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English Pages 127 [105] Year 2022
THE BOOK WITH NO ANSWERS Unlocking the Power of Questions for a Better Life
ROBERT JAMES MAIOLO
Copyright © 2022 Robert James Maiolo The Book with No Answers Unlocking the Power of Questions for a Better Life All rights reserved. No part of this publication may be reproduced, distributed, or transmitted in any form or by any means, including photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the publisher, except in the case of brief quotations embodied in critical reviews and certain other non-commercial uses permitted by copyright law. Robert James Maiolo [email protected] First Edition 2022 The Book With No Answers is a work of Non-Fiction. Some names and identifying characteristics have been changed to protect privacy.
To Enzo, and anyone else that never got a fair shot at life.
Table of Contents Introduction PART 1 THE ROADMAP Chapter One Who am I? Chapter Two Who do I want to be? Chapter Three How do I get there? Chapter Four How do I stay on track? Summary of Part One PART 2 THE BACKPACK Chapter Five Questions for when you feel lost Chapter Six Questions for when you need motivation Chapter Seven Questions for when faced with adversity or loss Chapter Eight Questions for when you need a laugh Chapter Nine Questions for when things are going great Chapter Ten Questions for when you feel like being introspective Chapter Eleven Tactics on how to help find answers Summary of Part Two Conclusion Acknowledgements About the Author
Introduction Congrats! You just bought a book with no answers. I respect your love for adventure. In this heroic quest, there may be a few reasons you decided to pick up this book. One reason may be that you have a discontent with books written by “know-it-all” authors who claim to have all the answers in life. Five tips on how to wake up earlier, ten tricks on how to be a better partner, seven hacks to pay more attention to your kids, etc. Some books in that genre can come off as pretentious and preachy and can get tiring and old pretty quick. Another reason you picked up this book may be that you were intrigued by the title of the book. If a book has no answers, what could it possibly be about? The funny thing about this title is that I originally wanted to call the book People Don’t Listen . I realize this is an overgeneralization, but we all know one person that asks everybody and their mother for advice, and then doesn't take any of it. I know I’m guilty of it. I’m sure you have been too in the past. I think the correct term is “Askhole.” There have been countless times where I’ve given people advice, only to see them go and do the opposite. Although discouraging, it was the inspiration for this book. Throughout my life, in my attempts to give people advice, I’ve noticed one thing that does have a high success rate. If someone thinks it was their own advice that they thought of, they just might listen and act. People are willing to put more emphasis on a plan they’ve devised through self-discovery than a plan they read about on the internet. To do this, you need to enable that person to ask themselves the right questions. If someone asks themselves the right questions, this will expand their consciousness and enable them to find the right answers and advice all on their own. That is the goal of this book — to ask the right questions. The title didn’t mislead you; there will be no answers in this book. If you’re looking for “Five life hacks to make your high-school sweetheart more
interesting after ten years of dating,” you might be in the wrong place. What I do have for you is a series of questions I have asked myself that have enabled me to find some answers in life. Questions that planted a seed in my brain and allowed me to ponder and wonder for weeks, months, and sometimes years. Through that time, I started to find some answers to these difficult and lifelong questions. This has expanded my understanding of myself, my life, my goals, and the actions I'm taking to achieve them. I know these questions can do the same for you. Throughout this book, I’ll go into detail about the deeper meaning to these questions, how you can break them down into a more digestible format, and even use a made-up character as an example to show how this process could work for you. We will also organize these questions in a way that gives you a clearer gameplan in life, often referred to as a Roadmap. More on this later. Most of the questions will be open-ended with no right answer. A couple of them are simple questions you’ve heard a lot in the past. The goal of this book isn't for you to have all the answers to your life and your future; the goal is for you to start thinking about the right questions about your life and your future. I’d recommend having a journal nearby; you may want to write down some thoughts as we go through the questions. If you’ve ever been to a therapist, you know that despite what people believe, they offer very little answers to your problems. Most of the words therapists use are in the form of a question. They almost never say “That's happening because…” Instead, they'll say something like “Why do you think that is?” This is the spirit of what I’m trying to accomplish here — thought-provoking, answer-provoking questions. This book will help those feeling a bit lost, those who need some guidance and direction, who are struggling to find answers, or may not even be asking the right questions. Even if you feel like you're in control of your life and are doing exactly what you need to be doing, this book will help you add some depth and structure to your life and actions. This book will also prepare you for life's twists and turns when they inevitably come your way. I believe everyone needs to take a step back and ask themselves some questions occasionally. This book will help you do that in a structured and productive way.
You might be thinking, what's wrong with listening to other people's answers? Why are questions so important? Asking ourselves questions can expand our consciousness. It allows us to understand more about ourselves and the world around us. It also allows us to teach ourselves lessons through self-discovery. If you try to learn something from an influencer on Instagram, it may never sink in. Their answers are based on their life and experiences, not yours. However, if you can teach yourself something through questions and discovery, you’ll remember it forever. Questions can also shine a light on our problems and insecurities, which although may be scary, is a great way to deal with them — sunlight is nature’s best disinfectant. Before we figure out where we are and where we’re going in life, we need to understand ourselves. I truly believe that asking ourselves questions is the best way to do that. If you don’t agree with me, I know this book can convince you otherwise. If you do agree with me, this book is going to take you on a wild ride. Typically, the idea for books have a grandiose story of timing, passion and opportunity slamming into each other like some sort of magical car crash, however that isn't the case here. It’s much more mundane and boring. It happened while working as an associate for a bank (ugh) in Toronto. Let's call them Big Green Bank (BGB). During a quarterly meeting, I was asked to give a talk that would motivate my fellow associates to perform better in their role. As I started to work through what the speech would be, I realized quickly that it was coming off as pretentious and preachy. The content made it seem as though I had this all figured out and I was about to drop some mind-blowing knowledge on these young-ins. I soon realized that wasn't true, and that wasn't me. I was in the same boat as them, still trying to figure out my career and life. However, there was one difference between me and the 200 people in the audience; I was a little further on in my career, so I knew I had something to offer. On the day of the talk, I wore my best suit, got up on stage, faced the audience, and said, “I’ve been told to come up here and motivate you all to be the best at your jobs; however, I don't really know how to do that.” I saw my boss across the room. If he had a poison dart and a bamboo shoot, I likely would’ve been dead on the spot.
“What I do have is a series of questions I’ve asked myself, and encourage you to ask yourself. This might help you find your own answers to your life and career.” My PowerPoint (ugh) was simple. I had five slides with a cool picture and one question on each of the slides. As I went through the slides, I explained my process of understanding the deeper meaning of these questions, how to frame them properly, and how to begin the journey of answering them on your own. Not one piece of advice was given, just questions asked. Right after my talk, we broke for a late lunch. The response was incredible. People came up to me saying they really enjoyed the speech, that they took a lot of notes to ponder over, and that it was the best speech of the day. I was flattered by the response and the impact my talk had on my colleagues. As the days passed, I wondered who else would benefit from the lessons I talked about. It inspired me to find a way to get this message out to more people. This book is a distillation of the talk I gave that day. So let me start this book the same way I started that speech. In the book The Hitchhiker's Guide to the Galaxy by Douglas Adams, a supercomputer named Deep Thought is commissioned to provide the answer to the question “What is the meaning of life?” After spending millions of years calculating this problem, the computer finally spit out the answer. The answer was “42.” Everyone looked disappointed and underwhelmed. The computer continued by saying,
“I think the problem, to be quite honest with you, is that you’ve never actually known what the question is.” I truly believe we all need to focus more time on finding the right questions to ask. The better we can frame the questions in our life, the more successful we will be in finding the right answers. So, if I didn't make it clear enough already, there will be no answers here, just a bunch of questions I know will help you find your own answers.
Just promise me when you’re done, you won’t write another fucking selfhelp book.
PART 1
The Roadmap This book is going to prepare you for an adventure. A long adventure filled with many twists and turns. It’s called “the rest of your life.” Much like any good adventure, there are two things you’ll need to be prepared — a map to guide you and a backpack full of supplies. Part one of this book will be all about creating your map, or as we’ll refer to it in this book, your Roadmap. Like any traditional map, your Roadmap will have three things: 1. A starting point, referred to as point A 2. A path 3. An end point, referred to as point B However, instead of getting you from your house to your job or a local coffee shop, this Roadmap will be much more meaningful. This Roadmap will get you from where you are today as a person to where you want to be in the future. By the end of part one, you’ll have a Roadmap with a clear indication of where you are today, where you want to be in the future, and a path to help you get there. Even if it's not perfectly laid out, I'm confident you’ll at least be able to begin the process of drawing your Roadmap and thinking about what you want it to look like. Regardless, at no point am I going to tell you who you are or who you need to be. I’m merely offering a series of articulately organized questions that will enable you to find out these answers on your own. I don’t know you, so I’m in no position to offer answers; that part is on you. The last thing we’ll do in part one is help you make the Roadmap as efficient as possible. When you use Google Maps, it tells you the fastest way to get there with the least amount of traffic and turns. A straight line is
the shortest distance between two points. We won't get a perfectly straight line; there are no straight lines in life, but we can do our best to find the optimal route. This is what your Roadmap looks like right now. It’s blank, and oddly looks like a pirate map, but that's OK. Pirate maps are fun, and it won't be blank for long. Let’s get started.
Chapter One
Who am I? This might sound like an easy question to answer because it seems basic. You've also probably heard it asked often. Someone may have even asked you this question a couple of times in the past. Whether it be on a date, in a job interview, or maybe from a therapist, a version of this question has come up in conversation. It was likely framed as “Tell me about yourself?” or “What's something cool about you?” However, it can all be boiled down to a question I believe everyone needs to ask themselves in their life, early and often. Who am I? This is the starting point in trying to find some answers in your life. If you don't know who you are, it makes it very hard to find answers to the other questions later in the book, and later in life. Think of this as your starting point on your Roadmap, your Point A. When answering this question, a lot of people start out with basic descriptive answers about themselves: “I'm a guy.” “I like yoga.” “I went to University of Michigan.” (Go blue!) “I work at Bed Bath and Beyond.” These can be great answers to start with and to get the ball rolling, but they're surface level and won't get you far. This is a big question, and a lot of people get distracted by the complexity of the meaning. It's difficult for someone to summarize their whole life into a few short sentences, especially with little notice. What might help with this is to break down the question “Who am I?” which can be broad and tough to narrow down into smaller sub-questions that are easier to digest and find answers to.
What I’ve done to help with this is broken it down into four sub-questions. I’ll go over them in detail so you can understand what they're asking and why they're important. After we go through these four sub-questions, we can use our answers to help with solving the larger “Who am I?” question. Let's get started. 1. What do I care about? I’m sure something popped in your head when you read that question. If it didn't, feel free to read it again. Oftentimes, people can help define who they are by the person(s), places, causes, and hobbies they care about. For example, if you read that question and thought about your kids or siblings, then maybe you’re a family-oriented individual. If you think about work, then maybe you’re a career-driven maven. Did you think about your summer plans to visit Banff? You could be an outdoorsy person with a love for adventure. I realize caring is a subjective term. I think deep down you know what things you care about, and what things you sometimes pretend to care about. Asking yourself what you truly care about in life will help remind you about the things you spend your time doing/thinking about. It's only natural that this will start to define who you are. 2. What do I offer to the world? Please don’t say “I have nothing to offer” because that's just not true. If you've already said it, then take it back. I'm waiting… Perfect, thank you. I also agree that you have something to offer. It doesn't have to be a unique talent that gets you a million views on YouTube. It's probably something you’ve taken for granted because it's always been part of you. Smart people often say they’re “dumb.” Good listeners sometimes don't realize that being a good listener is unique. Being reliable is something that’s only noticed when you've been around unreliable people. If you’re struggling to find this answer, it may be a good idea to ask someone else. Sometimes our friends know more about us than we think. Love? Guidance? Entertainment? Compassion? It can be anything. Ask around if you have to, but you offer something to the world, and it's a big part of who you are. Go find it. 3. What have I been through that not many others have? This doesn't have to be traumatic or life-changing, but it can be a useful tool in finding what's unique about yourself. Everyone goes through ups and
downs, but I can imagine there's something about your past that not many people have been through. Maybe you used to sell baseball cards on weekends, used to make birdhouses with your grandmother or ate Popeyes chicken every day for a week to win a bet. What about that one weekend where all you did was play video games, that rough patch where you drove your aunt to chemo treatments every day for a month? What about the fact that your cousin played for the Chicago Blackhawks and you partied with him when he won the cup? As you can see, the examples can widely vary, but there's a unique part of your story that needs to be shared. Like the previous question, people often think things in their life are typical because it's always been part of them. Going to sailing camp every summer as a kid doesn't seem that unique to someone who sailed their whole life. But for someone like me, who still doesn't fully understand how sailboats work, it is unique. Look through some pictures, ask a friend or family member, read an old journal. There's something unique about your past, and it has likely shaped who you are today. 4. What do I want people to know about me? (Careful with this one) This question comes with a warning sign for a reason. Notice this question does not say “What are the carefully selected things I want people to know about me?” If not careful, this question can lead to cherry-picking and create a fake facade about your life. This question is asking you to think of what you want people to know about you because it's a reflection of who you really are. Please don't stretch the truth. The truth matters here, the whole truth. Use your answer as a tool to advertise something about yourself that the world needs to know. Just don't forget to make it true to who you are. Now that you've spent some time thinking about these four questions, they can offer you some insight into who you are. As you’ve noticed, who you are is composed of many different things, and put together, can offer a robust and informative answer. One exercise you can do a little later in the chapter is to take the main highlights of each answer to the four questions, the most poignant and important parts, and string them together in a sentence or short paragraph.
Again, don’t cherry-pick your favourite parts of your answers and turn it into a McDonald’s commercial. This must be real and true to who you are. Feel free to put this book down if you need to and think about the questions you just read. If the answers don't feel obvious, then you may need more time to find them. What might help make this process a bit clearer is to go through an example. To do this, I’d like to introduce you to someone. His name is James. What I will do at the end of every chapter is apply the principles we learned in the chapter to James’ life. We’ll call it “James’ Journey.” This will allow you to see a case-study example of how these principles can work for you. Sometimes it helps seeing an example of the theory being practiced to help drive home the point, so this should definitely add some value to what you've learned already. James’ Journey James is in his early thirties and lives in the city with his girlfriend. He works as a relationship manager in the finance industry. He works from home (thanks a lot, ‘rona) and tries to see his friends and family as often as he can. He balances friendships with his relationship, his uncle duties, trying to start his own real estate business on the side, while also trying to be a physically and mentally healthy individual. Sounds easy enough, right? James has been feeling a bit lost at work and in his personal life. At times, he struggles to find meaning in this seemingly random world, and he's not sure where to turn or how to find the answers in his life. After months of feeling like a lost puppy, he's determined to act and make a change. James has decided a good first step would be trying to figure out who he is. He wants to start asking himself some hard-hitting questions that will force him to look at himself objectively and in a new light. The first question that he wants to tackle is... Who am I? Well, since James bought a book called The Book with No Answers (nice, James, nice) he learned this daunting question is easier to tackle when broken up into four smaller sub-questions. It's not quick and easy, but, over time, James starts to think deeply about these questions until he's able to find some answers. Here are some of James’ answers: 1.
What do I care about? I care a lot about my girlfriend and my family. I want to be there for them and be around for the important stuff. Birthdays, weddings, soccer practice, I don't want to miss any of it. However, I realize I need to take care of myself, too, so physical exercise and meditation are things I try not to skip. I don’t feel like the best version of myself when I skip those things. I also have several groups of friends from different parts of my life. Although I don't see them as often as I’d like, I try to text as often as I can and tag them in things they might like on Instagram. This is my way of showing I care; it's the best I can offer right now. With all of this, I do my best to make sure work isn’t taking a back seat. I put in a good effort when I'm logged on, but I’m not sure if it’s my best, and I know that, and that's OK right now. Juggling priorities in life isn’t always easy. 2. What do I offer the world? I think I offer a kind soul. It sounds lame, but I really try to be a good person to those around me. Being a jerk just never feels good. I'm human, and have my moments, but I think what I offer to my community is kindness and candor. I sometimes lose it but remind myself of it often. 3. What have I been through that not many others have? Somehow, although only thirty-one, I've been a pallbearer seven times. I've also been a best man twice and was at the hospital when my niece and nephew were born. I've seen the beginning of a lot of great things and the sometimes beautiful, sometimes tragic end to a lot of things. This gives me a lot of understanding and a unique perspective on how fragile life is. I think I could teach a course on grieving — how to deal with it, how to learn from it, and how to grow from it. I don’t know who would attend that course though; kind of depressing. 4. What do I want people to know about me? I try. I don’t always deliver, and I sometimes disappoint people, but I really try. I know this because I'm my own toughest critic, sometimes to a fault.
Sometimes, I'm not there for people; sometimes, I lose patience, but I really try not to. I'm aware of who I am and my emotions, so I do my best to control them. It's not easy, I work on it daily. As you can see, some of the answers are well thought out and meaningful while some are short and to the point. However, they all took a lot of soul searching, self fact-finding, and most importantly, time. There's no substitute for time and you can't avoid deep, meaningful thought when it comes to self-awareness. Sometimes, even planting the seed of a question will allow answers to form quietly in the back of your mind. I’m sure the above answers are still a work in progress, but it's a start, and something James can build on. After going through this exercise, James can now come up with a decent answer to the question Who Am I? To do this, he takes the most important parts of the above four answers, and strings them together into a short paragraph. He doesn’t cherry-pick and he doesn't act like his own personal publicist. He instead finds the deep and meaningful parts of his answers that truly reveal who he is. When James asks himself “Who am I?” he now answers with the following: My name is James and I work in finance on the relationship management side. I live in the city with my girlfriend who I love spending time with. You can find me at my nephew’s soccer practice, my buddies’ birthday parties, and my cousin's wedding. I always make time for family. My friends often call me the “go-to” guy, always around for a chat or to listen, sometimes over a glass of scotch or two. Although I try my best to be there for others, I also make sure I take care of myself, too. I’ve seen a lot in life, the good and the bad. I wouldn't change any of it because it made me who I am today. I think the reason people feel comfortable leaning on me is because not only have I seen a lot in life, but I take the time to digest and understand it. I guess what I'm trying to say is, I try to put in a good effort in everything I do. And although I don’t always succeed, I don't let it stop me from trying.
Notice how the answer to the larger “Who am I?” question is made up of the same answers he gave to the previous four sub-questions. All James had to do was take those four answers, mush them together, format it into a paragraph, and he was left with a robust answer to the question “Who am I?” Feel free to use the same method and see if it works for you. Also notice how James starts out soft, gives some basic information about himself, and then dives deeper into who he is and how he got that way. James knows this
definition isn’t stagnant. Who he was at the age of twelve isn’t who he is at the age of thirty-one, and certainly won't be who he is at the age of fifty. It's a dynamic, fluid response that changes as time goes on. It reminds me of my favorite quote from John Maynard Keynes:
“When the facts change, I change my mind. What do you do, sir?” As time goes on, and the facts of your life change, your answer will change. For example, James may get a promotion next year that requires more of his time at work, which will then start to take away from his time with his friends and family. He may also have less time to work out if he suddenly needs to spend his evenings doing his day job. These changes may sound like changes for the worse to some or sound like a change for the better to others. That isn’t super important here. This isn't “Who do I want to be?” That's coming later. This question is based purely on fact and circumstance, and as the facts change, the answers change. Another thing I want you to notice in James' answer was that he barely mentioned his career. This is something I want you to challenge yourself with. Most people struggle to define themselves outside of their career, so try to push yourself to go beyond just talking about what you do for a living. Career is important, I don't deny that. In fact, I will talk about it a lot in the book because this is something most of us have in common, but what are you beyond your career? I’m fully aware James made this process look easy when it isn't. Again, James spent days, months, and years sifting through his past and coming up with the answers you see above. I also realize James’ answer was personal and gave a lot of information about himself. You don't have to advertise this to the world if it makes you uncomfortable; the answer is for you and anyone you choose to share it with. Don't let your discomfort of sharing personal information distract you from finding the deeper meaning to this question. If you want to share this information with the world, great, tweet it. If you don't, that's great too, keep it to yourself. Neither of these are an excuse for avoiding the adventure of self-discovery. Although this is uncomfortable at times, you
need to have a relentless pursuit of the truth. Remember, this is your Point A, your starting point. You can't have a successful adventure through anything in life if you don't know where you started from. James gave a great response to the questions above, but please don't just focus on the answer he gave; focus more on the questions he asked himself, the thought he put into it, and the process he took to get there. This is what I’m hoping you leave this chapter with. The journey to finding the answer, and the self-awareness it takes to find those answers is much more important than the answer itself.
Map Update You've got the most important part, where you're starting from. It’s OK if you haven't marked your Point A yet; you'll get there with time. Even if you have marked your Point A, your map still looks bare, but we've made progress, so let's keep going!
Chapter Two
Who do I want to be? Naturally, if we started the book with figuring out who we are today, the next step would be to think about who we want to be tomorrow. If chapter 1 is Point A on your Roadmap, then think of this chapter as your Point B. This is where our Roadmap is leading to. You’ve been asked this question a lot in the past. People on first dates love to ask it, friends and family enjoy asking it too. People often ask more specific versions of the question such as “Where do you see yourself in five years?” or “What's your dream job?” This is people's attempt to strip down a broad question into something more digestible and specific. I'm a big fan of this. People often freeze when you ask them big life questions. They are much more willing to talk when it's a small and fun question. However, I want to start at the most basic version of this important question. Who do I want to be? Notice a key word in this question — want. Unlike its boring younger sibling, this question isn’t based in fact. It's not based on circumstance, setting, your past, obligations, current mindset, or any sort of literal reality. No, no, this question is way more fun. This isn't, who am I? This is who do I want to be? I can't stress the word “want” enough. This is the question where you get to have a lot of fun. You get to dream, hope, wonder, and fantasize about your future. The sky's the limit, and even that seems too low. This question allows you to think beyond your current potential and launch yourself one, five, ten, fifty years into the future. Much like the last chapter, this question has a lot of depth to it, and breaking it down into smaller sub-questions will help us understand it better. However, before we do that, I think it's
important to highlight what this question doesn’t ask. This question does not ask the following: How much money do I want to make? Do I want to be a vice president or senior vice president? Do I want to drive an Audi or a Benz? Do I want the lake house in Banff or a beach house in Malibu? This question has nothing to do with how much money you want to make, what title you want to have, what ocean you want to live besides, or what version of the Real Housewives you want to have a guest appearance on. This question goes far deeper than that. It asks, “Who do you want to be as a person?” It's a question of reputation, of legacy, of passion, and interest. It's a question of what chapters you want to write in your autobiography, how interesting will your diary be, how proud will you be of the progress you've made, and, quite simply, what do you want your days to look like when you're older? Before we start to break it down, I need you to do something for me. I need you to go into this with a growth mindset. If you're not happy with who you are, there are things you can do in the future to change that. Even if you're happy with who you are today, I'm confident there are bigger goals you want to achieve in the future. The way we're going to get there is with a growth mindset. We can't stagnate; we must continuously grow to find our future. If this mindset doesn't come natural to you, join the club. I wasn't always like this, either, but we can change for the better. A growth mindset helps make that happen. My second ask of you is that you throw every ounce of realisticness (I can’t believe that's a word) out the window. There’s little room for practicality here. This chapter is for dreaming. If the answers you came up with in chapter one didn't make you happy, here's where we change them. If they seemed mediocre, here's where we improve them. And if they seemed like they were heading somewhere great, here's where we can set them on fire and blaze you into an incredible future (I told you all practicality is gone here). So, if you're ready to dream, then let's start breaking this down into four sub-questions that will make this big question a little easier to understand.
1. What does success mean to you? This question is probably the easiest to grasp; there are no tricks here. What does success mean to you? What comes to mind when I ask that question? Sometimes, it might help thinking of a successful person you know. Or make one up if you must. What does a successful person look like? What do they have? What does their life look like? Who are they surrounded by? How do they make you feel when they speak to you? What do they do for their community? There's no right answer here. If a boatful of money, liquor, and models looks like success to you, then cheers, save me a seat and I'll bring the beer pong table. However, I will challenge you to look a bit beyond the artificial surface and dig deeper. Try to think about what you hope success will feel like. Sometimes, it's easier to chase feelings than things. Your gut will tell you a lot about whether something is right for you. The reason this question matters is because I'm going to assume you want to be successful in the future. However, “success” is a broad term, and difficult to chase if you don't know what it is. The first step to being successful is defining what success means to you. Once you have that, it will give you an idea of what person you need to become in the future to achieve that success. 2. What do you want your legacy to be? This question is significantly more difficult, because it requires you to go into the future while also looking back at your life; that's like four different dimensions of time. What I’d like you to do is imagine yourself when you're “older.” I’ll let you decide the age. Let’s say the age of eighty, for example. Now that you're eighty, I want you to look back at the previous forty years of your life, age forty to eighty. What legacy did you leave behind? Or better yet, what legacy do you want to leave behind? Maybe you cured a disease, became a philanthropist, raised four amazing children, built a successful company, fell in love with your soulmate, sailed from Newfoundland to Ireland, or broke the record for most beers chugged in ten minutes (you legend, you.) You can also think about what type of person you were during those times. Rather than what you did with your life, how did you make people feel?
What stories will they tell about you? What did they say to each other when you left the room? You don't have to have a life full of achievements to have a great legacy. Many times when people talk about legacy, they talk about who they were as a person, not just what they did. The eulogies I've heard and personally delivered mostly talk about how they'll miss the person, their energy, and how they lived their life, not how much money they made. If a eulogy sounds too dire, then think about your retirement party. What toasts and speeches would you like for people to deliver about you? What do you want them to say? There's no right answer here; this is the legacy you want . When you start to think about what you want your legacy to be, it will start to shape the person you want to become. Many people believe in “reverse-engineering,” meaning you imagine the final product and work backwards. In this case, if the legacy you hope to leave is being a great philanthropist, what actions will you need to take in the future to make that happen? If you want your legacy to be one of compassion and empathy toward others, are you that type of person today? These answers will start to highlight the change you need to make that gets you from Point A to Point B on your Roadmap. This will come in handy during the next chapter. 3. What's something you went through that you don't want anyone else to go through? I once saw an incredible interview where someone explained the difference between the hero and the villain in a story. You see, the hero and the villain typically have the same backstory; they both experience a tremendous amount of pain that shapes who they are. Where they differ is how they respond to it, or as the interviewee in the video explained:
The villain says “The world hurt me, I'm gonna hurt it back.” The hero says “The world hurt me, I'm not gonna let this happen to anybody else.”
It’s literally how you decide to react to pain that causes you to become the hero or the villain. I’m going to go out on a limb here and assume you want to become the hero in your life and the lives of those around you. Hopefully, the above text proves to you that just because you went through pain in the past doesn't mean you can't become the hero in your life. In fact, you unfortunately had to go through that pain to become the hero today and in the future. I know it's uncomfortable, but this may be a good time to think about the pain in your past that you went through. If it's a small pain, like having to use cumbersome software or doing a boring manual task, this can be the spark for an idea in the future. It can shape who you become and what you do with your life. Maybe you make a better software or a better “mousetrap” to help reduce the pain for everyone else. If it's a big pain, like childhood trauma or losing a loved one, this can and will shape who you become in the future. It may make you a more empathetic person, someone who listens to people and is always around to help. Maybe you take that one step further and become a counselor or social worker, helping people get through trauma or confusion in their life. Remember what Batman said in The Dark Knight Rises :
“A hero can be anyone. Even a man doing something as simple and reassuring as putting a coat around a young boy’s shoulders to let him know his world hadn’t ended.” You can be that hero. Maybe it's a smaller version, maybe it's a gigantic version; that's for you to decide. However, a good way to start finding that path is to think about the pain in your past, and let it be the fuel you need to become someone's hero. Ideally, your own. Once you identify the pain in your past that you don't want anybody else to go through, you can then
decide the person you need to become to be that hero. Will you become an engineer? A police officer? a personal support worker? An awesome team manager? Or maybe it doesn’t impact your career and it just changes what kind of person you become. Maybe it turns you into a sympathetic individual that other people can always count on. Maybe you turn into the awesome parent you always wanted. The way you can find this out is to think about the pain in your past that you hope to make right for others. 4. What do you want your days to look like in the future? Alright, let's finish off with a lighthearted question after that rough one. I want you to think about this one quite literally. What do you want your days to look like in the future? Like…literally. In the future, ten or twenty years from now, what do you want to do when you wake up in the morning? What do you want to do for lunch? What do you want your nights to look like? What do you want to spend your summers doing? New Years? Christmas? In fact, I want you to get so practical, I want you to schedule out an ideal day in the future. What time are you going to wake up? Are you going to drive your kids to school? Do you even have kids? Are you working from home or at the office? What are you doing after dinner? What about your summer? Are you going on vacation? Taking your kids camping? Going to Cabo with your soulmate? Maybe you'll be retired, and that opens another can of worms. What do you want your retirement to look like? I worked at a bank for almost ten years and spoke to hundreds of financial planners, most of whom dealt with peoples’ retirement plans. They’d always stress to their clients, “Don't just think about saving enough money, think about what you’re going to do with all that free time. You can only watch so many reruns of Seinfeld.” Although I disagree with the Seinfeld part, I agree with the rest. If you start to think about what you want your days to look like in the future, it will help you start to think about who you want to be in the future. Who you are is a sum of your actions. What you do in the future is who you will be in the future. This type of planning will help you start working toward those goals.
Is your goal to sail the world when you're fifty? Well, not only do you have to save for a sailboat, but you better start taking some bloody sailing lessons. Want to retire at forty-five? Maybe you should start figuring out multiple streams of income or start working on that grand-slam idea you're going to sell for millions. Want kids? May need to find a partner for that. Or think about starting the process of adopting on your own. Want to drive those kids to school? You better find a job that allows for that kind of flexibility. So, go ahead, start writing in your day planner. But not for this Monday, write it for this Monday ten years from now. What does that day look like ten years from now? Doing this will give you a good idea of what you will look like ten years from now. Now that you've thought about the four sub-questions, you can start going through the same process as the previous chapter. Think about each of the questions and their descriptions and begin thinking about some answers. Again, don't worry so much about having the perfect answer, or any answer. You’re not going to figure out your entire future in the time it took to read this chapter. The important thing is that you start the process of discovering those answers. James’ Journey Alright, let’s cut the BS. I’m James. I don't know why I felt inclined to make you believe it was a fictional character; maybe I was scared of being too polarizing or that I’d get trashed in the Amazon reviews. Regardless, if you didn't figure it out already, I’m James. I wasn't even being that clever; James is my middle name, and it's literally on the book cover. Anyway, I’ll stop with the generic answers and give some real answers based on my life. Once I started to feel confident in my answer to the question “Who am I?” it made it a lot easier to take on new challenges in my adventure of selfdiscovery. It also helps me feel a lot more confident in my day-to-day life. Once you know who you are, you can’t get pulled in different directions
and be swayed by temptation. I’m getting a better idea of who I am and am using that as a stable foundation for the future. I’m now feeling confident enough to tackle the next major hurdle, which is coming up with an answer to “Who do I want to be?” To start, I’ll answers the four sub questions. 1. What does success mean to you? The first thing that comes to mind is happiness. Money is great but being miserable in a Porsche doesn’t sound that great to me. I’d rather smile in a Toyota. I realize “happiness” is a vague term that's hard to drill down, but it's something I work on finding, and will likely be a lifelong venture. When I think of a successful person(s), I think of my parents. They don't have all the money in the world, but they built a great life with whatever it is they do have. They raised me and my two siblings, have a great marriage, always found money for a small family vacation, roof over our head, everything. My parents are two of my heroes and I hope I can replicate their success in my future. 2. What do you want your legacy to be? When I think about what I want my legacy to be, I focus more on what effect I want to have on the people around me. I want people to think about me as someone they can count on. Someone who was a good husband and a good father. Someone who did his best in his career, but never let it overshadow his friends, family, or personal interests. Someone who was inquisitive, never scared to try new things, and never scared of adventure, even if the destination was unsure. I want my girlfriend to be proud to call me her boyfriend (and eventually husband). I want my parents to be proud to call me their son, and I want my future kids, nieces, and nephews to look up to me the way I look up to my parents. 3. What's something you went through that you don't want anyone else to go through?
When I was twenty-three years old, I lost my brother to heart failure; he was thirty-two. It was horrible, and easily the worst part of my life. I’ll share more details later in the book; I don’t want to get too depressing too quickly. Unfortunately, death has promised us that everyone we love will one day pass away, so there's nothing I can do about that. However, what I don't want anyone else to go through is the loneliness. Not only did my brother pass away, but I was on the other side of the world in university when it happened. I remember being at a travel agency in downtown Manchester trying to book a flight home. It took ten minutes for me to tell the agent I was trying to go to Toronto, I couldn't stop crying. I’ve never felt so alone. I was lucky I had a family to come back to and lean on, but I realize not everyone is so lucky in life to have that support system. Some people have to deal with loss by themselves and can end up internalizing it for a long time, sometimes forever. I think this is why being available to friends and family is so important to me. I never want people in my life to feel like I did that day. 4. What do you want your days to look like in the future? Well, if you really want me to get practical, let me write an ideal schedule for me fifteen years from now when I'm in my mid-forties. Morning: wake up early, get a workout in before anyone is awake. Make breakfast for my family, help my kids get ready for school while my wife gets ready for work. Take the kids to school and stop off for a walk in the park on the way home. During the day: work, either from home or in an office, not picky. Eat a good lunch, maybe find time to go for a walk or partake in one of my hobbies (going for kayak ride would be awesome.) Afternoon: Pick up my kids from school, either bring them home or take them to an activity. Hang out with my wife, talk about our day, and have some dinner. Maybe go for a walk or bike ride as a family. Night: Watch some TV, chat with a friend, go for a drive to the waterfront with the family, maybe get in some yoga or
meditation and get to bed early to do it all over again tomorrow. All in all, I want it to be centered around my family, my hobbies, and our health. Work is part of it, but it's not the main attraction. I want to be more than my career, and I want to show my kids the importance of taking care of yourself and your family. I also want to be ready and available for my wife, whenever she needs me to be. I know some of these answers can seem grand and imaginative, and that's good! That was the goal of this chapter, to dream about a great future. In addition to just dreaming, I tried to be specific about what it is I want my life to look like, all the way down to a specific schedule. It's OK if you can't get this narrow; it's sometimes hard to think of these things on the spot. It's also OK if your answers seem boring or mundane. This isn't a popularity contest; this is your life and the only approval you need is your own. I will remind you again that although the above answers seem like they came easy, they didn't. I’ve spent a tremendous amount of time thinking about these answers and did the best I can at making them robust and well thought out. You also need to spend a tremendous amount of time if you want to do the same. Now that I’ve answered the four sub-questions, let me take a shot at answering “Who do I want to be?” In the future I only want one thing, to be happy. Not just me, but my family and friends too. I want to be a reliable person my immediate circle can lean on and count on. I want to be a good husband and father. I want to be the guy that people feel comfortable calling not only when times are rough but when they are good too. I want to be the guy that chases his goals and dreams, lives his life purposefully, and makes time for his hobbies and interests. This may sound selfish, but I think I need to be happy and fulfilled before I can do the same for others. I want to be a good spouse and parent, just like my parents. When I think about my life fifteen years from now, I want to be able to make time for the important things, like driving my kids to school, seeing my wife when she gets home from work, and having time for hobbies and exercise. I realize this type of life and freedom doesn't come easy but thinking about what my life will look like in my forties allows me to think about what I need to do today to make that happen.
I tried to keep my answers deep and meaningful. Not a lot of talk about how much money I’ll have one day or what car I want to drive. When I think about being a good dad, I don’t think about having a big house or massive
backyard. It's very emotional and qualitative. I encourage you to do the same. I’m also well-aware of the amount of work it will take to get to where I want to be and acknowledge that the work to get there starts with my actions today. Again, there's nothing wrong with money. In fact, I’ll need a decent income to afford this kind of freedom and lifestyle, but that's not what I talk about or think about. I’m only focusing on what that money and freedom will do for me and my family. If this lifestyle does require a lot of money, then I can put this into my game plan for getting to my Point B (more on this in the next chapter). What I’m trying to get at is, if you want to make a lot of money in the future, great, but what you are doing with that time and money will dictate what kind of person you become in that future — I think that's just as important. There's another thing I want to highlight in my answer. I talked about not only my happiness but the happiness of those around me. I find it interesting that my happiness is tied to other people's happiness. I’ve noticed in life that it can be exhausting to have your happiness be reliant on others, and sometimes feels like a pointless endeavor. However, I believe the acknowledgement that happiness starts with yourself is a good first step. I have found a lot of unhappiness in my life when I felt like I was giving to everyone else more than I was giving myself. Think of it as when the masks drop in an airplane during an oxygen deficiency. You need to put on your own mask first before you can take care of a child or an elderly person. Happiness works the same way. You can't make others happy unless you make yourself happy first. This will take some time and patience when figuring out your answer to who you want to be in the future. I'd recommend writing down your thoughts as time goes on. I'd also recommend emulating what some successful people in your life have. Don't be afraid to be a copycat in the beginning; you'll tailor it toward yourself as time goes on. If you say, for example, you want to be like Elon Musk one day, that can be a good start. As the days go on, you'll realize there's things about his life that you do like, and things that you don't. Over time, you'll start to chisel away at this future self until you come up with an answer that suits you. As time goes on, this answer will change as your priorities, interests, and wants change with it. Maybe right now you don't want kids, but five years
from now you might meet the right person, and can imagine starting a family with them. This will result in your answers changing about who you want to be in the future. This will likely happen often. I'd learn to embrace it as soon as you can. I’ll end the chapter by saying this. I don't expect you to figure out your future in the time it took you to read this chapter. I just want you to start deeply thinking about your future. These questions will help pinpoint the person you want to become. Once you get an idea of who that person is, the path to get there will be a lot clearer.
Map Update Alright! Look at your map now! Not only do we have a starting point, but we also have an end point. These are two important parts of a map, and we’ve already got them down. There's just one thing missing. If only there was a way to connect them. Some sort of path perhaps…
Interlude — Music While writing this book, I was listening to Eminem, the Red Hot Chili Peppers, Bruce Springsteen, Logic, MDymez, The Lumineers, Harry Styles and Jay-Z. Music has answers to problems we didn't even know we had.
Chapter Three
How do I get there? OK, great. You're working on who you are, Point A. You're working on who you want to be, Point B. This is great progress. Maybe you even have some pretty good answers to those two questions, which is even better. So proud of us. There's just one missing part, how are we going to connect the points? You need a path to connect the two points; that's kinda the whole point of a map. Imagine you live in Toronto, and you want to do a road trip to Los Angeles. With Google Maps, it's easy. It tells you every turn and highway. Now imagine doing that trip in the year 400 B.C. A little tougher, eh? Not only is it tough because Toronto and Los Angeles didn't exist then, it's also tough because there's no paved path to get there. Not too many people have done this trip before, and there are no signs, highways, or Google Maps to take you there. Now also imagine that Los Angeles has legs and moves randomly from one side of the country to the other. That's what this adventure may feel like. Getting from your Point A to your Point B will not be easy and will be a lifelong adventure. There are no signs, travel blogs, or hippy uncles that can tell you how to get there. And seeing as your Point A and Point B will be a dynamic location that changes as time goes on, it will be tough to pinpoint their locations and get to them. All this boils down to our third question: How do I get there? This question is often asked as “What's your five-year plan?” which inevitably turns into me rambling for ten minutes about a five-year plan that doesn't exist but I'm trying to make up so I can get this job that I applied to for reasons I can't remember. However, I don't care for that question because it's too generic, too corporate, too narrow, too…. ugh. Let's stick with “How do I get there?”
For the purposes of this chapter, we will define this as your path. There are a few ways to begin the process of figuring out what this path will look like, but before we do, I want to remind you of something. This is supposed to be the fun part. Life isn’t just about the destination. I know you've heard that before, and it sounds cliche, and maybe a little nauseating. To be honest, even writing it down makes me want to punch myself in the face. Regardless, it's true. Your life really is an adventure and is meant to be enjoyed. This isn't the means to an end. You can't just put your head down and hope to wake up rich in twenty years. Even if that did work, that sounds like an unfulfilling way to live your life and is a terrible waste of your time, especially if you're in your late teens or in your twenties. Some of the best days of your life are coming soon; you may even be in them right now. Don't forget to enjoy them. Please don't say “I can’t wait till I'm in my thirties and have money and ain’t a broke college student anymore.” Some of my best days were being a broke college student. I used to make bologna and cheese sandwiches, but without the bread. Literally, just roll a piece of bologna around a piece of cheese. It was delicious. Hard to get away with that now, though. If your future self is twenty years down the road, you have a lot of driving and living ahead of you. Your path will have a lot of U- turns, red lights, train crossings, potholes, roadkill, dead ends, detours, dirt roads, speed limits, and even a couple of bridges that collapse when you're on them. Yikes. Let's be sure we spend most of our time on this path living and learning. We’ll be on this path for a while, so it's a good idea to take in the view. Or as my mom would always say during a road trip,
“Don't forget to look out the window, this is part of the trip too.” Don't get so busy driving that you forget to take in the view. (Maybe wait for a red light for insurance purposes.)
Alright, now that the kumbaya stuff is out of the way, let's get down to business. You've got a long ride ahead of you and you need to start getting some miles on the odometer if you plan on ever getting to that destination. I know I said that the destination is not the most important part, but we do want to get there eventually. The hard part will be figuring out what this path will look like. It's tough to know how to get somewhere you've never been before. And seeing as everyone's life is different, you're trying to go down a path that nobody else has gone down. You're the pioneer of your own life, so you're going to be traveling down an unpaved and potentially unforged path. Although other people will have a similar journey that you can learn from (more on that later), this is the first time anyone is going from where you came from to where you want to be. There's only one you, remember that. Driver’s Education Course Even though everyone's path looks different, goes in different directions and speeds, are made of different materials, have different views, etc. Everyone's paths do have a few things in common. What I'd like to do is list a few things that will be on everyone's path in life, including yours and mine. Think of this as your driver’s education course. ● U-turns : You thought you were going the right way, “turns” out you weren't. That's OK, no shame in going back. At least you get to see what this part of the world was like. Looks like it’s not for you, time to turn back. It's better to take a U-turn then to go on for a long time in the wrong direction. CAUTION: Making a U-turn while you’re on the right path can be a real disrupter to your adventure. Make sure you’re going the wrong way before you make a U-turn. ● Red Lights: A moment to stop and think. Think about how far you’ve come, where you're going next, all the while taking a breath and taking it all in. Just be ready to go when it hits green again. ● Train Crossings: In a way, the long version of a redlight. Except now there's a nice train going by to distract you. This was also unplanned, as it's hard to know when the train was scheduled to go by. No worries, you've stopped, adapted, and are ready to go whenever the train gets out of the way.
● Potholes: They slow you down but also wake you up. You've probably driven through a bunch of these in your life. Sometimes, we need a suspension-shaking pothole to wake us up and focus on the path ahead. By the way, I wouldn't recommend trying to avoid them; that can be even more dangerous than driving through them. ● Roadkill: A reminder that life is short. Dark, I know. We all need a reminder of that occasionally. It's not fun to think about, but you’re going to join that raccoon one day. Enjoy the path and be thankful you're still on it. ● Dead Ends: Similar to U-turns because you're forced to turn around; however, dead ends are a little easier to deal with. There is no other option, you must turn around. A U-turn was your decision; however, the road (and life) decides when there's a dead end. Could you have seen it coming? Maybe. And maybe that's a lesson for next time. But for now, don't harp on it, just do a three-point turn and get out of there. ● Detours : Nothing wrong with these, it's all part of being a driver. Sometimes, you think you're going the right way, you learn new information, or something changes in your life, and you need to change the direction you're driving. Sometimes, it's better to take a detour than to go down a path that ends with a U-turn or a dead end. If you see trouble coming, a detour can save you. Some detours happen because you know what's coming and try to avoid it. Some detours happen because other people did things, and you now need to react. Either way, detours are coming in your future and there's not much you can do about them. The sooner you make your peace with it, the sooner you can get back on track. ● Dirt Roads : Dirt roads can be annoying because you were just on a nicely paved road with no bumps. Now you're on a rough dirt road, dust is flying, you spilled your drink on your seat, your cell phone fell out of its cup holder, an absolute pain. However, don't forget that just because you're on a dirt road doesn’t mean you’re going the wrong way. These rough times will remind you how good you have it when you're back on the smooth, paved roads again. This too shall pass. ● Speed Limits: These can be frustrating. You feel like you got it all figured out, you know where you need to be and you know how to get there, it's just taking forever. Speed limits keep you safe, annoying as they may be. They keep you from getting too confident in yourself. Just because
you know where you're going, doesn’t mean you're ready to go 200 clicks an hour with your arm out the window. I know you're excited, you'll get there, the destination is coming. Patience really is a virtue. ● Bridges that collapse when you're on them: This one is a bit extreme but stick with me. You're driving, the sun is shining, you're going over a bridge looking at the beautiful waters below, and then BAM the whole thing collapses from underneath you. Now, thankfully, this doesn't happen when you're driving in real life (not yet anyway, knock on wood.) However, this will likely happen in your adventure through life. You think you're going down the right path, everything is working great, you're on top of the world, nothing but smooth driving ahead. Suddenly, the bridge you were driving over collapses. Or in real life, that business venture doesn't work out, your partner leaves you, you lose a loved one, something you never saw coming hits you right in the face. These are hard to go through, but unavoidable in life. Don't get too down on yourself. Heal, recover, take the time you need, but get back on track because you've got a lot more driving to do. Next time, maybe take the ferry instead. Now that we all know the basics of driving, we can start planning our path. Remember, we have Point A and we have Point B, so let's draw a big line to connect the two. To do this, I’ve broken down the question “How will I get there?” into …. you guessed it, four sub-questions. You know the drill as to why we're doing this, so let's just get started. 1. What steps do I need to take? You may not think of it, but if you walk from your home to a coffee shop, it's a cumulation of a bunch of individual steps. Every path is taken one step at a time. To create the path to your future, you need to think about the individual steps to get there. Although it's against the rules, I do have some advice for this one. Remember earlier when I talked about reverse engineering? This is usually what people do to answer this question. Think about where you want to be in ten years, and work backwards to find the path. For example, if you want to be an electrician, you need to finish your five-year apprenticeship. To finish a five-year apprenticeship, you need to have someone take you on as an apprentice. To have someone take
you on as an apprentice, you may need to go to trade school, or start as a general laborer. To go to trade school, you need to… well, I think you get it. It's tough to connect the dots looking forward; it's much easier to look back and connect the dots to how you got there. Reverse engineering is a common way to think about doing this. Where it gets tough is when it comes to the person you want to be. Not the job you want to have, but the qualities you want to have. If you want to be an attentive parent that’s actively involved in your kids' lives, that's a little tougher to plan and reverse engineer. However, it may not be impossible. Can you reverse engineer being a good parent? If you think about someone in your life that's a good parent, were there steps they took, things they did in their life, and priorities they made that you could emulate? It's not easy, but there’s a lot of value you can gain in working backwards from any goals you have. While I’m in an advice-giving mood, I’d also recommend trying new things. If you can’t figure out what steps to take, then trying something new can help you get in the process of taking steps, regardless of direction. This might motivate you to find the right steps forward. There's a limit to this, which we will talk about later. However, trying new things, or as some influencers on the internet call it, “trying shit” may help you find the correct path forward. 2. How do I know if I’m going the right way? This is tied for first place for the hardest question in the book. It's easy to walk in any direction; the hard part is walking in the right direction. Let’s try not to confuse movement with progress. The quote “If you don't know where you're going, any road will get you there” comes to mind. This question is trying to get you thinking about direction instead of speed. I’ll admit that it's difficult to be certain you're going in the right direction in life, regardless of how much planning you've done. I think the goal here is to at least be going in the right vicinity of your goals, not to be spot on. It's kind of like horseshoes or curling — getting close will get you some points. The reason I want you to ask yourself this question is because it's easy to let time pass you by. The adage “time flies” really is true. If you're not paying attention, months can pass by like days. If you're not checking in on your
Roadmap to make sure you're going in the right direction, you may be walking for months and years in the wrong direction, and a U-turn may be in your future. Or worse, be so far gone you can't even remember what your goals or dreams were. It's easy to get pulled into a life that you never wanted simply because you didn't pay attention to the direction you were going. I think we all know someone that this happened too. It can happen to you too, so be careful. Like I mentioned in the last question, sometimes it's nice to take a walk in a random direction to find what's out there. It can be fun to “try shit.” It's especially useful when you don't have an idea what you want in life; this is a good way to find out what the world has to offer. The same way you may walk down a busy street while on vacation to find a good restaurant, you can do the same thing in your adventure through life. Just be sure to check in with yourself on occasion to make sure you're happy with the direction it's taking you. 3. What changes do I need to make? Our old friend, the detour! This is a question all about the U-turns, detours, dead ends, and every other change in direction we’ll need to make during our adventure. This question typically follows the “How do I know I’m going the right way?” question, which is why they're back-to-back. If you think about whether you're going in the right direction, and you decide you are indeed going in the wrong direction, the next step is to decide what changes you need to make. This varies widely based on the situation you're in. If you're mostly happy with your life, but there's a few things that don't feel right, maybe you need a slight change. Maybe a new wardrobe, a vacation, or a new hobby will do the trick. On the other hand, if you’re dramatically unhappy with your life, then maybe you need to make a dramatic change in your life to combat that. Drastic times call for drastic measures. Maybe you need a big change in your life, such as a new job, leaving a spouse, or maybe even moving to a new city. Thinking about this ahead of time is always advisable. Remember, it's often better to make a detour than a U-turn. However, during this adventure, shit happens and you'll need to adjust. Maybe it's not a change in direction you need as much as a change in speed. If you're going too fast,
it's easy to ignore life around you. This can lead to unhealthy relationships and a feeling of not being in control of your life. On the other hand, if you feel like you're going too slow, you can feel like you're being left behind. This can lead to unhappiness with the progress you're making on your path. It's up for you to decide if the speed and direction in your life is where it needs to be. This question will help you think about what changes you need to make to get yourself back on the path to point B. 4. Who am I going to ask for help? This is also tied for the hardest question in the book; funny how they both came in the same chapter. There are two pieces of advice floated around often that you've likely heard before: The first is, “Be sure to get feedback from your peers and ask for help.” And the second is, “Stay in your zone and don't let people's opinions disrupt your goals.” These are opposite pieces of advice, and they're both common in our society. Knowing who to listen to and who to ignore is incredibly difficult to figure out in life. In our case, when trying to find a path to our future, this is especially true. Sometimes, when you have an idea, and you ask for people's opinion, it can get homogenized. Everyone gives their opinion, they cast doubts, make you second-guess yourself, and may completely kill all excitement you had. Whenever people tell me, “Ninety percent of all businesses fail,” I always mention an important stat that's forgotten. Not only do ninety percent of businesses fail, ninety percent of businesses never start in the first place. You know where most businesses fail? Someone has a business idea, tells their friend, their friend says it’s stupid, and it ends there. Most businesses fail at “That idea will never work, don't waste your time and money.” Being loose with who you talk to and listen to can really make your path confusing and uncertain. It can even stop it dead in its tracks. On the other hand, not asking for any help has its pitfalls too. Although your journey is unique, it's likely not 100 percent unique. If you want to open an ice cream store by the beach, that's been done before, thousands of times. So, if you have an idea for an ice cream store, and you ask someone that owns a successful ice cream store, their advice may be valid. They may be able to tell you things you didn't know, point out holes in your business
plan, and maybe even let you work for them for a few months to see how things are run. However, if that person has been jaded by the cold world of entrepreneurship, they may discourage you from opening the store and tell you to just “get a job.” So maybe they aren't the best person to get advice from? I think you know where I'm getting at with this question. Everyone has opinions and objections about every subject. Be careful and think consciously about who you’re listening to and why you're listening to them. Taking bad advice from the wrong people can send you down a path you were never meant to go down. And there we go, another four sub-questions for you to think about and ponder. I know we’re rifling through these pretty quick, but please take your time. This book is purposefully short. The reason there aren’t a lot of words in this book is because I want you to take your time going through it and think deeply about your life and goals. Much like a job interview, I want you to do a lot of the talking and thinking. I’m just guiding you along the process.
James’ Journey Now that we've broken down the “How do I get there?” question, I’ll tackle these questions myself for your reading pleasure. I really feel like I’m on a roll. I’m happy with the answers regarding who I am and who I want to be. It's time to connect the dots. I want to start moving my life in the right direction, but I need a path to get there. These four sub-questions will help me do that. Here are my answers: 1. What steps do I need to take? I want two things in life — financial independence and a great family. The best way I feel like I can obtain financial independence is through real estate. I've seen a few people in my life and on the internet do the same, and it seems like a great way to go about it. To do this, I know I have to learn about real estate, gather funds from banks or investors, buy real estate, learn how to renovate, and then learn how to manage tenants. This seems like a lot, and it probably will be, but breaking it down into tasks (step by step) will help make that happen. The second part, having a great family, isn’t as straightforward. I have an amazing girlfriend that I want to spend the rest of my life with, but where do we go from there? When will be the right time to have kids? How will we take care of them? How do we have a happy family as opposed to a broken home? I have a few examples I can learn from, especially my family, but it's harder to emulate those steps, especially when I’ve seen a lot of scenarios where great people, who live great lives, can sometimes create broken families. How much of this is in my control? One thing I do know is that spending time and being present with your family is a good way to help have a happy family (based on what I've seen). The steps are a little less clear with this goal, but I think I have enough ideas to at least get started. 2. How do I know if I’m going the right way? Oh man, I have no idea. It's hard to find any road to travel on, much less the right one. I like to think that doing something is better than doing nothing, but I guess there's a limit to that. Eventually, you need to check in on your
road to make sure it's taking you in the right direction. I don't know how I'll know if I'm going the right way, to be honest. I think my gut will tell me. I know that's not a very solid plan, but it's done me well in the past. I think the key will be not only to listen to my gut, but to check in with my goals and progress. My gut can say all it wants, but if I don't check in with myself and double check my plan, I can see this going the wrong way. I've seen a ton of people in my life build lives they never wanted and aren't happy with, I really don't want that to be me. Feeling trapped is one of my worst fears in life. I don’t know where it came from, but I like having options, and do my best to avoid being backed into a corner. It’s easy to feel trapped when you go down the wrong path and fall into a life you never wanted. I’ve come close in the past, but I have been able to get it back on track. Thinking of this question as often as I can should help keep me on the right path. 3. What changes do I need to make? It seems the goal of this question is to think about not only direction but speed as well. Right now, I'm just starting out, so I'm more focused on starting on my road than changing it. Maybe in the future it will be more clear what changes I need to make. The one thing I can do now is make sure I don't back myself into a corner financially. Some people need to make changes in life, but they can't because they buried themselves financially. Keeping up with the Joneses can really hurt your Roadmap from what I've seen. I’ve seen friends and family that never followed their dream because they over extended themselves with a big house and cars. This leads to taking jobs that they may not even enjoy, all for the sake of paying for things they don't even want. This sounds like a nightmare. Hopefully, if I do need to make changes in the future, I'm in the position where I can financially do it. I mentioned this before but backing myself into a corner may prevent me from making the changes I need to make in the future. This could seriously harm the happiness of myself and my family. This is an easy trap to fall into. 4. Who am I going to ask for help?
This is tough. There's so much noise in this world. Everybody's an expert and everyone somehow has experience in everything. Social media and the internet, in general, makes this a thousand times worse. I think my best strategy would be to stick with only taking advice from people I admire or have the things I want in life. If someone has achieved financial independence, especially through real estate, then I think it's a good idea to listen to them. If someone I know has a great family, then maybe I can take their advice when it comes to starting and raising a family. I also need to be careful who I tell my goals and dreams to. I love all my family and friends, but some of them are wet blankets. Some of them can't be told certain things, or they'll stomp all over it. I know me, if they start crushing my dreams, I'll start defending it, we'll get into a fight, it'll get ugly, I'll get discouraged, etc. It may be better to avoid listening to certain people and talking to certain people, especially when it comes to big parts of my life, such as lifelong dreams and goals. I don't wanna go in alone, but I do have to be careful who I bring along with me. I’m so proud of James. He's honing and articulating what he does and doesn't want in life. Oh wait, I forgot, I’m James. I should probably stop with the ego stroking. There are a few things I want to point out in the above answer that I think you can use. Notice the acknowledgement that I can't possibly figure it all out today. When I talk about what changes I need to make in the future, I’m aware of the fact that I can't make those decisions on day one. I can try to help prepare for them, but some decisions need to be made when the moment is right. I think this mix of certainty and uncertainty will serve me well in the future. I hope you apply the same certainty/uncertainty mix in your Roadmap. Please don't let the metaphor of a Roadmap lead you to believe you have to have it perfectly planned from day one. This is a dynamic adventure that will throw a lot of obstacles in your way, so it's OK to have uncertainty. That's what makes this so fun! To keep with tradition, I’m going to take all my answers to the four subquestions and put them into my answer to the “How will I get there?” question.
I’ll first need to start with small steps. When it comes to my financial situation, I need to do a better job at learning about real estate and what it takes to be a smart investor. There's a lot to learn but I need to start now with some baby steps. Maybe attend a seminar or buy a book. When it comes to raising a family, I’ve already started by finding an amazing girlfriend. I can’t wait to keep building on our relationship so we can get to the point of starting our own family. I’m not sure how I’ll know if I'm going the right way, or how we will do this, but I know I can trust my gut and my partner during these moments. Although I'm still starting out, I know I'll need to make changes in the future. The best thing I can do now is keep an open mind and realize that the plan I have now will need to change and adapt as time goes on and I gain more information. As I think about this plan, I know there's no chance I can do it alone. I’ll need to be careful whose advice I seek and whose advice I ignore. There's a lot of noise in this world and not everybody wants the best for me, so being selective about who I keep around will be important.
I tried to be humble when plotting out my path. I realize I need a plan, but it doesn't have to be perfect. Instead of focusing on the unknown, I’m focusing on what I can control today and what steps I can take with the information I currently have. I don’t think pretending like I’ve got this all figured out is a good idea. One part I want to highlight is the acknowledgement that I need to be OK with changing my plan and accepting that my path will have a lot of twists and turns. The fact that I’ve already accepted it will allow me to be better able to handle these obstacles when they come my way. Have you also accepted that your path will have twists and turns that you can’t possibly predict today? Knowing how to get from where you are today to where you want to be in the future can be a daunting task. For some people, this may be the hardest part in the book. Anyone can dream, but there are few people that can plan the steps it takes to get to their dreams. However, instead of being buried by the intensity of the path ahead of us, we may find more success by focusing on the small and meaningful actions we can do today. When there are a million steps ahead, the first five steps can seem daunting and almost pointless. However, anywhere we have ever traveled to has been done step by step; achieving our goals in life will be no different. When I was a kid, my neighbour was a bricklayer. When I asked him how he built houses, he gave me a very simple and inspiring answer.
“You lay one brick as perfect and straight as you possibly can. You then lay the next brick as perfect and straight as you possibly can. You then keep repeating that until the project is done.” I like to think of that as a metaphor for your adventure through life. Step by step, brick by brick. Let’s focus on applying the information we have today, and acknowledge there’s a wild path ahead of us. If we can do that, not only can we start making great progress immediately, we can also be prepared for detours and U-turns when they inevitably come in the future.
Map Update This is the first time it looks like a full Roadmap. We have a starting point, a clear-ish path, and an endpoint. These are the three things that every Roadmap needs, and we finally have it. If you’ve made it this far, you should be proud of the work you've done here. Most people don't have this sort of clarity in their life. Well done.
Now that we have this, you’ll notice the path between your two points is a bit inefficient. A lot of dead ends, wrong turns, circling back — this looks like a rough adventure. In all honesty, this is probably what it will actually look like. There are no straight lines in life and there are no Google Maps to help you find the fastest route. However, I’m sure we can do a bit better. I think we can make it a bit more efficient. At the very least, we should talk about how you're going to stick to this Roadmap and stay on track.
Interlude — Repetition If you feel the flow of the book is coming off a bit repetitive, that's because it's supposed to. There are no magic tricks here; it's a simple process. Ask yourself a question, understand the true meaning, see it applied in a real-life example, and then think about how you can apply it to yourself. Rinse and repeat. Like I said before, you have most of the responsibility in this book, I'm just guiding you through the process. This book takes work and so does your life and goals. This all takes work, and sometimes work can feel repetitive. However, I promise if you stick with this process, you can gain a lot of good from it. It worked for me. I know it can work for you.
Chapter Four
How do I stay on track? Look at how far we’ve come! You finally have the three aspects of the Roadmap. You should be proud of the progress you've made to get here. I know I am. It’s a work in progress, and we’re making great strides so far. This brings us to the final chapter in part one, and the last thing we’ll talk about regarding creating your Roadmap. Once you start traveling on your path from where you are today to where you want to be in the future, you’re going to notice something pretty quick. You’ll notice yourself being pulled in a billion different directions. A friend’s housewarming, family birthday party, your partner wants to go for a walk, your boss has a strict deadline, your nephew's first football game, tax season, washing the dishes, the new season of that show, and that awesome party at your friend's place that you “can't” miss. And this is all on one weekend. This happens to also be the same weekend where you were going to take an important step in your Roadmap. You were going to register for a continuing education program, you were going to go to that class on basket weaving, call your friend to see if they're interested in starting a paint studio, or maybe relax for a couple days because you're burnt out from the progress you've made.
Sadly, and inevitably, there will be an overlap of responsibility between the things you’d like to do and the things you need to do.
These are tests of your dedication, and much like tests in school, it's good to study and be prepared. This brings us to our last question: How do I stay on track? Having a plan is great, and necessary, but if we throw that plan out the window on the first minor inconvenience or overlap, then that plan isn't worth much. Knowing how to stay on track is key to one day reaching our destination and the awesome milestones along the way. I want to make a key distinction here. In the third chapter, we took a drivers ed course and I talked about U-turns, detours, and other obstacles on our path. Those still exist, and always will. We're not trying to avoid hitting any obstacles on our path; we're trying to avoid going so far off track that we can't even find the path anymore. A lot of good can happen off the beaten path, but you can also get lost out there, so lost you'll never find your way back. We need to be careful and do our best to stay on track. There's also the issue of speed. I've said before that it's not just about the end goal, Point B, but also the adventure to get there. I still believe this to be true; however, if we don't feel like we’re making progress to our Point B, the adventure can get tiresome and unmotivating. The better we can stay on track and stick to our plan, the faster we can get to our goals and milestones. This chapter will not only help you stay on track but may increase your speed while on your path. I know I've thrown a lot (a lot a lot) of questions your way so far. In fact, in part two of the book, there's going to be more questions coming your way, rapid-fire style. However, what I would like to do in this chapter is give both of us a break from the questions. We're about to get a little less philosophical and a little more tactical. This chapter will talk about some thoughts I have when it comes to staying on track and achieving your goals and milestones along the way. This is mostly anecdotal and consists of observations I've made of my life and of those around me. I’m drawing inspiration from the times I've stayed on track, the times I've gotten lost, and the times I've noticed other people do the same. So rather than four questions, here are four observations I want you to think of when you strategize how you will stay on your path. In fact, let's make it
five; we deserve it. 1. Good is the enemy of great This is first on the list for a reason. Right now, you’re on a path to greatness. I don't know where you started, but I can imagine you're trying to get somewhere great. If you followed my advice in chapter two, the plans for your future are the things legends are made of. If this is true, and you are indeed in the pursuit of greatness, then you now have a new sworn enemy: “Good.” Or what it's sometimes referred to: “Good Enough” Good is indeed the enemy of great. If you want to achieve greatness, you have to avoid the “good” in life. This can rear its ugly head in many ways. If you want to be a great entrepreneur, your enemy may come in the form of a “good” job offer. Why struggle and work for 100 hours a week as an entrepreneur when you can get a good job and make a good living and have a good life? A good job is the enemy of great entrepreneurs. If you want to learn a new skill, your enemy may come in the form of a good television show with a good cast while sitting on your good couch. Why struggle trying to figure out how to complete a Rubik's cube or take a difficult class on hotel management, when you can watch The Office for the four thousandth time? Good television is the enemy of great personal development. If you want to improve your physique, your enemy will inevitably show up as an invite for a night out with your friends filled with drinking, eating junk food, and gossiping about nonsense. Why do a thirty-minute run when you can get drunk and talk shit about that person that did that thing that one time? A good night out is the enemy of a great body (with exceptions, of course). You need to be careful when it comes to settling for things that are just good enough. There will be a lot of moments where you can “cash-out” and give
up on your goal. Maybe you've built up enough skills to get a good job at an accounting firm but haven't quite gotten enough skills to start your own firm like you originally wanted. Maybe you decided to become the manager of a restaurant when you really wanted to start your own restaurant. It can be tempting to settle, and it's up to you to decide what's right for you and what isn't. Another term for this is “honeypots.” Things like a pension, solid retirement, dental benefits, and free company cars can seem like good incentives to have in life. You have to remember that when you decide to take one thing, you're giving up another. Beware of these honeypots in life. A stable retirement and a company car sound great, but when it comes at the expense of giving up your dreams in life, they don't sound so great. They barely even sound good at that point. Again, beware of honeypots. I'm looking at this from a career standpoint because it's relatable and easy for everyone to understand, but “good” can rear its ugly head in other aspects of your life too. A good partner. A good friend. A good body. A good mindset. A good pizza. There's a lot of good in life, and there will always be plenty of good you can take in your life. I’m not saying there's anything wrong with a good job or good pizza. I’ve had plenty of both in my life. I just encourage you to think about the decision you're about to make when you take something that's “good enough.” Are you taking a great opportunity? Or are you settling for something less? Oh no, there we go again with the questions. 2. Remember why you did this When you inevitably screw up and make a mistake, you're going to get discouraged. It's going to happen; don't bother trying to avoid it. Failure is going to happen, regardless whose fault it is. When you’ve failed or suffered a loss, it's easy to let the “give up” thoughts start to cloud your head and judgment. The best way I've seen people get through this is remembering why they started the task in the first place. Your “why” can be used as the motivation to keep going forward. Nietzsche was right; a person with a why can overcome almost any how.
There are anywhere from ten to 100 million books that talk about your “why.” Because of this, I’ll spare you the details. What I’d like to do instead is show you an example from my life. Earlier in the book, I talked about my brother passing away and promised to revisit it, so here goes. It's a story that I don't like telling but I think it will help you get through failure, or loss, when it comes your way. Nine years ago, my brother Enzo passed away at the age of thirty-two from a heart condition. It was horrible, and the worst day of my life by a fucking mile. My mom called me at 7 a.m. to tell me the news. My phone was on silent, but I somehow woke up to her call. I answered. She was crying harder than I’ve ever heard somebody cry. The only words she could say repeatedly was “I’m sorry.” She didn’t have to say much more; I knew what that meant. I somehow held back the tears on that phone call and told her I’ll be on the next flight home. It’s amazing how strong you can be for someone you love. I’ll never forget the sadness I saw in my friends and family when I got to Toronto. The funeral and wake were spread out over three days but felt like three years. I’ve never hugged my mom so hard and haven't since. I saw who my real friends were, I hugged them, told them stories about my brother, and cried on their shoulders. I'm crying right now just typing about it. I wouldn't wish it upon anyone. If something similar happened to you, I understand the pain, and I’m sorry. Here's something that might help both of us. As I tried to digest what happened in the following years since my brother passed away, I've bounced around a lot of things in my head. Life can seem meaningless. Life can be unfair. Life can sometimes seem like a sick joke written by a bad writer. None of these served any good in my life. As more time has passed, and clarity has slowly come back, I’ve thought of something new. Something that this experience has taught me. It’s my why . It’s a motto I carry with me and want you to carry with you as well. Adversity can be a great motivator. Notice the word “can.” This is your decision.
Adversity can be the straw that breaks the camel's back. It can be the thing that buries you. The thing that causes you to settle, give up, turn bitter or go back to mediocre. I've seen all of this happen before. However, adversity can be the thing that sets you on fire. That makes you work harder, that ignites your passion for the goals and dreams you have. It can make you realize that life is short and that all you have is now. It can be the thing that doesn't bury you into the ground but launches you higher than you ever thought possible. But only if you let it. Remember the word “can.” It works both ways. Adversity is a doubleedged sword. It's up to you to decide. You control the narrative, you control the next chapter, you control how you react to it. When I think of my Why, I think of my brother, and it enables me to overcome almost any setback, any adversity, any how. Remember the difference between the hero and the villain. It's all about how you respond to adversity in your life. It doesn't have to be as big and devastating as losing a loved one. Adversity shows up in many forms. Failing a class, getting dumped, getting fired, your investment tanks, or someone you counted on let you down. There will be a lot of adversity, loss, failure, tribulations, and any other word you can think of to describe it. Bad days will happen. Remembering why you started can help you move on to a good day. So, on this amazing adventure you're about to embark on, when failure, pain, and adversity kicks you in the stomach, remember that something great can come from it, or something bad can come from it. It's up to you. When this happens, I encourage you to find a way to be your own hero. 3. Track your progress Warning, this can be boring. Who has time to write down progress reports outside of work and school? As if I'm going to write down “I ate four vegetables today” in my little journal. Stay with me. Remember when I talked about the adversity you're going to face in the future? One of the most common forms of adversity is selfinflicted. It’s called “a random lack of motivation.” One day, you'll be
chugging along, making ground toward your goal, everything will be great. The next morning, you wake up, and your first thought is “Ugh… screw it” You'll lose motivation and struggle to find a catalyst to get moving again. Momentum is a great thing, but it sucks when you lose it. Something that can help solve this problem is to track your progress. Writing down the progress you’ve made in a particular goal will help you realize how far you've come. Let's say, for example, your goal is to do fifty pushups in succession. On day one, you did two pushups. Day five, you did ten pushups. Day ten, you did twenty. Day eleven, you don't feel like doing any. Screw it. What's the point? Pushups are overrated. This is dumb, I’m just going to go for a walk instead. *Insert other excuses here.* Rather than giving up on day eleven, try picking up your workout journal and looking at the progress you've made in your pushups. You got from two pushups to twenty pushups in less than two weeks. You’re on track to achieve your goal in less than a month! You don't want to lose all that progress and give up now, do you? Didn't think so. Let’s see you hit twentyfive today, my friend. If you feel like you're stuck or unsure as to what actions to take next, writing down your goals can help you understand what the next step should be. There's a lot of research you can find that shows writing down your goals will make you much more likely to achieve them. You may want to consider writing SMART (Specific, Measurable, Achievable, Relevant, and Time-Bound) goals so you have something tangible to work toward. You can then track your progress toward those goals to keep you motivated along the way. Revisit those progress reports whenever the ugly beast of “just give up” knocks on your door. I encourage you to write it all down. The achievements, the failures, actions that make you happy, actions that make you sad. The more, the better. You're not only writing a great story, but you’re making a playbook you can use in the future if you're ever feeling unmotivated or lost. What really helped me find more time in my day is documenting my hours. To do this, write down everything you did yesterday in thirty-minute blocks. If you can't remember what you did yesterday, then start doing this tomorrow.
Whenever I did this, you know what I realized? I had plenty of time, I just chose the wrong things. I had plenty of time for my goals, I just chose something else. I had plenty of time for the gym, I just chose Netflix. I had plenty of time for writing, I just chose to scroll on Instagram I had plenty of time to talk to my girlfriend, I just chose to yell at people on Twitter. I'm not saying you’re wasting time in your life, but writing down your schedule might help show if you are wasting valuable moments. Whatever it may be, tracking your progress can help you get motivated, plan your actions, and keep you on track with your goals. The best time to start is, well, now! 4. Take any motivation you can get This adventure will be daunting. It will be grueling. It can zap you of your energy and willingness to keep going. And like I said, it can be unmotivating at many points along the way. My advice? Take any motivation you can get. If a ten-minute motivational Gary Vee or Tony Robbins video helps get you through a task, take it. If watching David Goggins running on Instagram motivates you to run, take it. If reading Michelle Obama's biography motivates you to start creating your own great story, take it. Take any motivation you can, and as often as you can. Getting motivated is like showering — you should probably do it often, ideally daily. My warning here will be that although showering has immediate benefits, motivation takes a bit more work. It's great to be motivated. Sometimes I'll sit around with my pals and we'll gas each other up about what we're going to do in life. But the next morning? Back to hitting snooze and eating Oreos. Capitalizing on motivation is equally (if not more) important than being motivated to do something. Being motivated to run doesn't get you many health benefits. Running is where the benefits start to happen.
Motivation can be a powerful tool in your journey. But just like any tool, it's only useful if you do something with it, so be sure to capitalize on moments of motivation. Something else that can be motivating is to spend a little time celebrating your accomplishments. My friend Tyrone once told me I should “celebrate better.” I think about this often. Achieving one goal after another is great, but if you go years without celebrating the progress you've made, then it can feel mundane and occasionally pointless. My advice? Celebrate better. Cut the “no time to celebrate, I’m too focused” bullshit. You're not The Rock. Even he has tequila and cookies sometimes. Next time you achieve a goal, order dinner with someone special and enjoy it. It won't kill you. In fact, it may get you more motivated to achieve the next goal. The one caution flag I will wave about the topic of motivation is that motivation is just a feeling, not a lifestyle. The ultimate goal is to achieve discipline, meaning you can do things in life without needing motivation. This takes years and is hard to achieve. You know the person on your street that goes for runs when it's boiling hot out in July, and when it's freezing in February? That's got nothing to do with motivation; that's discipline. Going to the gym when you don't feel motivated would be great but isn’t easy. Finding motivation can be the boost you need to get in the gym on mornings where you don't feel like it. This will in turn build on your discipline and turn you into the workout machine you’ve always wanted to become. This applies to everything in life, not just your fitness. 5. Don’t confuse movement with progress I mentioned this earlier in the book, but I wanted to bring it up again. It’s easy to think that just because you’re doing something or working on something that it’s helping you achieve your goals. When I was working at Big Green Bank, there was a lot of movement. I worked a lot. Was I making progress toward my goals? I wasn’t. I was making progress for someone else’s goals, sure, but they sure as shootin’ weren’t my goals. From the outside looking in, I may have seemed like I was making a lot of progress, but it was just a lot of movement. Be careful not to fall into the same trap. When you’re about to take on a new activity, skill, or movement, spend some time thinking about whether it’s making you progress toward your goals. Try to avoid movement for
movement's sake. The only exception to this is if you’re in a rut. If you haven’t made any progress in a long time, maybe then it's time for some movement, regardless of if it's helping or not. Sometimes, just getting up and going for a coffee can springboard some progress. However, for the most part, don’t let the busyness of movement lead you into a false sense of achievement. Work smarter. This is by no means an exhaustive list. You need a lot of focus and determination if you're going to stay on track. Remember that the goal of this is to not stray too far off the beaten path. It's also important to be making consistent progress on your journey. Before we move on, I want to address both those things so we're on the same page. Regarding “don't stray off the beaten path” . . . I know you may be thinking “But that's where the magic happens. If people never wandered then we’d never have The Hobbit and all those other magical…” Yeah, yeah, yeah I get it, Dr. Suess. I'm not saying you shouldn't explore and have fun. In fact, I encourage it. What I'm saying is that if you go too far off the beaten path, you can wander into the forest of mediocrity. You see, not every forest is full of adventure and learning. Some forests suck. Some forests are full of shitty jobs, unhappy marriages, and shopping carts with one broken wheel. Staying on track doesn't mean you shouldn't explore; it means you need to be careful where you’re exploring. There are plenty of traps (and honeypots) in those forests. If you're not careful, you can get lost in a bad forest and never find your way back. The second idea I want to address is “making consistent progress.” This doesn't mean you have to be perfectly clear with what you want. It also doesn't mean you have to sprint through all your adversities to get to your goal and be in the top thirty under thirty. I want to make one thing crystalfreaking-clear; there are no timelines on any of the goals you have in life. Please don't confuse my mention of efficiency and speed to lead you to believe that you need to have everything figured out and achieved by a certain date. It's important you understand this because you may be in your thirties, forties, fifties, sixties+ and your dreams may have yet to be achieved, and that's OK.
Georgio Armani didn't start his clothing line until he was forty years old and he went on to make the best damn suit anyone has seen in the past halfcentury. There are thousands of examples of people achieving great things later in life. Please don’t think I’m preaching that you need to achieve everything you want in a timely fashion. I just want you to understand the power of progress. You’ll feel much better about the actions you’re taking if you feel like it's leading somewhere (Point B). It doesn't matter how fast you're traveling along your path, it's much more important that you're traveling on a path and making some sort of progress toward a goal. James’ Journey I’ve thrown a lot of observations and a little bit of advice at you in this chapter. I think it was a nice change of pace from the barrage of questions. What I’d like to do is bring back James (me?) one last time. There are no questions to answer; instead, I’m going to talk about my game plan for staying on track in my Roadmap. Here are my thoughts. “I feel like I'm getting a bit ahead of myself. I’ve barely started the journey of achieving my goals, so it seems silly to worry about how I'm going to stay on my path. I just got on the path! There will be tough times in the future. This seems fun and exciting now, but I'm sure there will be tiresome days in the future. It's kind of like getting a new gym membership. The first week is fun, the next fiftyone aren’t so fun. I think the first step is acceptance that bad days will come. Once I accept that, I can prepare for it. Pretending this will be rainbows and butterflies the whole time doesn't do me any good. However, I don't want to worry about something that hasn't happened yet. That's like paying interest on a loan you haven't taken out yet (my uncle’s favourite quote). When the bad days do come, I'll be sure to come back and reference the materials in the book. Remembering why I started, not settling for less, tracking my progress and finding any motivation I can get all seem like great strategies that I can apply one day. However, for now, I'm just excited to get started.”
I’m aware a lot of this advice will find itself useful a little later in life. Right now, this journey seems fresh and exciting, so the idea of being unmotivated seems unlikely. The power of this chapter will be revealed later on when I revisit it in the future any time I feel unmotivated or unsure what to do next. This was the last time we will talk about James’ journey in this book, so I think it's only fitting we say goodbye. Sometimes, I like to write messages to myself that I can read later on. It’s fun and a little weird, the perfect combination. Here's my message to me:
Please don't worry so much about having a perfectly straight path, worry more about starting that path. We can figure out the fancy stuff a little later. Allow the space between where you are today and where you want to be in the future inspire you rather than drag on you. Thanks for hanging out, James. I'm proud of the progress you've made and the growth you’ve shown. The work you’ve done on yourself throughout this book is something some people avoid their entire lives. You should be proud of the progress you've made in part one of the book. This is just the beginning; you have an incredible adventure ahead. Godspeed. (Am I talking to James or myself? I'm not even sure at this point. Writing is hard.)
Summary of Part One Let's do one final map update.
That's one good looking Roadmap! Not only do we have all the elements of a map, it's also a somewhat direct route that will be easy to stay on. Well, easy-ish (remember what we learned in our drivers ed course). We went through a lot in part one of the book, so I want to do a quick recap so we can realize how far we've come. We started at Point A, Who am I? We talked about what's important to you, what you spend time doing, what you've been through, and what people should know about you. This was based in fact and was a current snapshot of who you are as a person. The next step was to find out where we wanted to go. In this case, that was called Point B, Who do I want to be? We talked about what you wanted to get out of life, what success means to you, what you want your legacy to be,
and what do you want your days to look like in the future. This was less based in current circumstances and more based on future goals and dreams. Once we figured out where we started (Point A) and where we want to go (Point B) The next step was to find our path to connect the two points. Or as we called it, How do I get there? We talked about what steps we needed to take, what changes we needed to make, how we were going to know if we were going the right way, and whose help we were going to ask for. To get from one point to the next, we knew something needed to change; this question helped us map out those changes. Lastly, we needed something to keep us on the right path. A straight line is the shortest distance between two points. It would be nice for our path to be as close to a straight arrow as possible. It won't be, but we want to do our best. This led to our last question in part one, How do I stay on track? How can I avoid distractions? How can I avoid honey pots? What metrics am I using to keep myself on track and accountable? This section was a little more specific and tactical, and that's OK. Without it, we may find ourselves drifting too far off the beaten path. A lot of good can happen off the beaten path, but you can also get lost and never find your way back to the goal. Tread carefully. Hopefully, this summary reminds you of how far you’ve come in this process and how much you’ve learned about yourself. See? Tracking your progress can be useful! These are deep and powerful questions a lot of people have shied away from their entire life, so good on you for tackling them head on. This wasn't easy, but it’ll be worth it. Feel free to spend some more time in part one if you need to. Please don't get caught up in feeling like your Roadmap needs to be fully planned out and ready to travel with. Don't forget the title of this book, the answers aren't important here. All we did was ask the right questions so you can begin discovering your own answers and your own Roadmap. Next, we’ll talk about the second thing you’ll need for your life's adventure. Your Backpack.
Interlude – Warning about questions Hold up! I forgot something We’ve made great progress and you’ve had to absorb a lot. You've thought about who you are, who you want to be, your game plan for getting there, and your strategy for staying on track. These are all deep, meaningful questions and problems that will keep you busy for some time as you work through them to find some answers. Before we get into part two, I have one warning about the power of questions. They can bury you. It's easy to fall into the trap of sitting around, thinking about your past, your future, your family, Zendaya, your job, death, Seinfeld , why isn’t my phone working, on and on and on. This can lead to overthinking and can lead to inaction. The whole point of self-discovery is so you can act. This isn’t high school; you're not finding answers so you can get a good grade. You're finding answers so you can act and make things happen. I don't really have any rules, strategies, or answers here (remember the title of the book). You know yourself better than I do. Feel free to call yourself out on your own bullshit. If you are sitting around doing some deep thinking about who you are and what you want in life then that's great! Keep going! However, if you're using thought as an excuse for inaction then that's a problem. You need to take action to get out of that overthinking funk. There’s a fine line between planning and inaction, you'll find it, but only if you’re mindful of it. This is your reminder. Good luck. I probably should’ve put this in the beginning of the book, eh.
PART 2
The Backpack Now that you have your Roadmap, or have at least started the process of drawing it out, you need a Backpack full of supplies. Every good explorer knows bringing the right supplies in your backpack is the key for a good adventure, so that's what we're going to work on in part two. However, instead of water, food, and a good pair of shoes, this Backpack will be filled with, you guessed it, questions. I’ll list and explain some of my favorite questions. They aren’t big enough for their own chapters, so they'll have short(er) descriptions and summaries. These questions will guide you along your adventure by helping you stay focused, remind you what's important, remember why you're doing this, and have a little fun along the way. This will have similar vibes to chapter four. The main difference will be everything is formed into a question. This is because I want you to draw your own answers and conclusions. This is your Backpack; it needs to be tailored to fit you and your life. If at any point you feel tired, unhappy, unmotivated, lost, anxious, or any other adjective I can't think of, then don't worry, you have your Backpack! Full of great questions you can use to refuel, motivate, and keep you on your path. For the sake of clarity, organization, and to make the editor happy, I’ve grouped these questions into categories. Each category will explain the situation you may be going through, and the corresponding questions that will help you overcome that situation. This will also make it easier for you to come back to these questions in the future. Now, let's get packing!
Chapter Five
Questions for when you feel lost I think it's safe to say we’ve all been here at some point in our lives. Likely multiple times, and likely not for the last time. Lost. Not necessarily unhappy or unmotivated, just not sure what to do next. Not sure where to turn, who to listen to, or what the next step should be. Feeling lost can be a tough emotion to overcome. Being lost with a map can be an even worse feeling. You may be thinking “I had a plan, I had a map, I had all the directions I needed, how did I get so lost?” No amount of planning and road-mapping can eliminate the possibility of you getting lost. The first step is admitting you're lost. Pretending everything is “fine” and “going according to plan” can do more harm than good. I’m really good at this. If you ever hear me say “I’m fine,” I am absolutely, 100 percent without question, not fine. Now that you’ve admitted you’re lost, the second step is to get out of it. Don't worry so much about trying to feel like you're completely found again; let's focus more on some actions we can take to get back on track and in control. Ask yourself the following questions to help start this process. If I had to give advice to someone experiencing my current problem, what would I say to them? This question should be handled exactly as it sounds. If someone you knew and cared about was going through the exact same problem you're going through, what advice would you give them? I like this question because it removes your emotions from the situation. A lot of times we can get caught up in the emotion of the problem and think illogically. When you give someone else advice, you're likely doing it based on the facts of the situation, not the emotions of the situation. Do you
remember a time when you acted out of emotion instead of logic? Did it work out the way you wanted it to? If you can remove yourself from the equation, and make a decision based solely on facts, you're likely to come up with a better plan. However, it's tough to not act with emotion when you’re the one in the situation. Pretending it's somebody else in this situation may help solve these problems. Everything was made in this world by someone no smarter than you, so why can’t you be next? This sounds a little more philosophical than you might want, but it's a good thing to think about. Specifically, it's a good question to ask yourself when you're feeling lost due to a daunting endeavor. Let's say you want to open a new restaurant but are lost as to whether or not you can pull it off. Oftentimes, we build up the people that did it, and belittle our ability to match their success. You may look at Gordon Ramsey or Wolfgang Puck and wonder if you could ever be like them. I think it's important to remember they didn't start out successful. They started out just like you. Maybe they had a little more money or opportunity than you, but they didn’t start with the knowledge needed to do what they've done; that was learned over time. If Gordon Ramsey started out as just a common line cook with a dream, and turned that into over thirty high-end restaurants, what's to say you can't do the same? If he started out no smarter than you, and achieved what you wanted, what's to say you can't emulate that success? I thought about this a lot when writing this book. I looked at other authors of self-help books and felt like a phony. They were all doctors, influencers, and experts. However, if they wrote great books, why couldn’t I? People aren't just looking for advice that they could probably find on Google anyway. People respond to authenticity, which is all I was able to offer you in this book. It made me realize that regardless of title, I was just as qualified to write this book as anyone else. If you're feeling lost by the size of your dream and aren't sure what to do next, just remember the people who achieved what you want also felt the same. They all started as kids with a dream, just like you.
If I didn't need money, what would I do? This question can help anyone, but I especially like it for people just starting out and struggling to find their goal. If you're struggling with finding your answer to “Who do I want to be?” from chapter two, this might help. In my ten years in the corporate world, I’ve seen countless people take a job for money. Like I said earlier in the book, I don't discount the importance of money. You need it to live and eat, and some people have friends and family to take care of. I don't doubt the importance of that. However, one thing I noticed is that people who joined the corporate world solely for the purpose of making money can sometimes struggle to find happiness. They can never quite feel fulfilled, regardless of how many promotions they get and the perks that come with it. It's just never enough; they always felt lost. The only people I saw happy in the corporate world are the people that wanted to be there. They wanted to be a leader, help others with their financial plans, and genuinely enjoyed feeling like they are part of something bigger than themselves. I'm glad those people are doing what they love, but I believe those are the minority rather than the majority. For the people that took those roles for the money and can't find happiness in their job, I wished they asked themselves this question when they were first starting their career. This question allows you to dream, to ponder, to think about what you're good at, what makes you happy, and the change you want to make in the world. This isn't a perfect question, because the fact is you will need to make money in the future. However, this question lets you entertain the possibility of choosing a future based on what you want to do with your life, not what amount of money you want to make. It lets you entertain the option of a life based on passion, rather than just financial gain. What's a skill, big or small, that I’ve always wanted to learn but never have? What's one step I can take to achieve that skill? Name a skill you want or need to learn in life. You may want to learn how to juggle, golf, paint, surf, snowboard, or practice yoga. You may need to learn how to be comfortable with public speaking, use a certain software program, or become a better leader.
Regardless of what it is, there's a skill you’ve been wanting to learn for a while, but you haven't. I believe the most common reason people don't learn new skills is because of how daunting it can feel in the beginning. I’ve been learning how to play golf in the past few months, and although fun, it feels like a herculean task. There are so many nuances, rules, unnatural motions, etiquettes, outfits, and sunburns involved that it's hard to know where to start and how to start. If you feel the same way, I challenge you to ask yourself this. What's one step I can take, regardless of size, that will help me achieve that goal? Don't think about the order or importance, just take one step toward learning. When I wanted to learn how to play golf, the first thing I did was ask my dad to borrow his clubs. Step one. I then bought a golf shirt. Step two. I then watched a YouTube video on technique. Step three. I then booked a lesson with a local golf instructor. Step four. Individually, those steps seemed small and insignificant at the time. However, looking back, it feels like I’ve made a lot of progress toward my goal of learning to play golf. I can take my dad's clubs, put on my golf shirt, and go to the driving range to practice the skills I learned from YouTube and my lessons. What seemed like an impossible task in the beginning seems much more achievable now that I've taken small steps forward. It all started with that first step, and that's all it takes sometimes. So, if you want to learn a new skill, what is one step you can take to begin the process? Don't worry about order or size, just take one step. It will lead to a snowball of activities that will help you make significant progress to learning that skill. Just start. Are you excited to be spending time the way you're spending it? If not, what needs to change? This is a simple question to end this section. When you woke up this morning, were you excited? When you looked at your schedule for the day, was there anything that you were looking forward to? You can’t just wake up and solve every miserable problem in your life; there needs to be things to look forward to. It’s easy to feel lost when every task you complete is done out of necessity and not interest. If you're not excited to be spending time the way you're spending it, what needs to change? What can you remove, add, or change in your day that
will make you a little more excited to wake up in the morning? Remember how hard it was to wake up at 8 a.m. for school on a Tuesday? Remember how easy it was to wake up at 5 a.m. on a Tuesday to go to the airport for that awesome vacation? The difference between those two days was the excitement you had for what was coming in your future. So, if you’re feeling lost, look at your schedule. Does it excite you? If not, it may be time to remove, add, or change something in your day.
Chapter Six
Questions for when you need motivation We talked about this before, and it's a bummer. I think everyone runs out of motivation at some point, regardless of who we are and what we’re doing. The worst part for me is how hard I can be on myself when I lose motivation. I often compare myself to others, especially to people on TV and in the media. I look at Elon Musk and think about how hard he works and wonder why I’m not like that. “Elon never gets unmotivated, why am I getting unmotivated?” I don't know Elon, but I'm sure he gets unmotivated from time to time. Even if he doesn't, who cares, this isn't his life, it's mine. I need to focus less on what others are doing and more on getting motivated and back on track. If you’re like me, and are trying to find motivation, then let's stop being so rough on ourselves, stop comparing ourselves to others, and look at some questions that might help us. While reading through, please don't forget my warning about motivation. Motivation isn’t the goal, discipline is.
What would I do if I only had one year left to live? A common reason for a decrease in motivation is a lack of urgency or timelines. In most cases, people don't have to achieve their dreams. Remember when I talked about our enemy, good enough? Well, you can always just have a good life and ignore your dreams. You can always give up. You can always say “good enough” and take a nap on your couch. This can result in a lack of motivation. Why bother trying hard for greatness when so many people in your life just settle for good enough? One solution to combat this can be to make your goals more time-sensitive. This is my version of the “if today was your last day” question. I think where some people go wrong with that question is they put too much pressure on themselves. Sometimes, that creates results; a lot of times it doesn't. If I lived every day like it was my last, I'd be bankrupt in six weeks. But what's much more reasonable is to live every year like it's your last. It gives you a few days to think, miss a step, make a mistake. I like to call it my yearly bucket list, a list of things you want to do if this was your last year on earth. The best thing that comes out of this question is a healthy sense of urgency. Not a tremendous or unhealthy amount of pressure to have everything done in a month, but a much-needed timeline on your goals. Like setting a SMART goal, this puts a time stamp on the actions you need to take to achieve your goals. Beeple, an artist that's famous for creating a daily piece of art for 5000+ days straight (you read that right), has a great quote about this: “You don’t have a lack of motivation. You don’t have a lack of ideas. You have a lack of deadlines.” So, if you only had one year left to live, what are some things you would need to accomplish? Well, why wait for your last year? If it's this important, why not start now? How am I making the world a better place? We know you offer something to the world, you contribute something to your community and the people around you, but what? Finding this answer may help you get motivated to apply and home in on that skill to the world around you. Is the world a better place because you're a good parent and are being purposeful in raising your kids? Good. Double down on that. Is the
world a better place because you help your neighbors? Are you often there for a friend in need? Work overtime at the hospital? Motivate friends and family to live a healthy lifestyle? What is it that you do that makes the world a better place? This will not only remind you that you have purpose, but it will also remind you that you have a gift that needs to be nurtured and expressed. Even better, it can lead to you doing other things in life that will help contribute to the world. Even if you can't think of anything, even if your gift and contribution don't seem obvious, this question can be a great reminder that you're here for a reason. If you don't know that reason, that's fine. Let's spend some more time finding it. Would “future me” be proud of the decisions I’m making today? If there are things you want to accomplish in the future, would “future you” be proud of the progress you're making today? Who you are today was once the future. Your five-year plan you created five years ago is now complete. Did you accomplish what you wanted? Did you do what was necessary to complete that plan? I like to think of it in the reverse. If you're unhappy with something about your life right now, aren't you pissed that “past you” didn't do anything about it? If you don't have a lot of savings, aren't you mad you didn't save more money three years ago? If you're unhappy with your body, aren't you pissed you didn't join the gym with your co-workers when they asked you to join two years ago? Aren't you sick of paying for the mistakes of the past? At some point, you have to wake up and be tired of being a slave to your past and the mistakes you made. At some point, you have to draw a line in the sand and start making changes in your life for a better future. Well, this is where you make those changes. This is where we make “future you” proud of who you are today and the things you did today. A classic example is a hangover. This is you in the past screwing over you in the present. However, you can get over a hangover in a few hours or days (depending on age.) It's tougher to get over a bad physical or financial situation just as quickly. The next time you want to skip the gym or buy something you know you shouldn't be buying, think about whether “future you” would be proud of the decision you're making today.
What decisions have you made in the past month that you never want to make again? This is similar to the previous question, just a little more dire. Drinking too much and then having a brutal hangover the next morning may seem like a bad decision, but I don't think it would stop you from ever drinking again, so that's not what we're talking about here. This is a more intense version of that question. What’s something that you did in the past month that you never want to do again? This question allows any bad decisions you made this month to turn into a lesson learned. If you dated the wrong person and you knew you weren't supposed to be together, then so long as you don't make the same mistake again, then it wasn't a bad relationship, it was a lesson learned. Did you trust someone in business or in your personal life when you knew you shouldn't? Being more careful in future situations can be the lesson learned. This question is trying to make you realize that mistakes of the past don't have to be meaningless mistakes, they can be lessons learned, so long as you don't repeat them. Fool me once… My words of encouragement, in the event this question makes you upset, is that you’re not your past. Use your past mistakes as motivation to move forward, but don’t think you’re that person. You’re not. You’re the person that's learned from those mistakes. This is your chance to build on it. What if you have no haters? What if you have no haters to prove wrong? When you said to yourself “I’ll show them,” who are you referring to? What if they don’t exist? What if you have no haters, and nobody cares what you do? This sounds depressing, and it is, but in a good way. When you realize most people are indifferent about whether you achieve great things, or achieve nothing, it brings the attention back to yourself. Rather than trying to prove people wrong, you focus on making yourself happy. Instead of doing things to prove the haters wrong, what if you did something to prove the people that care about you right? A lot of people get so caught up in trying to show their former high-school bullies they’re not a loser. They get so caught up in living by the “success is the best revenge” motto. This can often lead to completely ignoring the people that are in
your corner and cheering for you. I wish we, myself included, spent more time focusing on showing the people that believed in us that they were right to do so. I wish we realized that we probably don't have any haters, and the people we’re so focused on proving wrong don't know or care about what we do. It’ll free us up to be motivated out of happiness instead of having a misguided chip on our shoulder.
Interlude — Locations I wrote this book at the following locations: My apartment in midtown Toronto, ON My parents’ place in Scarborough, ON An Airbnb in Chicago A cottage in Huntsville, ON Various coffee shops and bars in Toronto The Rogers Centre during a Toronto Blue Jays’ game I knew switching up where I wrote the book would help inspire me to write about people. Changing your perspective can literally change your perspective.
Chapter Seven
Questions for when faced with adversity or loss This is a tough part of everyone's life. There’s no exception to this. Although we all share it and go through it, it doesn't take away the pain. Loss and adversity. The two things that make life memorable and painful at the same time. Whether it's personal or in your career/business, it's going to happen in your life, in all shapes and sizes. Although hard to prepare for, accepting that it's coming is a great way to help make it easier to deal with when the time comes. Another thing that may make it easier is knowing you're not alone. To help with this, let me tell you another story about the adversity that I faced in the past. Feel free to learn from my pain. When I was nineteen years old, I started working for a Big Green Bank in Toronto (remember BGB?) It was a dream come true at the time. To still be a teenager and working for the biggest bank in the country was a great feeling. You see, I was a terrible student, constantly worried if I’d ever make anything of myself, so to work at a bank while still being a teenager was incredible. I worked there for ten years, slowly climbing the ranks, working in various departments, meeting new people, living a good (not great) life. On October 28, 2019, that all came crashing down. I came to work as I always did. Same train, same suit, same office, same everything. Except this time, my boss was waiting for me at my desk. She said I had to go to the eighth floor and that the department manager was waiting for me. Uh oh. I went up, saw the manager, and we started walking toward a meeting room. Uh oh. I asked, “How was your weekend?” He said, “To be honest, pretty shit.”
When you hear a suit say a curse word on company time, you know it's bad news. I get into the office, they sit me down; there's someone there from HR. Uh oh. “Robert, due to corporate restructuring and the current climate, we’ve decided to let you and your whole team go.” “Well, then, this is a rough start to the week,” I thought. The department manager continued by saying, “This person is here from HR to give you your severance package and walk you out. I’ll need your pass card and we will mail you your belongings later this week.” He got up and left. That was it. Ten years, all of my twenties, all of my energy, effort, relationships, loyalty — gone. I was escorted to the elevator and out the door with nothing but papers in my hand and tears in my eyes. The managers I tried hard for and went to bat for never contacted me again. Some of the people I spoke to every day for years never even messaged me after the fact to see if I was OK. Just nothing. People I thought I could trust never even said sorry. Never asked how I was, never checked on me, just nothing. I got a whole lot of nothing. I'm not dragging on about this to make you feel bad for me. I’m telling you this because I understand what adversity looks like in both the professional and personal sense. I went home that day completely clueless as to what happened, how it happened, and what to do next. I was sad, lost, and most of all, angry. Although I was angry at a lot of people and a lot of things, I (in hindsight) was the angriest with myself. Relying on a company and a paycheque to secure my financial future was foolish and irresponsible. I spent the next year making sure that never happens again. Although I have found a great company to work for now, I will never rely on them to fund my hobbies, retirement, future children's education, or anything else I deem important. Nobody on this planet is going to take care of you other than you. Although I’ve made my peace with it and sound like I’ve spinned it into something positive, it wasn't easy and it didn't happen overnight. I spent a lot of time looking at the blackbox of my career to figure out what happened and where to go next. The following questions helped me through that process.
Have you spent enough time digesting what happened? It was tempting for me to think “I’ll show them” and get a job at some other bank on Bay Street. The best way to get over one bank is to get under another one. Wait, that might be the wrong expression. Regardless, as someone who has a lot of experience with loss and adversity, I knew that wasn't a good idea. Moving on without digesting what just happened is a sure-fire way to make the wrong decision. I knew I eventually had to deal with what happened. Whether it be today, or five years down the road, you can't outrun your demons; you have to face them head on. This took a while, but it was worth it. Before you try to move on from loss, make sure you spend the right amount of time dealing with it. You don't have to do this alone; a partner, friend or therapist are great ways to find peace. If you’re still going through adversity, the same rules apply. Have you accepted what's currently happening? Or are you pretending everything is OK? You can't deal with problems without admitting they exist. If you're in a tough spot right now, spend time accepting and analyzing what's happening. It's the first step to getting out of it. What is one thing you learned from this situation? This allows you to take a loss and turn it into something productive. I believe this is a good step in moving forward. Rather than accepting this as just a loss and something you can't learn anything from, I encourage you to look deeper. Earlier I talked about learning the power of adversity after my brother passed away. When I lost my job, I learned that I need to take care of my own financial future and not to rely on a company. There has to be something from your loss or adversity that you can learn from. A lesson that has been passed on, something you could have done differently, or a memory you can carry. This loss wasn't for nothing; realizing this can help springboard you forward. Now what? Sounds basic, but it helped put me in the right frame of mind. I’d spent enough time processing what happened; I needed to act. Asking myself “now what?” as often as I could helped me think about next steps. It took me out of that office on the 8th floor and brought me to today. It helped me think of the steps I needed to take to move on from the situation. Every time
I had a thought rooted in the past, I countered it by asking “OK, now what?” “I can't believe they did that to me.” OK, now what? “I can't believe they can treat people like that. ” OK, now what? “I can't believe I trusted them with my future.” OK, now what? This may seem harsh, and that's not my intention. I think you should take as much time as you need to digest and comprehend the loss and adversity you went through. However, when you feel like you’ve spent enough time dealing with the situation and are ready to move on, it may be time to ask yourself now what? What's one thing you can do tomorrow to make yourself feel better? This is the more descriptive version of now what? It's more specific and enables you to create a plan you can act upon. Rather than trying to fix all your problems at once, what is one specific thing you can do to make yourself feel better tomorrow? Can you go for a walk? Can you make your favourite dish? Can you do a puzzle? Call a friend? Look for a job? Paint a picture? Watch your favourite movie? There's something tangible you can do that will make yourself feel better. When we feel better, it's easier to build upon the momentum and keep moving forward. I like to make it something you can do tomorrow because it allows you to think beyond today. The number of times I thought “I’m going to get in shape” is plentiful. I then proceeded to go for a walk that day and then never again for the next month. The way I combat that is to think of a plan for tomorrow. If you still want it in the morning, you're already showing good dedication. You're already building momentum. I’m proud of you, let's keep this going. We can do this. By the way, while we're on the topic of things to make you feel better. When I got let go from BGB, I texted a handful of people. All the texts were the same. I just wrote “Can I call you?” All of them responded with varying versions of “absolutely.” I took screenshots of those text exchanges, and they still sit in a folder on my iPhone. I look at it whenever I need to be reminded what a true friend looks like. It always makes me feel better. I hope you can find your own version of that.
Chapter Eight
Questions for when you need a laugh Life can be rough. This book asked a lot of you. This isn’t easy. Don’t forget to laugh sometimes, ideally often. Here's my attempt at humour. Hope it helps. What's your biggest weakness? This is arguably my least favourite question of all time. I know there’s no such thing as dumb questions, but this question is really testing that theory. For the record, I like asking this question introspectively. When you ask yourself this question, you can be honest with yourself and give a great answer. My anger comes when it's asked in a job interview. If you get asked this question in a job interview, I give you permission to walk out the door and never answer the HR reps communications ever again for the rest of eternity. One time I was asked this question and I answered honestly. I said, “My lack of organization skills” which, at the time, was true. I thought the HR rep would appreciate my honesty. They did not. We spent the next twenty minutes talking about how that's a problem. After that experience, anytime someone asked me that question, I’d jokingly respond with “That's entrapment” or “What's your angle?” It probably doesn't do much for my candidacy, but I think it's funny, and hopefully sends a message as to how ridiculous the question is. So, the next time you’re feeling down, just imagine someone asking me “What's your biggest weakness?” and then picture me answering with “What's your angle here?” like I'm on a cheesy weeknight crime drama, aviators and all. Why did you and your ex break up?
Yet another form of entrapment. This time, in the form of a common first date question. I guess you could answer with honesty; however, that would mostly apply if you had a fully amicable breakup. Raise your hand if your last breakup was mutual and amicable. Nobody? Thought so. It then relies on you to harness your J. Jonah Jameson from The Daily Bugle . How can you spin this story to still reveal elements of truth while also making you look like a great candidate. I like the “we just grew apart” story. It shows you like to work on yourself while also refusing to settle for less. I think this looks like a good reason to a potential mate. My friend was once on a date and said that he and his ex broke up because she moved out of town. Later that night, as (un)luck would have it, his ex happened to be at the restaurant and introduced herself. Safe to say he had some explaining to do. Tell me that doesn't sound like an episode of Seinfeld . This question always makes me laugh because I imagine the ridiculous answers people have given while on a date. The image of Zach Galafanakis’ character in The Hangover computing complex math equations comes to mind. Have you ever given a “spun” version of the truth in this situation? If you have, email me. I’d love to hear it.
Interlude — My Journal A few years ago, my sister bought me a journal as a Christmas gift. The cover of the journal was black, and on it said Fucking Brilliant Ideas . When someone gets you a gift like that, the pressure is on. You can’t write “Walk 3000 steps tomorrow” in a journal that demands you only write fucking brilliant ideas. As soon as I got the gift, I knew something special was going to come of it. I didn’t know what, but I knew it was going to be special, maybe even brilliant. I started journaling about myself and my life. Nothing crazy, just my daily events and occurrences, hoping something inspiring would come, and it did. On March 5, 2021 I wrote the following:
That was it. That’s all the page said. However, as I've said repeatedly in this book, sometimes all you need is a seed. And in this case, that's all I needed. Over the coming weeks, that seed grew into more and more pages of ideas about what the book could be. It reminded me of the speech I gave at work, the lessons I tried to get across, and the goals I was trying to help people achieve. Slowly, but surely, that one page of almost gibberish turned into the book you’re currently reading. All it took was a sister that cared, a journal that motivated, and one Fucking Brilliant Idea.
Chapter Nine
Questions for when things are going great Now, although we talked about adversity and loss a lot in this book, it's not always like this. A lot of life can and will be great. We can be firing on all cylinders for weeks, months and sometimes years. It's a great feeling to know where you came from, know where you're going, and know how to get there. But, guess what, it's likely not always going to be like this. Remember your driver's education course, the U-turns and detours are coming. While we are on this smooth highway, it's important to appreciate it. It's also important to take notes and notice the things we’re doing right. This will make a great reference to look at when things inevitably go wrong at some point in the future. Let’s ask ourselves some questions to get a gauge of what we're doing and how we got on this great track. We can also ask ourselves some questions to remind us how lucky we are, just so we appreciate our fortunes a little more. What does your daily routine look like? Since we are rolling along at top speed, we must be doing something right. We must be listening to the right music, hanging out with the right people, eating well, putting our energy in the right places, and spending our time wisely. It all seems so obvious now, doesn't it? Well, it may not seem so obvious when things start going south. So, let's write down the things we are doing today that are leading to this sort of success. Here are a few subquestions (not this again) that you can ask yourself when things are going great. Keep this handy the next time you need direction on how to get back to the highway.
What music/podcasts am I listening to? What TV shows/movies am I watching? What exercises, if any, am I doing? What is most of my energy going toward? How much time am I spending hanging out with my friends and family? What does my diet look like? How often am I writing in my journal? What does my work/life balance look like? Writing down these answers will be your game plan for success. Keep it close by. By the way, you can also ask yourself these questions when things aren't going so great. When you're not being productive, when you're not happy, when you're not motivated to be better, you can ask yourself these questions. Compare the answers to when things were going great. Look at the difference between the answers and that might help you make a change for the better. For example, if when you're feeling great, you work out three times a week, eat salad daily, and listen to The Killers every morning, then that's likely part of your success. If when things aren't going so well you find yourself not exercising, not eating well, and not listening to your favourite music, then you now have a game plan to make things better. Get on the treadmill, have some kale, and listen to Mr. Brightside for the 8000th time. It may be all you need to get rolling again. What's your game plan to stay on track? When things are going great, it's best to keep rolling. Momentum is a great thing and should be kept for as long as you can hold on to it. Asking yourself how you plan to keep rolling is a good way to remind yourself this won't last forever, and it will take work to stay on this path. How will you stay on track? Maybe it's time to re-read chapter four and look at some of the things we talked about. I listed them here to save you some page flips; however, you may want to spend more time in chapter four to really digest these. Good is the enemy of great Remember why you did this
Track your progress Take any motivation you can get Don’t confuse movement with progress Whether it be the above pieces of advice, or other ones not mentioned here, don't forget that you can't just stay in autopilot and expect for things to keep going great. It's hard to get to the top; it's even harder to stay there. Keep your foot on the gas. What are you most thankful for? What’s something you have today that you wanted five years ago? You probably only get asked this question once a year around Thanksgiving if you celebrate. Why is that? Why don't we count our blessings more often? I don’t have a great theory as to why, but I do let it motivate me to practice gratitude more often. The reason there are two separate questions is because they’re both asking similar things, just formatted differently based on your perspective. I prefer the five-year question because it allows you to look back and see how far you've come. It makes you realize that thoughts can become things. It can make you believe that setting goals and wanting a better life is a good thing. Most importantly, it can motivate you to create new goals. Maybe a new five-year goal. If it feels great to want something five years ago and have it today, then imagine how great it will be when you do it again in the next five years. Asking “What are you most thankful for?” is a little less about game plan and strategy, and more about building a character of gratitude. If you want to be a person that appreciates things in life, that's grateful for what you have, that realizes there will come a day where you might not have what you have today, then this question achieves that. I think we can objectively agree that being grateful is a good quality to have as a person. There’s nothing worse than helping someone who doesn’t appreciate it. Asking yourself this question often is a great way to avoid becoming the person that takes everything for granted. Count your blessings while you still have them.
Chapter Ten
Questions for when you feel like being introspective I busted out the Talisker whisky for this one. Be careful going down this path; you might not like what you see. I like to think most of this book was introspective. To get the most out of this book, you had to be willing to strip away the superficial layers of yourself and get deep into who you are and what you want. In case you didn't get enough, I’ve got some more for you. Much like the rest of this book, these questions are best tackled when being honest, vulnerable, and willing to learn and grow. Even if you don't get anything from these questions, sometimes they're just fun to think about. Socrates would be proud. Enjoy. What do you think other people see when they look at you? My first inclination when I heard this question was to respond with “who cares?” I do my best to not let other people's opinions change who I am and what I do in life. However, I’m human, and so are you. Because we’re human, we likely care, to varying degrees, what other humans think of us. This question isn't quite rooted in people's opinions, as much as their impressions. There's the first impression, which consists of how we look, how we approach them, and how we carry ourselves in the first few moments. There's the second impression, which is rooted in the words we say in our first conversation, how we look the next time we see someone, and if our personality carries over into the second meeting. And then there's the lasting impression, which is what people see when they look at us on a continuing basis. I like to break it up in three parts because I’m interested in the progression of how people see me. I don't think I've ever made a good first impression. I don't usually dress well, I struggle with eye contact, I never really have
anything clever to say. I’m just not that kind of guy. What I focus more on is my lasting impression. The people who have known me for years, what do they see when they look at me? That's mostly what I focus on and what I try to improve. What do you think people see when they look at you? What do you think their first, second, and lasting impression of you is? How much does that matter to you and why? I find it interesting how much or how little some people care about the impression they make on others. I think it will tell you a lot about who you are and where your priorities lie. You can always cheat and just ask people, but I much prefer to think of it on my own first. From there, it's fun to see if people's impression of you matches what you thought of in your head, or what you hope they see in you. For me, this is sometimes rooted in fear. I don't want people to see me as uncaring. I don't want them to see me as indifferent or aloof. My biggest fear is that some people see me as wasted potential. Someone who could have done great things but didn’t. It’s part of the reason I’m writing this book. To make others, along with myself, proud of the effort I'm putting in. I let this be a motivator to do more, which leads perfectly into the next question. How do you want people to see you? This is the flip side of the previous question. Forget about what people see in you, what do you want them to see? What do you want their first, second, and lasting impression to be of you? Do you want their first impression to be that you're a well-dressed person with a firm handshake and a nice smile? Do you want their second impression of you to be the person that remembered their name and remembered to ask about their trip to New York? Do you want the lasting impression to be that you're the person they can call to be fun at parties and always start a round of shots? Forget about what people see in you, what do you want them to see in you? This is where we can turn a bad first, second, tenth, and lasting impression into a great one. This is where you can make the impression that you’ve always wanted to. This is where I decided to write a book. This is where I decided to dress better, even when going to Walmart. This is where I worked on my handshake, started reaching out more, being kind for no reason, and spending as much time as possible with friends and family. I
wanted people to see me differently than they had in the past; this question helped me act on that. It can do the same for you if you want it to. You don't have to be what other people think of you, and you can change their perception of who you are and what you stand for. This applies to work, your relationships and life. I firmly believe a great second impression erases a bad first impression. People's minds can change, and you can change. Never fear change; it gave you all you have, it will give you all you’ll get. This question might help jumpstart that change. It’s never too late to be what you might have been. Would you believe what you believe if you were the only one that believed it? Imagine taking everything you believe. Not facts, just opinions, ideas, thoughts, theories, stances. Everything that's not based in fact. Let's call that “things you believe.” How many of those beliefs are a product of group thought? Meaning, how many of your beliefs only exist because other people believe it. An even scarier way to look at it is how many of those beliefs would you still have if you were the only person on the planet that believed them? This question makes me think about how much I am influenced by others, how much research I do into my beliefs, how important the acceptance of others is to me, and how comfortable I am being alone in thought. These beliefs can be about business. For example, Jeff Bezos really believed everyone would buy everything online. Plenty of people didn’t believe that, but it didn't seem to bother Jeff that much. Would it have bothered me? Would I have the fortitude to stick it out and pursue the business venture of creating an online bookstore? These beliefs can be political. Would I protest on the streets against an injustice if I was the only one protesting? These beliefs can be about anything. Would I go to church if it was just me and the priest in an empty cathedral? Would I cheer for my favourite sports team if I was the only one in the stands? Would I buy this investment if I was the only buyer in the market? This question can show you how much you're willing to hold on to what you believe. It shows you whether you’re on board with something just because it's cool or saw someone else do it. More importantly, it shows how strong you will be in the face of adversity. In your life, if you're the only
one that believes you can do what you want to do, will you still have the strength to go after it? If you're the only one that thinks you will be able to get to your Point B will you give up under the lack of support? Or does the lack of support fuel you to dig in and fight harder for your beliefs? It's an interesting question to ask as it may foreshadow how you will handle adversity in the future. Why does it matter what other people have? Here's a quote that I love sharing with people: “You don’t look in your neighbor's bowl to see how much they have; you only look in their bowl to make sure they have enough.” I don’t know where I heard that quote, but it sticks with me. I often ask myself why it matters what other people have, and, to be honest, I still haven't found a great answer. My first inclination is to blame Instagram. It breeds jealousy, envy, and this notion of “keeping up with the Joneses/Kardashians.” However, as tempting as it is, I can't blame Instagram for my thoughts. In fact, Instagram is likely just exposing my insecurities. The fact that part of the reason I follow people on that app is partially just to “keep score” is pretty sickening when I think about it. It's not part of me that I'm proud of but it's true. However, the part I'm most curious about isn't that I keep tabs on people’s progress, it's that I care in the first place. When it's people who are close to me, I understand. It's important to keep tabs on your loved ones to see how they’re doing. But what about people I haven't seen in ten years? Why does it matter what they're doing and what they have? I believe this question is step one in solving this insecurity. This question helped expose my unhealthy relationship with envy. I'm thankful that it did. I now focus more time on checking in on those that are close to me and worry less about Tim and Tina from high school. When you ask yourself this question, does it expose anything about you that you don’t like? If not, then that's good. If it does, then that's good too. You found the unhealthy insecurity; maybe now you can focus on the why. I don't have much advice on why. I’m still struggling with that myself. However, you’ve taken the first step; keep the momentum of self-discovery going.
What's something others value that you don’t? What’s something that other people place a lot of care and value in that you never understood or found appealing? What do others spend their time worrying about that you never do? Money? Acceptance? Being understood? I’ll give my own answer just to get the ball rolling. I never worried much about following timelines in life. It never bothered me that people were getting married at twenty-four and I was single. Even currently, it doesn’t bother me that I’m in my early thirties and don't have kids yet. I noticed a lot of people around me have these timelines that they obsess over hitting. Having a career by age twenty-two, making six figures by age thirty, having kids by age thirty-two, owning a house by age thirty-four. None of these things ever really bothered me. I always felt like I had a strange relationship with time. I always feel like there's simultaneously too much and too little time in a day, so I think this screwed up any timeline projections I have for my life. Regardless, I always did things when it felt right, not when I was “supposed” to do it. What about you? What's your version of this? I’d be curious to hear about it.
Interlude — Books I made a list of my favourite books in the event you’re looking for more books to read after you're finished this one. (And finished recommending it to your friends. And finished giving it a five-star review). I hope they inspire you as much as they inspired me. Man's Search for Meaning by Viktor Frankl (You will never complain about your life again. It also shows how strength in adversity is a person's greatest asset.) Originals by Adam Grant (Helps you dream and makes you rethink entrepreneurship.) The Last Lecture by Randy Pausch (Life is short, this book is a beautiful and stark reminder.) Scar Tissue by Anthony Kiedis (The only thing more astounding than his life is the fact that he's still alive.) Greenlights by Matthew McConaughey (Teaches you the art of keepin’ on livin’ man. It also motivates you to live a great life with lots of stories.) Option B by Sheryl Sandberg (If you need more help dealing with loss and adversity.)
Chapter Eleven
Tactics on how to help find answers Alright, you made it to the last part of the book, you put up with a billion questions being thrown at you, I think you deserve something different.
Here are my tips on finding answers to these tough questions you’ve been tasked with solving. I purposely left this for the end as a treat for those that stuck it out this long. I’ll even turn it into a top ten so it's easier to read and maybe will get posted on Gary Vee’s Instagram (love you, Gary.) 1. Think. I know, it seems obvious. But I’m just reminding you that there's no substitute for thinking. Sorry. 2. Read Deep Work by Cal Newport. It helps you shed distractions and teaches you how to think and work at a level you never thought possible. Take notes while reading. 3. Start a journal and write through your thoughts. Your thoughts will start to clutter your mind and make it tough to think about other ideas. Writing down those thoughts will help clear things up a bit and keep you from forgetting them. 4. Unplug and isolate . Even for an hour. No TV, phone, tablet, smart watch. Just you and your thoughts, and maybe a journal… and maybe some scotch….and some Oreos. You get the idea. Shed the distractions and focus on you. Twitter won't miss you, it's fine. Also, don’t be afraid to isolate yourself. There’s a beauty in being alone with your thoughts, and it will allow you to find answers that wouldn’t otherwise be possible in a crowded environment. Some people are afraid to be
alone, but if you can manage to do it, there are great rewards waiting for you. 5. Write a review for this book . It won't help you find any answers. But do it anyway, please! It will help me help others, which is the whole reason I wrote this book. This book has heart, algorithms don’t. They only care about sales and reviews, please help. Thank you 6. Ask for help . Much like how I just asked for your help, you should do the same. It gives you a break and allows someone to give a unique perspective. Ease up on the “nobody knows me better than me” bullshit. It may be true, but it doesn’t mean others don't have a useful perspective on who you are and what you've been through. Ask a friend, family member, or even start seeing a therapist. Outside perspectives can help. If you think the information they give you is garbage, ignore it, but at least you have more information to consider and use if needed. 7. Be willing to be honest with yourself. Not only is it easy to lie about how great you are to others, it's easy to lie about it to yourself. I am great at making excuses to myself as to why I didn't go to the gym, eat healthy, or any other task I'm trying to complete. Somewhere deep down, you know when you're bullshitting. It's OK to call yourself out on that; you'll need to do so if you're going to find deep, meaningful, and accurate answers in life. 8. Study others . In the early stages, it’s sometimes easier to follow someone else’s Roadmap than to find your own. Every biography (especially autobiographies) is a window into someone's life. It allows you to borrow their brain. It shows the person from the beginning, when they were lost and clueless, just like how we all started. It may also show how they solved problems, worked on themselves, and eventually found answers in their life. A good biography can often be read as a playbook for success and may help you find your own success in life.
9. Start a hobby that involves solving complex problems. Chess, Martial arts, a Rubik’s cube, improv, coding, rock climbing, crossword puzzles. The list is endless. Problem solving is a skill. It's a function of the brain we are born with but still need to exercise and improve. If solving the problems in your life can feel too daunting, even when broken down to smaller problems as this book did, feel free to try problem solving in another function. Learning how to solve a Rubik's cube can build confidence in your ability to solve complex problems. This shows you that you have an ability to solve problems and can motivate you to solve more. It may start as small as solving a crossword puzzle but can quickly snowball into finding the answers to your own life's questions. 10. Be kind to yourself. You will struggle to find answers in life if you beat yourself up every time you hit a roadblock. This takes time and isn't easy. You should be proud of yourself for even attempting to find these answers. Socrates said that the unexamined life isn’t worth living. He’d be so proud of the work you're doing. I know I am, and you should too. If you find that you're being hard on yourself, take a moment, breathe, remember why you're doing this, remember that it's hard, be proud of yourself, and keep going. Kindness to others is a great way to find success in your life. Please don't forget to show it to yourself too.
Summary of Part Two There you have it, your Backpack. We crammed every pocket, every hidden compartment, every nook, every cranny full of questions. Please don't hesitate to come back to this whenever you need to. No point in bringing water with you if you don't drink it. Highlight your favourites, take pictures on your phone, whatever works for you. Just don't hesitate to use these as often as needed. The main purpose of this is to remind you that you're not alone on this adventure. You have a Backpack full of questions to support you during any emotion you'll inevitably feel on your path to Point B. Feel free to add more, ignore the ones you don't like, whatever you need to tailor it toward you and your goals. Now throw it on your back, tighten the straps, and get going!
Conclusion Phew! We did it! We asked questions, we dug deep, we exposed insecurities, thought about dreams, and dared to plan how to make them happen. We asked ourselves more questions in this book than some people ask themselves in their whole life. We didn't shy away from the uncertainty, we embraced it. We didn't let our weaknesses stop us from dreaming, we worked with them to create a better path forward. We have a Roadmap showing where we are, where we want to be, and how we’ll get there. It’s still rough, and not very efficient, but it's a start. It’s something we can work with and start making progress on. We also have a Backpack filled with questions we can use to help us whenever we need it. Anytime we get lonely, lost, tired, or sad, we can always reach into our backpack for the fuel we need to keep going forward. This might leave you thinking now what? Well, my friend, for the past 30,000+ words, this is now your time to shine. This is where you take charge. This is where you get to make peace with who you are and where you're starting from. This is where you dream about the person you want to be, the career you want to have, the family you want to raise, the places you want to go, and the world you want to live in. Most importantly, this is the moment you take your first step forward. This book has done all it can for you at this point. It has prepared you as much as words on a piece of paper are able to. It's time for action. That action starts with you. That action starts with one step. I’m in tears of joy right now thinking about the progress you’ve made so far, and the progress you're about to make. I’m so proud of you. I hope you are equally as proud of yourself. You can do this. Before I go, here are some final questions: Are you insecure about where you're starting from?
Are you uncertain about your future? Are you worried you might not have the perfect path forward? You are? Good.
Embrace this uncertainty, embrace the fear of the unknown. Embrace it all. You’ve prepared as much as one can; it's time to start your adventure. My contact info is at the end of this book. If you ever need me or have questions, please reach out. I’ll do the best I can. Helping you plan out your Roadmap has helped me make progress on my own Roadmap. Thank you for helping me take one step closer to reaching my Point B. I look forward to hearing about you doing the same.
Acknowledgements This part of the book is mostly to make the author feel better, so I understand if you want to skip it. If you're reading this hoping your name will be here, I'm sorry if it isn't; there are only so many pages. I first have to thank my parents, Maria and Cosimo. They’re the reason I’m here and the reason I have the confidence to know I belong here. They make parenting seem easy when we all know it very well isn't. Thank you. I’d like to thank the love of my life, Indigo, for making me realize that the most important thing in a partner is respect and support. You're the biggest proponent of those two in my life. I don't know how I got so lucky, but I sure don't take it for granted. I also appreciate that you didn't laugh in my face when I told you I wanted to write a book. I know I would have if I were in your shoes. Thanks for seeing the best in me, even when I don't. I’d like to thank my sister, Daniela, for being a fun sister and also a responsible third parent. Slightly cooler, slightly more understanding, way worse at cooking. My brother-in-law Paul, my nephew, Alex, and my niece, Gabriella, are reminders that family is the most important thing around. I'm lucky I get to call you family. I also want to thank my brother, Enzo, for the countless memories we had in our seemingly cut short time together. Thank you for being a beautiful reminder that life is short and meant to be lived. In the interest of time, I’ll make the rest a little more rapid fire. Just imagine they all start with “I’d like to thank...” My friends for sticking with me through the really good and really bad times. I don't take your support for granted. I just wish I was as good at it as you are. Anna and Richie for showing the world that love can be fun, even if it means dancing in the kitchen at 4 a.m. on a Sunday.
The Bad Decisions Boys for showing me that bad decisions can be a good thing. My high school pals for showing me that time doesn't have to pull people apart; it can bring them closer. Casey, for being the best cat ever, taking care of Indigo for twenty years, and teaching me that pet love is the exact same as family love. Rest easy, buddy. My friends from former workplaces for showing me not all friendships are just friendships of convenience. Scarborough for letting me call you home and making the lyric “I can't love you more than my hometown” the truest lyric I've heard to date. My goddaughter, Gabriella, for not laughing when I cried the first time I held you. Everyone that left me a review on this book's Amazon page. Wink. Bruce Springsteen for proving that art can indeed make a grown man cry. Italy for showing me that beauty doesn't have to fade with age. Adventures in other countries for showing me how small my problems are. My extended family for showing that time between seeing each other has nothing to do with the amount of love and support you can show someone. My favourite comedians for making me laugh when I was lonely. My favourite sports teams for letting me get lost in competition and community for sixty minutes at a time. Wendy’s for making a damn fine hamburger. Lastly, I’d like to thank the HR reps that didn’t respond to my applications, the former managers that didn't think I could handle it, the dates that never texted back, the former friends that didn’t think I was worthy of their time, and the bouncers that never let me into “that cool place.” You all taught me the most important lesson I’ve ever learned: There's a tremendous amount of power in being the one nobody would vouch for. Now how's that shit for an outro?
About the Author My name is Robert James Maiolo. Son, brother, uncle, partner, friend, cousin, former banker, lifelong learner, hopeless explorer and with all that, a sweetheart of a guy (my girlfriend says this daily). I’ve been a best man two times, a pallbearer seven times, had my heart broken a few times, and have broken hearts a lot less than that. I’ve been to over twenty countries, went to university abroad, but will always call Scarborough home. I’m not coming to you with a psychology degree, or years of research in the field. I'm not a life coach, a former CEO, or a crypto millionaire (not yet anyway — come on LollypopCoin!) I’m coming at you as an average guy who spends an above-average amount of time thinking about the world around him. I'm not an expert in anything, so all I can do is be myself and be authentic. I’ve often been mistaken as a quiet guy, but the chatter in my head never stops. I believe being a deep thinker while also having something to say makes me a great candidate to write this book. So, if you're scared that I'm a “know-it-all” author, I promise you I'm not. In fact, I'm the complete opposite. I'm the “question-it-all” author (sadly, this is just as annoying and even more pretentious.) If you want to reach me, please hit me up at [email protected] . You can also reach me on Instagram @robbieaxelrod. Hey! Remember when you told yourself you were going to leave a review? This is your reminder. The book is finished. There are no more words to read. You can leave a review by accessing your orders page in your Amazon account or wherever you bought this book. Thank you!