Taking myself off autopilot.

Photo by Dino Reichmuth on Unsplash

For as long as I can remember, I have woken up each morning determined to build things of real value in this world. 12 months ago, I woke up, and for the first time in my life asked myself “why?” This Article is the culmination of what I have learned since asking myself that simple question.

The catalyst

At 2 pm (CST) on April 30th, 2020, my life changed. This was the result of a conversation with a man I have never met before, and through a Zoom-call to boot. The man, Randy Fisher, reached out to me on LinkedIn as a result of something I was quoted saying in an article a week prior. Randy was interested in what I had to say regarding a government policy that would support early-stage startups in Canada through the pandemic. I showed up 10 minutes late and after the first 20 minutes of speaking with one another, I figured the conversation would end there and we would likely never speak again. I was wrong.

Just before we ended our call, Randy said to me “Jordan, if I may, I would like to give you some unsolicited advice.” When someone you don’t know says something like that to you over Zoom, any rational person would be curious as to what that advice may be, so I complied. Randy proceeded “I think that you have something to say that people need to hear.” I sat there flattered as one would, but also without a clue as to how to respond. I imagine I said something self-deprecating as has been my custom upon receiving compliments for as long as I can remember. See, his comment itself was by no means revelatory, but it was what came next that took me by surprise.

As I proceeded with my customary downplaying his kind words, he began to take notes on his screen. After I would finish speaking, he would recite back to me exactly what I said. Each time I would try to explain myself to Randy, using whatever form of self-awareness I believed I had as armour, he would read back my comments to me like I was a book and would proceed to give me compounding advice. A man I have never met, who wasn’t even in the same country as me (New Jersey, USA) somehow after repeatedly regurgitating back at me my platitude salad, knew me better than anyone I have ever met, including myself. For years I had been collecting all of the individual pieces, but this conversation and the epiphany it yielded was the final piece that exposed the full picture.

The affliction

Growing up, I recall watching movies portraying the wealthy CEO or investment banker who had all of the money and success in the world but who was alone, unfulfilled, and unhappy. In tandem, I remember sitting with my mom watching Entertainment Tonight in my young teens and seeing all of these celebrities (actors/actresses, musicians, writers, athletes) who were getting divorced, on drug benders, and even committing suicide. I wondered “how on earth could you be that unhappy with all of that money, fame, and success?” This isn’t a new notion, but it becomes ever more apparent as you grow up and find your calling and throw everything you have at it, all while life becomes increasingly more complex.

High-performers exist in everything from sports to art to business but share a similar core driver. If you sit down with any high-performer and ask them “what motivates you?” often they will say something like “the love of the (blank)”. However, if you dig a little deeper you will come to find that almost all of them have encountered some form of trauma in their early years, which has been the fuel that has propelled them to their success.

Parents ignored you as a kid? Win a gold medal. Siblings picked on you? Run for Public Office. Teachers told you that you won’t succeed? Build a unicorn company…and on and on it goes. High-performers, for whatever their unique reasons, almost universally apply themselves and achieve what others cannot because their trauma fuels them to do so. They achieve, but for the wrong reasons.

My story is no different. Growing up I was the fifth of five children and throughout my entire life have had some form of a chip on my shoulder. My elementary school years were normal enough but by the time I got to high school the bullying started and persisted even into my university years. I remember building my first company in Grade 5. I still have the booklet where I went around my classroom and asked everyone what they want (typically electronics) and what their bottom price was. From there I would search online and see if I could find it for under that price and if so, I would buy it, sell it to my classmate, and keep the margin. This was followed by another 15 businesses before the age of 26 (not including jobs) and encompassed everything from a snow plowing business, a clothing brand, a local deals website, a venture capital fund, a 3D printing MedTech startup, and no less than four non-profits. At no point did I ever stop to think “why am I doing this and who am I doing this for?”

After three years of lobbying and fundraising, in 2017 we finally incorporated and built the non-profit technology incubator I had been trying to create for our local tech community. Three years later, a total of six years since the inception of the idea, we have built one of the fastest-growing tech hubs in Canadian history. This did not come without its challenges and many sacrifices. However, it only became apparent to me two years in (2019) that something was wrong. We had launched the rocket ship and things were going amazingly well, but I would get home late each night and feel empty. I began to search for a “solution” to this problem in the form of 3 trillion Tim Ferris podcasts, books on Buddhism and childhood trauma, and the penultimate “fix”, hours of therapy. The thing is though, none of it worked for me. I would drive to the mountains alone on a Friday night and listen to 7 hours of podcasts before I would climb a mountain and feel a moment of complete stillness and peace. However, give it 48 hours, and all of the presumable “progress” I had made in believing I was “fixed” would be gone.

You may be asking yourself, what do I mean by “fixed”, what’s broken? The funny thing is, nothing is broken per se. You hit a point as a high-performer where you are so driven to succeed and conquer and for so long, that once you begin to reach the summit of whatever mountain you were climbing, the skies clear and you realize you were actually on a treadmill all along.

I am not alone in this. The pandemic has created a unique moment in time where high-performers have the opportunity to gain perspective as to their why while they are still on their journeys. In my role running a technology incubator over the last three years, I have worked with hundreds of tech founders, almost all of them high-performers. On March 18th, 2020 each of them was given a unique opportunity which still exits to this day four months later, to evaluate why they are building their companies all whilst the economy is on pause. This is a perspective that is typically only achieved when your company sells or shuts down. So, what did they find? Well, my data is anecdotal at best, but the vast majority of them, like me, have been in existential free-fall. Questions like “Why am I building this?”, “What happens if I succeed?”, “What happens if I fail?”, and the most important question “Who do I want to be at the end of all of this?” These are incredibly important questions as the answers are what prevents a high-performer from reaching their summit, only to find that it was all done for the wrong reasons.

The remedy

I believe there are two things that every high-performer needs to consider to solve for the aforementioned existential quandaries:

1. How did I become like this?
2. How do I become the person I want to be?

Let us begin with #1. As mentioned earlier, the traumas that we encounter early in our lives shape our core drivers and motivations. One of the most compelling explanations of these traumas and their effect on high-performers is outlined in a book titled The Drama of the Gifted Child by Alice Miller. In this book, A. Miller explains that the relationship between a child and their parents, specifically their mother, in the early years of their lives becomes the foundation of that child’s “false self”.

Before the age of 5, your parents are your entire world. They are your access to food, shelter, love, affection, warmth, and all other human needs. As such, when your parents do not satisfy those needs, for example, your mother ignores you or mistreats you, your survival instincts kick in. You are presented with two options: 1) express your feelings such as crying or screaming or 2) repress these emotions. Given that your mother is your entire world, your survival instincts inform you that to express your emotions would sacrifice losing her love for you and therefore you hold them in. Ironically, we’re surprised that years later that same child, now 30 years old, struggles to communicate with those most important to them and instead dedicates themselves to building something that will make their parents proud of them. Further, high-performers who experience this kind of childhood trauma oftentimes pursue grandiosity as a supplement for the attention they did not get as a child. The challenge with grandiosity however is that it acts as a dopamine hit, and when the attention and accolades fade, all that is left is a hole oftentimes leading to depression; like a balloon that falls to the ground as it loses air.

The cycle repeats through children who become parents and repeat this behavior with their children. It can only stop once a person reflects on their early years and mourns for the person they wanted themselves and their parents to be. Only then can they become their “true self”.

When I applied this framework to my own life I realized two things:

1. My father was a CEO and would rarely be home in time for dinner. When he was home he was constantly busy reading documents, emails, or on phone calls. As early as I can remember I would try to take an interest in business and develop ideas that he would be interested in, all to get his attention and admiration.
2. My mother was a principal all whilst raising 5 children. Often she was overwhelmed with the responsibilities this entailed and to gain her affection, I would do things to make her life easier. For example, I would pretend to be sick to stay home from school so that I could clean the entire house for her.

Applying these realizations, along with those not suitable for a Medium Article, I realized why I am the way I am. For years people have asked me “why do you do what you do?” and I have even had peers ask me “do you hate money?”, as I give to others and rarely expect to receive in return. Now it all makes sense; I do things for other people in my life, personally and professionally, to receive their admiration which in turn forms my own identity. Upon realizing this, for the first time in my life, I could without judgment, understand my core drivers. This understanding has now given me the freedom to become the person I want to be.

Now #2, how do you become that person. There are six tools that I have collected and actively apply to my life daily to become that person. Every day I wake up and as I walk out the door I look at them on my whiteboard and think about which ones I will need to apply that day.

A Whiteboard Guide to Self-Actualization :)

1. Positive Self Talk: As I spoke with Randy, the one thing he and I both noticed was just how negative I was when speaking about myself and my accomplishments. What I have found is that I, like many high-performers, have been my greatest critic and have used that negativity as fuel. The problem is, however, if you always undervalue yourself and what you have accomplished, it doesn’t matter what you achieve as you will always reach summit after summit and not give yourself permission to enjoy the destination, let alone the journey. The day after my conversation with Randy I took note of each time I was negative to myself either in conversation or in my internal self-talk. I hit 50 instances in one day before I realized the magnitude of this behavior. As such, each time I undervalue myself or am critical I stop, change the narrative, and find a way to instead celebrate what I have done rather than what I have not.
2. Question Assumptions: One of the most dangerous parts of being a high-performer is the artificial assumptions and parameters we place on ourselves and our potential. Every time we climb further up the mountain we tell ourselves that we cannot start at the bottom again. This kind of thinking affects both our short-term and long-term decision making. For example, recently I asked myself “Why do I feel the need to order an entire meal when I am only slighting hungry?” This behavior derived from habit I developed and may seem insignificant, but to question it I gave myself a low-risk alternative. I told myself that I would simply order an appetizer and if I am still hungry after I would permit myself to order more. 99% of the time you don’t. This manifests itself in our largest decisions such as our careers. A senior bureaucrat friend of mine told themselves that they could not leave their job and move to another city unless they secured a role that is more senior than the one they currently hold. These kinds of artificial assumptions and parameters we place on ourselves shackle us from change and realizing our infinite potential. In this situation, I asked him a series of “What ifs” such as “What if you didn’t need to move into a more senior role?”, “What if you moved to another city?”, “What if you didn’t need to work in government?” Layer by layer we pulled back these artificial assumptions until they realized their options were infinite if they questioned and removed the parameters they had placed on themselves.
3. Happiness Framework: For years I have constantly thought to myself “What’s next” even when I was still building the venture I was currently involved in. Whenever I was unhappy or felt that hollowness I spoke of earlier, I always blamed it on what I was currently doing professionally. Thus, in my mind the solution to this fleeting problem was the “next thing” and I would fixate on that. However, what Randy explained to me during our conversation was that I had it backward. Instead of fixating on what solution (company, job, city, etc.) would make me happy, I should instead fixate on the framework of which I measure my happiness. Ask yourself, how do you measure how happy you are? I have to admit, when he first asked me this question, I could not readily answer. As such, whenever I now feel unhappy I don’t blame it on my current situation, but rather contemplate how I am measuring my happiness. I then compare my options or “solutions” against that framework to make a decision that may improve my overall happiness.
4. Multi-spectral Decisions: My personality has always been such that I am either 0% or 100% committed, all or nothing. This is incredibly valuable when you do commit to something, but makes progress in things that require dedication incredibly difficult to achieve. Thus, when I do not have the desire to do something that I know I should, I ask myself “What am I willing to commit to on the scale between 0% and 100%?” This has led to gradual progress in leaning into behaviours, taking steps in 10% or 20% increments, which over time will change my habits and routines.
5. Action=Inspiration=Outcome: One of the most important lessons I took away from a book titled The Subtle Art of Not Giving a F*ck by Mark Manson, was the idea that our approach to behavioural change is backward. People will often say “I am not in the mood” or “I do not have the motivation” to do things like write, paint, or workout. What M. Manson pontificates, however, is that people think the path to achieving the desired outcome is Inspiration=Action=Outcome, when the process is actually Action=Inspiration=Outcome. Think about it, when you go for a run you immediately feel inspired and energized to do other activities. I was recently listening to a podcast between Tim Ferris and Malcolm Gladwell where Gladwell, a famous writer, said that he writes between 500–1000 “shit words” every day to get himself in the right mindset to write. Objects in motion tend to stay in motion. A perfect example of this dynamic is this Medium Article itself. For weeks I have been talking with friends about my findings and would have to recite the same 30-minutes worth of information each time. I knew it would be easier to just write it all down and send it to them but at no point did I feel like I was in the “right mood” to do so. After a month of procrastinating, I finally opened my laptop and started writing on a Saturday night. I woke up the next morning to find that most of what I wrote was complete hogwash, but I carried on none the less. 6 hours later I had completed my “impossible task” all because I dared to begin without judgment of how terrible the results may be.
6. Run towards suffering: The second most important lesson I took away from Mark Mason’s book was the idea that humans need to suffer to have a purpose. Think about, when we face adversity and suffering we have a purpose, everything from having to get up at 6 am to go to the gym to staying at the office until midnight to finish a proposal. It is only when we have no suffering, no real problems, that we create them. Ever heard the term “Californian problems”? Neither have I, I just made it up, but the theory holds. When you have all of the money in the world and no real role in society, you create artificial problems to solve. Just watch The Real Housewives of (blank) and you will see my point. Thus, suffering and pain are where we find fulfillment in our lives and we must not try to run away from it but rather run towards it.

It should be noted that all six of these tools have a direct correlation between them. There are, however, too many to list, but if you try to apply each to any particular situation you’re encountering you will do well to find the balance between them.

The outcome

My life changed the day Randy and I had that conversation, not because of one thing he said, but because he said things in a way I could understand; like pieces fitting together in a puzzle. Understanding why you are the way you are and using these tools to become the person you want to be will never change who you are; your personality, your interests, even your ambition. It will however allow you to wake up from the years of “autopilot” that you may have been on and of which, may have led to lonely nights, hollow success, and even depression. I have seen so many high-performers, especially tech founders given my role and the profession’s overall volatility, experience these feelings, and not know how to find the answers. My hope with this Article is to impart some of the lessons I have learned so that you too may be able to apply them to your life in your unique way.

Even now things are not perfect, and they never will be as life is a shit-show and it’s beautiful, but at least now I feel like I am an active participant in it all, eyes wide open.