“You know that you are a motivational speaker, right?”
She said.
Her affectionate tone carried a tenderness, half-joking, that I tried to rationalize as merely polite. Sitting in the cafe holding a short cup of cacao, unknowingly, she had struck the vein of a very old source rock in the story of my life, one that she probably did not realize how far into the past it ran.
I’m standing alone in a University Community Center basement classroom. Beige, brown and black tiled, dull, and lifeless walls enclose the space with a cast of around 18 empty chairs and tables. Overhead, a projector scatters light onto a white screen with a PowerPoint presentation reading “Expect The Unexpected” in black font to an orange background (apparently I failed the Intro to Perfect PowerPoint Presentations 101 class). It’s intensely quiet, only the sound of my inner monologue and what I have to do holds next. It’s around 7PM in the evening, not many students are on campus, voluntarily. It’s the third time I’ve run through my speech, enunciating the words and accentuating the tone and points. I practice my walk. I practice my pacing. I practice a confident grin and pause held before I drop the next devastating idea. I try to assure myself that animations and reveals are on time, for dramatic effect. Yet, I’m terrified, I can’t tell you why on earth the undergraduate students at Richard Ivey’s Business School picked me to do a speech. As I inch my way towards the end, I slow down and add tentative heartbeats to the cadence of my words, Ba-dum—Ba-dum—Ba-dum, preparing for the big ending. As I rattle off my conclusion and close the speech, I imagine a roaring applause and cheers. I try to feel some pride, I stop and take a sip of water. The timer reads just a few minutes under the cut off time. I resolve that I need to try it again to make sure it’s right this time.
My honest, yet most hidden ambition in life, was to be a motivational speaker. The vanity and hilarity of it aside, it’s true. I even at one point attempted to, imitating a posthumous mentor Jim Rohn, write my own self-help book. The title of it was something like Developing Personal Magnetism and Charisma, as if I had any clue what those things meant at the ripe age of 20. I genuinely, despite insecurities surrounding personal confidence and esteem, imagined myself one day on a stage talking about how to live. That vision was the end state performance of a life that I rehearsed for over half a decade and forgot about for even longer. So what got in my way and why did I forget about it after all? It all started, with the basic problem of: what could a twenty-year-old student attending one of Canada’s lesser-known institutions, unremarkably so, really have to say about anything related to life? I needed a story, mission and life, worth talking about first.
The New Face of Entrepreneurship
Read the cover of Entrepreneur Magazine.
A bold upfront mocha coloured font in the magazine’s iconic typography extended over a front spread photograph: a young, bright looking gentleman with a grin; the image of my 19 year old self stood arms folded, upright and smiling in triumph. It was a mangled photo that I took with a selfie-timer in my bedroom, poorly photoshopped onto the magazine cover. The printout hung on my dark green university bedroom wall so that I would see it, first thing when I awoke and the last thing when I went to bed.
It was the early evening in the fall of a new school semester, where leaves fell from the trees and the feeling of open possibility held in the air. After a long walk home to my Richmond Street dwelling, my body felt tired and ready to sleep. But, as I turned the door handle to my bedroom, I knew I had one more task to complete. The task always felt like a nuisance, but I knew that trading these 5 minutes, ritualized every night, would be oh-so-worth it to bring it all together. I opened the small side-table hidden to the left of my bed. Inside, a secret Ziplock bag full of looseleaf paper, contained scribblings and markings in multiple ink colours. Next to the bag was a stack of single sided blank paper, recycled from academic notes. A neatly cut collection of small strips measuring the size of two fingers. Climbing into bed I selected a pen, blue was the colour of choice this evening, then pulled the covers over me and angled my body awkwardly to write on the table’s surface.
The Secret of Success
I could hear the voice from a cheerful everyman 1950s narrator echo in my thoughts. It was the voice from the start of Napoleon Hill’s audiobook Think & Grow Rich. I recalled the task the book had specified:
Write down the precise amount of money you desire and the work for which you will do to acquire it.
I wrote out the sum and the work I would do, autographing my name like a piece of memorabilia. Holding the small paper, I then visualized my future, before stuffing the signed affidavit to my future-self into the trade secret plastic bag. My little repository of ambition, a secret reveal once I had made it. I shut the side table, and felt the pang of doubt again. How exactly is this going to work? Brushing the doubt aside, I didn’t know… but magnificent magic was my guess. Hill’s book made a compelling case that you think, you do, you get rich, to that transaction, at least, I did my part and my eyes closed to sleep.
I’m fairly certain that the amount of money and work I would do changed from week to week. Sometimes I wrote management consulting; other times, computers and technology hit the page in ink. Under exceeding circumstances of limited imagination, I simply wrote “business”, then like a dismissive child, shooed away the unfair test question. While drowsiness won over invention often, admittedly I did not miss many recitals. But, these magical life purpose statements really fed into a story that the photoshopped magazine cover alluded towards, it was the story of my life, worth telling. It was a narrative I was trying to build on the coat tails of two myths that I held to be worth hearing.
When Andrew Carnegie died, his estate found a scrap of paper in his desk from his youth: for the first half of my life, I will spend it making a fortune. For the second half, I will spend it giving it all away. The image of a magnanimous character, lauded for his philanthropic claims, held strong in my imagination, though I borrowed it for less selfless aims. In sincerity, I did want to be a philanthropist and do good in the world. I still do believe it to be a high expression of virtue, and I was also probably partly motivated to follow Carnegie’s plan for the authority to speak from the podium. Yet, it was the second story that created a greater weight for me in the end. The image is of a young Jim Carrey sitting alone in a car after striking out yet another audition; he decides to visualize a cheque for $10 million, telling himself that if he can cash a cheque that big, he made it. In his later Dumb and Dumber appearance his dream came true. So, I decided to write myself a cheque, several actually. My visualizations had been coming up short recently, so I set my sights on realism. After a series of self-negotiations, I bid my cheque value down, especially as doubt surmounted. Finally it settled somewhere in the fantastically delusional range of $300 million, dated in 2035. I had taken ~Rittenhouse’s poem~ seriously. That folded promissory note occupied the same place in my wallet, tucked under a series of talismans and good luck charms for years, lugged persistently, and with heaviness, as the objective to meet.
I buzzed myself into the cool corporate lab area, the early summertime heat had me sweating from the bike-ride in. Corporate innovation was hip at the moment, so office furnishings were excessively modern: no fixed desks or chairs, standup tables for stand ups, bar stools and couches. Before entering another rehearsal in the theater of innovation, I slid devilishly to an accessibility bathroom on the righthand side. Another 5AM morning to a venture before work had me exhausted as I sighed and locked the door. My newly birthed drop-shipping business was struggling under its light weight and my impatience; the shoddycopia of AliExpress trinkets I marketed weren’t selling, and only I was to blame. Sitting on the shower stool, the dark blue interior bath tile reflected my figure, as I stared at the promissory note between my thumbs, an intense doubt weighing on my shoulders. Bringing the cheque to my forehead, praying for things to go right, I whispered motivating things to myself in low sobs. Nobody answered.
That 6 by 2.75 inch personal cheque weighed what I imagined the earth on Atlas’ shoulders to be. A feeling of always-on edge, intense urgency and need to prove myself to its persistent ticking sound; a reminder that time was passing by in the light of my self-conceived destiny. I needed to be an entrepreneur. But, why? That wasn’t a question to think about at this moment. What mattered was that I found the perfect start-up idea and means to make the cheque real. Strangely, the truth was, I didn’t believe any of this. I wanted to believe it, I rehearsed my performance continually: networking, searching for the start-up idea, trying to seem smarter than I was. And yet, the sentinel at my shoulder gnawed at me as if I had taken the wrong direction somewhere. That was doubt, I confidently tried to convince myself, but the eerie sense of being offtrack or misaligned held within me still.
Affirmations, manifestation, fake it till you make it, but does any of it work? Wrapped as it is in the reverence of metaphysical projection, visualization, my guess, is a tool that helps, just not in the way self-help claims. The brain’s default mode network is a powerful place, the repository of self-referential thought (i.e., the “~Me~”), particularly recurring beliefs. Visualization and affirmations aim to refactor our self-concept in ways that align to stated goals. In theory, a self-concept primed on a target gets better at noticing the events and openings already pointed that way. It’s a subtle recalibration of cognitive focus that systematically alters what the default network registers as self-relevant, reshaping selective attention, risk tolerance, and daily micro-decisions. By training perception to recognize the openings hiding in plain sight, visualization turns itself into a self-fulfilling prophecy. What you don’t realize, however, is the road to the visualization end state might be a lot bumpier than you imagine.
PLEASE SEE ATTACHED CEASE AND DESIST.
The e-mail header froze the breath in my throat so cold that I might have been better off on Pluto. I stood paralyzed as a wave of dread ripped through me, my insides felt as if someone had turned on a buzzsaw and stabbed me with it twelve times before deciding it was enough. The small app I taught myself to code had started getting some attention and the C&D letter arrived a few months after launch and weeks leading up to my birthday. By this time, I had become enraptured with silicon dreams, rehearsing daily affirmations aimed at one day going to The Valley of Industrial Make-Believe. As I panicked internally trying not to hyperventilate, was THIS what it felt like to be successful!?, I looked for help. The letter ended as a minor bump resolving without issue, but it gave me the first taste of terror that would come from big goals and business. For someone with grand ambitions, in that moment, I didn’t quite feel like the one with the iron stomach for it. But it was also a success, at least, right? A few more trials and I would be on my way to moment where the cheque gets cashed.
V just looked at me through the video call screen for a second and asked point blank:
Usually, when someone is a business owner or entrepreneur there is a driving motivation to build or see something be built in the world – what is that something for you?
The question needled me as honest inquiry does. I was here because something was wrong with me. I’d been rehearsing for years into this secret of success business, why couldn’t I just get it together, go “beast mode” and just deliver the grand performance already? I recalled my photoshopped feature on Entrepreneur magazine from years ago, how proud I wanted to feel to call myself an entrepreneur on Linkedin (cringy). But as I really started to turn it over, I didn’t have any deep reason. I just wanted to be free and respected.
I don’t really know I just want to be an entrepreneur. It’s always been there, I can’t exactly remember where it came from.
I replied. We had been working through the Enneagram as a personal development tool. My type, The Three or “Achiever”, had a particular backsliding tendency into image. As I sat on my neon green papasan chair, staring into the cyberspace built by the San Francisco transplants and beyond, V paused and replied:
That sounds a bit vain doesn’t it?
I felt a hairline fracture to my ego crack wide open.
Where did this ambition to entrepreneurship come from? I recalled the cheque and intention to “do good”, but I could not remember the origins. The Type 3 is described as ambitious, competent, and energetic while equally status-conscious and driven to advance, with the ultimate fear of worthless. At unhealthy levels they try to impress through superiority, self-promotion, and making themselves sound better than they are. I knew how to do a lot of that, with the exception of self-promotion which without genuine interest is my downfall. Sometimes, three’s are even called the “Performer” as they lose touch with what they feel so as to conform to the image or desired persona as needed. The disconnect between my obsessive success rehearsals, self-conceived image and reality of my conceit was menacing. But, this revelation had just peeked open a small door, to the more rapid demolition that was to come on that same neon green chair a few months later.
The Papasan Chair in Question
I’m sitting in my dim red mood-lit studio, my laptop in hand, and the clock reading around 11PM late December. The on-call rotation alarm has just notified me that something has gone wrong again. It was the end of one full year of pandemic lockdown across the world while working for a hyper-growth company that provided me opportunities and stresses I never would have imagined taking on in my 20s. Working on systems responsible for millions of dollars and securing assets, my team had been undergoing a brutal trial of downed systems and problems for the past several months. As I sat in my papasan chair during the holiday season, thousands of kilometers from my family, a few tears pooled in my eyes in front of the keyboard. I could not think straight. The application dashboard piled logs in with a cascade of requests and errors. The screen flashes with computer text so quickly, you could not catch a beat to read without interfering to make it stop. Two messages tag me in quick succession: “@oncall: can you look at this”, “hey @oncall: errors on the system – any advice here?”. Peeling my eyes from the pings, my phone suddenly burst again into that God forsaken robotic voice claiming another “On call alert”. The pressure in my head was growing and my face hot. I felt like I was being torn in two pieces. The skeleton crew running the holiday season only amplified the loneliness in this digital workspace. No one to call or lean on. Just another alert and another issue to solve, and I was paralyzed.
But it wasn’t just the alerts that brought me to this point, it was that on-top of everything else. I was working in the world’s most competitive city, with some of the smartest people I’ve ever met, in a global pandemic, where crying in my storage closet on a casual Tuesday was normalized, and a persistent worldly chaos and escalating civil unrest led to a feeling of apocalyptic prophecy. That even a few months earlier, San Francisco had experienced a plausible warning sign to the cataclysm as the city awoke to orange skies and dusk at 8AM caused by wild fires, it was enough to convince anyone the world was at its end.
September 2020: San Francisco 8AM Wild Fire Sky
Yet, the most deafening screech came not from the sounds of worldly foreclosure, but in the quiet subtle ticks sounding the seconds fleeting by from my time-bound cheque. Despite all the projects, ventures and attempts nothing had worked yet, and here I was trying to hold it together and believe. I looked at the software logs and felt an honest drop in my being, asking myself a question I had kept asking myself for all the years up to that point: can I handle this?
That is the stone wall that I ground myself against for 7 years. The only baptismal truth I knew, having circulated and evangelized for it without rest in The Church of Success I had built from the media I consumed, was to: persist always, work harder, endure, discipline yourself, and never give up. If I quit on this thing, it would all come crashing down. I could lose almost every thread of faith, but so long as I had one in that dream, I could hold on for dear life, because… that’s how the magic of “The Secret of Success”, worked. But truthfully, it was probably because I didn’t know who I was without it, or more clearly, how I could be worthwhile, without it.
The studio apartment was quiet, the night sky held above the city and the glimmer of lights sparkled around. By all measures it was a serene sight. Yet, the logs flooded into my screen now faster and another message tagged me with: Hey @oncall Any update here? I kept asking myself over and over, What do I do!? What do I do?! I don’t know what to do! I have to handle this!
While I wish this story was a heroic triumph, it’s not.
After an agonizing negotiation, feeling my being split apart, I opened my messages and typed my manager’s name. In a short and comically understated message, I tell my manager that I’m not doing so well and I don’t think I can complete the on-call. Finishing the draft, I read it over, uncertain fingers holding over the Enter key carefully. The force 0.65 newtons would be all it took to commit this act of personal self-destruction. All the nights, all the rehearsals, all the recitals held in hope and pushing against doubts, would be gone. My fingertip shook as I felt the nausea and panic pour through me again. The voice in my head barked at me like a drill sergeant, promising menacing forms of corporal punishment if I chose to go through with this:
If you can’t handle this, you can’t handle being an entrepreneur, period!
The message sent and within a few minutes I was off call. While I ought to have felt relieved, something deep inside me had broken. It was the admission of real defeat and resignation, I did the one thing you’re never supposed to do: I quit.
I didn’t feel much. Just a sense of profound shock, shame and numbness. Words were not really forming in my thoughts let alone able to be spoken out loud. I closed the laptop and put it on the floor, stepped cautiously to the front hallway next to my bathroom. Inside the key bowl, I saw and held my small black leather wallet. Opening its soft texture, I sifted my finger into the hidden pocket to find a four way folded personal cheque. I scanned the payee name, the sum, the memo signed with black in the red atmosphere, feeling the weight of time, emotion and cost held, and tore it in two, scattering the pieces. Sitting back in my papasan chair, I didn’t speak or open my laptop. Just the soft moody glow, low hum of my open exposed red lamp, and I stared into the room.
The next day, I went for a morning run and listening to Wake Me Up by Tim Bergling (aka “Avicii”), the once ambitious musician driven by unrelenting tour schedule that tragically passed at the age of 28. In the song, I heard the story of someone who had gone to sleep in the process of working towards the success they wanted, which at times was so overwhelming, they wished themselves to just be asleep until it was over and they had arrived where they were “supposed to be”. I heard Avicii’s tragic story quietly underneath the pop sensation, and a recognition of my own, that I didn’t know I was lost, either.
My story was a dress rehearsal for a life I hoped would one day be worth talking about. A performance I kept waiting for permission to give, waiting for someone else’s authority, that never came. Throughout all the recitals, I lost track of what I was even practicing for. An actor so consumed by his role that he forgot what the role was for, whether he was even enjoying the part, or whether he’d wandered onto the wrong stage entirely. The revelation was hidden under a 1 gram personal cheque, signed and payable to myself, for the sale of a company I’d thought I’d build one day. I never would have guessed it would weigh so much. I didn’t realize yet how insane the situation around me actually was, I thought the problem was just me.
The strange part is, I still rehearse, write daily affirmations, and even visualize from time to time. 50 Cent’s The Hustler’s Ambition is still one of my favourite rap tracks. One final lesson I got from V, the one I still have not integrated into my life after all these years, was: what if the big stage isn’t the stage meant for me? I’d spent so long fixated on the big stage, but maybe there is a smaller, humbler side stage where I am better suited.
I paused a moment, then turned to her, the same cup of cacao between us now as it was then, and back to the desserts on the table. The afternoon sun had set on the Thai island with day turning into night: my oversized fisherman pants adorned, barefoot sitting on accent pillows in front of the small coffee table. The image of a self-assured half-smiling student hell-bent on a place in the world was replaced by the sincere goofy smile of an older man without a job, purpose or any clue what he was in life. My voice shook as I tried to reply:
“Ha. A motivational speak… you think so? You know it’s funny you say that…”