Memento Mori

How My World Has Changed

Ignition: Leaving the Garage

I’m walking away from my life as a corporate wage slave. 

I’m giving up the illusion of job security. 

No more predictable pay cheque. No deposit every second Friday.

Friends ask me what I’m doing with my life and I tell them the truth:

That I’m becoming a writer. 

That I welcome their encouragement.

That I feel their disdain.

With a young family to support, I have always felt like I need to be the grown up in the room. 

Do the right thing. Take the safe route of another VP job in real estate. 

But I realized something: People’s perception of risk is frequently backwards. What appears to be the safe bet, is actually quite risky. So by going down the entrepreneurial route, I’m betting my family’s future on me.

Starting Line: The Engine Stalls

I grew up as the first born son of first generation immigrants.  They came to Canada with next to nothing. Arriving with desire to build a life here and leave the old one behind.  

My father? A med student.  

My mother? An ex-nurse.  

She told me her stories.

About how she wandered up and down the streets of Toronto. 

About how desperate she was, in search of a paycheque.

About how she was told no, and only no, over and over again.  

Eventually, she had to beg the manager where they did their banking.  

“Please help me. I have nowhere else to go.  I don’t know what else to do.”  

It was the quiet desperation of new immigrants.

Luckily, the bank manager took pity on her, gave her a job and eventually, she became the best at what she did.

Detours: Steering Through Darkness

One day, they had me.

Her new banking career came to a stop. She became a devoted stay-at-home mom...all for me. 

My father…he finished his specialist training in internal medicine and we moved to Vancouver to start a new life. Dad opened up a new medical practice and looked forward to receiving new patients.

But no one came.  

I was too young to remember.  I was only three.  

He would come home dejected and anxious, asking my mom:

“Did I do the right thing for us, for our family?”  

Days and weeks went by. Still, no one came.  

Fifty years ago there was no LinkedIn, no social media, no WhatsApp, no shout-outs, no likes and no connections. Networking with the GPs was the only way to get referrals.  

Mom had to remind Dad, “Have confidence.  They will come. Believe in yourself.”

Eventually patients came and his practice grew.  

Cruise Control: On Easy Street

By the time I was in primary school, I was privileged. 

I had the lifestyle, the lifestyle of an upper middle-class family in a good neighbourhood. My younger sister and I went to good private schools. We had smart tutors, great music teachers, and great weekends spent at our ski cabin up at Whistler. 

Our cabin was ski on, ski off. We could wake up, get dressed, and be on the ski lift in one minute. 

“I thought that poor kids were the ones who had to do 5am day trips.”

The “poor kids'' were the ones whose families had to wake up when it was pitch black and drive two hours from suburbia up to Whistler. They’d change in the parking lot and after a hard day of skiing had to drive two hours back to the city on the Sea to Sky Highway without falling asleep at the wheel.

The nickname for the highway?  Ski to Die Highway as it was one of the most dangerous highways. The poor kids? Upper middle class kids who didn’t have a ski cabin.

Such a statement reflected a certain amount of naivety, arrogance and shelter from the real world. My attitude in my teens and early 20’s weren’t that different.

I was the embodiment of economic privilege and I never realized it.

My parents made enormous sacrifices for my sister and me.  

But I never did much with my life for the first 30 years of it.  

It was an endless carousel of dead-end jobs, too much TV, internet and video games.  

That was how I repaid them.

Dead End: A Wrong Turn

Eventually, I became an adult at the age of 40. 

I finally got married, settled down, and had a beautiful daughter of my own.  

A few years later, I was let go — Vice President of a Real Estate Investment Trust. 

Up until then I thought I had finally made it. Then the company wound up operations in the province and I was packaged out. Shortly afterwards, I found a new job, but it only last three months.

“You’re not a good fit.”

No explanation, no apologies and no severance.

Over the next several months, I sent out multiple job applications. Few interviews came. Nothing panned out.  

Pit Stop: Risking an Upgrade

All along, I had secretly wanted to become a writer.  

I had even set up the Substack www.reinventingdad.com.  But I barely made a single post. I was drifting and not achieving any traction. 

I reached out to a contact I had known for years for a job of last resort.  It was civil service. I was offered the role of a public sector consultant and worked as one over the next 18 months.  

Imagine four to six hours per day on Teams, PowerPoint presentations to no end, and ten signatures for every approval. Staff would complain that 50-person video conferences were like YouTube podcasts – two people doing the bulk of the talking, everyone else listening passively.

I was paid to watch corporate YouTube.

This was the job that would take me all the way to retirement.

The story of my life was reading like a slide deck instead of the Declaration of Independence.

People told me:

“Grow up. You’re not paid to follow your dream.” 

“You’re paid to do what you’re extremely good at.”  

In my mind I agonized over whether I should behave like a grown-up and do the responsible thing.

“Do I keep a stable government job?”

Changing Lanes: Steering Towards Uncertainty

But my soul was bleeding from the inside out.

I wanted to do something with my life.

Let’s intersect my 20+ years of real estate with something more world-changing than a new subway line! 

This time, I was committed to becoming a writer.  

I had taken David Perrel’s Write of Passage course and dissected online newsletter operators from A to Z.  Hours were spent researching the most successful newsletter operators making six and seven figures . 

No smarter or educated than I was, they usually came from more humble beginnings, often stumbling their way to incredible success.  

Looking in the mirror, I asked myself:

“Instead of accidentally finding my own success, why don’t I just follow someone else’s playbook and intentionally succeed?”

Empty Tank: Ignoring the Warnings 

The road to this destination was paved by one realization:  

I had no drive.

For most of my life I had taken so many things for granted:  

No pressure to succeed, no threat of extinction, no rent to pay, and no tiger parents.  

That was me for most of my young adult life. 

I was living on cruise control as the child of immigrant parents. 

Green lights were everywhere only to be overshadowed by the tunnel vision of seeing stop signs. 

Fueling Up: Finding the Drive

As mentioned earlier, the little one came into my life four years ago.  Or, as my wife kept insisting, our lives. 

So back then, when the little one opened her eyes for the very first time, she opened mine.

But at that time, I was looking in the wrong direction.

I could see, but had no vision.

I could hear the winds of change, but wasn’t listening.

Then I saw this last month:

Memento Mori - “One day you will die.”  

That hit me in the chest. I did not want to die having never lived.

This is how my world has changed:

I am a Reinvented Dad…just like my dad before me. 

P.S. Men really don’t grow up until they get married and have a kid. Formula and diapers are expensive!!!

P.P.S.  In honour of my Dad’s 80th birthday