Field note
Do it for the lore
The accepted playbook for success is pretty simple: you work hard in school, you get accepted to the right college, you get internships at the right companies, you secure the return offer, and then work your way up the corporate ladder for the next 30 years.
When applied across a population, this advice is directionally correct. You follow these steps, and you’re likely not to end up homeless.
But for an individual, this advice sucks if you have any ambition to not peak as a “Senior VP of Digital Transformation” at an insurance company at 55. To achieve asymmetric outcomes, you need to make some weird decisions along the way. If you play the safe game — don’t be surprised when you achieve the safe outcome.
There’s two stories of men that have influenced the way I’ve thought about these things.
Go east, young man.
The first is the late Bill Webb, the owner of the Toronto Arrows Rugby Club.
His story started out normal:
- ✅ Went to university
- ✅ Did 3 internships at IBM, got a return offer
- ❓ Went on holiday to England and stumbled on a financial futures course. Turned down the job in Canada to pursue the course.
- ✅ Finished course; got hired at Credit Suisse as an investment banker
- ❓ Quit his job after only a year, and spent the next two years backpacking through the Middle East, China, India, and Nepal — learning Mandarin along the way
- ✅ Experience led him to McGill, where he did an MBA with a focus on East Asian studies
- ✅ Hired by Gluskin Sheff + Associates, he became one of the first western investors in China
Each “irrational” decision he made also opened new doors for him. If he stayed at IBM → he never goes into investment banking → never spends two years bumming around the eastern hemisphere → never goes to McGill (where he met his wife), and the butterfly effect continues.
Beyond the career that it opened doors to, spending two years adventuring around the world is a priceless experience.
Don’t be afraid to bet big.
The second story is of Jack Cowin, a great-uncle of mine. His story went a little something like this:
- ✅ Went to university, starred on the football team
- ✅ Got a job out of college as an insurance salesman
- ❓ Convinced thirty people to loan him (a 26 year old) $10,000 each, to secure a franchising agreement to open the first 10 KFC’s in Australia in 1969
Now, 56 years later — having continued to expand his fast food portfolio to include a large stake in Domino’s Pizza and Hungry Jacks, he’s one of the wealthiest men in Australia.
But imagine if he’d stuck with his insurance job — by all accounts, that would have been a safer path. He had a good white collar job. He had a wife and young kid to look after. The responsible thing would be to keep the steady paycheque coming, and slowly work your way up the company.
Seek out lore.
This brings me to the main point I have — in almost every case I can think of — seeking out unique circumstances will not hurt as much as you think.
In my own experience:
- ✅ Went to university
- ✅ Did a bunch of internships
- ✅ Got a job out of college at a fintech unicorn
- ❓ Went and played professional rugby for a year
On paper, was it the best “next move” for my white collar career?
Probably not.
And yet, when I went back to applying for jobs after the season ended, I found interviewers interested in the experience.
In a pile of AI-generated resumes boasting of “increasing user engagement by 37% in core metrics”, playing a professional sport was a pattern interrupt. And it showed an ability to reach the peak of my chosen craft.
Your lore doesn’t have to be sports though.
Start that business with a friend.
Move to a new country.
Create something beautiful.
Apprentice for a dying art form.
Make the uncomfortable choice to grow.
Have stories to tell your grandkids.
One of the most gratifying parts of seeking out lore — is the lifelong memories it brings with it.
I’d like someday to be able to regale my grandkids with the wild things I did over the years, and the full life that I lived.
The trip I survived off only peanut butter and slept in a tent for two weeks traveling the circumference of Iceland.
The time I hiked up Mount Rainier at 2am to catch the sunrise.
The company I started with my brother that sold digital fish.
The underground poker game in Costa Rica where I won, and lost big.
The scar where I split my eyebrow playing rugby, and needed 10 stitches.
Life is meant to be lived.
Don’t be scared.