Design the life you want
4 min read

Design the life you want

Design the life you want

From an early age, I often felt like an alien.

I played well within the system - getting good grades, not doing anything too stupid as a kid, and not fighting too much with my teachers.

I just always felt a layer removed. Like the whole thing was kind of pointless.

You sleepwalk through the first 16 years of your life, then the wonderful distractions of sports, alcohol, and women keep you from asking the important questions like - what are we even doing here?

My first day of University made it abundantly clear that I didn't fit in.

Standing in a circle of my peers at business school, everyone spontaneously broke into a synchronized chant that chilled me to the bone.

"Sauder is hot to Go! H-O-T-G-O-G-O. Aaaa whoop. Hot to go!"

Wtf, man. All so excited to be a part of this elite group of diverse kids who all thought the same. I felt so alone.

Yet, I continued to work within the system - getting good grades while thinking how strange it all was.

I tamed some of that ennui by spending a lot of time at the bar, but never lost that niggling feeling that something was wrong.

Two books I read during that time were formative:

“Happy Hour is for Amateurs,” an obscure story about a disgruntled, drug-fueled lawyer that hated his life - resonated. I could see the path so many of my peers were on, and it terrified me.

“The Four Hour Work Week” was the biggest catalyst for my future career. Who wouldn’t want to shrug off the pressures of corporate life to travel, learn, and explore the world?

I secretly plotted my exit while everyone else was suiting up to attend “recruiting events” where 25-year olds in suits tried to convince 20 year-olds in suits that working for KPMG was the key to happiness.

Instead of summer internships at prestigious firms, I did manual labour. I chopped trees. Washed windows. Anything to avoid that life.

That window cleaning business made me enough money to graduate without any debt, and spend 3 years hustling by any means necessary to avoid getting a job.

I sold compost at farmers markets. Started a web agency. Built multiple websites/apps that didn’t go anywhere.

My goals were simple - create a business that allowed me to travel and avoid getting a job as long as possible.

At some point I decided I wanted to be a millionaire by 30 (should’ve adjusted for inflation, but whatever).

2 years in and floundering, we got selected for Canada's version of YCombinator.

We raised $25,000 - which felt like $10m at the time.

I was renting my bedroom out on AirBnb and sleeping on the couch - a $1500/mo salary made me feel like royalty.

Those 3 months at a startup accelerator permanently changed my mindset.

It taught me to think bigger, dream bigger, and execute faster.

It also scared the shit out of me, and was the most stressful period of my life.

But despite the stress, I started to feel like I had found a world in which I belonged.

One morning I looked around the shared office and felt, for the first time, that I belonged. I actually fit in to this group of misfits.

Still an alien, but sharing an office with other aliens.

Matt and his brother Greg - hacking away at Thinkific (IPOd last year!).

Dan exploring new ideas before starting Koho (raised ~$150m!).

Collin working on a CRM that he pivoted into Predictable Revenue .

Kalv building a killer Rails agency.

What an incredible community.

I was inspired to build something successful, and did I ever try.

11 pivots and 1 company later, I owned an online business that made $10,000/month - twice my original goal.

The goal in 2014.

That was my freedom line, and I moved to Buenos Aires for 3 months.

Over the next 3 years that business grew to millions in revenue while I travelled to South America & Europe - living the proverbial dream.  

I did what I set out to do - an incredible feeling that you quickly normalize.

(Of course it wasn't all it was cracked up to be, but that's the subject for another essay).

This isn't a how-to post, and I wouldn't suggest blindly following any path.

Mine was hard. Stressful. Lucky.

But I do hope that everyone who's so inclined gets to experience seeing cracks in the worldview we're taught is normal. Or better yet, creates those cracks.

I hold strongly these three convictions:

You can create the world you want.

There is a group of people in which you'll fit.

If you work at it long enough, you will succeed.

Enjoying these posts? Subscribe for more

Subscribe now
Already have an account? Sign in
You've successfully subscribed to Mistakes of Ambition.
Success! Your account is fully activated, you now have access to all content.
Success! Your billing info is updated.