Into The Unknown: Leaving Shopify to Build a Business

I’m leaving Shopify today. I’m saying farewell to an amazing job, a known career path, and a constant paycheque. I want to build my own business.

I’m turning my eye towards a wide and uncharted path before me. I want to welcome uncertainty and master the fear that comes along with it. I want to reconnect with my artistic side. I want to look at a blank calendar and see a blank canvas. I want to connect with new people, new ideas, and new opportunities.

The Shopify arc

I began working at Shopify as a front end developer in 2015, 3 months before the company went public. I became a lead in my first year. Since then I’ve been managing dev teams and experiencing rapid personal growth. I had to sharpen my skills as the company scaled around me. I was learning to perform at an amazing tech company filled with high performers. In addition to those demands, I became a father and experienced the beautiful, painful transformation that comes along with that.

It is safe to say that my time at Shopify was not just another job. It was a phase of my life. A major arc of my story. It provided me with the skills, the confidence, and the financial leverage to try something bigger.

The beginning of the end

This career change was a complicated and difficult decision. I did not begin with the end in mind. It began with a few questions that popped into my head one day, approximately 2 years ago:

“What will I do AFTER Shopify? What could possibly surpass this?”

“How will I leverage my assets?”

The questions are a testament to how great Shopify is. It was working so well for me that I became I afraid. I was afraid that one day I would move on to some other, lesser tech company and forever look back.

Over time these questions evolved and lead to other questions. They became a meditation on what I wanted in life. By now Shopify had imbued me with the allure of entrepreneurship. I started to discover creators on the internet who spoke to my values while describing their own journeys in entrepreneurship.

A list of reasons

By November of last year, I knew that I was restless. I had to either change what I was doing at the company, or explore another path. By this time I had compiled a list of reasons to start my own business. It was assembled from many scraps of articles and my own journals. Here is that list:

Working 50 hours a week is unacceptable. I would like 20-30 of those hours back. I believe building a company will be the most fulfilling path to this outcome. I can already hear the experienced entrepreneurs laughing their heads off. I also want to clarify that 50 hours included commute time and outside office hours thinking - something you should always add to your time on the clock.
Shopify has been my greatest professional challenge but I feel ready for something harder. I think company building might be it. Shopify is not motivating me enough right now. This turned out to be the most important item.
Increased freedom. As I increase in seniority at Shopify, I increase the number of stakeholders and people interested in what I’m doing. It makes it harder to simply execute or choose my own work. In addition, my time is getting harder and harder to own - I spend most of my week in meetings with the various people I support or connect to. Daniel Vassalo describes this really well
Decouple my time from my income. By decoupling I can apply higher leverage to spend more time with my family.
Owning a company is a good long term investment because it is an asset that compounds. Employment does not create that kind of asset since a corporation owns my output.
Work on my area of ultimate passion and build my own thing. The pursuit of unbridled self-expression.
Decouple myself from Ottawa. More opportunities to travel with family for extended lengths of time.

Discarded options

I had considered other options to increase my freedom and wealth.

I considered freelancing but noticed that it would keep me tightly bound to the schedules of clients. Freelancing does not separate time from income. It may yet play an important role through the transition but it is not the goal.

I considered asking for more money and a reduced schedule from Shopify. A tough sell. I rejected that idea because I was on the manager’s path at Shopify and wanted to stay there if I stayed at the company. The job seemed too difficult to execute with less time and attention, even if Shopify approved it.

Finally, I considered bunkering down and saving up a nest egg to live off of. This path was achievable, especially with a high tech salary and the stocks performing the way they had were. But the time horizon was too long. When I’m restless, I need change soon. When I make a decision, I need change immediately. I refuse to wait years to “retire” and then live the life I want. Life is for living right now.

Unignorable assets

As for my assets, I am wise enough to know that you should not let things like that sit around. When you have assets, you should deploy them. You should put them to work and grow them. I had two that I had to contend with: the skillset I had developed and my shares.

I was not the most savvy shareholder but no one was. Hindsight is 20/20. None of us could have thought that the $SHOP stock would grow like that. I’ll never forget doing my first trade. I traded a big chunk of stocks at $27 USD a share and counted myself lucky. I used the proceeds to pay off some small debt.

Thankfully, I did not trade everything. Random luck and the unbelievable success of Shopify has served me well here. I acknowledge I am in a privileged position, and I must strive to live up to it.

The real reason

Between the time I came up with the idea to build my own business, with the long list of reasons, and today, COVID19 happened. Shopify became “digital by default”. For many people, this was a massive challenge. Personally, it meant dramatic improvements in my daily work life.

I want to acknowledge that I was, through random luck again, in a priviledged position. My wife and I had decided to homeschool about 3 years ago (a topic I will write at length about soon). We had no adjustments to make with childcare. We had also decided to buy a big house in the country 2 years ago, giving us lots of space and access to nature. The only downside of our new home was my commute – close to 3 hours a day. That time dropped to 0.

My engagement at work skyrocketed. Managing a team through the changes was HARD. Everyone at Shopify felt the urgency to put in extra effort to help our merchants and partners any way we could. Employees who were not caring for their family, or getting sick themselves, were eager to pick up the slack. The challenge motivated me.

But as the dust settled, my engagement went back to baseline. I spoke with my trusted friend and colleague Tejas to figure out what was next for me at Shopify. It became clear what my one real reason for leaving would be: I had lost my motivation to work on Shopify problems.

Looking back at my original list of reasons, I noticed how many had disappeared because of the shift to remote work. I also noticed how many of them were on shakey ground (entrepreneurship as a path to working less, a new company as a sound investment, hmmmm…). But it didn’t matter. I had one reason, and it mattered most: I am not motivated to work at Shopify. I am motivated to build my own business.

It might be the least effective path to some of the outcomes I’m after, but it seems to me like the most fun.

What’s next?

I remember the early part of my life being creative and spontaneous. As a young man I took risks. I explored. I danced and sang a whole lot. In the next phase of my life, when my “career” began, I shifted into a more disciplined mode. Since then I’ve been developing my ability to learn new skills and execute. Discipline and execution are very important things, but life has so much more to offer. In the next phase, I want to try and integrate those two sides of myself: the artist and the dependable doer. My career so far has been a story of incremental, inevitable progress. It’s time for some uncertainty – some big wins and crushing losses.

I will enter into a mode of exploration and creative openness. I am still working on how I will adjust my personal systems to become more like rhythms. I’m looking for a way of working that will keep me accountable to making progress, without constraining me. I will observe the market for opportunities. I like the idea of starting with many small bets: noticing opportunities and then challenging myself to ship solutions that need little investment. One day I will find something that truly excites me and go all in.

I imagine myself beginning as a bootstrapped solopreneur who is aiming for a lifestyle business. But I don’t want to be a slave to that model. If the right opportunity presents itself, I will let the nature of the work guide me. I will remain open to partnering with others, or raising money to grow if it is warranted. The only thing I will strictly avoid is becoming an employee. I want to be an owner, even if I end up owning something small.

Fantasy RPGs and Homeschooling

There are two areas of interest I will focus on to bound myself. I will start with tabletop roleplaying games like Dungeons & Dragons. Fantasy has always been an important part of my life. I see a real opportunity to bring the Old Magic you find in the books into online products. I have already begun under the name Sword & Source.

My second area of interest is homeschooling and future models of education. It was clear to me and my wife years ago that the current public education system does not make sense for a lot of kids. It does not fit in our modern context. COVID19 has made that clear to many other people. If I can think of some way to help in this area, I will.

Thank you

I expect that this will be difficult. Very difficult. But through difficulty I will experience radical personal growth. I want to develop my character, test my mettle, and find my life’s work.

Thank you for sharing in this small part of my journey. I will be writing about it a lot more.