Well… there’s only one direction in which this letter can go.

After sitting on the decision for a few months, I have decided to leave the best company in the world, Shopify.

I could go down the traditional route of sharing my biggest lessons from working at a company like Shopify, or why it’s the greatest company in the world, but I feel like my biggest contribution to this conversation is to share the other side of it: what happens when you start to feel that your dream job is no longer the dream. I hope you don’t mind me taking you on that journey instead.

I’ve been very intentional each week to share the unpolished and still-in-the-throes-of-it updates of navigating a less traditional and more adventurous career path. As a society, we’re still a little quiet about this style of work and we’re often left to figure it out on our own: what this non-linear career path really looks and feels like. The kind where you’re on a staircase that shifts to a new landing before you even reach the top. Shopify itself celebrates the spiral career path—a big reason why I’m sure many of us joined years ago. There’s even a term for it: “the jungle gym”. Many of us have “jungle gym-ed” at Shopify. In fact, I don’t think you can succeed very much without the context of having experienced the company from different perspectives.

But there also comes a time when the jungle gym stretches beyond company territory. That’s where I happened to find myself over the past few months: do I look for the next challenge internally or externally?

The former is an easier decision to make: choose the next step and move forward without my identity or environment changing too much.

The latter is a more complex decision to make: choose the next step AND close out an entire chapter of my life. What I was most fearful of was making the easy decision. Convincing myself to make a small change when in my heart I knew I needed to make the bigger one. How did I know this? Well, in hindsight, I’ve been getting little nudges from the Universe all year:

The first crumb came in early August from another woman in tech. She left her company because “it had successfully grown up”. I immediately knew what she meant. My sweet spot, like hers, is in early-stage companies where you are responsible for both creating the strategy and executing on the strategy. A scope that becomes too stretched at larger companies, making it impossible to be both the strategist and the one who gets shit done. For some reason, I was beginning to convince myself that something was wrong with me for wanting this. That I should change myself to fit into the grown up version of Shopify where you had to pick a side. Her story gave me permission to double down on my strengths and bid farewell to a company that was no longer aligned with my genius zone.

The second crumb was a month later from a fellow Shopifolk who was leaving because he had lost his motivation “to work on Shopify problems”. I took a screenshot of this and still have it on my phone. He wrote words that I wasn’t ready to say out loud myself, but ones that resonated deeply. As much as I love the company, the problems that I really want to solve are no longer aligned with the problems that I have to solve. The reality is, Shopify has grown into the second largest Canadian company. The white spaces we once had to explore are becoming more defined (and rightfully so!) to support the millions of merchants who need a grown up and more corporate kind of company to continue building their livelihoods on.

It’s easy being a multi-passionate when you’re taking on new exciting projects, but it’s much harder when it’s time to start letting go of them. That’s the nuance of being a highly functioning human in multiple lanes—you have to choose which lanes to prioritize and which ones to wind down, even when you’d rather hold on to all of them.

When I quit my very first “real” job in finance to move to Malaysia, I found a quote by Rockefeller: “Don’t be afraid to give up the good to go for the great“. It’s been my emotional compass since, reminding me that the pursuit of greatness will require many bittersweet moments. That saying farewell is going to become a muscle that I will need to flex regularly.

I’ve also learned that despite how much we might intellectually know we’re ready for a change, the emotional aspect is much, much harder to navigate. I think it’s why we often have our breakthroughs after we’ve unplugged from our every day life. We can let our guard down, our adrenaline slows, our ego takes a break, and we reconnect with a version of ourselves that has no label. That’s how I felt over my two weeks of holiday in December. Just little old me, sitting on the couch with a good book, wondering if I should have chocolate for breakfast. After the year we’ve had in 2020, those two weeks were bliss. They also helped me cut through my own bullshit and look at my decision with an uncluttered perspective.

2020 taught me the term “privilege”, so I know better than to skim over the most important parts of my decision making:

First, I have free healthcare here in Canada. Something I’ve always taken for granted, not realizing how much harder of a decision it must be for our American friends who rely on employment for their basic healthcare protection.

Second, I live with my boyfriend. Even if the worst case scenario happened, I wouldn’t be out on the streets, nor would my lifestyle change very much.

And third, I’ve been investing in my side hustle for over three years now. I’ve been bringing in a portion of my salary already, so aside from potentially having to cut back on the Veuve and online shopping (the horror!), I wasn’t starting from scratch financially.

So then, what first world problems were keeping me up at night?!

Mainly, it was giving up my identity as a Shopifolk and working at Canada’s tech darling. A label I’m deeply proud of. Who would I be without my network of Shopify partners and colleagues? I have always respected our leadership team, but watching Tobi navigate Shopify’s rocket ship in 2020? I was blown away. His rational optimism and Stoic view of the world is something I didn’t want to let go of. But as we all know, those aren’t good enough reasons to stay in a job, in the same way that we shouldn’t stay in a relationship with someone because we love their parents.

That’s probably the biggest hurdle all of us ambitious professionals will face. We know we have the network and support systems in place to make pivots, but my god is releasing our identities hard!

I don’t have my next title. Entrepreneur? Freelancer? Consultant? Writer?

God damn those titles. We feel safe with them, don’t we? They’re our billboard to the world that we’re important. And right now? I feel a tad naked. Like a newborn, with magic and wonder in my eyes.

For today at least, that’s enough of a label for me.

Perhaps I should have kept this newsletter a little fluffier, sharing my 4 awesome lessons from 4 years at Shopify. Did you want that? Was my rambling today pointless? I hope not. I tried to share everything that I wish I could have read in my own decision making process. Apart from the two or three people with whom I confided in from the very beginning, the others I looked to were strangers on the internet who shared their stories. Putting into words what I wasn’t ready to articulate myself.

Next week I’ll share more about what I’ll be getting up to, but if you have questions or thoughts in the meantime, please send them my way! I love having deep conversations with you in my inbox.

I’m excited for 2021 and adding more creativity, adventure, and growth into my life. And I can’t wait to share it all with you.

I guess it’s time now to shut my laptop, hang up my Shopify cloak, and do a little happy dance. Cheers to all of you!