Why I Quit, And What's Next

So, tomorrow's the one-month anniversary of me quitting my job at Shopify. It was as amicable as these things can go.

To answer the one question I've heard more than any other since making my decision, why did I leave an amazing company with great perks? To be clear, Shopify is a great company, easily the best I've worked for. I'd be lying if I said I didn't miss the catered lunches, snacks, and camaraderie. But without diving into exact numbers, here's why:

Not the most elegant graph, but I'll try to explain. Joining Shopify in 2011 was a greater risk than joining (or continuing at) Shopify today, so people joining in those days got significantly more stock options, which in my case wound up being worth more than all the salary and bonuses I earned in my entire time at Shopify combined. Post-IPO and with my 2011 options fully vested, the total return on my time became a function of my salary and the day's stock price. I ran the model a few different ways, and whether my salary doubled, halved, or even disappeared didn't really have a huge impact on the total gains. With that in mind, I had to ask myself: what kind of marginal return on my time and energy am I getting by staying at Shopify, and what am I actually doing this for? What's the endgame? Once I realized my reason for being wasn't to work at Shopify forever (as much as I've enjoyed it) and that I'd be financially okay if I left (as nice as the benefits were), the job started to become a grind, and it became really hard to motivate myself. At that point I knew I needed to either shake things up or leave, and when it became clear the former wasn't likely, leaving was the right call.

So: from years of hard work and a lot of luck, I can feed myself and keep paying the bills without needing to work for a while. Not forever, but a while. And given this time, I should probably work on whatever I was put on this earth to do, that one overarching purpose, that thing I can do that no one else can, that thing which will make the world a slightly better place and which simply won't happen unless I step up and do it. What is that thing?

I don't know. I couldn't name it with any certainty if you put a gun to my head. But I read this James Altucher piece recently and through some synthesis of his thoughts and my own, I've drifted towards the following as a central idea that drives a lot of my day-to-day actions:

It's almost impossible for me to become the best stand-up comic in the world. The odds of me being the best programmer, the best politician, the best salesperson... all extremely long. I sure as hell will never be the world's foremost economist, and I'm okay with that. But I can absolutely point to times where some knowledge of economics has made me far better as a salesperson, where knowing how to tell a joke has helped me disarm people who disagree with me on politics, where understanding programming basics has helped me understand bigger systems, even if I couldn't write them from scratch.

It's a bit frustrating to say this, because I always believed (and I kinda still do) that someone who says they're a Promoter/DJ/Model/Actor/Web Designer/Social Media Guru/DJ/Writer is almost certainly full of shit and unlikely to offer much value to anyone. They're a failed DJ (you can tell, they mentioned it twice) and they're just flailing to find anything they enjoy that someone will pay them to do. Because if it's just a slash, if all these distinct interests fail to inform and build upon one another, then you're just spreading yourself thin and limiting the upside because in any given domain there's going to be people doing what you do, only better. A full-time DJ will kick your ass if you spend 80% of your time not DJing.

So as I go on through life, what am I doing? I'm telling jokes, I'm keeping up on politics, and I'm noodling around with the latest technology, but none of these things are in any way siloed. That's my intersection, and it's one I can aspire to be the best in the world at. My sales background is how I apply that intersection to the world, and my econ background is how I measure the effectiveness of that application.

I'm someone who can crack jokes backed up by hard data, who knows how to win people over to my way of thinking, and who has the applied skills to not only fit that persuasion into larger business or political objectives, but accurately measure its effectiveness. I'm someone you almost certainly want on your team, and I really didn't mean for this to turn into a "Hire me!" post. But here we are. Could I sit on my ass for a while? Sure, but that's nowhere near as much fun. There are things on the horizon I'm thinking about, none of which I'm anywhere near ready to announce, but I'm keeping my options open and trying new things that complement my existing skill-set.

Along those lines, I attended PAX last weekend, and if you haven't seen the latest VR stuff from Valve or Oculus, you're missing out on the future. The controller interaction and visual fidelity are getting to a point where it's starting to cross the uncanny valley. It was always virtual, but the state of the art no longer feels that way. It just feels right. And knowing that makes you think about potential applications and how big this is going to become in 3-5 years once the cost comes down enough for it to go mass market, which is likely inevitable... knowing that will absolutely impact on decisions I make about my career in the future.

I'm also more politically involved than I've ever been, canvassing a couple times a day with one of the local Liberal candidates in the lead up to the next election. As someone who's observed from the sidelines, following it closely through the media for most of my life, I can tell you that getting elected really isn't anything at all like it's often portrayed. It's much more local and personal, and all the national storylines people try to craft to get more play in the media... don't really hold a candle to making meaningful connections with the constituents you want to represent you.

Suffice to say, I'm keeping busy, I'm happy, life is good. 

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