So you want to leave the mothership: follow up

Last week, I wrote a post about my time after leaving Shopify. I received a bunch of feedback – almost all of it positive. There was some negative feedback that I’ve heard, both directly and through the proverbial grapevine, that I want to address.

  1. I’m not attempting to convince anyone to leave their job, Shopifolk or otherwise. I do think, though, that there’s a feeling at many big companies that this is “as good as it gets”. Using the Shopify example is particularly easy – Ottawa isn’t exactly known as a tech hub, so I get the impression people feel like if they want a great job, they have limited options. I used to feel this way too – it was either Shopify, or move away. This is no longer the case, and shouldn’t be a reason to stay if you’re feeling antsy. Remote work has opened up tons of opportunities, and there’s companies in Ottawa worth working for.
  2. I heard someone say that they disliked that I said I “was Partnerships”. I have no illusions of being incredibly important at Shopify. I could have sworn in writing this post that I had used “lowercase-p partnerships”, but looking back I used “Partnerships”. My intention was to use the lowercase form to enforce that I thought I was hot-shit and knew everything about the discipline then received a wake up call, not that I thought I was the foundation of the team. This was a mistake and not what I meant to put forward.
  3. I also got some pushback around my thesis that there are people at Shopify who succeed despite being bad at their job. First: I tried to put at least the possibility forward of myself being in that camp. I think the point stands that when a company is growing incredibly fast, it can cover up for a lot of errors in decision making, performance, etc. Also: there are totally people at Shopify who are bad at their job and still succeed. They’re fairly easy to identify, especially retroactively. It would be impossible to hire 5000 people and not have some underperformers who are good at playing The Game. I stand by this point.

So you want to leave the mothership

In the year and a half since I left Shopify, I’ve had countless people come to me asking for advice on how and when they should make the jump. The bulk of these people are looking to leave Shopify, but not all of them. I believe it’s a combination of the strong culture Shopify has built, the pretty insane long term retention (people get really comfortable there and stay for years), and the fact that huge swaths of my network are from there that result in so many people from there asking me. It’s not exclusively Shopify, though – people from other companies that I worked with in my Partnerships role have approached me looking for advice on making the leap. After countless coffee dates and meals out, I figured I’d write some thoughts down on this to make their – and my! – life easier.

Disclaimer: I’m not an expert on this, and this isn’t exactly groundbreaking stuff. I don’t even think I did a particularly good job of leaving gracefully. Now, on to the listicle:

1. Just leave.

You might have been there one year, two, five – it doesn’t matter. If you’re thinking about it, it’s time. I thought about it seriously for a year before I pulled the trigger, and afterwards I wished I had done it when those thoughts first crept up. Just make sure you’re leaving for the right reasons. A bad manager is *a* reason, but it’s not the *best* reason.

I left because I had a great day. Seriously. I got home on a Thursday, looked in the mirror, and told myself: “Now that was a great day. I learned a lot, and I feel accomplished.”

The problem was, it took a great day for me to realize that I hadn’t had a Really Great Day™️ in a long time. I wanted to be moving forward (i.e. a string of Really Great Days) and it was clear that a Really Great Day had become the exception, not the rule. I put in my notice the next day.

If you have one foot in and one foot out, it’s not fair for anyone: it’s not fair for you because you’re holding yourself back from your full potential. It’s not fair to your team, because you’re not able to be fully present as a leader. It’s not fair to your company because you’re not able to provide what they want without being fully committed.

2. Take some time.

The first thing I did when I put in my notice was work my network. I let a couple of trusted people outside of the company know that I was looking to make moves. Working in Partnerships is a bit of a blessing when it comes to switching roles. I knew a lot of people who worked for startups and were growing – they were also almost all looking to start partner programs of their own, and had seen my team grow one of the best in the world. It didn’t take long to get some initial interest, and I had all but signed a contract with Pixel Union within a week of leaving.

As you might expect, I should have taken some time off. That’s what most people I’ve seen leave a post-exit startup do. I like working, so I didn’t see any appeal in taking an extended holiday, and solopreneurship wasn’t something I was ready for yet.

That first role at Pixel Union wasn’t the best decision, for them or for me. I ended up essentially firing myself after just a few months because I knew I wasn’t producing. I wasn’t passionate about the product(s), and I was still a bit burnt out from my time at Shopify. People who take six months off in between 1-2 year stints at a job make me roll my eyes a bit, but there’s no shame in taking time off when you’ve been somewhere for years.

After Pixel Union, I did take some time off – about six months. This was too long for me. If I was to do it all again, I would either take one month off and do nothing, or six months with a plan for how to spend my time. Without a plan, I spent most of those six months off doing very light consulting to cover the bills, occasional short trips, and channeling my anxiety and mild depression in to impulsive trips to Bed Bath & Beyond to overoptimise my house. It was a disaster.

When I was ready, I was ready, though, and got to choose between two great roles at two great companies.

3. Pick your next move.

When I was ready to start looking, I didn’t actually look very hard. As I mentioned above, Partnerships as a career opens you up to all kinds of positions. I feel very grateful that I never had to truly join the job hunt, and had companies approaching me. I can’t advise much on going out and looking for jobs. However, I did have to evaluate opportunities, and I think I learned some things to look for.

Look for roles that will expose you to new things. This is obvious. New things can mean doing a similar role in a new industry. New things can mean a completely different type of company (like agency vs. SaaS). New things can mean a different size of company (counting on both hands vs thousands of employees). New things can mean a Director role with leadership responsibilities in a field that you already understand well. I took a role at Shogun that has provided a variety of these New Things. I don’t think I would have gained any ground by going to lead partnerships at an ecommerce-related company that had hundreds of employees.

There is one piece of nuance here that I think is important: doing the Same Things that you did wherever you’re coming from doesn’t mean that there won’t be New Things in a similar role at a similar company. This is something that I learned the hard way. Using Shopify as an example is all I can do, and I don’t mean to be insulting, but you might not be as good at your job as you think you are. I thought I *was* Partnerships. I thought I knew everything there was to know about partnerships. Turns out, I didn’t – I just knew Partnerships at Shopify. In the real world, I still had a lot to learn. What worked at Shopify wouldn’t necessarily work elsewhere. I truly believe that you can be genuinely terrible at your job in a place like Shopify and still succeed. Growth will atone for many sins, and Shopify grows like hell. Be ready for a humble slap-in-the-face when you go join a startup that isn’t having one of the strongest, longest growth runs in history.

4. Brace yourself.

Continuing on that theme, be ready for everything to be different. Some of the changes that hit me the hardest were the soft things. It’s the trite stuff like making my own lunch again. It was the more personal things like not seeing some of my best friends every day. It was working remote for the first time and never really getting to spend much time with my coworkers. It was discovering books on my own again because the company library wasn’t there.

But, it’s not all bad. It was also going back to being an individual contributor and feeling like I actually accomplished something at the end of a day. Wrapping my head around a completely new challenge again. It was a higher salary than Shopify was willing to give. It was a chance at another big adventure.

All-in-all, the last year and a half has been an adventure with more ups than downs. I feel like I’ve landed at a really good place with Shogun, and I feel like I’m contributing in real ways. My life satisfaction is way up. And that’s not because Shopify is a bad place – in fact, it’s an incredible place. I will always look back at those days as “the good old days” – but these days are pretty bananas too.

Book review: Digital Minimalism by Cal Newport

I’ve been a Cal Newport fan for longer than I knew – he came back on my radar in 2016 with his release of Deep Work, but I immediately recognized his name as the author of a book I read about student success back in high school. I wasn’t ready for his wisdom back then (I did terribly in school despite the book), but Deep Work was a work that had a great impact on me. When I heard that Cal was working on a new book about digital minimalism, I immediately preordered it. It’s almost exactly what I hoped it would be – Deep Work, but for your personal life.

In a similar but more explicit way to Deep Work, Digital Minimalism is a great blend of narrative, examples, and concrete advice. That last bit – concrete advice – is where this book really shines. Some of it seems obvious, like deleting social media on your phone, but it’s built on and elaborated on in a way that drives the point home. Repetition is something I’ve found valuable in my own retention efforts, and Cal is a master in writing in a way that really improves retention for me.

One of the common complaints about books like this is that they’re blog posts blown up to 250 pages, and therefore a waste of time. Although it’s never mentioned in the book, Digital Minimalism is a book that proves this point wrong. You could take all of the practices, all of the discussion, all of the heart out of this book and strip it down to a 10 minute blog read, but you’d lose so much. You’d get the same information, but not the same opportunity to digest it slowly, consider it, and hear the various angles and subtleties. This is a book best read on paper, in a nice chair, with a highlighter in your hand, a notebook by your side, and your phone in another room. That’s how you’re going to get the most out of it, and will be your first taste of how true Cal’s thesis is that screens are a constant distraction and there is value in getting information slowly and more thoughtfully.

Digital Minimalism came at an interesting time for me. I think part of what helped the book resonate so well was that I was already halfway down his path, and had spent a lot of time thinking about the themes in it. I had deleted most of my social media in December – aside from Twitter – and had already dabbled in ways to block my biggest time wasters, Hacker News and Reddit, out of my life. What it really did was provide a better thought out, more thorough framework to grow this practice.