👔 Quit With Positivity

• 6 min read

There have been many times I’ve quit for the wrong reasons, either because things got too hard or I was afraid. But there were also times I’ve quit for the right reasons as a means to get somewhere better.

Perhaps it was the time I quit competitive soccer to go back to the league with my friends; the time I was switched university degrees to pursue an interest in software; or the time I told my roommate—after our landlords kicked us out to sell our apartment—that I wanted to look for a place on my own.

Quitting is always difficult but it’s a necessary part of life. When done for the right reasons, it acts as a transition, taking us from where we are to somewhere better. It plays a huge role in helping us get to the best version of ourselves. 🦾

My Dream Job

In 2015, I’d been at my day-job for two years. Having joined as one of the first employees, I had a huge hand in growing the company from a scrappy startup to a 20-person team. In the beginning, work was extremely challenging and rewarding. I learned so much about business—from both technical and non-technical perspectives—and was able to meet a lot of amazing people from the industry. It was my dream job.

But things had changed a lot in those two years. Growth wasn’t nearly as fast, our technology stack stabilized, and unexpected problems weren’t nearly as dire. That would have been great on its own—I could have used a break—but there was a new problem to contend with.

Being a VC-funded startup forced us to move quickly, prioritizing features over quality; our technical debt was piling up fast. And, since I was the most senior, it was natural for me to take on the responsibility of paying off the debt. Eventually, and without realizing it, that became my entire job.

Deciding to Leave

In my weekly one-on-one meetings with one of the co-founders, I expressed my unhappiness like a broken record. Every week, we’d come up with new ways to dig me out of the rut, but nothing seemed to stick. When problems inevitably surfaced—like when the servers suddenly stopped working—I would jump in and just fix the damn thing myself.

I was too attached to the company to sit back and watch someone else fix the problem, knowing it could be resolved sooner if I did it. It was a self-destructive habit that became harder and harder to escape.

To make matters worse, I was also using my free time to work a side-project Insomnia, which had amassed a few thousand users in its first year. So, not only was I draining myself at work, I was also working hard in my spare time—burning the candle at both ends. Because Insomnia was doing well, I made less of an effort at work, and started fantasizing about leaving to pursue self-employment.

I’ll tell you what, I’ve never gone back-and-fourth on something for so long. The game of mental tug-of-war continued for six months before I seriously considered quitting. Quitting felt like an admission of defeat—that I wasn’t tough enough to handle the job. I didn’t want be that person; I didn’t want take the easy way out and force everyone else to carry the load.

Eventually, a trip was approaching that my partner and I had planned together. We were heading up north to visit family and take a break from everything. I had to make up my mind right then; either I quit and enjoy the trip, or push it off again and waste a month-long vacation dreading the return to work.

So I quit. But not because I was giving up (even though that was part of it) but because I wanted to get somewhere better. I was finally going to start my own company.

Leaving with Confidence

I couldn’t just leave without a plan, however. It would have been humiliating to take such a risk on quitting, only to fall on my face and have to come crawling back to the workforce. So I did a few things to reduce the risk of failure as much as possible.

Here’s what I left with:

  • Two years of living expenses ($35k)
  • A side-project with 5000 users
  • The skills required to build a great product
  • A supportive partner ❤️

Those things would ensure I good starting point, but there was still a big question weighing on my mind: would it actually be possible to turn Insomnia into a profitable business?

To find out, I did a ton of market research and analyzed countless pricing models. Could I charge money for what I already had? Should it be paid up-front, or a monthly subscription? What new features should I add?

I decided it would be safest to model Insomnia’s business after its main competitor, Postman.

Postman had roughly 20 employees at the time so I concluded that, if I adopted a similar business model, Insomnia’s user-base would only need to grow to 1/20th the size in order to be financially sustainable. It seemed simple enough. I already had a popular product that was growing quickly, so it seemed like a safe bet.

Hindsight is 2020

It’s been four years since then and I’m happy to report that the plan worked! I can definitely say that quitting was the right choice.

And, six months ago, I actually quit Insomnia too, accepting an acquisition offer to sell the company. I’m still working on it as an employee but I’ve offloaded a lot of the day-to-day responsibilities, setting myself up for a smoother transition later. Even though I don’t know when I’ll quit next, it feels good to already be planning for it. I’m now able to look at quitting in a positive light, instead of simply dreading the experience.

And that’s the biggest thing I learned from all this, which is to focus on the positive parts quitting, instead of dwelling on the negatives. Doing that would have made my self-employment transition easier for everyone involved; I would have been in a better mood, had more energy to help the company prepare, and been able to celebrate with my coworkers instead of isolating myself in guilt.

Transitions are always hard, especially when they involve people we care about, but they’re usually quick. So, do your best to focus the goal, even though it’s hard, to work towards becoming the best version of yourself.

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