As part of our recent move to Scotland, I resigned from Microsoft after 13 years of being at the company and I recently started new work as a support engineer (aka Happiness Engineer) with a company called Automattic, a company that’s so different it’s hard to see a resemblance past the fact that they are both “tech companies”. I didn’t leave for any single grievance with my prior employer, it was for my own reasons. That’s mostly true.

After only a few weeks working with Automattic, I can say it’s been a hugely refreshing change from Microsoft. But what exactly is so refreshing in leaving one of the most successful companies in existence in the middle of it’s resurgence? I’ll preface this all with the fact that I have nothing but love for the company and the many wonderful folks I worked with over the years. That being said, I needed a change.

For starters, I was tired of the way in which work had to be done. A highly synchronous, always-connected culture persists at Microsoft (as it does in many/most tech companies). Yes, there is a push towards more asynchronous communication (as there should be), but most work still happens in one’s email inbox, good written communication and sharing isn’t widely valued and rewarded, and incessant in-person meetings dominate people’s schedules. The result is that people need to find their own time to do real work, largely outside of work. There are other issues I could mention, but every place or thing worth working on must have it’s challenges, otherwise it isn’t interesting.

The second and probably main thing was that after a point, and I can’t quite put my finger on when exactly this started, I didn’t feel like I was really challenged in my work. I was building a great resume but I had grown very comfortable in my previous roles and knew what I needed to do in order to be “good” in that environment. There was very little incentive for me to push myself into uncomfortable areas required to learn. I would go so far as to say that I was incentivised to not push hard into new territory as those who did were frequently ostracised or ousted. This was not good and I could feel it.I needed to do something drastic to create the conditions for me to have to develop a new skillset. Doing a “learning and development” commitment in my spare time and having a cushion and reputation to fall back on meant that learning could always fell to the back burner.

“When I’m learning a new mathematical technique…the uncomfortable sensation in my head is best approximated as a physical strain, as if my neurons are physically re-forming into new configurations…this stretching feels much different than applying a technique you’ve already mastered, which can be quite enjoyable. But this stretching, as any mathematician will also admit, is the precondition to getting better. This is what you should experience in your own pursuit of “good.” If you’re not uncomfortable, then you’re probably stuck at an “acceptable level.””

Cal Newport, So Good They Can’t Ignore You

Some people create artificial constraints by paying for school and doing night classes. I did by moving country and resigning. It was this do or die challenge that was and still is invigorating and something I rarely had in my previous roles.

Did I give up a ton of money, security, and comfort? Yes. Do I think my most challenging and rewarding work is still ahead of me? Yes.

I need to prove that I can do great work in a different way and in an entirely different domain. The process is still ongoing and whether I’m successful or not is yet-to-be determined, but one thing is for sure, it’s a refreshing change.