One year of self-employment: a retro

November 9, 2021 • Reading time: 5 minutes

A year ago today, I left my last job to do a 3-month batch at the Recurse Center, followed by... something. I never really articulated what that something was going to be, which was part of the point. I wanted to take some time to discover what really motivated me as a person.

A big part of the "something" has turned out to be initiative.sh, a project that I launched recently and continue to develop full-time.

I expect to be on that journey for the rest of my life, but a year on, I do have a few thoughts to share. In honour of one tradition I don't miss, the sprint retro, I'll structure my insights according to the good ol' liked/lacked/learned/longed for format.

Liked

• Setting my own direction. It's a big change to be able to work on projects that I actually care about, doing work that interests me. In response to my grumbling about some tedious/complicated work that I was going to have to work on, my wife asked why I was doing it. After some reflection, I told her that it's because I wasn't coding for fun - the project was what I wanted to be doing, even if each individual task was not.
• My velocity. It's a truism that one developer can do in one month what six developers can do in six months. The release cadence I've been able to maintain has been remarkable: 22 releases in the past month alone. And they aren't all small changes, either: things like permissive parsing, creating and editing things, and undo history have involved substantial work.

Lacked

• Hobbies. Okay, it's not exactly an original discovery that the fastest way to kill enjoyment in a hobby is to do it for your job. But my experience has been a bit different: I enjoy this work as much today as I did a year ago, maybe more now that I've found my footing. However, by promoting the hobby of tinkering on side projects to my full-time preoccupation, I ended up leaving a void in my evenings and weekends. I'm still working on finding ways to fill that time, but I'm making progress. I've done a lot of canoeing over the past year and finished my first woodworking project this summer: a pair of Adirondack chairs.
• Service. I've written a lot of code this year, but I don't feel like I've done enough to support others. Some of this comes from not having users, some from not having coworkers, but maybe those were both distractions from a real lack that predates my self-employment.

Learned

• I'm in the right field. I could have done anything after leaving my job, and I ended up getting up at the same time in the morning, sitting down at the same desk, doing more or less the same work (albeit with more code and less meetings), and working about the same hours as I had before. So either I'm well and truly embedded in this rut, or this work really is my calling.
• This doesn't have to be forever. The notion of getting a "real job" again one day doesn't frighten me. I was afraid that once I'd had a taste of freedom, I wouldn't be able to go back. But really, while I would want to choose an employer that is doing something I care about, the idea of reversing course and re-entering the working world isn't that scary. It's even kind of appealing, to once again work with others to build something bigger than I am.

Longed for

• Users. Until recently, I could count my user base on one hand, which carried with it a lot of challenges. For one thing, it's hard to stay focused on building something without the reward of seeing people use and enjoy it. For another, it's hard to find the right direction for development without users to offer feedback and suggestions. When I launched, there were two small features that people asked for over and over: case-insensitivity and command history. They were both already on my roadmap, but having so many people asking for a thing made it much easier for me to prioritize my work.
• Colleagues. The Recurse Center community has been great for supporting me technically, but I do miss working alongside other people. I miss teaching new developers, and I miss whiteboarding out problems with developers of all levels.

Action items

No retro would be complete without action items, right?

• Volunteer. As hinted at before, I'm going to start volunteering my time with a non-tech-related charity on a regular basis.
• Open-source initiative.sh. Oof, this is a scary one. I started this project in the hopes that it would one day generate a bit of passive income. I don't know for sure if this is the right move, but ultimately I would rather maximize the number of people using my work rather than the amount of money I'm making from it. And I do miss collaborating with others.
• Start something new. I have plenty of other project ideas. Once initiative.sh is in a stable place, I want to start dividing my time between it and another project.