Reflections on my sabbatical

In March, I retired. Sort of.

I don’t have enough saved up to never work again, and I’m not interested in just relaxing by the beach for the rest of my life. But, after 15 years working in tech, I have enough saved up that I could afford to try something different.

So, I “retired” from my career as a software engineer. And then I took a sabbatical.

I wasn’t planning to take a break. I had an idea that I wanted to chase immediately after quitting my day job. But, my wife made me promise to take some time off work as a pre-condition of her support for me quitting. I’m glad she did.

At first I thought I’d just take a few weeks, but I was a lot more exhausted than I thought. Once I had some time to decompress from work, I realized I was being silly. My wife is a teacher, and my kids are in school, so they were all about to have the summer off. I haven’t taken a summer off since high school, and I don’t know if or when I’ll get to take one again. So I decided to make this an extended pause from work — aka, a sabbatical.

This break enabled me to do a few things I’m really grateful for:

• I spent a lot more time with my family, including two fun vacations (1,2), and a lot of day trips to hike or camp.
• I was able to help Strong Towns through a major organizational change. As Board Chair, my involvement wasn’t optional, and it would have been really difficult to fit the extra hours had I been working full time simultaneously.
• I was able to take better care of my health. While I still don’t enjoy exercise, I’ve been doing more of it.
• I wrote a novel! I’ve enjoyed writing fiction now and then, and have attempted this in the past, but I never ended up with a finished book that I was proud of. This time I did, and I’m really excited about it.

Now my kids are back in school, and Labor Day feels like the right symbolic moment for me to declare my sabbatical over and shift back to work mode.

Reflections on taking a sabbatical

I wish I had some profound insight to share with you, or some story about the deep insights I gained while taking an extended break, but… I don’t.

My main reflection is that life is full of difficult tradeoffs.

Early in adulthood, I had a set of big dreams that were impossibly out of reach. After several years chasing those goals head-on and always being worried about paying the next month’s rent, I noticed that most of the people who got to do cool work were “old”, and had retired from some first career that paid well.

I hated the idea of having to wait decades to have a chance at work I found meaningful (and I still hate it), but I didn’t have an alternative. So I went full mercenary, learned to code, and got to work in software.

Now, standing mostly on the other side of that decision, I would tell you: (a) it seems that it worked, (b) it was exhausting and miserable, and (c) I wouldn’t necessarily recommend it.

I’m deeply grateful for my years in software. I worked with many wonderful, brilliant people, and I learned so much. And, as jobs go, it was an easy job with great pay.

But the thing about finding little-or-no fulfillment in your day job is, your day job consumes most of your life. So my life was always over-busy as I tried to squeeze in as much “stuff worth doing” as I could into all the gaps in my schedule.

That constant overcommitment took a toll on my mental and physical health. Now that I’m no longer trying to live that dual life, my stress level is way down, and so is my blood pressure. My primary care doctor tsk’d at me and said I should have quit years ago for the sake of my heart.

And yet, I wouldn’t say I quit at the perfect moment. I don’t have “never work again” money, nor do I have “self-fund an ambitious project” money. If I’m prudent, I have “don’t worry about your house” and “help your kids through college” money. If I could have stuck it out a few more years, I could have reached a higher level of financial independence. But, we’re secure enough, and life is too short to keep waiting.

What’s next?

Now that I have a degree of freedom, actually having to decide exactly what to do next is a bit overwhelming, but I have a general direction.

A few things I believe are true:

• We could make neighborhoods so much better for families and kids by making our neighborhood streets fully safe. If kids could walk to and from their daily activities, they’d have more fun and independence, and parents would be far less stressed.
• We’re nowhere near ambitious enough about housing. The whole industry is anchored on the idea that housing “ought” to consume about a third of household income, but that’s silly. There’s no amount that food, shelter, education, healthcare, transportation, or any other basic human need ought to cost. The goal should be to make decent housing attainable to all.
• Micromobility and autonomy change what’s possible in our cities and neighborhoods. The pioneers who figure out ways to incorporate these new technologies today are likely to re-shape the built environment just as much as the car did.
• There’s so much room for progress in municipal policy, from better alternatives to zoning to better tax systems, and there’s tremendous momentum for reform. I’m optimistic that cities will be far better governed in the decades to come.

My goal is to make a dent in one or more of these.

There’s obviously some overlap here: if I was building new family-oriented housing, then I’d have to keep costs in check, I’d have opportunities to incorporate new technology, and I’d be dealing with local regulation. But I’m not sure yet if it will be more viable to focus primarily on just one of these issues, or if there’s a productive synergy in combining them.

For now, I’m mainly meeting with smart people and learning everything I can as I iterate towards a business plan. If you have ideas or suggestions, please reach out. I’m happy to talk!

I’m grateful to have reached this milestone, and excited to shift my time toward work that actually matters to me. And I’ll be excited to share more as ideas and opportunities come together.

Thanks for reading. The best way to support my work is to share it. If you enjoyed this post, please consider passing it along to a friend.

For Labor Day we went on a 4 mile hike with about 1,000 ft. of elevation gain. I’m sore, but I survived!

It’s a sci-fi mystery called “Time Traveler’s Insurance.” Since many people ask: I wrote it for myself, and I haven’t decided if I’m going to try publishing it yet. But, if you love John Scalzi you would probably enjoy this book. If you’d like to read it, message me and I can send you a link.

Working to try and change the world rarely pays well, if it pays anything at all.

“Old” from my perspective at the time, though now I realize many of them were in their 40’s and 50’s, which… suddenly doesn’t seem so bad!

Though I will say, AI has already upended software, and the job today is suddenly very different than it was for most of my time in the field.

To further illustrate this point: consider what happened to food in the 20th century.

Per the Bureau of Labor Statistics, food and clothing consumed nearly half of household income in 1901, but fell below 15% by 2001. We didn’t get there by magic, we got there because millions of people worked hard to make it happen. Why not try to achieve for housing in the 21st century what we did for food in the 20th?