2023 in review.

Published on December 18, 2023. career (45), blog (21), year-in-review (8)

This was an eventful year. My son went to preschool, I joined Carta, left Calm, and wrote my third book. It was also a logistically intensive year, with our toddler heading to preschool, more work travel, and a bunch of other little bits and pieces. Here is my year in review summary.

I love to read other folks’ year-in-review writeups – if you write one, please send it my way!

Previously: 2022, 2021, 2020, 2019, 2018, 2017

Goals

Evaluating my goals for the year:

[Completed] Write at least four good blog posts each year.
I wrote a lot this year, including adding five to my popular posts page, including: Writing an engineering strategy, Measuring an engineering organization, Setting organizational values, and Writers who operate.
[Completed] Write another book about engineering or leadership.
I did this: The Engineering Executive’s Primer goes to print in late January, and should be available for purchase in February. The complete digital version will be available via O’Reilly in January.
I am currently brainstorming a bit on a fourth book, very likely my last on the topic of engineering leadership, although it’ll take a bit of time to decide whether and when to take that on. Right now mostly thinking about the topic of engineering strategy.
[Mixed] Do something substantial and new every year that provides new perspective or deeper practice.
Like clockwork, I struggle to give myself a passing grade on this one. Joining Carta has greatly expanded my perspective on executive leadership. I also worked with a new publisher, O’Reilly, which provided a different view into the book creation process than self-publishing or working with Stripe Press. This was also the first year I gave a keynote, this one at QCon, which maybe qualifies?
[In progress] 20+ folks who I’ve managed or meaningfully supported move into VPE or CTO roles at 50+ person or $100M+ valuation companies.
This goal is due in 2029. Without spending much time thinking this through, there are at least five folks who qualify here, and I bet I could get to at least ten if I spent long enough digging into it
[Completed] Work towards a clear goal for physical exercise. (Hitting the goal isn’t important.)
Discussed a bit more below, but I reset my running habit and worked back up to doing a few eight mile runs. I’m mostly doing four milers now that I’m working full-time again, but it was very validating to stretch mileage a bit!

Carta & Calm

I left Calm earlier this year. I planned to take a year off, but ended up joining Carta after a couple months. When I explain this to folks, particularly those who I’d already told that I wasn’t going to go back to work immediately, what I tell them is: I felt confident that I would regret declining the offer to join Carta.

That’s still how I feel ~nine months into the job. Personally, learning and impact are the two things I value most in my work, and Carta remains the highest indexing job I’ve ever had on both counts.

An Engineering Executive’s Primer

I started and finished An Engineering Executive’s Primer this year. Coming into the year, I expected to write another book this decade, but it wasn’t this book, instead it was Infrastructure Engineering, which I ended up not making much progress on. I wrote up notes on writing Primer, and altogether I’m proud of the book and how quickly it came together.

Other books

It feels good to finish #3, and I think I could put down the pen at this point and not feel like a fraud to consider myself a writer, but I’m not done quite yet. I still have at least one more topic I want to spend some words on, engineering strategy. (I have no idea if I’ll ever get back to the Infrastructure Engineering book, I’m finding it hard to marshal the focus onto a topic that I’m not working on directly day to day.)

My first two books, An Elegant Puzzle and Staff Engineer are both doing well. Have been translated a few more times and so on, but nothing too wild. As I mentioned last year, I’m working hard to focus on the new things I do, and not to spend much time thinking about stuff I’ve already done, hence not reporting on book sales and such anymore.

First keynote

I gave my first first keynote, Solving the Engineering Strategy crisis at QCon SF. You can see a video recording of that talk on Youtube. I’m mostly avoiding conference talks these days, but it was impossible to pass up the opportunity to give my first keynote, particularly a keynote that didn’t require traveling for the conference.

There aren’t any conference talks on my schedule for 2024 but if I do some it’ll probably be focused on the topic of engineering strategy.

Advent of Code

I made it through day twelve of Advent of Code this year before deciding I needed to bail out. Some years ago I read Tanya Reilly’s ode to Advent of Code, and attempted it that year before getting busy, and decided to try again this year as quite a few work, professional and friend groups participated. I really enjoy working on these, but they’re competing for writing project time, and that’s just hard to fit in with the work travel, family visits, and so on that happen around the holidays. Maybe next year.

Angel investments

I did four angel investments this year, and invested in one fund as a limited partner. This is, give or take, roughly the sort of angel investing year I expect to have most years going forward, but it’s not a goal or a priority. I just evaluate the interesting things that come my way and occasionally invest. (I am mostly interested in developer experience, productivity, and infrastructure startups, as it’s the space I understand best and where I think my input is most useful.)

Reading

After finishing up Primer, I’ve been doing a bunch of professional reading. Much of this has been related to collecting my thoughts on engineering strategy, but some of it has been mining for ideas (including structural and presentation ideas) both as a leader and as an author who writes books.

The professional books I’ve read in the last few months are:

Year of personal admin

In addition to various work stuff, this was also a year of personal admin for me, where I tried to catch up on a few years of neglected tasks and ambitions around the house and my body.

Wearing glasses

I wore glasses until I was 13 or so, then I stopped wearing them, essentially on a whim. My vision was good enough for most purposes, including getting a drivers license, so I just didn’t think about it much for the following 20-plus years. Not thinking about it was nice.

When I started my new job, I started getting frequent migraines. Trying to diagnose what might be going wrong, it was clear that I was spending more time looking directly at a computer monitor than I had for several years, and I tried wearing a pair of old glasses that I had made about fifteen years ago as a last resort if I needed them to pass the vision portion of the California driving exam.

It turned out, this worked very well, and my eyes and head have felt much better since returning to wearing glasses. I don’t wear them all the time, but I do wear them whenever I sit down to do more than a few minutes of work on the computer. Age is, I suppose, more than just a number.

Running

Since graduating college, I’ve always been a frequent runner, although rarely been a serious runner. More concretely, other than a detour for a stress fracture, I’ve gone on 2-3 runs a week, averaging 3-4 miles, for quite a long time. In roughly 2013, I ramped up my runs for a while, building up to 6-8 mile runs twice a week for a few months, before ramping back down to my shorter runs. The shorter runs are nice because they take less time, and they also put a bit less strain on my knees which have at times been a bit unreliable. Plus, I generally prefer to stress my knees playing basketball instead of running.

This year, I wanted to build up my running distance and pace, with the goal of reestablishing a higher fitness baseline. Starting from my 3-4 mile runs, I rebuilt up to 8 mile runs, with my fastest average pace at 8 miles being 8 minutes and 42 seconds. I intended to spend more time working on my pace doing short runs, but I got distracted by the new job.

Relatedly, I’ve long been on the fence about buying an Apple Watch, but decided to buy one to help track my runs, and it’s been a surprisingly delightful piece of hardware. (I specifically bought the Apple Watch Ultra.) If I hadn’t bought it, I would absolutely not know how much I’d run, or the pace I ran at. It’s safe to say that I wouldn’t have even tried to do a pace goal, which would have considerably reduced the impact of my running workouts (e.g. only doing slow, long runs, rather than a mix of slow/long and fast/short) and results.

These are, on an absolute scale, not particularly big achievements. I know many runners who are much faster, go much longer, and are even much faster while going much longer, but it still felt good for me! I have no ambitions to be a competitive racer, I just like to push myself a bit occasionally, and particularly to continue pushing myself as I get older to remember that physical decline is in many ways a sum of choices rather than an inevitability.

Invisalign

In January, I started on Invisalign to improve parts of my bite, along with crowding in my lower front teeth. The plan was that I’d only wear them for four months, but twelve months later I’m still wearing them as the original set of trays didn’t fully work out. I’m scheduled to finish in February now, and am looking forward to no longer timing coffee consumption quite so carefully.

That’s my annual year in review for 2023! If you’re writing one, please send it my way! Love to hear what folks are working on and thinking about over the course of years.