2024 in review.

Published on December 14, 2024. career (38), blog (19), year-in-review (7)

A lot happened for me this year. I continued learning the details of fund accounting at Carta, which is likely the most complex product domain I’ve worked in. My third book was published, and I did a small speaking tour to support it. We started the unironically daunting San Francisco kindergarten application process. I was diagnosed with skin cancer and had successful surgery to remove it. All things considered, it was a much messier year than I intended, but with many good pockets mixed in with the mess.

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

Previously: 2023, 2022, 2021, 2020, 2019, 2018, 2017

Goals

Evaluating my goals for this year and decade:

[Completed] Write at least four good blog posts each year.
How to create software quality, Layers of context, Useful tradeoffs are multi-dimensional, Notes on how to use LLMs in your product, Eng org seniority-mix model.
[Completed] Write another book about engineering or leadership.
I did this in either 2023 or 2024, as I released The Engineering Executive’s Primer this year, and finishing writing it late last year. Either way, it’s complete.
[New] Write three books about engineering or leadership in 2020s.
I’ve already written two this decade, so committing to writing one more feels pretty attainable. At that point, I’ll have written four total including An Elegant Puzzle in 2019, and I’m pretty sure I will be “booked out,” perhaps permanently, but I think I have one more good one left in me on the topic of engineering strategy.
[Completed] Do something substantial and new every year that provides new perspective or deeper practice.
Started working with a physical trainer for first time, significantly helping me improve on a number of my lifts. On a totally different dimension, I finally spent time to learn Wardley mapping which is something I’ve been intending to do, but not doing, for at least five years.
[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 is a decade goal ending in 2029. I previously increased the goal in 2022 from 3-5 to 20. A strict count is at 10 today, so I think I’m on track.

For backstory on these goals: I originally set them in 2019, and then revised them in 2022. I’ve generally come to the point of view that I should be revising these every year, but also not sure it’s worth doing it. Maybe one day!

Published Engineering Executive’s Primer

My third book was published in March, The Engineering Executive’s Primer. I wrote up notes on publishing it with O’Reilly, and I’m altogether very happy to have written and published it. I’m also glad that work is in the past, rather than the present, as finishing a book is a fair amount of work to juggle with a full-time job and parenting.

Relative to my last two books, this is a bit more of a niche topic, so my mental model for sales was that they’d likely be a bit lower, which seems to be accurate so far, with a bit over 10,000 copies sold through October. The real question for a book like this is whether it maintains sales after the first six-month bump, which I’ll be watching with curiosity. It may also be true that book sales are not a particularly effective way to evaluate a book like this, which aims to advance the state of the industry by reaching decision makers within the industry. That said, it’s hard not to evaluate your book that way, even when you know that you shouldn’t.

As an aside, determining accurate numbers for O’Reilly titles is a bit tricky. There are things like the online version of the book, where you’re paid by usage (similar to Amazon Kindle Unlimited) but don’t have a non-dollar indicator of usage. I’m similarly unclear how audiobook usage is calculated, as it doesn’t show up in my royalties. To deal with all that, I’ve just focused on sold physical books and ebooks.

Other book updates

A few other book related updates:

I broke through 1,000 ratings on Amazon for Staff Engineer this year, which is a cool milestone to pass for two distinct books. (AEP passed 1,000 a year or two ago.)
Both earlier books continued to sell fairly well. I believe An Elegant Puzzle passed 100k copies sold either late last 2023 or early 2024 (the sales data I get is not particularly high granularity), which is a nice number. Staff Engineer is also doing well, passing 89k copies sold as of today. I think it’ll pass 100k sometime in 2026, assuming it can mostly maintain its velocity from over the last couple years.
I wrote the High-Context Triad which I view as an additional set of chapters for a second edition of Staff Engineer whenever I get to that project, probably my second side project in the queue after finishing the engineering strategy book. Of those chapters, I think Useful tradeoffs are multi-dimensional and Layers of context are particularly useful.
I’ve been pulling together notes and writing on engineering strategy, which has a real chance of turning into my next book, but there’s no guarantee on these things, e.g Infrastructure Engineering certainly went off the rails.

Public speaking, etc

Generally, I am not very focused on public speaking, but my stance on this topic changes the years when I publish a new book, and I did quite a bit of speaking, writing, podcast attendee-ing, and so on. I was featured on Gergely Orosz’s Pragmatic Engineer mailing list, First Round Review, and Lenny Rachitsky’s Lenny’s Newsletter.

I also gave talks at:

If you’re wondering why I do more speaking on the years I publish new books, it’s pretty straightforward: it helps sell more copies of the books, and books live on momentum. A good start in the first year contributes forever to its sales, as long as it’s a timeless book (“engineering leadership”) rather than a timely one (“details about the current version of a database”).

Videos

I’ve been playing around with creating YouTube videos for my conference talks. My approach is pretty basic: whenever I give a talk, I record a practice run ahead of time, and then post it online after I’ve given the talk at the conference. I don’t ever expect my YouTube channel to go anywhere–hence the low production values–but I do think it’s worthwhile to keep recordings as conference videos often disappear. Worst case, this means I have some recording of my talks since late 2023.

Health

This has been a pretty challenging year for me from a health perspective. I had two major vacations planned this year, and both got derailed by health concerns. The first I was recouperating with stitches from successful skin cancer surgery, and the second I was in bed with a fever for five day straight until my doctors were convinced my sickness was bacterial.

The skin cancer diagnosis was unexpected, and was a pretty unsettling several months to go from detection through surgery. As I write this, I am treating myself with topical chemotherapy to prevent another swath of skin requiring surgery in the future, which is far less serious than it sounds, but unsettling nonetheless. The good news is that a few months out, I am likely on the other side of this batch of skin cancer risk, and one large scar on my neck is a small price to pay for good health.

Probably the most challenging thing with the surgery and recovery, sickness and recovery, and so on, is that it just throws off the larger health routine. For the first time in my life, I’m working with a personal trainer, which has been quite nice. I’ve been an off and on lifter for the past several decades, and feel comfortable withi most lifts, but there have been a handful where I’ve just never quite gotten the form right, and I’m finally getting it now after working with my trainer. Similarly, there are some mobility issues preventing e.g. deep squatting, which I’ve certainly not fixed, but I’m able to better understand and make progress on.

I’m still running 1-2 times a week, although I’ve dropped milleage down to 4 mile runs, and playing basketball for a couple hours each weekend. I’m hopeful I’ll be able to both extend milleage and incorporate a speed session, but I’m honestly struggling to find the time (or perhaps, energy) to make those happen. Fingers crossed for 2025.

Kindergarten search in San Francisco

Without saying too much, I can say that I’ve never experienced anything like the San Francisco process of applying to public and private kindergartens. That said, the schools themselves are just remarkable. Looking back at the schools I went to in North Carolina… comparing them to these schools is almost impossible. I’m excited to see my son start next year, and will be excited to have this process behind us in a few months.

Tracking family cashflow

It’s slightly embarassing to admit, but I’ve had a relatively bad grasp of the details of my financial situation over the past few years. Specifically, I was very comfortable with how we were invested, but was having a hard time with the details of cash management. How much were we cash flowing? How much were our high spend months the result of obvious annual expenses (e.g. property tax) versus one-off purchases?

Our income streams are sufficiently complex, and I shuffle money between several bank accounts (one for bills, one for higher interest), that answering these questions had generally gotten beyond my ability to answer with conviction. This is a problem, because I’m the family CFO, and I became increasingly uncomfortable that I didn’t understand the financial consequences of various theoretical scenarios. For example, if I lost my job (or died, I suppose), where would that leave my family?

I wanted to reclaim my confidence in our finances this year, and did a fair amount of research to determine a tool that would make this possible. Ultimately, I went with Monarch Money (but do your own research before picking one!), and was pretty impressed with how quickly I was able to correctly represent our cashflows. The most important part was marking the various flows to and from bank and investment accounts as transfers rather than in or outflows of cash.

Altogether, I probably spent four or five hours over a week to get it fully configured, and now I can see my family’s cashflow for the first time in my life. This is pretty powerful, and now I have a pretty clear understanding of how much we’re spending (a bit more than I realized), and how much we would need to have invested to fully cover that spend. This has also made it much easier to sit down once or twice a year as a family and update our mental models on how things are going.

Reading

The profession-adjacent related reading I did this year (by which I mean, most of my reading is fiction that I don’t include here):

Financial Accounting, 11th Edition by Weygandt, Kimmel, and Kieso
Hardcore Software by Steven Sinofsky
The Big Score by Michael S. Malone
How Asia Works by Joe Studwell
Loonshots by Safi Bahcall
Chip War by Chris Miller
Practical TLA+: Planning Driven Development by Hillel Wayne (I thought that I’d read this previously, but I’m pretty sure I’d just bought the Kindle version and struggled to get into it in that format. I actually read it this time as a paperback book.)
Architecture Modernization by Nick Tune with Jean-Georges Perrin
Superforecasting by Philip Tetlock and Dan Gardner
Accounting Made Simple by Mike Piper
Partnership Accounting - Financial Accounting by Robert Steele (This is a Udemy course, not a book, but very much professional content.)
Team Topologies by Matthew Skelton and Manuel Pais
Super Founders by Ali Tamaseb
Zero to One by Peter Thiel
Poor Charlie’s Almanack by Charles T. Munger
Domain-Driven Software Distilled by Vaughn Vernon
How Will You Measure Your Life? by Christensen, Allworth, and Dillon
Write Useful Books by Rob Fitzpatrick
Building Green Software by Anne Currie, Sarah Hsu, and Sara Bergman
Unit X by Raj Shah and Christopher Kirchhoff
What You Do Is You Who Are by Ben Horowitz
Read Write Own by Chris Dixon
Co-intelligence: Living and Working with AI by Ethan Mollick
The Cold Start Problem by Andrew Chen
The End of Loyalty by Rick Wartzman
You Deserve a Tech Union by Ethan Marcotte
Build by Tony Fadell