Year in Review — 2023

I started Year in Review articles for this blog back in 2014, as an exercise to look back through the year and coerce reflection by writing. This would make our post here the 10th one of these things, a milestone that I’d like to think establishes consistency and cadence—increasingly rare in a world with fleeting fame and short attention spans.

I’m also changing the format a bit: less focused on broad events better explained elsewhere, replaced by more navel-gazing and personal updates. As usual, here are all the posts for the year.

Smarter Reading

This year, I pulled back from spending my reading time on inconsequential articles and uninformed editorials to reallocate the time towards books. There was a good mix of fiction and non-fiction in my literary diet this year; my habit is to write mini-book reviews for each one I either feel strongly about or find something interesting to say:

• How to Take Smart Notes
• The Culture Code
• Excellent Advice for Living
• Silo
• Of Boys and Men
• Road to Nowhere
• Friends, Lovers, and the Big Terrible Thing
• Exadelic

In particular, the first one—How to Take Smart Notes—introduced the Zettelkasten system of note-taking, a practice that helps enforce active reading ]similar to writing reviews, while enabling reflection by connecting related themes and domains. I have not been as consistent as I should be to get the most value out of this exercise, so this is an area I’m working on in 2024: improving not only in what to read but also how to read.

Consistent Writing

Including this post, I will have published 47 posts this year here on in|retrospect, which is in line with what I’ve written for the prior 3–4 years. The consistency and iterative refinement continue to pay dividends, for both personal and professional writing tasks. At this point, having established my style and voice and the topics to write about, the next thing to work on is improving process and efficiency.

The rise of AI and its ability to generate passably good prose adds another dimension. Although I’ve been playing around with image generation for a while1, I haven’t made the same deep-dive into textual generation, particularly with the fine-tuning techniques currently used to emulate style and tone. And sure, there’s a lot of potential here to streamline the writing process, but I’m cognizant of the importance of retaining the core activity of putting thoughts on digital paper: it remains a powerful forcing function to think through issues, and the time spent reflects the effort for stray thoughts to coalesce.

My longer-term goal is still to collect enough thoughts and real-world operational experience to author a book on the topic. Right now, I don’t have plans to execute that goal within the next year—but I’m also running out of excuses to not start.

The Tech Community

I participated in a pair of conferences this year, both organized around the engineering management community in San Francisco: ELC Annual and Plato Elevate. I’ve been involved with both organizations on and off over the years, and have helped with panel discussions and keynotes in the past when the communities were in nascent and ascending. This year, I led discussions on a few management topics in my wheelhouse: managing upwards and outwards2, as well as shifting team culture to address tech debt.

It’s been a while since I’ve attended a conference in person. With COVID halting all physical gatherings for the past few years, I had forgotten that despite all the new interfaces created for video calls and gathering in VR, the act of talking with someone in physical space—shuffling from conference halls to presentation rooms, awkwardly stumbling past the vendors eager to sell SaaS solutions—is still an unapologetically physical experience. Even the swag was fun to grab3. And the influence of tech in San Francisco, for something as niche as engineering management, nonetheless was on full display. It is, after all, a small town; I caught some familiar faces from years and jobs past, a spontaneity elusive to virtual gatherings.

Due to a combination of work and burnout and personal stuff, I’ve pulled back from engaging with this community of engineers and engineering managers, coinciding with how the communities themselves meandered a bit in the wake of the disruption brought on by COVID. As things normalize, it’s an area I want to spend more time redeveloping in the coming year and look for opportunities to volunteer.

New Generation of Startups

In 2023, I connected with more startup founders than in the past few years, which I think speaks mostly to the increasing number of folks building their own companies. A few factors are converging:

• More tech layoffs, along with fewer job openings,
• AI-enabled capability and hype driving investment dollars,
• Major startup exits in 2020 and 2021, giving would-be founders more personal runway to pursue ideas.

On that last point, just as it took a few years for Square’s IPO to create its cohort of startup founders, I’m seeing the same pattern play out in the shadow of Affirm’s IPO in early 2021. Some of my former colleagues who joined the company early in its startup journey are now entering YC, or taking on C-level roles themselves in the next generation of early-stage startups. For those who enjoyed more spectacular exits, a couple straight-up retired from their equity stakes, and an additional handful of folks shifted into venture capital. In Silicon Valley, new generations of tech companies arise from the ashes of the previous downturn, and we’re right in the middle of this startup formation.

One additional reason why I’m getting pinged is that the tighter venture capital environment made it harder for startups to de facto hire their way out of problems. I joined Continuum last year out of curiosity, but in talking with their support reps, it sounds like they’re seeing an uptick in demand due to their clientele looking for ways to leverage expertise without fully committing to an expensive executive hire. At the same time, conversations with retained search firms confirm the trend from a different vantage point: fewer full-time jobs are available, and hiring managers get to choose from a bigger talent pool. Combined with the current macroeconomic backdrop, entrepreneurship may also be the path of least resistance.

Hobbies and Side Projects

Somehow, I found time this year to work on a couple of undeniably geeky projects:

• An E-ink Kitchen Calendar
• The Dygma Defy Keyboard4

These were also some of my most popular posts, so y’all are more receptive to hardware discussions—or at least find it more fun than the vicissitudes of people management. I’m far from being a product reviewer5 or a career hobbyist, but I’m hoping that the research write-ups and informative links inspire some of you to try out similar projects.

On the flip side, I wrote about and played fewer video games this year than in years past. There were a couple of epic single-player games on the PS5 that I enjoyed—Final Fantasy XVI; God of War: Ragnarök; Horizon: Forbidden West—but the full adulting schedule with work and kids’ activities and home renovations cut into available free time. Whereas 40+ hours of playtime through a story-driven adventure was a selling point to my teenage self, now it’s become an overriding cost of commitment, especially in comparison to 2-hour movies and 4-hour novels in entertainment value. More recently, I’ve taken more to smaller, portable games that are easy to pick up and drop: silly titles like Retro Bowl on my phone, or relaxing ones like PowerWash Simulator on the Steam Deck.

West Coast Travel

Whereas most people got their post-COVID revenge travel out of the way the last 2 years, we largely stayed put during this time and didn’t extend our travel beyond business trips and short car rides. This year, we made a more concerted effort to get out of town more often, but the kids’ activities and school schedule constrained our travel plans; as a compromise6, we took this opportunity to wander up and down the west coast.

There was an EV-powered road trip down to Death Valley and Las Vegas at the beginning of the year. Spring break took us on a short week in Hawaii, stopping by Volcanoes National Park while taking advantage of my son’s 4th-grade national parks pass. Summertime took us up the Pacific Northwest to my childhood in Seattle and Vancouver, the one time of the year when it matched my nostalgic memories of rainless, sunny skies. For the new year, we’re about to hop back down south to revisit San Diego and check out Joshua Tree National Park.

I’m admittedly late to the party when it comes to traveling, but I’m starting to understand why some of these travel amenities are so valued. The AmEx lounges are a welcome reprieve for business travel; TSA Precheck streamlines what is usually a long, stressful line for kids; keeping a dedicated travel tech bag makes packing much easier. I also added some new bags and backpacks so I could carry my A7III full-frame camera on flights, ensuring that I looked the part of a tourist. Now that we’ve gotten our travel legs under us by practicing on this coast, we’ll look to venture further afield in 2024.