Advancing the industry, part two.

I’m turning forty in a few weeks, and there’s a listicle archetype along the lines of “Things I’ve learned in the first half of my career as I turn forty and have now worked roughly twenty years in the technology industry.” How do you write that and make it good? Don’t ask me. I don’t know!

As I considered what I would write to summarize my career learnings so far, I kept thinking about updating my post Advancing the industry from a few years ago, where I described using that concept as a north star for my major career decisions. So I wrote about that instead.

Recapping the concept

Adopting advancing the industry as my framework for career decisions came down to three things:

1. The opportunity to be more intentional: After ~15 years in the industry, I entered a “third stage” of my career where neither financial considerations (1st stage) nor controlling pace to support an infant/toddler (2nd stage) were my highest priorities. Although I might not be working wholly by choice, I had enough flexibility that I could no longer hide behind “maximizing financial return” to guide, or excuse, my decision making.

2. My decade goals kept going stale. Since 2020, I’ve tracked against my decade goals for the 2020s, and annual tracking has been extremely valuable. Part of that value was realizing that I’d made enough progress on several initial goals that they weren’t meaningful to continue measuring.

   For example, I had written and published three professional books. Publishing another book was not a goal for me. That’s not to say I wouldn’t write another—in fact, I have—but it would serve another goal, not be a goal in itself. As a second example, I set a goal to get twenty people I’ve managed or mentored into VPE/CTO roles running engineering organizations of 50+ people or $100M+ valuation. By the end of last year, ten people met that criteria after four years. Based on that, it seems quite likely I’ll reach twenty within the next six years, and I’d already increased that goal from ten to twenty a few years ago, so I’m not interested in raising it again.

3. “Advancing the industry” offered a solution to both, giving me a broader goal to work toward and reframe my decade and annual goals.

That mission still resonates with me: it’s large, broad, and ambiguous enough to support many avenues of progress while feeling achievable within two decades. Though the goal resonates, my thinking about the best mechanism to make progress toward it has shifted over the past few years.

Writing from primary to secondary mechanism

Roughly a decade ago, I discovered the most effective mechanism I’ve found to advance the industry: learn at work, write blog posts about those learnings, and then aggregate the posts into a book.

An Elegant Puzzle was the literal output of that loop. Staff Engineer was a more intentional effort but still the figurative output. My last two books have been more designed than aggregated, but still generally followed this pattern. That said, as I finish up Crafting Engineering Strategy, I think the loop remains valid, but it’s run its course for me personally. There are several reasons:

First, what was energizing four books ago feels like a slog today. Making a book is a lot of work, and much of it isn’t fun, so you need to be really excited about the fun parts to balance it out. I used to check my Amazon sales standing every day, thrilled to see it move up and down the charts. Each royalty payment felt magical: something I created that people paid real money for. It’s still cool, but the excitement has tempered over six years.

Second, most of my original thinking is already captured in my books or fits shorter-form content like blog posts. I won’t get much incremental leverage from another book. I do continue to get leverage from shorter-form writing and will keep doing it.

Finally, as I wrote in Writers who operate, professional writing quality often suffers when writing becomes the “first thing” rather than the “second thing.” Chasing distribution subtly damages quality. I’ve tried hard to keep writing as a second thing, but over the past few years my topic choices have been overly pulled toward filling book chapters instead of what’s most relevant to my day-to-day work.

If writing is second, what is first?

My current thinking on how to best advance the industry rests on four pillars:

1. Industry leadership and management practices are generally poor.
2. We can improve these by making better practices more accessible (my primary focus in years past but where I’ve seen diminishing returns).
3. We can improve practices by growing the next generation of industry leaders (the rationale behind my decade goal to mentor/manage people into senior roles, but I can’t scale it much through executive roles alone)
4. We can improve practices by modeling them authentically in a very successful company and engineering organization.

The fourth pillar is my current focus and likely will remain so for the upcoming decade, though who knows—your focus can change a lot over ten years.

Why now? Six years ago, I wouldn’t have believed I could influence my company enough to make this impact, but the head of engineering roles I’ve pursued are exactly those that can. With access to such roles at companies with significant upward trajectories, I have the best laboratory to validate and evolve ways to advance the industry: leading engineering in great companies. Cargo-culting often spreads the most influential ideas—20% time at Google, AI adoption patterns at Spotify, memo culture at Amazon, writing culture at Stripe, etc. Hopefully, developing and documenting ideas with integrity will hopefully be even more effective than publicity-driven cargo-culting. That said, I’d be glad to accept the “mere” success of ideas like 20% time.

Returning to the details

Most importantly for me personally, focusing on modeling ideas in my own organization aligns “advancing the industry” with something I’ve been craving for a long time now: spending more time in the details of the work. Writing for broad audiences is a process of generalizing, but day-to-day execution succeeds or fails on particulars. I’ve spent much of the past decade translating between the general and the particular, and I’m relieved to return fully to the particulars.

Joining Imprint six weeks ago gave me a chance to practice this: I’ve written/merged/deployed six pull requests at work, tweaked our incident tooling to eliminate gaps in handoff with Zapier integrations, written an RFC, debugged a production incident, and generally been two or three layers deeper than at Carta. Part of that is that Imprint’s engineering team is currently much smaller— 40 rather than 350—and another part is that industry expectations in the post-ZIRP reentrenchment and LLM boom pull leaders towards the details. But mostly, it’s just where my energy is pulling me lately.