Irrational Exuberance - 2022 in review. @ Irrational Exuberance

Hi folks,

This is the weekly digest for my blog, Irrational Exuberance. Reach out with thoughts on Twitter at @lethain, or reply to this email.

Posts from this week:

- 2022 in review.
- 2019 - 2022 reading recap.
- When shouldn't you roll out business reviews?

2022 in review.

Previously: 2021, 2020, 2019, 2018, 2017

After the past two years, it’s odd to write an annual reflection where my first thoughts are happy rather than bleak. The truth is that there is a lot of bleak out there right now–just look at the layoffs and the funding environment–but while last year was an unusual and challenging one for me, this one was relatively quiet for me and my family.

That said, even a quiet year is worth a bit of introspection, so here is my annual note.

(If you’re writing a year in review of your own, please send it my way! Love to read folks' thoughts on their own years. Also particularly curious about how you are thinking about setting personal goals, either your own goals or your thoughts on the goals that I’ve set below for myself.)

Goals

In 2019, I set goals for the upcoming decade, which I’ve been working against for the past three years. For the record, those have been three very strange years, but nonetheless a worthwhile exercise to check-in on progress:

• [Fail] Do more learning experiments. Try new technologies, software, etc.

  Hmm, I did take up the piano again this year, but that wasn’t my intent when I wrote this goal, so I’m marking it as a failure. I also struggled with this one in 2021, so I’ll need to take some time in 2023 to reflect on how to make more time for this work.

• [Completed]. Write at least four good blog posts each year.

  I did write four posts that I list this past year: Reading a P&L statement, Founding Uber SRE, Hard to work with, and Trunk and Branches. I also wrote a bunch of other haphazard stuff that wasn’t objectively very good!

• [Some progress] Write a book about infrastructure engineering.

  I started work on Infrastructure Engineering. I then got a bit distracted with other work and such, but optimistic that this is on track to get published this decade.

• [Completed, 2022] 3-5 folks who I’ve managed or “mentored” move into VPE or CTO roles at 100+ person or $1B+ companies.

  I’ve definitively met the goal here, even following a strict definition, e.g. excluding folks I only managed for a month or two, and taking the other requirements literally. I increasingly think this goal is the most interesting one from the original list.

• [Completed, 2021] Write another book about engineering or engineering management. Completed with release of Staff Engineer

• [Completed, 2021] Invest money in 3-5 startups. I made two more angel investments this year.

• [No progress] Become a board member of a small company, or startup.

• [No progress] Start a small but real business that I can run with a small amount of ongoing time investment.

• [Dropped, 2022] Become an official advisor for 1-3 startups.

  I had the opportunity to become the advisor for several companies this past year, and what I came to understand is that advising is not a cool, high status thing to brag about, but instead advising is consulting, with a different name, and that’s (sometimes) paid with equity. I’m not looking for more part-time work, so I dropped this.

  I’ve also seen a handful of scenario where an advisor asks for a lot of equity and then doesn’t do much for the company afterwards. The incentives just don’t seem well-aligned between the company and the advisor in most scenarios.

I’ve been thinking more about revamping my goals going forward, which I’ll talk a bit more in the next section.

Updating my goals

At the end of 2019, I rolled out my “decade goals”, which are the goals I listed above. I’ve generally really enjoyed them, and have found them quite helpful. I particularly value the breadth that decade goals give relative to annual goals: if you don’t make progress on a given area one year, no big deal, just make sure you’re making progress somewhere!

That said, I also appreciate that some of the goals I picked were subtly misguided. For example, the idea of advising companies is an interesting one, but as I came to understand what advising really was, it’s a lot closer to a job than I’d appreciated. I could imagine a future where I spent much of my time advising, but I have no interest in having part-time advising roles in addition to working a full-time role.

In that goal and several others, I arguably was too specific (“start a new business”) rather than capturing what I really meant (“do something new and novel that fosters personal growth”). As I spent time thinking about what I wanted my goals to accomplish, I want them to help direct me towards three themes:

1. “Advancing the industry.” I believe that I can improve practice in the technology industry. Examples: writing good blog posts, writing books that are read, supporting strong leaders in finding larger roles
2. “Personal growth & practice.” I am energized by doing new things and getting better at things I find meaningful. Examples: writing (even if it isn’t read by others), running further or lifting more weight, practicing the piano, programming more
3. “Endurance for the long-run.” I see many talented folks burn out on their work and hobbies. I want to continue doing both long-term, even if it means slowing down in the short-term. Examples: creating space to do less, rest, vacation, breaking routine

Reflecting on those over the past few days, I’ve decided on this set of new goals for the next decade. I’m certain these goals will adjust a bit over time, but I’m happy with them as a starting point:

• Write at least four good blog posts each year. This goal is a carryover. It does a good job on focusing on what I care about (writing good blog posts) without getting caught up in what I don’t care about (writing more posts)
• Write another book about engineering or leadership. This could be Infrastructure Engineering, it could be something else, but I would like to continue writing books. I’ve updated the goal to give me more space to be motivated by what energizes me rather than assuming what will energize me
• Do something substantial and new every year that provides new perspective or deeper practice. This is deliberately open-ended to support play and exploration, but some examples of what would qualify: join a board for the first time; launch a small personal business selling something other than a book; found a company; move from 1-2 angel investments one year to doing 10+ in that year; etc
• 20+ folks who I’ve managed or meaningfully supported move into VPE or CTO roles at 50+ person or $100M+ valuation companies. Although an imperfect goal, I do see this as one of the most direct and meaningful ways I can advance the industry, by helping more excellent folks rise to top-most leadership roles
• Work towards a clear goal for physical exercise. (Hitting the goal isn’t important.) I find that my workouts are much better when I pursue a clear goal. At one point this was running distance, and I built up to longer runs over a year. At another point it was strength in various lifts. This past year it’s been a focus on improving my basketball shooting. It’s not at all important to me that I attain my workout goals, but it is important to me that I have a goal to aim towards.

The one major gap for me is that I really want to do more programming, but I keep squeezing it out of my calendar to do other things. I’d like to figure out a goal that helps me create space in my life to write more software, and anticipate adding one more goal here as I experiment with ways to accomplish that.

Calm

A lot has happened this year at Calm. In February, we acquired Ripple Health Group, and got a new CEO, David Ko, who became my direct manager. Working with David has been life changingly good. He has a very different style than the other CEO’s I’ve worked with, and he’s taught me a lot.

We also announced Calm Health, got a handful of rewards for our iOS and Android applications, and had by far our best year in our B2B business line. Within all that, our increased deployment of machine learning–in combination with getting a good feel for the product, engineering, and data science partnership to iterating on machine learning products–has been a highlight for me personally.

Like every company this year, the macro-economic environment has impacted Calm. Along with many of my peers, much of my work and energy this year has been devoted to positioning Calm within that turbulence. At points, it’s been some of the more challenging work I’ve ever done, but I’m really proud of, and grateful to, the folks I’ve gotten to work with through all of it.

There’s more to be written here, which I hope to get around to in early 2023!

Infrastructure Engineer

As I mentioned in the goals section, the next book I am working on is tentatively titled Infrastructure Engineering, and is very, very early. As such, I really only have two major thoughts to share on it at the moment.

The first is straightforward: I’ve been pretty busy so I haven’t made quite as much progress on it as I would have liked!

The second is slightly more nuanced, and is a natural part of trying to get to the core of a book. An aspect of the book that I’m very excited about is documenting tools and meetings for operating an infrastructure organization–like this tool for organizational design, or this business review template– but many of them are just such general topics that I’m struggling with whether they’re really an infrastructure engineering topic!

It’s easy to argue that they’re really not an infrastructure topic, but so much of what I’ve seen effective in running an infrastructure organization is applying these sorts of basics with the occasional modification. I’m going to keep pondering this for a bit longer, but either I’ll embrace those elements despite being somewhat general or I’ll pull them into another book around executive leadership (removing them from Infrastructure Engineering).

Staff Engineer (2021) and AEP (2019)

All numbers are through December 11th, 2022 unless otherwise stated.

This was Staff Engineer’s first full year in release, and it did well. Through October of 2021, it had sold 20,000 copies, and lifetime sales are now at 48,000 copies (34k on Amazon, 9k audiobooks, 5k on Gumroad). I was also very excited to see Tanya Reilly publish The Staff Engineer’s Path, which is a fantastic addition to the topic of Staff Engineering, and well worth a read if you haven’t already done so.

By Q3, 2021, An Elegant Puzzle had sold 44,000 copies. At the end of Q2, 2022, it’s sold 58,000 copies. I won’t have the Q3 or Q4 numbers for 2022 for a few more months, but looking at the recent sales I’d estimate that it’ll end up something around 62,000 copies sold by the end of this year. Combined with the sales numbers from Staff Engineer, that would push the lifetime combined sales a bit over 100,000. A pretty neat milestone. (Another quick vanity metric: 1,436 ratings on Amazon. People actually read these things!)

I’m taking reaching 100,000 books sold as an opportunity to stop tracking or talking about book metrics for Staff Engineer and An Elegant Puzzle. When I next publish something of note, I may track it for a bit, but I probably won’t. I wrote about this a bit earlier this year in Time and Energy, but I think there’s a real risk in spending too much energy or time thinking about one’s past accomplishments instead of working on your future accomplishments. If I have energy, I’d rather work on something new. If I’m tired, I’d rather rest with more intention.

Irrational Exuberance

As mentioned before, my favorite blog posts of the year were: Time and Energy, Reading a P&L statement, Founding Uber SRE, Hard to work with, and Trunk and Branches.

Pulling stats for the blog has gotten trickier as I had to upgrade to Google Analytics 4, which I simply have not found particularly helpful for tracking blog analytics. The political and legal bodies striving to protect the internet are definitely pushing against 3rd party analytics, which is generally a cause I’m supportive of, but it does make pageviews a bit trickier to measure.

Because this blog is currently hosted as a static page via GitHub Pages, there isn’t really a great alternative approach to analytics outside of 3rd party tracking, so I’m leaning towards deleting analytics and not worrying about it much. This might seem extreme, but it’s what I did from roughly 2012 to 2017, and I wasn’t particularly harmed by the loss. It does make it tricky to detect what’s genuinely popular, but I can probably rely on direct reach out to solve that particular usecase.

Other stuff

• Our kid turned two! We don’t post pictures or talk about him on the internet, but it’s been a good time. (If you’re in San Francisco and want to hang around Saturday mornings with a two year old, send me a note!)
• I made three angel investments this year. I’m pretty excited about all three of them for different reasons! This is a much higher hit rate than last year, and it’s thanks to some of the investments I somewhat regret from last year that I was able to place more thoughtful bets. For the record, it’s not that I expect all these bets to turn into major successes, that’s unnrealistic, but rather they are businesses that I want to exist, have a chance to be successful, and with founders that I’m glad to support
• I got the chance to audit Sequoia Capital’s scout program, which was a fantastic learning opportunity. I thought about writing something up from that experience directly, but ultimately think I’m just too early in the angel investing process to write much about it
• The CTO/VPE Learning circle that I put together in early 2020 is continuing to go well for its third year, still meeting every other week. I do occasionally ask myself if I should wind it down, or fully transition ownership, but it has a surprising capacity for becoming better whenever it gets a bit less focused. I do wonder if it would benefit from a summer vacation! Attendance drops a bit and discussion quality drops a bit if sessions get too small
• I wrote up a recap of my non-fiction reading from 2018 to 2022. The significant majority of my reading is fiction, but I can’t claim any particular insight into what I read there, but I thought it might be interesting to share the more professional-ish books I read, hence the list

That’s my annual year in review for 2022. 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.

2019 - 2022 reading recap.

If this seems redundant, I did indeed accidentally release a draft version of this list earlier in the year.

In 2018, I put together my book recommendations, and while I don’t currently have any ambition to reflesh that list (those are pretty timeless books!), I decided to collect the non-fiction books I’ve read since writing that list through the end of 2022, which is roughly 2019 through 2022. I’m certain that I’ll miss a few, but here is a fairly representative list, particularly those where I read a physical copy.

Altogether, this is 57 “books about work” over the past four years, or just over one per month. I don’t set reading goals, but this isn’t a startling number that I’m concerned about one way or another. I’ll also note that I read more fiction than non-fiction, but have omitted those because that’s not really what this blog is about.

For books that I still think about somewhat frequently, I’ll preface with a star emoji, “⭐”.

• When McKinsey Comes to Town by Walt Bogdanich
• Talent by Cohen and Gross. As someone who is primarily focused on scalable, repeatable hiring processes (like hiring a team of engineers), this book’s focus on hiring one-off individuals (e.g. founders) was an interesting one, although most lessons would be difficult to translate
• Atomic Habits by James Clear. Have seen recommendations for years on this one, but never actually read it. A quick read with some interesting ideas
• An Everyone Culture: Becoming a Deliberately Developmental Organization by Kegan and Lahey. A recommendation from my father stemming from a discussion about dead-end jobs
• ⭐ The Staff Engineer’s Path by Tanya Reilly. An excellent book on succeeding as a Staff Engineer, with a deeper focus of on doing the day-to-day, month-to-month assignments that a Staff Engineer is likely to be focused on (both those literally assigned and those implicitly necessary but never assigned).
• Never Search Alone by Phyl Terry. I saw someone recommend this as an interesting read, and it was. The premise of the book is that you should search for jobs in a circle of other folks concurrently searching for jobs, and that feedback from this circle will prevent you from wasting a tremendous amount of time pursuing jobs you’re not qualified for, help you negotiate, and so on
• Inside the Tornado by Geoffrey Moore
• Invent and Wnader: The Collected Writings of Jeff Bezos by Jeff Besos, Walter Isaacson.
• ⭐ System Design Interview – An Insider’s Guide: Volume 2 by Alex Xu and Sahm Lam. I’ve gotten to know Alex Xu from a distance as someone doing interesting and very successful independent publishing work, and wanted to both support and learn from his work.
• System Design Interview – An insider’s guide by Alex Xu. Same as the previous book, although this is the first volume.
• Startup CXO by Matt Blumberg. I really like what this book aims to do, but I found it wasn’t quite at the right depth for me, personally.
• The End of Loyalty by Rick Wartzman. Interesting context behind the social contract between employees and businesses.
• ⭐ The Power Law by Sebastian Mallaby. I learned a lot about the history of venture capital from this book. It’s absolutely the history of venture capitalists from the perspective of venture capitalists, so take it with a grain of salt, but I enjoyed it.
• Amp It Up by Frank Slootman. An interesting read of one CEO’s perspective on good leadership. My personal opinion on “the value of intensity” has changed quite a bit over time (not in a consistent direction), and I appreciate reading folks’ opinions on it. More of an aspirational book than a tactical one.
• Doing Good Even Better by Edgar Stoesz. A primer on how to be an effective non-profit board member, which I read while refining my approach to personal altruism.
• Couples That Work by Jennifer Petriglieri. Read while looking for more perspectives on navigating dual career parenthood. I thought it was good, but I’m hard pressed to identify a novel takeaway that changed our approach. (The biggest idea–be explicit–was an idea we’d heard a lot.)
• Startup Wealth by Josh Maher.
• Fool’s Gold? by Scott Shane. A skeptical review of data on angel investing.
• Venture Deals by Brad Feld and Jason Mendelson.
• ⭐ The Bogleheads’ Guide to Investing by Mel Lindauer, Taylor Larimore, and Michael LeBoeuf. A useful summayr of the approach to personal finance that we follow as a family.
• The Trauma of Everyday Life by Mark Epstein.
• Lean Analytics by Alistair Croll and Benjamin Yoskovitz.
• Empowered by Marty Cagan.
• Working Backwards by Colin Bryar and Bill Carr.
• Who: The A Method for Hiring by Geoff Smart and Randy Street.
• Pivot by Jenny Blake.
• Ruined by Design by Mike Monteiro.
• Seeing Like a State by James Scott.
• Weinberg on Writing by Gerald Weinberg.
• How to Be an Antiracist by Ibram X. Kendi.
• The Unicorn Project by Gene Kim.
• Designing Data-Intensive Applications by Martin Kleppmann.
• White Fragility by Robin DiAngelo.
• Billion Dollar Brand Club by Lawrence Ingrassia.
• ⭐ All the Shah’s Men by Stephen Kinzer.
• Traction by Gino Wickman.
• Super Pumped by Mike Isaac.
• Building Evolutionary Architectures by Neal Ford, Rebecca Parsons, Patrick Kua.
• The Lean Product Playbook by Dan Olsen.
• Enterprise Strategy by Jeanne Ross, Peter Weill, David Robertson.
• The Principles of Scientific Management by Frederick Taylor.
• Secrets of Sand Hill Road by Scott Kupor, Eric Ries.
• The Broken Ladder by Keith Payne.
• Late Bloomers by Rich Karlgaard.
• ⭐ Escaping the Build Trap by Melissa Perri. I wrote up notes on this book when I finished reading it.
• Practical TLA+ by Hillel Wayne.
• The Rust Programming Language by Steve Klabnik, Carols Nichols.
• Angel by Jason Calacanis.
• ⭐ The Two-Income Trap by Elizabeth Warren, Amelia Warren Tyagi.
• Company of One by Paul Jarvis.
• Silk Road by Eileen Ormsby.
• ⭐ The Soul of A New Machine by Tracy Kiddler. I wrote notes on this one as well.
• Swipe to Unlock by Parth Detroja, Aditya Agashe, Neel Mehta.
• Move by Patty Azzarello.
• The Advantage by Patrick Lencioni. This is sort of a sumamry of his other books, many of which I love.
• Principles by Ray Dalio.
• What Works for Women at Work by Joan Williams, Rachel Dempsey, Anne-Mare Slaughter.

When shouldn't you roll out business reviews?

Earlier this week I got an email from a friend asking whether they should roll out business reviews at the company they’d just joined as the head of engineering, and inevitably the answer is, “Maybe!”

I recently pulled together a template for Monthly Business Reviews, which are an exceptionally effective meeting format for operating a business: each functional leader writes a metrics-heavy report about their past month, and discusses it with the other functional leaders. A well-run business review gives you a good sense of what’s happening, a checkpoint to ensure everyone is headed in the same direction, and an opportunity for teams and stakeholders to raise the alarm when they notice something going wrong.

As much as I think highly of these meetings, I’ve also seen business review rollouts go quite badly, so I took that email as an invitation to write a few notes on why you might not want to roll out. Some anti-patterns to avoid are:

1. Business reviews don’t solve a relevant problem. If teams are highly aligned, execution is strong, and existing leaders have strong judgment, then it’s unclear why you’d want to roll out business reviews. You’ll be spending time on something you’re already quite good at!
2. Missing leaders to write the business reviews. Sometimes folks want to roll out business reviews, but they simply don’t have the existing team to run constructive business reviews. This happens most frequently when the existing team is small and the existing leader is so consumed by operating their part of the business that they can’t step out to think about improving it.
   
   You don’t necessarily need to replace those existing leaders, rather they need your help creating mental space before they’ll be able to absorb a shift in the business’ operations like moving from ad-hoc execution to a business review-driven approach.
3. Your CEO isn’t committed to doing the work. Business Reviews are particularly valuable when the organizational tie-breaker is present in the review and engaged in breaking ties. This takes a lot of time, although it generally takes less time than not doing it. If the CEO doesn’t commit to the necessary time to prepare, participate, and engage during the sessions, then your business review is unlikely to succeed.
   
   (If you’re doing a business review for e.g. teams within engineering, then you don’t need the CEO there, but in that case you do need the head of engineering to be heavily engaged.)
4. You can’t agree on a standard format. It’s my lived experience that the format itself is important but there are many different formats that can succeed. However, the inability to agree on and enforce a standard format means that no one sufficiently important in your company is paying enough attention to the format for it to succeed.
5. Presentation quality doesn’t rapidly increase over time. When you initially roll out business reviews, the presentations are going to be rough. That’s expected and normal. Don’t get discouraged if the first pass isn’t good. What is concerning is when the quality doesn’t improve. Someone must be giving feedback to presenters and holding them accountable for the quality of their presentations. Further, this feedback needs to be good feedback. Again, this is a sign that senior leadership is either not paying attention or not aligned on the business review’s goals, both of which are good predictors of a bad outcome
6. Presenters are allowed to persist in meeting anti-patterns. The discussion’s format must focus on introducing concerns and new information to the review-writer. It must not be a reporting forum that consists primarily of presenting the written report. For example, a great session is when stakeholders in the audience flag concerns about execution, say, flagging that a recent partner launch went more poorly than represented in the written report–this means you’re creating alignment. Conversely, it’s a perfunctory waste of time when it’s dominated by someone “sharing context” about their execution in the live session. That should be in the written report. Doing it live is wasteful disrespect of the others gathered to improve organizational alignment and execution.
7. Attendees are allowed to be unprepared or otherwise disruptive. You cannot build alignment across a leadership team if some members are unwilling to prepare for the peers’ business reviews. At best, this means significant meeting time will be consumed with irrelevant or misguided discussion.

In summary, business reviews require significant maintenance from senior-most leadership or someone that senior-most leadership has empowered to operate in their stead. Without that maintaining attention, business reviews will rapidly become overhead rather than leverage.

That's all for now! Hope to hear your thoughts on Twitter at @lethain!

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