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.)
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:
- “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
- “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
- “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.
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!
As I mentioned in the goals section, the next book I am working on is tentatively titled
and is very, very early. As such, I really only have two major thoughts to share on it at
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.
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.
- 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.