Grab bag of random thoughts.

A bit over a week from now, I’ll be joining a company to start a new role, and I wanted to ramble a bit to braindump the numerous loose threads in my head as I transitioned from Calm to the past month of full-time writing, and then into this new role. This isn’t really a job announcement post per se, as I won’t share any details about the job itself until I’ve officially started. Instead, this is a snapshot of what’s top of mind for me, particularly driven by the dozens of discussions with friends and colleagues as I thought about what’s next for me over the past few months.

Job search

My last day at Calm was in early March, and I was planning to take three to six months off before starting my next job search. My initial goal was to specifically avoid talking to anyone about open roles until I was ready to start, because there is a certain momentum to executive searches that is hard to avoid: if you’re an eligible candidate who interviews reasonably well, once you start talking to VCs and recruiters, you’re going to end up placed somewhere. If you fight against that momentum for too long, you’ll eventually annoy the folks trying to place you, turning supporters into neutral parties at best.

If you disagree that there’s some risk to resisting executive search momentum, a quick aside for you. At this point in my career, I am selected as a backchannel reference for a number of folks. If you’ve worked with me, and you interview for an executive role at companies backed by a certain handful of venture firms or staffed with executives whose network overlaps with mine, it’s fairly likely I will get a call about you. I try extremely hard to center the positive for everyone I’ve worked with, even in the rare case that I didn’t love working together with them, but it highlights something important: even if you’re trying to spare me from performing too many references on your behalf, if you run a long executive search and we’re worked together, then I am getting a lot of pings. It’s not that I’m special, this is how the executive recruiting ecosystem works. If you run a long search–even if you don’t personally pull many people in–you will tire out your network. The VCs and recruiters will get tired too.

Back to my own search: Talking to friends, a recurring theme was the lack of exceptionally good executive openings in 2023 relative to searches in prior years, especially relative to the 2020-2021 era. There were still many open executives roles, but many were in deeply challenged businesses or very early businesses (e.g. Series A). There were still some executive roles in thriving businesses, but there simply weren’t very many of them. This made me rethink my planned three to six months break before talking with recruiters.

I ended up deciding to talk with companies about roles that I felt confident I would accept, barring uncovering major flags in the interview process, and where I could accept an offer without experiencing FOMO about the other companies I didn’t speak with. In other words, set a high bar,, and let it take as long as it takes to find an opportunity. This worked a bit faster than anticipated, and I’m quite excited about the role and company I’m starting next Monday. I’m confident that I wouldn’t have found a better opportunity for me, even if I’d spent the next six months talking with companies, and equally confident I would hae regretted saying no.

Leaving Calm & how I thought about my next role

When I was thinking through my decision to leave Stripe (the role I left to join Calm), I wrote A forty-year career, which describes each role as a mix of profit, people, prestige, learning and pace. This framework continues to resonate with me. The nuance I’d add to it, as I’ve gotten better at managing my own energy, is that pace is often more of a ratio between energizing and draining work rather than an absolute speed.

My time at Calm was very rewarding, and the hardest part was leaving the leaders, peers and team that I got to work. What solidified my decision to leave was my belief that my rate of contribution to the business and my rate of learning were both tapering off. If I could go back in time to 2020 and pick any available job, I’d pick Calm again, because I have learned so much over the past three years, but it also felt like the right moment for me to move on to something new.

As I thought about what I would do next, finding an opportunity with a significant rate of both contribution and learning was the foremost criteria, and I believe that four years from now I’ll have learned just as much as I learned over the past four. This isn’t a precise science, but if I keep learning enough to write a new book every four years, that will be good evidence that my learning at work remains at the right pace.

Sabbatical

As mentioned above, I left Calm planning to take a three to six month sabbatical, aiming to finish writing my next book. I’d say that I’m about 60% done writing the initial draft, and will slow down a bit as I start my new job. I remain optimistic that I’ll finish it over the next four months or so, which was the timeline I established with O’Reilly, admittedly under the assumption that I wouldn’t be returning to work quite so early.

The book’s first chapters will be up for early release very soon, at which point I’ll write more about that project. It just feels a wee bit premature to write about something I can’t link to. (For the record, this upcoming book is not going to be Infrastructure Engineer, which has fallen a bit down my priority list. My hope at this point is to pick it back up in late 2024, I don’t think I’ll see much progress on it until then.)

A number of people have asked me for sabbatical advice, and I’ve established absolutely no credibility in terms of doing the sabbatical I intended to, but I’ll still share what was important to me when thinking about the sabbatical and then implementing it:

• Particularly in 2023, you should have a financial position to support a six month job search. That is in addition to the resources to pay for the sabbatical itself. The job market out there is just very strange right now. I’m seeing some folks find new jobs very quickly, and others struggle to find new jobs for months.

• Figure out whether others in your family will or won’t have time to do it with you, and adjust for that. My wife was continuing to work, so this meant I had more time to myself, but also that I needed to keep to my existing child care and family schedules. Life is long and complex, don’t try to make others take time when you’re taking time, let people live!

• Give yourself a few weeks, maybe two, to do absolutely nothing productive. Don’t have a schedule, don’t have meetings, don’t take calls, don’t catch up with friends. Just relax. Maybe go somewhere else.

• Don’t get anxious and start scheduling lots of meetings. You can easily spend all of your time taking meetings. You could just keep working and get paid to take meetings if that’s what you want.

• Have a clear set of goals to focus on. I kept a strict writing schedule during my time, which helped me feel productive. I occasionally “cheated” on the schedule sometimes to take care of my son, work on a fun project, meet up with a friend or whatever, but I mostly kept to the schedule. It was not a brutal schedule by any means. It was peaceful, but focused.

  I also had a running goal, to get back up to an 8-mile weekly “long run”, which I hit last week as the deadline started to get uncomfortably close. As someone who’d fallen into three mile maintenance runs for the past decade, it was a good to remember that running further is mostly about not stopping when it gets uncomfortable.

• Remember that rest is about resting. There have been days when I didn’t get stuff done, or even get stuff started, and I just gave myself permission to rest. When working, I would have pushed through and gotten it all done, but my goal for this time was essentially to heal and recuperate from the last ~15 years of working full-time, so I didn’t ever push. If it felt like I needed to push productivity harder, I just relaxed the constraints instead. I wanted to be ready to utilize my higher gears when I returned to work, rather than to exhaust them during my break.

If I could do it again, I think I’d do it the same way! Life comes at you fast, and rarely according to plan, but I don’t think I could have planned it more with better results.

Who’s successful anyway?

Recently when I chatted with a friend about our careers, we got onto what I think is an interesting topic, which is the inscrutability of success. There are people in the industry who appear extremely successful, but who are not. There’s two different dimensions to consider here.

1. First, there are individuals who you’d assume are financially very successful but who are working out of necessity despite working very high prestige roles (e.g. head of engineering at a trendy company for years, but still working out of necessity 25-30 years into their career).
2. Second, there are individuals who are widely considered very successful by folks without detailed context of their work, but who are considered very unsuccessful by those with concrete awareness of their work (e.g. well-known on conference circuit but considered a poor performer in role by former colleagues).

As I’ve gotten deeper into the industry and a bit better networked, it’s less common that I’m shocked by someone’s performance–usually I know someone who knows someone who worked with them–but I remain constantly surprised at the industry’s inconsistent financial outcomes. I don’t have any concrete lesson to share, but I think it’s interesting to note that I’m still frequently surprised at how little financial success is extended to some nominally extremely successful people in the industry. Conversely, there are also many, many folks who are financially successful, without a clear correlation between that success and their various contributions. Downturns make this phenomenon even more extreme, with many excellent folks failing to “cash out” of their work, largely due to timing constraints out of their control.

Culturally, there’s a strong pull towards using financial success as a sort of moral compass, but it’s my experience that luck plays far too high a role. Even if you think you’re appropriately discounting the role of luck, I suspect you are still underestimating its impact.

Executives without much range

There are a number of executives out there who are very good at some things, but lack the flexibility to operate in varied environments. Sometimes this is because they are stubborn, and have a specific working style that they insist on following independently of the company. Another major contributor, in my experience, is executives who lack experience working in middle management.

Middle management is, of course, something that people often view as fake work, but it’s the critical work of translating an executive’s stated plan into a series of real plans that the company can actually implement. Executives who don’t understand this are doomed to create systems and processes that impede organizational execution, often screwing things up while claiming to improve organizational execution. Based on my experience, I don’t think you can be an excellent executive at a scaled (or scaling) company without middle management experience.

There are lots of details here, but the two biggest ones I’d mention are: I find that executives without middle management experience often rely on trust rather than inspection, and then generally a lack of understanding of how to design useful processes (usually viewing process as a one-off thing rather than an ongoing evolution).

LLMs

I had fun playing around with the OpenAI API this past week. I summarized my view of this technology shift as, “LLMs are showing significant promise at mediocre solutions to very general problems.” This captures my perspective pretty fully, but there’s one other nuance I’ll throw in for the moment: chat hasn’t yet proven itself as a durable paradigm for serious interactions. It’s a good paradigm for broad discussions that can tolerate some loss of meaning, e.g. initial communication about intent to purchase a SaaS product or customer support for a user who’s ordered two specific items, but not a good interface for areas where meaning is fundamental, e.g. here is how you should write a legal document. This is similar to the issues Alexa and Siri as meaningful product lines, when they’re largely stuck playing music, setting timers, and checking the weather.

The issues with chat absolutely don’t mean that LLMs won’t find a sweet spot, I’m just a bit skeptical that chat’s the sweet spot. Most valuable applications are trying to do valuable work where correctness matters, and I don’t see this technology as likely to upend those sorts of interactions. I’m not in the rooms making these decisions, but my personal hypothesis is that chat is a very smart use case where you can show significant value while minimizing costs (e.g. imagine the price of evaluating LLM responses for each of your ten million users every night as opposed to only incurring those costs when a human directly asks for one).

That said, it’s clear that LLMs are going to absolutely break the current paradigms of writing, editing and evaluating written work. Publishers are already getting overwhelmed with generated submissions, and it will be instructive to see where that ends up. I’m personally a bit concerned about it, not because I think it’ll impact me in a major way, but because I think it has the potential to make it much more difficult for new writers to distinguish themselves. That said, it’s exciting for the world to keep changing, and it was never going to statically remain the same to prioritize my comfort over technology’s drive to innovate.

That’s all folks

OK, I’ve gotten my random thoughts out of my head for now. I’ve been publishing on pretty much a weekly cadence for the past few months, and suspect my cadence will slip a bit as I ramp up in my new role, but hopefully not too much!