Personally? If I were you, I would return to engineering as a regular old software engineer, writing and shipping code every day in the trenches with (this cannot be emphasized enough) a really, really good team.

Your rustiest skill sets are always going to be the most tactical ones — writing software, reviewing code, reproducing bugs, understanding a new production system.

As a former CTO, you have many other skill sets to pull from — management, strategy, architecture, coaching, staffing, fundraising, etc. These skills are valuable. But they don’t degrade the way hands-on development does. You’ll still remember how to write a performance review two (or twenty) years from now, but writing code is like speaking a language: you use it or lose it. And just like with a language, the best way to freshen up is full immersion.

It’s not just about refreshing your technical chops, it’s also about re-acclimating yourself to the rhythms of hours, days, and weeks spent in focus mode, building and creating.

Think back to the time you first moved from engineering into a management role. Do you remember how exhausting and intrusive it was at first, having meeting after meeting after meeting on your calendar? You had to context switch twenty times a day — you were context switching constantly. You had to walk into room after room after room full of people and their words and emotions. By the end of the day you would be drained dry (and the days felt so long).

As an engineer, you spent your days in stretches of deep focus and concentration, punctuated by the occasional meal, meeting or interruption. But as a manager, your life is nothing but interruptions (and time boxes, and time-boxed interruptions). It took time to for you adjust to manager life and learn where to seek out new dopamine hits. And it’s going to take time for you to adjust back.

How much time? About six months, at least for me. I don’t think it’s being overly dramatic to say that you have to allow enough time to become a different version of yourself. You can’t just change personas and entire ways of being like you change your clothing. The process is more like…a snake shedding its skin, or a caterpillar turning into a butterfly. Don’t rush the process.

And don’t just pick up where you left off as an engineer. This is a beautiful opportunity for you to enjoy the terrible frustration of beginner eyes. ☺️ Learn a new language, learn a new framework, learn a new way of packaging and deploying your code. Freshen up your toolchain. Try a new editor. Catch up on some new testing or validation ideas that have developed or gone mainstream since you were last in the coal mines. (Take modern observability for a test drive? 😉)

Shit moves fast. A lot will have changed.

If you try to pick up where you left off as an expert, it’s really going to suck as you stumble through the motions that used to feel effortless and automatic. But if you start with something new, the friction of learning will feel ordinary and predictable instead. And pretty soon you’ll feel the engine start to kick in: the accelerated learning curve you’ll remember from learning a new technical skill for the 50,000th time.

Because it’s not just about refreshing your technical skills and your daily cadence, either… it’s also about reconnecting with your curiosity, and your attachment to (and love for) technology.

And you better fucking love it, if you plan to inflict the world of agonies that is software development on yourself day after day. 😭 So you have to reconnect with that dopamine drip you get from learning things, fixing shit, and solving problems. And you have to reconnect with the emotional intensity of shipping code that will impact people’s lives — for better or for worse — and of being personally responsible for that code in production. Of knowing viscerally what it’s like to ship a diff that brings production down, or wakes up your coworker in the middle of the night, or corrupts user data.

So yes. It is absolutely possible to return to engineering after a few years away. And yeah, you could come back as a principal or staff engineer. Someone will definitely hire you. However, I suggest otherwise. I suggest you come back as a senior engineer, writing software every day, for a good 6-9 months.

Your grounding in the technical challenges and solution space will be much deeper and richer if you come back hands on than if you came in at a higher level, detached from the rhythms of daily development. Working closer to production and closer to users will give you the chance to rebuild the intense empathy and connectedness to your work and team that tends to seep away the higher you go up the food chain. You’ll be more confident in yourself as a technologist if you honor your need to relearn and rebuild. And you will earn much more respect from your fellow engineers this way. Engineers respect people who respect what they do.

It’s better than jumping straight into the role of a staff+ engineer and trying to refresh your tactical/technical skills on the side. And you’ll be an infinitely more effective staff+ engineer once you’ve done the refreshing.