👋 Hi there. In May, I decided to stop being a manager. Now I’m an engineer again. One of my emails this morning looked something like this:

This was my choice, no-one else’s, and I was not pressured into it. I’m staying on The Team because I love it here, and I’m excited about our next chapter together. The gist is, $big_scary_incident reminded me how much I love troubleshooting, research+writing work, and writing code. That was pretty sweet. See you in GitHub!

A brief primer on me: 19 years ago, I entered tech. Not Tech™ tech. Just an Oregon retail business you’ve never heard of. They needed some DB and desktop development, regular report-running, desktop support, and a dash of field support. Was I a Business Analyst? Programmer? IT Manager? Who knows. I got to make up whatever title I wanted. They didn’t care. In the grand scheme of things, the title really didn’t matter.

Twelve years of slinging code and hand-carving infra later (and several companies), I was confidently calling myself a Software Engineer. This isn’t a story about those twelve years, but rather the seven that followed as a Software Engineering Manager. This is:

  1. A story about deciding to pivot into Management, and what happened next.
  2. A story about leadership vs. management, and why they are most definitely not the same. (And how one is not for everybody, despite what you’ve been told.)
  3. A story about why being a manager for a while better prepares you for more senior levels of engineering. (🤞I hope.)
  4. A story on why delegation and letting go of control is one of the most important jobs of leadership.

How’d I get into management in the first place? Well, after twelve years as an Engineer, I got frustrated…

I used to be an engineer.

Eight years ago, I’m at a renewable energy company. (You haven’t heard of them, either.) EMS-SCADA systems, time-series databases, and a bunch of infra and ops. Just finished Giant Compliance Automation Project and Disaster Recovery/Business Continuity Project From Hell (won the “D.R. Prepper” award for that) and 😅 I need a break from that. Free cycles and a successful run gives me the street cred to go off and solve a problem that has been brewing in my head for a while. I spike out a proof of concept: $automate_thing. Pitch $automate_more_things to The People In Charge. Use all my Engineer Jedi Mind Tricks but fail my persuasion check. Headcount can’t magically appear, and there’s resistance. Lots of resistance. Bummer, but hang on here…

💡 These people with the Manager title seem to get their way a lot! (And they get paid more!1) I should go be one of them.

That’s when I decided to leave engineering and ops to pivot to management. Not right away. Went to some conference talk on being a Lead and they’re talking about this Michael Lopp (rands) guy and this Rands Leadership Slack community that’s a great place to learn from others about managing (coughLEADINGcough — I was naive) humans. Oh, and he wrote the book. (Managing Humans, I mean.) So I give that a read. Practiced this Lead thing for a while longer, mentored and organized bigger projects and Got Shit Done. Alright. Time to find a new job.

Then there were those years where I was a manager.

February, 2015. Interview at a startup… BOOM. Lead, Manager within the first month, took three years to grow a team from three engineers to 15. Startup, though, remember? So I’m coding a lot in the beginning, or writing design specs. Teaching the architecture to the New Guard as I hire them. Over time, I have more people to lead. Less time to code. Still the same pressure to code, to deliver. Why don’t I just start my own startup at the same time? No problem, I can handle it. Um, guess wife and I are starting fertility treatment… for two years. Oh……… wife and I are having twins. Wait, how many hours am I working every week? Is this what burnout feels like? Time to winnow.

October, 2018. Interview at Heroku. Data Team, Engineering Manager. I. Am. Excited. Interview with nice-human-who-was-going-to-be-my-boss-but-got-promoted-during-the-interview-process, then some other wonderful folks who aren’t at Heroku anymore and I dearly miss working with, and lastly a wonderful conversation about leading humans with a future peer manager. None of them wanted a manager that codes. They wanted a human who can help other humans thrive, get some projects going full-speed. Perfect role. Got the job.

Along the way, I learned a ton. Met a lot of really fascinating humans. Helped many of them accomplish cool things. Advised some of them towards accomplishing really awesome career goals. Got exposed to parts of The Business™ that I never would have seen otherwise. This foreign-to-me career pivot into Management has been one of the best and hardest chapters of my career.

Sounds awesome. What went sideways?

It’s 2022 now. What a… something… few years we’ve all been going through, huh?

So why am I pivoting back to engineering? Well… it turns out, Managers don’t actually have the power they think they do. I’m going to tell you a secret. When I got this job, I “found” this magic wand laying around. I can make people do anything with it! Projects just happen. People do things I ask. I can grease that squeaky bureaucratic wheel with it. With it, I was able to use it to do some really awesome things. Mostly for good. Some mistakes along the way, of course. Only a few singed eyebrows.

But the real power of that wand manifested when I started giving it away to others around me. First it was my directs. Engineers who worked for me—at first just the battle-scarred ones—who I trusted to lead a thing. Then things got spicy at work and I had to give up even more… so I started giving the wand to people who I didn’t necessarily know if they’d succeed or not.

When they succeeded, it was marvelous! When they failed… they learned. They did better the next time. Huh. Didn’t see that coming, for some reason. See, the battle-scarred engineers only got those scars from using the wand the wrong way in the past, or from making mistakes. Those scars stuck with them and became lasting memories of that time I plugged in an errant network cable and we lost control of four gigawatts of wind turbines. I was lucky enough to stumble into teams that were supportive and nurturing of the folks who made such mistakes. Not everyone has been so lucky.

What do you do when you give away all your magic wands?

At some point, the work of management felt… dull. My vision and strategy for the team was underway. We had some projects, some roadmaps, and lots of interesting things to go work on. I watched as engineers got to thrive in the work of design docs, PRs, mentoring each other, and working with our customers. And… I got a bit jealous. In giving everything fun away, I had left only the dull work for myself2: the expense reports, the offsite planning, the talent reviews and promotion packets, the continuous cycle of check-ins and planning.

All very important work, but not work that sparked joy in me. The work felt grueling sometimes, and stressful, and I had to work with a psychiatrist, a BetterUp coach, and an executive mindfulness coach to process all the myriad reactions I was having about work. I knew I needed a change again, but I wasn’t sure what yet. I had known since November. I didn’t know what I wanted. It took me a looooong time to process all of that.

Then in April, in the midst of The Incident That Shall Not Be Named, I had an insight that I was enjoying my work again, despite the hardship of a fully unreasonable (self-induced) work schedule and some of the most urgent and dynamic work I’ve ever been involved in. So, I decided to exit management. I do want to keep leading people, but I want to lead as an engineer instead of a manager. I’m excited about what’s next, but that’s a topic for another blog3.

My hypothesis: I’m going to be a better engineer because of this journey.

Here’s the second moral of the story. (The first is the magic wand mindset, which is actually a story about delegation, the constant search for personal growth, and shifting towards an Infinite Game mindset.)

See: I had left engineering to be a manager because I had the (mistaken) impression that only managers could get $thing_you_are_excited_about prioritized in an organization. It turns out that’s actually called influence and leadership, and you don’t have to pursue being a manager to learn and practice those skills. Also: the job of a manager is wayyyyyyy different than I expected4.

Whoops.

But through that journey, I now have deep empathy for my boss’s predicaments. I know the challenges she faces every day because I’ve lived them. I know how it impacts her when I don’t communicate my status, when I don’t ask my teams enough questions to understand what’s going on with the projects they’re leading, when I half-ass my Staff engineer’s promo pitch, when I don’t know what I’m doing and don’t say anything about it. As an early-career engineer, these things managers do irked me. They led to me leaving an engineering role.

All these scars I got while managing the best humans I’ve ever worked with? Those scars are teachers, and I’m optimistic that I can not only apply them myself (or learn to—after screwing up some more), but can also model them for the team that now sits next to me.


In retrospect, would I have chosen to be a manager again? Yeah. Totally would. I’m a better leader for it. Maybe a better engineer? We’ll see about that. But management is not for everyone, and our industry has got to find a way for that to be OK.

  1. Not all companies. Companies that optimize for the Engineer>Manager transition as the only path to making more money or working on more complex things are, IMHO, either lower-margin companies who can’t justify paying ICs more based on their business model or … are doing it wrong. Or both. Don’t make people take a job they don’t want as the sole means of career growth. 

  2. This is not to say the work was not rewarding. I thoroughly enjoyed seeing the outcomes of the work, I just didn’t like the process of getting there. Compare: I love seeing the outcome of a hard technical problem, but I also love the process of building it along the way. 

  3. I’m writing some internal Heroku Fanfic where an assortment of other Herokai and I are drafting one possible future. Keep your eyes peeled here for job openings and join us if you want to help pave this future: https://heroku.com/careers 

  4. Not all in a bad way! There were some genuinely beautiful moments of the gig, and a lot of good things happened for our team and for our customers as a result of the work I got to lead.