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> A CTO at even a small software company that is writing code is doing their job wrong if they aren't quickly evolving into a role where they don't even touch code.

hard disagree here. When I worked at Fastmail (less than 50 people), our entire leadership was technical. Even our least technical leadership person (CFO?) was more proficient than most junior developers.

It's a beautiful thing, because business goals get aligned with programming goals, on a long lasting technical project that is very important. No more jostling over what some person with product vision wants versus what needs to happen, refactoring, etc.

I actually think the biggest challenge for the leadership team at fastmail is the leadership part, not the programming part. A bunch of really really smart tenured developers suddenly navigating how to be managers, CEO, CTO, etc, is much more challenging than writing some fixes for a new Apple Calendar quirks. It was cool to see growth from the leadership who took the part of 'ok I am a real C level at a company with a growing headcount how do I do this right the first time?'

I think, having a leadership that still keeps their hands in the dirt is a good thing. Plus they happened to all be the best programmers we had. Leapyears better than anyone else I think.

> I actually think the biggest challenge for the leadership team at fastmail is the leadership part

…and you just identified why writing code in a leadership position is a problem, so actually it wasn’t working. There’s no doubt that leadership with previous experience in the trenches is a benefit, but they should not be actively doing it in that role. Leadership is a full time (or more) position, and coding is a distraction from that.

We have the phrase “can’t see the forest from the trees” for a reason; Leadership needs to be looking at the forest almost all the time, and they can’t be effective if they’re stuck in day to day coding issues (the trees).

Writing code is a different job from management. Of course you will be very successful if you have good management skills and you combine them with strong technical acumen. But writing code while being a manager is a recipe for failure.

What you saw at Fastmail is pretty much standard in the industry: above average intelligence in the worker ranks but way below average ability and intelligence in the management ranks.

> What you saw at Fastmail is pretty much standard in the industry: above average intelligence in the worker ranks but way below average ability and intelligence in the management ranks.

No, the opposite. Most of the C level is extremely smart. Smarter than when I worked at a research lab with all PhD's and Professors. All are or have been leads on successful open source projects, contribute to IETF, one guy ran the Perl project for years, and so forth. Very smart crew. One of the best things about working there was being around people smarter than me

I'll agree that being a manager sucks. Being managed is worse. Corporate is hell and it's an embarrassment to us as a species that we haven't managed to overthrow it. Our current system has all the bad things of Soviet-style socialism (bureaucracy, inept management, corruption) and all the bad things about capitalism (structural divergence, duplicated efforts, the widespread use of violence to maintain class divisions) but it has none of the good of either system. It should've been thrown in history's garbage pile decades ago.

If one has to survive in the shitpile we call corporate capitalism, though, then it's better to hold a higher rank, where the jobs are more lucrative, less demanding, and easier to keep.

I've been in multiple management roles at multiple places and, with one exception, the role is much more about managing expectations of leadership and playing political games to make sure your team survives.

Indeed, it sucks. But ICs suffer a high risk of random non-survival. The stress of being a manager comes from knowing what fecal garbage most of the people who run your company are. The stress of being a grunt comes from not knowing. It's hard to say which is worse.

On top of that mindlessly solving problems and getting to check out with only 3-5 hours of work is exactly what many of them want.

I find that, when the work is pointless, there's a hedonic adaptation to not having to do much of it, just as there is with everything else: whatever you have becomes, within 3 months, what you consider yourself entitled to. People who are used to 8 hours per day of pointless work might be happy at first to only have to do 5, but soon they'll grow to hate even that. I, on the other hand, don't mind working if there's a point to it. I want zero pointless work. Unfortunately, the current system, which celebrates the proliferation of malevolent bureaucracies, has nothing for people like me.

Jira jobs desirability are variable.

Some places allow you to have a say and decision in what comes into the queue and what gets worked on, I think those are a lot better.