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Ask HN: Going from CTO to Developer?

 5 months ago
source link: https://news.ycombinator.com/item?id=39873644
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Ask HN: Going from CTO to Developer?

Ask HN: Going from CTO to Developer?
22 points by thatguyagain 1 hour ago | hide | past | favorite | 17 comments
Let's say you work as a CTO at a failing startup, and you are tired of all the responsibilities, management, etc, and you just want to go back to being a productive developer and write code again. Will this be perceived as a stupid career move or will people understand? Is it a bad move? Asking for a friend.
I've done this. I have friends who have done this.

I'm personally a big fan of the "Engineer/Manager Pendulum" model described by Charity Majors: https://charity.wtf/2017/05/11/the-engineer-manager-pendulum...

Engineers who have spent some time in management are extremely valuable. They have a better grasp on how things work, they have better leadership skills (you don't need to be in a management role to provide useful leadership within a company) and they're generally useful as all-round contributors.

There will be people out there who will mark you down for this. That reflects poorly on those people, but that doesn't mean they won't be in positions of influence where their poor judgement can still impact you negatively.

There will be plenty of other people who get it, and who will respect the choices you have made.

And you can always swing the pendulum back again later.

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the only problem with this is that as an IC when your manager is really doing poorly and not grasping their job, its _really_ hard not to say 'dude wtf, that's just not right'. that can go pretty badly. so you really have to work hard to stay extra constructive and support them as if you were _their_ manager, without the authority that usually implies. and that's a heavy burden as an IC
I did this from a hands-on CTO role at a 20-person startup to a senior engineer at a 200 person e-commerce outfit known nationally in the UK.

I was miserable for a long time, and sat down one day and made a list of all the things I liked about the job and all the things I hated. Everything in the “like” column was dev work. Everything in the “hate” column was the management work. So I slept on it for one night, quit, and went hunting for a dev job - this was 2015 so not too shabby.

There were a lot of things about this move I regret. The pay cut, the fact that my office in London got shut down as a consequence of my quitting meaning nearly everyone was made redundant, the fact that at my new role I was kind of resented a fair bit by other engineers.

But I was a lot happier and settled in my life. And nobody else can do that for me. I had to own the actions to make my short life on this planet better.

I’ve done management work since, and I’m now back to being an IC at a FAANG, but not as a software dev. I am now thinking about getting back into dev but it’ll get harder for me now I’m in my mid-40s.

I say if you aren’t happy, do it, but realise there will be some pain points. Ride that out, keep your head down and stay focused and you could be a lot happier.

I’ve done this several times. I’ve also worked for and managed several.

In my opinion, it’s great because ex-CTO types know what their managers need and are typically very easy to manage.

If the start up is not well known and depending on where you interview, you can just change your title to Lead Engineer or something similar.

A small start up CTO is nothing like a CTO of a big successful company.

Yes, it will be perceived as a stupid career move.

No, people won't really understand.

Is it a bad move? There are no bad moves, only bad reasons?

I was not CTO, but I was basically doing that job without the title. My company was slowly failing (although no-one would admit that at the time, it did go bankrupt 9 months after I quit). We'd moved to NYC for the company, on a company-sponsored visa. My partner and I had just had our first child. Like your "friend", I was pretty tired of management, politics, the constant scramble, and trying to fit some actual building stuff in between.

So I quit, moved back to my home country, took a few contracting gigs for a while, and then went full-time as a software engineer at a medium-sized company.

It was absolutely a backwards step, career-wise. Less pay, disconnected from the startup scene, outside the networks I'd spent years building. It easily put me back 5 years, probably more like 10, in terms of career.

OTOH, I was working from home, with heaps of flexibility, which was perfect when my kid was little. For a while, we both worked 4 days, one weekday off each at home just hanging out with the kid. Work was fine, but I kicked the obsession that it had just about become.

10 years later, I haven't tried to climb back. I do 5 days full-time now, but I'm just a senior engineer. I miss the challenges, but not enough to want to go back. I get paid less, but I'll probably live longer, and certainly better, this way.

Everyone's different. Some people leave tech, and make furniture in the woods. Some people just pull back a bit. You can pause and then have another tilt at it once you've recovered a bit. There's no rule book, really. Do what feels right and good.

How big is your team?

People overestimate the importance of titles.

Anyone can start a company and call themselves a CTO. Plenty of line managers at big tech companies have more responsibilities than CTOs at start ups.

As long as you're not 5+ years into people management and have a team of less than ~50 it shouldn't raise any flags with most interviewers. People switch between manager and IC all the time.

Just have a good story ready, be humble, and demonstrate good self-awareness and you'll be fine.

I did exactly this, was CTO at a startup, it failed, went back to being IC at a large company, then went into management again and realized I am just not happy in that role.

Went back to IC roles, no regrets, much happier with what I am doing. Money isn't everything, as long as you have enough to live well, you don't need to make 7 figures, just make sure you are working toward a couple million in investments for retirement if you are in the US.

It’s going to lead to questions, especially if the time frame was long enough that they can’t just leave a gap on their resume.

One scenario I could see working is moving from CTO to founding IC for another startup, but that conserves a number of things your friend might be tired of. Like long hours, and sitting under the Sword of Damocles 24/7.

I'd love to hear about the other direction. What kind of skillsets or prep can a problem solved do to transition into more leadership roles? Is it primarily getting an MBA? Getting lucky?
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No need for an MBA. You can make your own luck here: start by taking on voluntary leadership roles such as mentorship, or running initiatives within your company (setting up an informal team to codify source code management practices, that kind of thing).

Make sure your own management know that you are interested in this path.

The book The Manager's path has excellent advice on ways you can prepare yourself for management positions: https://www.amazon.com/Managers-Path-Leaders-Navigating-Grow...

My career was a rollercoaster. You will never know what might have been, but it is important to be happy (enough). Ended my working days as a WFH contract developer which by then was perfect.
This is kind of what I did. I was VP of Engineering etc. at different companies and wanted to go back to coding, see: https://blog.jgc.org/2012/02/programmer.html.

Of course, I then ended up being CTO again!

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Cool, sounds like it worked out fine for you!
It might be considered a failure by some, but so what, do what you feel is best for you.
Does your friend think it is a stupid move?

That's what matters.

Life is much bigger than careers.

Good luck.

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