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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.
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.
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?
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...
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.
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'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 use…
A small start up CTO is nothing like a CTO of a big successful company.
In my opinion, it’s great because ex-CTO types know what their managers need and are typically very easy to manage.
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…
It sets a strange precedent sometimes too if not well communicated and managed.