I did this myself for a good 15 years or so, but eventually with a family, money became a bit more of a priority, and it's hard to get a good job if all you've worked at is small shops. Any next role in a larger tech company will likely be a downgrade until you can prove yourself out, which of course you may not be able to because things are so different, and motivation will run low because you're being tasked with all the stuff that caused you to leave big tech in the first place. It can be quite miserable to be grouped with a bunch of kids with 3-5 YOE that have no idea how to build something from scratch, and they're outperforming you because they know the system.
In my case it took a good five years and a couple job hops to rebalance. But eventually you get back to a reasonable tech leadership role and back to making some of the bigger decisions to help make the junior devs' lives less miserable.
No regrets, but the five years it takes to rebalance can be pretty hard.
I think that my work is honestly the most important factor in my happiness. I spend 8 hours a day (probably for the rest of my life) at work so it's going to be the thing that impacts me the most psychologically in my life.
After realizing that, I decided I'd try as hard as I possibly could to never have to work at a job that I didn't like. I already didn't want kids so that part is easy. The other part of the equation is saving lots of money. I'm not an ascetic by any means, but I live well below my means on a SWE salary which means I can save quite a bit of money each year.
I also recognize that not wanting to go corporate severely limits my options down the line. But capitalism is all about making money for other people. If I can make someone a lot of money, they're not going to care about if I have the chops to stand up a Kubernetes cluster or write a Next.js app or whatever (I hope).
I don't think I'm super smart, I'd say I'm pretty average for this line of work. But I reckon that most SWEs are focused on learning new technologies to get to their next job, or are overly concerned with technical problems. I like to think that I am pragmatic enough about only doing things that are going to deliver business value to make up for being average in smarts.
Anyways, there's not really a point to this rant. These are just some thoughts I have had about optimizing my career for my own happiness, and how I hope I can stay a hot commodity even though I hate working in the cloud and my software skills aren't bleeding edge.
In my case it took a good five years and a couple job hops to rebalance. But eventually you get back to a reasonable tech leadership role and back to making some of the bigger decisions to help make the junior devs' lives less miserable.
No regrets, but the five years it takes to rebalance can be pretty hard.