Now since about four years, I'm a freelance interim CTO and help companies that struggle inside and around the product development department.
What was the hardest hurdle to take when making the transition?
The switch to freelancing also sort of came naturally - a permanent job stopped very abrupt, and a headhunter that helped me find developers before approached me with the idea, because he had a customer who needed help.
I guess you also have to be "management material". Either you can do it or not. To a certain degree, you can learn management stuff, but honestly you have to be that kind of person.
Jus out of curiosity, what exactly do you mean by that kind of person.
Now I'm really intrigued by what it takes to get "freelance interim CTO" jobs - and whether this is with tiny one-person shops (where the CTO is also "the developer"), middle-size businesses (10-50), or enterprises that lost an executive to poaching or illness and need someone to plug the gap until their headhunter's got a new one lined up.
Right now, it's mid size businesses with 50-75 FTE product development departments, but when I will be 50+, I want to get also projects at bigger companies :)
I now analyze public policy for hedge funds.
Personal connections (even tenuous) make all the difference. One approach is to pick a vertical in which you have a secular interest that is unlikely to flag (e.g. finance for me), and be open to making the most of opportunities that might have non-obvious embedded call options. Then look for opportunities to be informally helpful to people working in that vertical (if starting at 0, look for a meetup or other public event to attend).
This can often look like a lateral or downward move to a job at which your outperformance is likely. In most analytics or adjacent roles there is still plenty of low-hanging fruit for automation, which frees up your time to add value on domain problems.
YMMV, but I found it helpful to not highlight the automation work (in fear of being pegged the "tech" guy). Instead, using the earned time to do exploratory analyses on root causes (or sensitivity or whatever) paid real dividends. Adding that kind of value has its own gravity, and my experience was that it opened other opportunities.
A friend of mine recently bailed out of software and is now a qualified mountain leader.
Having technical knowledge, yes. Very big plus. Not every developer has the other aspects of a Product owner or Product manager though.
I was a decent software engineer to boot but never really got into the super technical side of things. I enjoyed working with people and speaking to them about how technology can help solve their problems - hence, the role switch.
To scratch my itch, I do a bit of dev/machine learning work.
One of my buddies was a linux admin, but now he blows glass and does custom stained-glass windows. Still has a website and does other techy stuff but mostly just playing w/ fire and sand last I heard.