This 100x. If you go down the route of a generalist (and not just "generalist engineer" but generalist in marketing, engineering, back office, etc.), then you will quickly find yourself unemployable in the traditional sense since you will no longer ft any job description.

Maybe you can still wing it if you have a strong network, but if you plan on being employed rather than running a business, err on the side of being a specialist but keep your eye open for shifts in trends and don't become complacent on your existing skill set.

I'm feeling it. I'm a generalist working as a specialist, saving money until I can take my two related side-projects full-time.

Yup- we'll see what's in store for me if I ever have to go through the bigco PM interview gauntlet again! Not even sure I'll pass the resume screen even if I'm friends with the hiring manager! ;)

Yeah. I'll also need to work on personal branding once I go fulltime because otherwise it will be difficult to get a job next time.

This 100x also. I would just add that both approaches are risky:

You can become a 'Jack of all trades and master of none' without vocation to entrepreneur;

Or you can become a specialist in an outdated or irrelevant skill.

I like this idea. I am leaning more towards the entrepreneur side, because being employed is not my ultimate goal. Good thinking.