I would rather think hard about all possible easier pivots before thinking about a whole new career because I feel stuck. If your father were pushed by his pas

I would rather think hard about all possible easier pivots before thinking about a whole new career because I feel stuck. If your father were pushed by his passion for programming, then I could advise differently, but that does not seem the case. Can't you both think about creative ways to leverage his decades of experience as a top manager? Could it be that he is stuck in an employee's mindset and that's the true differentiator against your success? If so, why not help him in switching mindset instead? If everything else fails, then - sure! - why not go for the programming route... Becoming proficient at programming takes lots of time, but he would have the advantage of your mentorship. And as for our industry's ageism, screw it! I would just team up, be the "young face" of our duo and customers would be none the wiser about 50% of their software being written by a geezer. Oh, well... that's what I would if I were young. Good luck ;-)