I'm a millennial with boomer parents. Both got advanced degrees. Both ended up working in tech. Both ended up getting laid off and struggling to find a job again, partly because they were "overqualified" for many jobs. A takeaway for me was that if getting a good education and getting a responsible 9-5 job aren't going to guarantee success and stability, I might as well go after a career that makes me happy. In my case, comedy and writing.