> I feel very strongly that everyone should try, to the extent that it makes some kind of sense if you squint hard enough, to do what they want in work and life.
This is much much easier to say after an entire career in tech. However I wouldn't give this advice lightly to people just starting over.
Here is a counterexample. I started my career following my passion and "doing what I love", so I became an academic and joined a university.
After 7 years I was burnt out, broke and hated what used to be my passion. And I had to essentially start over my professional career in the private sector.
These days I don't necessarily always love my day to day job, but I do enjoy more the lifestyle it afford me as a whole.
My takeaway is that earning money and growing your career capital early on has compounding effect over time, and more importantly, it increases your optionality in the future. Going into comedy writing is less scary when you don't need to worry about sustaining your family.