[web99]

No generic answer to this but one way to think about it is over the long term would you value more depth (expert in something) or breadth (freedom to explore everything)?

If you value depth, specialize. In an industry (e.g security, healthcare, finance, etc.) or field (AI, distributed systems, scaling, etc.) You'll get intellectual satisfaction, emotional satisfaction if you intrinsically care about the space (e.g healthcare), and financial upside since people value specialization.

If you value breadth and wandering, generalize. You'll still get intellectual satisfaction from knowing a variety of things, emotional satisfaction from working on things you care w/o any industry constraints, and financial upside since generalists are valuable to startups and even though their failure rate is high, being in the right company at the right time could give you the same financial upside you'd get from say being at a large company in a specialized field.

I personally chose to speciailize because I value depth and find diving deep into a field more meaningful. I know many generalists with the same amount of experience who are doing equally well and I would hire them and value them in the same way if I built a company again.