For example, I've searched for but never been able to find actual advice about how to think about private company stock options. Everybody ends up writing them off with a, "Well, there's a decent chance they won't be worth anything, so just ignore them and try to operate within the world we do understand." Nobody quantifies the risk. Nobody talks about how to hedge against it prudently. Nobody talks about what to do when the piddly little number of shares the company tossed you as a customer support agent are suddenly worth half a million dollars and are a life-changing amount of money, never mind what to do if you had a real stake. Nobody talks about how to evaluate which early companies do have a strong shot at "making it" and which ones are doomed.
It's not impossible to think these things through and evaluate them. It's just hard, and not mainstream. For those of us for whom "instability" is a feature, not a bug, advice from someone who gets that and thinks it through would be infinitely more valuable than advice from the hordes who tell us we should just try to be different.
>But there's not much written for the people who know they're going to be in and out of work, how to maximize each while preparing for the other, stuff like that, and I wish there were.
like you said, a lot of financial advice is based on stability. The job hop strategy is inherently unstable. No traditional advisor is ever going to suggest going into a job with the mindset to quit in 2 years for better job.
It's also because it's an inherently unique bubble that is tech. Tech moves fast , blazing fast. You can have 3-4 different domains under your belt in a decade if you wanted, whereas you may not even be considered a master of a particular domain if you spent 10 years in more traditional prestige like doctors or lawyers (if you count school you'd just barely be starting in such careers!). And even in tech this is a pretty recent trend isolated to the mid-00's to now (minus a few housing crisis years). the oldest authority exposed to such trends would either be retired and still have spent most of their lives pre-boom, or still currently in the workforce. There's no formal advisor available yet.
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I say all this as someone who wanted to be a "long haul" type. I wanted to be that deep domain tech guru to uncover the various secrets in my field. The reality is I just get laid off every 2-3 years. so what's even the point?