> contribute to the vision of what could happen next, you're going to hate working under three layers of management, all of which have to be seen to be "doing something," so they tell you how to do your job even though they have no actual idea how to do your job.

This is by far the biggest frustration for smart people. You can't just have so many layers of mediocrity have authority over smart people. When you have so many mediocre people who want to be seen as "doing something", they are literally destroying the innovation by virtue of just existing in that company at that level.

The solution is actually pretty simple - make management track people go on call. That way, they develop empathy for customers, engineers and services. Make them spend less time on committees, promo packets, performance reviews and instead, spend more time on services. Make them fix bugs. Be close to the work that they are supposedly the face of.

I think it also behooves these smart people just to realize that they're not "one company for the long haul" people.

I'm one of the people who likes working in startups. My peers who like working in established companies are appalled by my resume, with 1-3 years each in a handful of different places, often separated by 6-12 months of unemployment.

But I've never had a hiring manager at the kind of startup I'm applying at raise an eyebrow over it.

I think there's a tangential tricky element here too, that most financial advice is written for the masses of people who do have predictable career paths and long-term plans. There's nothing wrong with that. Those people need to have plans too.

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. I could use decent advice, but "be a different kind of person, because the kind of person you are isn't like me" doesn't really help. I'm financially way ahead of my friends in traditional roles, because risk is often rewarded and ownership matters, but I've yet to find an advisor who has the first idea what to do with me.

A bit ironic because oods are the established companies are indeed the ones laying off people (which inevitably targets the 1-3 years more than the 5+ year seniority). If you're not an active detriment to a startup, you're probably not going to get fired unless you get caught in office politics (which can be much more personal and nasty than bigCo politics, admitedly).

>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?

It just seems like there are probably enough of us who do thrive in the early-stage startup atmosphere that someone could make good money targeting that niche with advice. We're different enough to be a subculture, but we're still working within a lot of the constraints of systems that weren't actually designed for people like us.

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.

Is there any company that has tried that idea? Sounds interesting (akin to DevOps).