I think to some extent there are always unknowns and there's a risk you'll choose wrong, but it's worth trying to choose correctly. In hindsight from your example it was a mistake not to do computers, your ROI calculation turned out to be short-sighted because of proximity to 99. Same thing might have happened to me had I been there at the time, it's hard to make the right choice in that kind of environment.
That's ignoring the cost of the research and planning, though. Even if that cost is only time + brain power that could be used on something else, in opting to engage in occupational planning, that time isn't being spent on something else.
> Same thing might have happened to me had I been there at the time, it's hard to make the right choice in that kind of environment.
I'd say for most people (but not most people at HN because the tech community is pretty unique in terms of labor relations), occupational planning is more akin the tech career planning in 99 where there are numerous big unknowns hitting people constantly (COVID, 08, etc.). Our informational environment is TERRIBLE to build a decent ROI model. Doing so would take the average person so much time to research and build that I think right now it's better to spend the time either:
a.) Planning outside of the current systems and their incentives. For example, I'm supplementing my conventional retirement savings by handing out a LOT of free money locally. Even if the stock market crashes in my 60s and I lose everything (which, based on my lifetime, will probably happen bc it always does...), hopefully there will be at least a few people/families/organizations around that view me kindly and will help (if 2000 people give me a dollar a month, I can make rent). This is also likely to be true even if society completely collapses, provided I'm alive.
b.) Focus on building better heuristics for reacting to sudden change and pivoting. Our culture and society doesn't care about being stable and will always change to chase the latest profit/dopamine hit, so instead of making plans that require and assume stability is possible and that the past is predictive, it's better to accept the future is NOT predictable and spend one's energy on building a great skill set to be flexible. Bending instead of breaking.
I can't find any agreement on who first said that, but it appears that several great generals have said something like that.