I think to the OP's point, if you are truly engaged in your work (and assuming your work carries healthcare benefits), it becomes a somewhat moot point to optimize for healthcare costs at some future age. I think your point on losing healthcare is predicated on the idea that you want to work less in the future (presumably in some job that doesn't carry those benefits).
I think part of the issue is that society in general (and tech in particular) are extremely productivity-focused which trains you to be future-biased in your thinking. Everything becomes about preparing for the next milestone rather than, as the OP advocated, optimizing for the present period of time.
> your point on losing healthcare is predicated on the idea that you want to work less in the future
No, it is predicated on the increasing probabilities of illness and injuries as one ages, as well as age discrimination resulting in more difficulty obtaining a job with sufficient pay and health insurance benefits.
To the OP's point, if you've optimized for engaging work and if you don't want to work less, you're already in a job that you want to continue working in. Your point is that you want to job-hop to get more money to pay for benefits...that you already have?
I've shared this elsewhere, but it's like the story from Oliver Burkeman's book about the NYC businessman chastising a Mexican fisherman for spending too much time on the beach drinking wine with friends instead of growing his fishing business. When the fisherman asked, "And once I have all that money from growing my business, then what should I do?" and the businessman said, "Well, then you can spend your time drinking wine on the beach with your friends."
> Your point is that you want to job-hop to get more money to pay for benefits...that you already have?
No. The goal is to be able to secure desired resources without needing a job, i.e. having enough wealth to not have to work in the event that I am unable or unwilling to work.
What am I supposed to do if my wife or I get hit with a cancer diagnosis in mid 50s?
The fisherman and NYC businessman story is missing the volatility component of life. Hence the utility of markets for futures trading, etc.
Fair enough, amend my first response to say it’s predicated on the desire for the option to work less in the future. The same concept applies, though. You’re optimizing for some future event while the OP was optimizing for something different. That is somewhat different than your post about the goal being "sufficient pay and health insurance benefits." Those you'd most likely already have without job hopping, even if your spouse gets sick.
There's probably something to be said about the systemic causes that create an environment where even tech workers are so financial insecure as to foster that mindset, but that’s a digression.
I think part of the issue is that society in general (and tech in particular) are extremely productivity-focused which trains you to be future-biased in your thinking. Everything becomes about preparing for the next milestone rather than, as the OP advocated, optimizing for the present period of time.