Well, there's only so much time I can spend on the internet convincing someone with an oversized sense of their own success that they're doing it wrong, so I'll try to be brief and I wish you all the best after this interaction.
If we're being frank, if the idea of picking a lane is doing something well, by choosing both lanes, you've actually chosen neither lane.
1. You are clearly not independently wealthy enough to have to never work again; otherwise you wouldn't care about "subsidized health insurance / contribute to an HSA" (both of which are things that the independently wealthy couldn't care less about), so either you are a) making up achieving outsized exits as a financier and you never actually achieved it, or b) worse, you made the outsized exit, became independently wealthy, and due to fiscal irresponsibility lost your position of independent wealth
2. You clearly aren't in a stable career position at a company with a long tenure steadily moving upward seeing as how you ended up having to take a job at a company with incompetent leadership that ultimately ended up firing you for making ultimately a reasonable suggestion
If anything, I think you have proven my point which is that you very much do need to pick a lane. There's the old saying that "startups don't die of starvation, they die because of indigestion" owing to the common and real risk of overly broad scope and dilution of focus. I think that same warning applies equally to careers -- your dilution in long-term focus may have played a role in you not achieving the success you might otherwise have been able to achieve. But I can't tell you for sure. Only you will be able to figure out that answer. And in order to figure out that answer, you have to be willing to be honest with yourself.
Best of luck.
