I really like this post. I've been noodling over a lot of similar career questions myself in light of the pandemic. All of a sudden, it became clear that I could just...bootstrap. With the rise of networks like Toptal and Facet, I get access to pretty high quality contracting opportunities and I don't need to commit to a "job" to pay the bills and make my money, which by proxy means I have much more time available than I used to.
Which means I can noodle around on that side business which all of a sudden...costs a lot less than it used to. Wonder how many other folks are in the same boat?