Great article by the way, I really resonated with the line: "Your job at Google used to impress people. Now, when people ask about your work, you awkwardly tell them, “Um, it’s a website where you type a food, and it tells you whether it’s keto…” Shouldn’t you do something that sounds more impressive?"
I've had this thought (about my own projects) all too often
"My living expenses were rapidly eating away at my personal savings. Between my $3.3k/month Manhattan apartment, private health insurance, food, and utilities, it cost $6-7k per month just to sustain myself."
If my experience (in California) is anything close, it costs somewhere around $500/mo for a single person his age. (If you have a spouse it gets up to around $1000/mo, and with kid(s) it goes up to about $1500/mo) This was 2013-2016 numbers, and was also with Covered California, not sure if that makes it any cheaper.
Further, a lot of people don't realize that employers get a discount on providing health insurance because they have a pool of people over which to distribute a bunch of uncertainty. When you buy individual insurance, the "pool" is you (and maybe any of your dependents), and the insurance companies charge you "full" price.
In NYC, I used Oscar for health insurance, which was $500/mo. In MA, plans are much cheaper, so I only pay $250/mo here.