All equity comes with risk. Doubly so for the type of equity that generates a lot of wealth. Stability is nice, but expect to pay through the nose for it. The only real exception I can think of are people with exceptional talent in an exceptionally in demand skill. E.g. Tom Brady or Linus Torvalds or a world-class neurosurgeon.
> His fortunes changed in 1999. Red Hat and VA Linux, both leading purveyors of Linux-based software packages tailored for large enterprises, had granted him stock options with no strings attached, thank-yous from entrepreneurs who hoped to grow rich off his creation. When Red Hat went public that year, Torvalds was suddenly worth $1 million. On the day VA Linux (now VA Software) went public, Torvalds was worth roughly $20 million, though by the time he could sell his shares, they were valued at only a fraction of that.
> Torvalds hesitated before buying himself his first expensive bauble, a two-seater BMW convertible. "I was a bit nervous about people's reaction," he confesses. "Are they going to think I've gone over to the dark side?" In the end he decided that the shape and price of the hunk of metal he drove to and from work each day was his own business. Despite counsel to the contrary, Torvalds wisely sold all of his stock and spent almost all of the windfall on his home and his cars, trusting that he'd always be able to earn a good salary as an engineer.
https://web.archive.org/web/20031127045640/https://www.wired...
If you're willing to take the short-term cap gains hit you can sell your stock immediately after vesting and reinvest in a total market index or w/e aligns with your investing philosophy. If we're talking hard numbers, you'd still be pulling in 150-200k+ in base salary/cash and let's say, in a non-ideal situation, what would've been your $125k of annual stock vest is now worth 30% less - still not a bad deal IMO.