> It was always worthless Options that could never be sold. One company's options I worked for 6 years, was worth about 4K after taxes, fully vested. There's y

> It was always worthless Options that could never be sold. One company's options I worked for 6 years, was worth about 4K after taxes, fully vested. There's your problem. Getting paid in options is the exact mistake I've warned about repeatedly in comments throughout this thread. Yours is a fairly common case in SV: worked in a series of startups that "paid" you in illiquid options that ended up being totally worthless. I'm willing to bet these very same startups encouraged you to value these options very highly: high 6 and even 7 figures, right? These places don't pay well, because why should they? Talent is apparently willing to work their ass off for these "worthless options" that are sold to them as vouchers for surefire multi-million-dollar jackpots.