But that is a large problem today, because you have no idea when, if ever, the liquidity event is going to happen. There are companies that spend a whole lot of

But that is a large problem today, because you have no idea when, if ever, the liquidity event is going to happen. There are companies that spend a whole lot of time private, and if said company is going well, it's going to be growing so fast that in 4 years, it might be unrecognizable. Even if you love the job you joined, you might hate the equivalent a few years later, and you probably still don't have a liquidity event. Quite a few years ago, a well known company was sending offers where the exercise cost of the shares was around $200k, plus whatever fun you'd have with AMT at exercise time. The company still hasn't seen an IPO, and I know quite a few people that didn't exercise their entire allocation just because it was just way too expensive for something illiquid... and that was with a company that was going (and still is!) going very well. Today you'll find companies that went for a decade without a liquidity event, and where a whole lot of options that were well in the money went back to the company, unused. Options would be far more worthwhile if there was a standing offer to, on departure, sell the options back to the company at departure time, but we all know this isn't how it works. So you end up in situations when two people join a company and leave at the same time, and their savings separate their final outcomes by 8 figures, because one could buy the shares and wait the necessary X years for the liquidity event, when someone else couldn't.