[RandomOpinion]

It's a good idea, in principle; I've seen people who stayed too long in rest-and-vest environments become completely unable to function when the gravy train ended.

The key questions you should be asking yourself is whether you're ready to withstand the stress of being "the dumbest guy in the room" (it's hard on the ego, to say the least), whether you're willing to make the commitment to learn an enormous amount of material in a relatively small amount of time, and whether you can come up to speed with the people in your new environment fast enough to avoid being penalized or even potentially laid off (having a financial cushion or some other backup plan in case things don't work out would probably be a good idea).

[tluyben2]

People who rest and vest hopefully would not care when the gravy train ends? You would have enough money to never work right? If not, why would you rest and vest? It is a waste of time then?

[toocool]

Not necessarily. If you would otherwise earn X in a fulfilling job but by resting and vesting in an unfulfilling environment you make 3X because of the vested equity, it might make sense to stay a few years in the latter and try to not completely waste your time by, for example, keeping learning other technologies not related to your actual tasks with the hope of remaining somewhat competitive. It's not "never work again" money, but it certainly can make a difference towards an early retirement.

[tluyben2]

Fair enough but would it not make sense doing something on the side which makes you learn new things? I guess I cannot imagine sitting still.

[muzani]

Also in some cases, you are morally bound to work on the startup when you've recovered and not waste time programming some side project. But too burnt out to code at all.

So, what many do is neither of the above - they read books, play games, have meetings, or some other time filling activity.

[toocool]

Agreed. In my case the side project was preparing 4 months to interview at the big 4 companies, and I interviewed with 3 of them and luckily got 3 offers :)