It’s tricky. Taking things to an obviously absurd extreme, being unemployed is clearly not worth $400k/year: people work for far, far less. As you say, longer

It’s tricky. Taking things to an obviously absurd extreme, being unemployed is clearly not worth $400k/year: people work for far, far less. As you say, longer blocks of vacation time definitely open up new possibilities, but perhaps there’s an inflection point: an 11-week trip seems like it’d be very nearly the same as a 10 week one. Things get weird when much of the total comp is in benefits. For example, if your cash salary is $50k, that limits what you can do with your $100k “worth” of vacation.