I would say this depends on what your aspirations are as a consumer and member of the economy (and apologies if this is a tangent, feel free to ignore). The ex

I would say this depends on what your aspirations are as a consumer and member of the economy (and apologies if this is a tangent, feel free to ignore). The explicit assumption in the OP is that you achieve this freedom though some form of large payoff. But how about achieving this freedom through a ratio, rather than a lump sum. For me, this is the ratio of how many days I need to work to earn a month's rent (currently 0.5 days for 1 months rent). This figure embodies both my earning power, and how much I need the money. I could become 'freer' (from work) by downgrading my living standards, or I could find a way to earn more per day. But, importantly, working more will not change this ratio. Of course, if learning to fly an airplane is your thing, then you could substitute rent for flying lessons.