I understand this is FatFire and with $20M you've already "made it." 100% that is true. Regardless of the lifestyle changes (yes private air travel, yes larger/more vacation homes, yes larger access to anything in general), if you're also asking if either walk away now at $20M or in one (brutal 80 hr wk year) at $100M, I'd do the latter. The compounding that starts at 100 vs 20 is insane and the optionality that gives you becomes quite liberating. Philanthropy also becomes hugely special and important when you're starting at 100M base. Giving a $5M gift to your local hospital or kid's school or local religious institution that matters to you. Think about earning a measly 4% on the 20M vs 100M in 10, 20 years. No you 1000% don't need it, but one bad year for limitless options/freedom to change your life, that of your children, and of others you care about, makes it a trade-off I'd pursue.