Skip the sympathy for millennials and Gen Z—they'll figure it out. The real story? Those hitting their 50s are staring down a completely different beast. Career disruption, stagnant pensions, late-stage inflation eating into savings, and the pressure of supporting both aging parents and struggling adult kids. Meanwhile, younger folks at least grew up digital-native, adapted faster to market shifts. It's the in-between generation catching the worst of both worlds—too old to pivot easily, too early to have built sufficient wealth buffers. That's where the real squeeze happens.