There’s a lot packed into your 20s. You’re getting an education — formal or otherwise. You’re figuring out what you believe about work, money, relationships, success, and who you want to become. Sure, that process doesn’t stop at 30, but your 20s are especially formative. And there’s no shortage of advice aimed at young adults. Commencement speeches. Career gurus. Personal finance influencers. But a lot of it misses the deeper question of what actually matters. And in a world full of noise, it’s getting harder to separate wisdom from status signaling. Today we’re joined by Jack Raines. He’s a young guy who made some pretty countercultural choices — walking away from prestigious jobs, big paychecks, and conventional definitions of success to build a life on his own terms. His new book, Young Money, is part memoir, part guidebook for the generation coming behind him and today we discuss:

• Embracing risk in your 20s
• Balancing financial responsibility and enjoyment
• Avoiding mindless toil
• Recognizing meaningful work
• FIRE as a mental illness
• Different goals for different life stages
• Why Jack believes “Am I having fun” is the most important question
• And much more!

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