Does more money make life easier, or does it just give you more expensive problems to solve? Most people assume that once they start earning more, their financial life will finally calm down and organize itself. Then they get the raise or the promotion or the business success, and somehow things feel just as chaotic as before, just with bigger numbers involved. Joe Saul-Sehy is joined by Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and OG to explore why "more" isn't always "simpler." The crew digs into early money mistakes they'd all like to forget, the weird psychological traps that show up as income grows, and why your brain doesn't automatically upgrade its money management skills just because your paycheck did. The conversation gets real about the hidden mental challenges that come with wealth growth. Decision fatigue gets worse, not better. Lifestyle creep sneaks in wearing a very convincing disguise. And suddenly you're agonizing over choices that used to be simple, because now you can afford multiple options and none of them feel obviously right. If you've ever wondered why your financial life didn't magically self-organize the moment you started earning more, this roundtable has your answers. The crew also tackles listener questions about building budgeting habits that actually stick, finding genuine financial confidence, and creating systems that scale with your life instead of working against it. Because the goal isn't just to make more money. It's to build a life that feels manageable and intentional at whatever income level you're at. Plus, Doug delivers a trivia showdown featuring fierce competition, questionable strategy, and what might be the most overthought trophy dilemma in basement history. What You'll Walk Away With: • Why more income doesn't automatically reduce financial stress and often creates new complications • The hidden mental traps people fall into as their wealth grows and how to spot them early • How Paula, Jesse, OG, and Joe think about building lasting financial confidence at any income level • Practical budgeting strategies that work whether you're making $50K or $500K • Why simple pleasures matter more (not less) as your money grows • The surprising ways earning more actually complicates everyday decisions • Listener Q&A on habits, organization, and creating systems that smooth out financial chaos • Permission to admit that making more money didn't solve everything like you thought it would This Episode Is For You If: • You're earning more than you used to but somehow don't feel more in control • You assumed financial stress would decrease with income but it just shifted to different problems • You're stuck between multiple good options and can't figure out why that's so paralyzing • You want to hear successful people admit that more money created complications they didn't expect • You're building wealth but want to make sure you're also building a life that feels good Before You Hit Play, Think About This: What's one financial decision that got harder (not easier) as you started earning more money? Drop your answer in the comments because this roundtable proves you're definitely not the only one experiencing this paradox. Learn more about your ad choices. Visit podcastchoices.com/adchoices