Ever notice how the smartest people you know sometimes make the worst financial decisions? In this episode, Pete Dame unpack why intelligence doesn’t always translate to good money habits. From overconfidence and analysis paralysis to emotional blind spots and ego-driven decisions, we explore the psychology behind financial self-sabotage.

This week on The Pete the Planner Show, we’re tackling one of the toughest money dilemmas families face today: when helping your adult children turns into hurting yourself. A listener writes in about her 31-year-old daughter who still lives at home, contributes nothing financially, and has become the center of a tug-of-war between supportive love and enabling behavior.

Pete, Kristen, and Damian unpack the concept of financial enmeshment—those blurred parent/child roles where support becomes indefinite, boundaries vanish, and retirement plans quietly suffer. Why is this happening more than ever? Sky-high housing costs, student debt, and the return of loan payments all play a role, but so do fear, guilt, and a desire to shield kids from failure.

We’ll explore the emotional conflict between partners who disagree on rules, the hidden cost of Parent PLUS loans, and why “support without structure is just deferred conflict.” Then, we’ll lay out practical tools for parents: aligning as a couple, having honest conversations with adult kids, and creating a phased transition plan that respects both love and limits.

If you’ve ever wondered where generosity ends and enabling begins, this is an episode you won’t want to miss.

Young adults are increasingly turning to risky bets — sports gambling, meme stocks, crypto, even leveraged ETFs — not just for the thrill, but because traditional wealth-building feels out of reach. In this episode, Pete, Damian, and Kristen dig into the rise of “financial nihilism,” a mindset fueled by housing costs, student loans, job market uncertainty, and fading confidence in the American Dream.

We’ll unpack the CNBC stories of 20-somethings chasing fast money on Discord and betting platforms, explore whether these strategies are truly new or just speculation repackaged, and debate whether they’re desperation or savvy risk-taking. Finally, we’ll look at healthier alternatives: ways to channel risk appetite without blowing up your future.

Because when people stop believing in long-term financial security, they don’t stop trying — they just look for shortcuts.

Claire and Ethan, a newly married couple in their early 30s, are sitting on $450,000 in cash after selling property and combining finances — and instead of feeling secure, they’re feeling anxious. With a baby on the way, strong incomes, no debt, and a net worth north of $2 million, their dilemma is how to balance competing goals: buying a home, investing for the future, keeping travel flexibility, and raising their child.

In this episode, Pete and Dame break down the psychology of “too much cash,” explain how to bucket money by time horizon, and show why timing often matters more than returns. They’ll also walk through the conversations every couple should have when life goals collide with financial uncertainty. If you’ve ever wondered how to turn money stress into money direction — whether you’ve got $4,500 or $450,000 — this episode is for you.

Americans are feeling strangely upbeat about retirement — maybe too upbeat. A new survey shows confidence is soaring, with fewer people saying it will take a “miracle” to retire comfortably. But optimism fueled by a hot stock market can be a dangerous thing if it leads to complacency. In this episode, Pete and the team break down the new retirement mood, the hidden worries still keeping people up at night, and the math behind what it actually takes to stop working for good. From the half-million-dollar savings gap to the real meaning of the 4% rule, this conversation cuts through the delusion and gets to what matters: how to build a plan that works even when the market doesn’t.

Are all financial red flags truly dealbreakers? Not necessarily. This week, Pete and the team dig into the money habits that look risky on paper—but can actually be fine if managed with discipline. From Buy Now, Pay Later to car leases to living paycheck-to-paycheck, we explore the nuance between a red flag in isolation and a pattern that leads to real trouble. You’ll learn how to spot the difference, set guardrails, and balance risks with financial strengths. Because sometimes the red flag is just a reminder, not a reason to panic.

When love and real estate collide, things can get messy. A new listener writes in after moving into their partner’s home—a home that’s been theirs for nearly a decade, kids and all. The couple is serious, even planning to elope, but the money side of the relationship? Totally unplanned.

How do you contribute fairly when you don’t technically own the house? How do you protect yourself without seeming selfish? And what conversations should couples really have before moving in together?

Pete and Kristen unpack the unwritten rules of cohabitation, from cohab agreements to avoiding the “floating system” trap. Whether you’re dating, shacking up, or already living in a blended household, this episode explores the fine line between romance and responsibility—because building a future together requires more than just sharing groceries.

This week’s listener email comes from a 40-something who admits they’ve fallen behind on retirement savings—and they’re wondering if it’s too late to catch up. Pete and the team tackle the emotional weight of realizing you’re behind, the math of what’s still possible, and the practical moves to make right now. From cutting expenses and boosting savings, to making the most of peak earning years and catch-up contributions, we’ll show how to turn midlife money panic into a realistic plan for retirement.

Downsizing sounds like a simple way to save money—sell the big house, pocket the cash, live leaner. But real life isn’t that tidy. In this week’s episode, Pete, Damian, and Kristen unpack the hidden math, emotional pull, and lifestyle trade-offs behind the “should we move?” question. From rising taxes and leaky roofs to property tax freezes and priceless neighborhood ties, we dig into when staying put might secretly be the better deal—and when it’s time to pack the boxes. Plus, we explore creative options for making your home (or your housing budget) work harder without automatically going smaller. Whether you’re a retiree with an empty nest or just wondering if your house fits your future, this conversation will help you decide what’s truly right for your wallet and your well-being.

When one listener gets a job offer in the Midwest with a 40% pay bump, it sparks more than just career contemplation—it opens the door to a bold family experiment: combining households with the in-laws. In this episode, Pete, Kristen, and Damian tackle the emotional and financial complexities of multigenerational living. From structuring ownership and avoiding sibling drama to protecting retirement assets and managing expectations, we walk through the pros, cons, and creative setups that can make this kind of arrangement work.

Spoiler: Loving your in-laws might be easier than figuring out who pays the property taxes.