The Pete the Planner® Show

Latest Episodes:

The truth about a mid-life crisis Oct 31, 2025

Show notes

Forget the convertible and the questionable haircut — the real midlife crisis happens when you open your retirement account and realize the math isn’t mathing. In this solo episode, Pete explores the emotional and financial crossroads that hit in your 40s and 50s — when time feels shorter, careers plateau, and money goals start bumping into real life. He unpacks why financial growth slows down, how priorities shift, and what to do when your sense of progress feels stuck on pause. From redefining success to right-sizing your lifestyle, this episode is part therapy session, part pep talk, and entirely relatable. Key takeaway: Your midlife crisis isn’t a breakdown — it’s a recalibration.

Spotting financial advisor red flags Oct 24, 2025

Show notes

Most people don’t know how to tell if their financial advisor is great—or just great at sounding confident. In this episode, Pete and Dame unpack the real red flags to watch for when you’re getting financial advice… without turning it into a witch hunt.

They’ll break down the difference between a bad actor and a bad fit, decode advisor-speak (“We’ll rebalance with a tactical overlay!”), and show you how to spot when someone’s more interested in selling than solving. Plus, they’ll explain what good advice actually feels like—clear, consistent, and curious about your life.

This isn’t an “advisors are evil” episode. It’s a smarter take on how to protect yourself and still believe in the power of good guidance.

AI vs Two Money Guys Oct 17, 2025

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💥 This week, Pete and Damian face off against their newest (and possibly most intimidating) competitor: Artificial Intelligence.

Can two seasoned money nerds outthink an algorithm? In each round, Pete or Dame tackles a real financial dilemma — from whether to raid an emergency fund to pay off debt, to deciding between a Roth or traditional 401(k). Then, they read the AI’s answer and debate which response wins on accuracy, empathy, and practicality.

It’s human experience versus machine logic — and the results might surprise you. Who gives the better advice: the pros with decades of experience or the robot with instant access to infinite data?

Tune in for laughs, sharp insights, and a fresh look at the future of financial guidance.

🎧 Featuring rounds like “The Credit Card Conundrum,” “The Roth Riddle,” and “The College Crunch.”

👾 Man. Machine. Money. Only one can win.

Why Smart People Do Dumb Things With Their Money Oct 10, 2025

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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. We’ll share real-life examples of “smart” money mistakes — from chasing complex investments to ignoring basic budgeting — and discuss why simplicity often wins. Plus, we’ll reveal the subtle ways our brains trick us into believing we’re the exception to every financial rule. 💡 Being smart with money isn’t about IQ — it’s about self-awareness.

When supporting your adult children turns bad Oct 03, 2025

Show notes

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.

If financial nihilism a thing? Sep 26, 2025

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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.

When Cash Feels Like a Burden Sep 19, 2025

Show notes

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.

The Delusional Retirement Confidence of Americans Sep 12, 2025

Show notes

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.

Financial Red Flags That You Think You Get Away With Sep 05, 2025

Show notes

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.

I just moved and I think I regret it Aug 29, 2025

Show notes

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.

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