The Pete the Planner® Show

Pete and Kristen read a listener email who seems to indicate they greatly regret their recent home purchase

This week on The Pete the Planner Show, Pete, Damian, and Kristen dive into one of the most universal workplace mysteries: why everyone treats HR like a certified financial planner… even though HR can barely tell you which parking pass to choose without checking a binder. Open enrollment, confusing benefits forms, retirement questions—employees fire all of it straight at HR hoping for guidance, cl...

As the calendar barrels toward its final pages, Pete sits down for a solo episode to talk about the strange, sloppy, wonderful chaos of the year’s final weeks. From an economy that can’t decide what mood it’s in, to holiday spending that threatens to turn December joy into January regret, Pete breaks down what Americans are really wrestling with right now — and how to keep your financial head on s...

On this week’s episode of The Pete the Planner Show, Pete tackles what might be the most misguided “solution” to housing affordability ever pitched: the 50-year mortgage. On the surface, it sounds like a clever way to make homes more affordable — smaller payments, easier approval, and a chance for more people to buy. But dig a little deeper, and it’s clear this “innovation” is really a long-term f...

This week, Pete is joined by veteran podcaster and political enthusiast Chris Spangle to wrestle with the myth and the muscle of willpower. Why do we think it’s the key to every success story—money, fitness, food, or habits—when in reality, it often lets us down? Pete and Chris explore how environment, emotion, and even exhaustion can overpower our best intentions. From political discipline to per...

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, ho...

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 y...

💥 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...

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 —...

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 un...

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 Dre...

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,...

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...

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 differe...

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 seemi...

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...

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...

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 retiremen...

After 40 years of saving diligently, listener Jeff is retiring next month—and like many new retirees, he’s asking the question the industry rarely answers: How do I actually spend my 401(k)? In this episode, Pete and Damian walk through the critical decisions that come after the last paycheck: how much to withdraw, which accounts to pull from first, and how to invest your portfolio for a retiremen...

This week on The Pete the Planner Show, we tackle a question from a listener couple in their 30s who’ve nailed the basics—no debt (besides the mortgage), a healthy emergency fund, steady retirement savings, and even monthly money check-ins that end in high fives, not fights. So… do they really need a financial planner? We dive into when DIY is good enough—and when a second set of (professional) ey...

This week’s episode begins with a heartfelt listener question that cuts to the core of a topic we all tend to avoid—death, and the financial planning that surrounds it. Pete, Kristen, and Damian explore whether prepaying for funeral arrangements is a sound financial decision—or an expensive emotional shortcut. With compassion and clarity, the team breaks down the pros (like locking in today’s pric...

Congress just dropped the “One Big Beautiful Bill” (yes, that’s really what they’re calling it), and it could reshape everything from your paycheck to your student loans. In this fast-moving episode, Pete, Kristen, and Damian unpack what OBBB actually is—and more importantly, how it affects you. Segment 1 sets the stage: from expiring 2017 tax cuts to new SALT caps, we simplify the headlines and h...

When the market is a rollercoaster and headlines won’t stop screaming, even the savviest investors can start second-guessing everything. In this episode, Pete, Damian, and Kristen unpack what confidence in investing actually means—and how to build it, rebuild it, and protect it when doubt creeps in. Segment 1 kicks off by normalizing the fear that even seasoned investors feel, especially in today’...

Summer break is here—which means your kids are home, your fridge is empty, and your wallet is… nervous. In this episode, Pete, Kristen, and Dame explore whether the old rules of teaching kids about money still hold up, or if today’s world demands something new. From toddler toy budgets to teen summer job paychecks, we break down how to raise money-smart kids without turning into a lecture machine...

In this episode, we tackle a sneaky problem: confusing financial motion with actual progress. Just because you’re constantly doing money-related tasks—paying bills, checking balances, moving money around—doesn’t mean you’re getting ahead. Pete opens with a gym analogy that hits a little too close to home, then brings in Kristen and Dame to break down why so many people feel stuck despite their eff...