Episodes

  • Financial Red Flags That You Think You Get Away With

    Financial Red Flags That You Think You Get Away With
    Sep 5 2025
    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.
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    1 hr and 6 mins
  • I just moved and I think I regret it

    I just moved and I think I regret it
    Aug 29 2025
    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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    1 hr and 4 mins
  • Midlife Money Panic

    Midlife Money Panic
    Aug 22 2025
    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.
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    1 hr and 4 mins
  • Does downsizing your house always make sense?

    Does downsizing your house always make sense?
    Aug 15 2025
    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.
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    1 hr and 8 mins
  • Should I buy a house with my in-laws?

    Should I buy a house with my in-laws?
    Aug 8 2025
    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.
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    1 hr and 9 mins
  • How Do I Spend My 401(k)? Turning a Lifetime of Saving Into a Retirement Paycheck

    How Do I Spend My 401(k)? Turning a Lifetime of Saving Into a Retirement Paycheck
    Aug 1 2025
    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 retirement that could last 30+ years. From the 4% rule to bucket strategies and tax-efficient withdrawal planning, we’re breaking down the complex into the practical. Whether retirement is right around the corner or still a decade away, this episode will help you think differently about what it means to turn savings into sustainable income.
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    1 hr and 13 mins
  • DIY Financial Planning: Can You Really Do It All Yourself?

    DIY Financial Planning: Can You Really Do It All Yourself?
    Jul 25 2025
    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) eyes might help you uncover what you don’t know you don’t know. Whether you love spreadsheets or break into a cold sweat at the word “fiduciary,” this episode will help you figure out if it’s time to level up your planning—or if you’re already crushing it on your own. You’ll learn: The tipping point between DIY and delegation What a financial planner can (and can’t) do for you How to avoid blind spots even when you're doing everything "right" It's a practical, honest conversation for anyone who's ever wondered: Do I need help, or am I just fine?
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    1 hr and 14 mins
  • Let’s Talk About the Thing No One Wants to Talk About -- Funerals

    Let’s Talk About the Thing No One Wants to Talk About -- Funerals
    Jul 18 2025
    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 prices and reducing stress on loved ones), cons (think: lack of flexibility and risk of mismanaged funds), and alternatives (including payable-on-death accounts and funeral trusts). We also explore Medicaid planning implications and what to watch for if you're in a state like Indiana with specific caps. Then in Segment 2, it’s Estate Planning 101—without the intimidating legalese. What documents matter most? Why is this an act of love, not just a legal to-do list? The trio walks through wills, powers of attorney, healthcare directives, and the often-overlooked step of updating beneficiaries. Finally, we wrap with the emotional labor of planning ahead. Why is it so hard to talk about money and mortality with family? How do you start the conversation without freaking everyone out? We offer gentle scripts, relatable stories, and encouragement to be the planner your future self—and your family—will thank. You’ll laugh, you’ll cry, and—if we do our job—you’ll make at least one meaningful step toward peace of mind.
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    1 hr and 13 mins