The Pete the Planner® Show

Latest Episodes:

Midlife Money Panic Aug 22, 2025

Show notes

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.

Does downsizing your house always make sense? Aug 15, 2025

Show notes

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.

Should I buy a house with my in-laws? Aug 08, 2025

Show notes

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.

How Do I Spend My 401(k)? Turning a Lifetime of Saving Into a Retirement Paycheck Aug 01, 2025

Show notes

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.

DIY Financial Planning: Can You Really Do It All Yourself? Jul 25, 2025

Show notes

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?

Let’s Talk About the Thing No One Wants to Talk About -- Funerals Jul 18, 2025

Show notes

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.

You down with OBBB? Jul 11, 2025

Show notes

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 help you emotionally prepare for what’s coming at tax time. Segment 2 dives into the biggest student loan shake-up in a generation: new repayment plans, forgiveness tweaks, and tighter borrowing limits that could change how families approach college altogether. And in Segment 3, we highlight the under-the-radar changes: boosted child tax credits, deductions for tipped workers, Social Security tax relief, and new Medicaid work rules you need to know. Whether you’re a student, a parent, a retiree, or just trying to keep up—this episode is your guide to navigating the chaos with clarity (and a few laughs along the way). Call to Action: What’s the one part of your financial life you hope this bill improves—or doesn’t mess up? Let us know!

How to trust your portfolio over the long haul Jun 27, 2025

Show notes

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’s world of economic whiplash and geopolitical uncertainty. Then in Segment 2, the team breaks down the four pillars of a trustworthy portfolio—clarity of purpose, evidence-based design, behavior as the engine, and regular (not obsessive) reviews. Finally, Segment 3 offers practical tools to reset your mindset when confidence takes a hit. Whether you’re a hands-on investor or someone who treats their 401(k) like a haunted house, this episode will help you shift your focus from predicting the market to trusting your plan. Because calm isn’t magic—it’s a skill.

Are the Rules for Teaching Kids About Money Different Now? Jun 20, 2025

Show notes

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 (or losing your mind). You’ll learn how to:

Use summer moments as money teaching tools
Talk to kids at different ages without getting eye-rolls
Help teens manage their own money—without a meltdown
Equip them for real life, not just allowance life

Plus, the team shares their favorite (and most hilarious) wins and fails from teaching their own kids about money.

Are You Actually Making Financial Progress… or Just Busy With Money? Jun 13, 2025

Show notes

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 efforts.

We explore what real progress looks like—both on paper and emotionally. From Power Percentage and savings rate to the peace of mind that comes with financial confidence, we’re separating the signal from the noise.

And with the year halfway over, we wrap with a "mid-year compass check" to help you course-correct before it’s too late. If January’s goals are now a blurry memory, this is your wake-up call. Don’t wait for December to figure out whether you made progress—let’s find out now.

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