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  • The Biggest Retirement Mistake: Over Saving and Under Living | Rachael Camp & Jesse Cramer | 198

    The Biggest Retirement Mistake: Over Saving and Under Living | Rachael Camp & Jesse Cramer | 198
    Feb 22 2026
    Don't be that person who becomes a hoarder in retirement! You know who you are and it's a big concern for those that are champs at saving but reluctant to spend. It almost seems like a good problem to have... but not really! Retirement planners Rachel Camp, CFP® and Jesse Cramer join the show for a tackle the topic and what's known as the "consumption gap"-- the mismatch between what retirees could safely spend and what they actually spend. They discuss how decades of frugality, and dopamine hits from watching net worth climb and similar types of thinking make it brutally hard to flip from saver to spender. In this episode we cover: ✅ The 4% rule's real origin story (it was built to avoid failure, not to optimize joy) ✅ The very human tendency to over solve for the worst-case market and under solve for lost health, time, and relationships ✅ Strategies Rachael and Jesse use with their clients to help them spend and not hoard their money in retirement ✅ Why talking through childhood money stories is often more powerful than another spreadsheet. ✅ Debunking the viral "retire later, die sooner" meme and zoom out to what actually affects longevity ✅ A challenge tailor-made for late starters: once the math says you've won, stop buy back your time, and don't die with the biggest net worth of your life. ==================== DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS MONARCH MONEY The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50 For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners SUPPORT THE SHOW 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.) 🌐 Rachael Camp Wealth Rachael Camp Wealth Youtube 🌐 The Best Interest Blog (Jesse Cramer) Personal Finance For Long-Term Investors (Jesse Cramer's podcast) 📄Debunked: The Later You Retire, The Earlier You Die?! ⏰ Related Episodes Smart Money Moves After 50 | Bill Yount | 142 Space Telescopes, Sunflowers, and Financial Gardening | Jesse Cramer | 105 If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.
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    59 Min.
  • Flashback to Episode 1: 'A Boat Named YOLO' | Bill Yount | 197

    Flashback to Episode 1: 'A Boat Named YOLO' | Bill Yount | 197
    Feb 18 2026

    This episode is a little time-travel experiment with a flashback to the first episode (A Boat Named YOLO) that started it all. We're celebrating three years of 'Catching Up to FI' and Bill officially coming out as reaching Financial Independence (FI). He started late at 50 but now FI at 60! Be sure to go back and listen to this past Sunday's episode, where Jackie interviews Bill and he openly shares all the juicy details.

    ➡️Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196

    ====================

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    For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners

    SUPPORT THE SHOW

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    If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!

    📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.
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    51 Min.
  • Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196

    Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196
    Feb 15 2026
    Don't miss this special 3-year anniversary of 'Catching Up to FI' as Bill marks the moment by doing something he's been helping everyone else do for years: officially 'coming out' as financially independent (FI)! It is hard to believe that the show has been around for 3 years, 196 episodes, 20k Facebook Community members, 1.4M audio downloads and 300k views on YouTube. Is this real? Today we celebrate Bill's journey from Episode #1: 'A Boat Named Yolo', to officially reaching FI, but feels more like the 'The Fog of FI'. During this interview, Jackie gets Bill to open up and venerably share details of his wake-up call at 50: burned out, sued, house-poor after a disastrous renovation and de-risking at the bottom of the Great Recession, and still living paycheck to paycheck despite a 'rich doctor' income. He walks through discovering FI via blogs and books, taking a full year to reclaim his money from private bankers and whole life policies (he's naming names!). Bill boosted his savings rate up to ~40% in his early 50s—using Mr. Money Mustache's 'shockingly simple math' to accept a 10–15-year slog. Fast-forward to 60 and a retirement-readiness check with a flat-fee, advice-only planner: after three years of expense tracking in Monarch Money, a comprehensive plan, and stress-testing with risk-parity portfolios, Bill gets the verdict every late starter dreams of, 'you could retire tomorrow'— and feels weirdly flat. We also dig into the emotional side: the identity crisis of possibly leaving medicine, using newfound leverage to negotiate work on his own terms, the choice to glide out over several years instead of cliff-retiring, and the shift from building wealth to giving with warm hands, mentoring younger docs, and helping his adult sons lay foundations he never had. We close with Bill's hard-earned advice: ➡️ Reverse-engineer your life from your tombstone ➡️ Focus on health span as fiercely as net worth ➡️ Stop over-identifying with your job or your number ➡️ Remember that for late starters, the real win is feeling less alone while you build a life you won't regret. ==================== DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS: MONARCH MONEY The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50 For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners SUPPORT THE SHOW 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question RESOURCES MENTIONED ON THE SHOW: 📄 Bill's 'Letter of Gratitude' and 'Financial Life Policy Statement' Bill's Financial Planner: Bryan Minogue CFP®, CFA (Kardinal Financial) ⏰ Related Episodes A Boat Named YOLO | Bill Yount | 001 The Power of Cash Flow Planning | Sarah-Catherine Gutierrez | 016 The Father of Financial Life Planning (Part 1) | George Kinder | 140 If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.
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    1 Std. und 12 Min.
  • Work Less, Live More: The New Paradigm of Financial Freedom | Andy Hill | 195

    Work Less, Live More: The New Paradigm of Financial Freedom | Andy Hill | 195
    Feb 8 2026

    Do you want to own your time, work less, and live more? What if the point isn't maxing out every account forever, but designing a week you don't want to escape from? This is the Coast FI life built by our guest today, Andy Hill. He shares the steps you can take to put your family first and escape the 9-5 grind: for good! He takes us through the full arc: starting married life at –$50K net worth, killing the debt in a year with budget parties, saving 40–50% to hit around $500K in investments by forty, then realizing that number was enough for Coast FI. With all that, he realized that what he really wanted was time.

    Andy is an award-winning blogger, podcaster, and family finance coach behind Marriage, Kids, and Money. He's also author of the new book 'Own Your Time: 10 Financial Steps to Put Your Family First and Escape the Corporate Grind', which walks readers through simple, yet highly effective steps families can take to achieve family financial independence. It also features real-life examples of couples who've conquered these family financial independence milestones and found better lives for themselves because of it.

    ====================

    DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS:

    MONARCH MONEY

    The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50

    For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners

    SUPPORT THE SHOW

    📩 Sign up for our newsletter

    🌐 Visit Catching Up to FI website

    🔗Connect with us

    ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"

    🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question

    RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)

    🌐 Marriage Kids and Money

    📕 Own Your Time: 10 Financial Steps to Put Your Family First and Escape the Corporate Grind

    ⏰ Related Episodes

    Generosity and Smart Spending: A Family Affair | Andy Hill | 103

    If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!

    📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.
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    1 Std. und 11 Min.
  • Back to FI Basics: How to Start Your Journey to Early Retirement | ChooseFI Crossover | 194

    Back to FI Basics: How to Start Your Journey to Early Retirement | ChooseFI Crossover | 194
    Feb 4 2026
    Strap in, because Jackie joins Brad Barrett for a crossover episode on the ChooseFI podcast, home of the world's largest FI community! Together, they rewind all the way back to 2017, when Jackie first stumbled onto ChooseFI… and everything changed. She recounts her journey to reaching early retirement by December 2019, and using that freedom to go back to school, get her CFP, and write 'F.I.R.E. for Dummies'. Then the two of them dive deep into the fundamentals and break down what financial independence really means. They explain why even ten dollars a month can spark a lifelong investing habit, and how Jackie's first investment club taught her the power of community and compounding. They decode 401(k)s, demystify fund selection, and spotlight the quiet villain of investing: expense ratios. The episode widens from there: debt payoff strategies, designing a modest but deeply rich life on $40–45K a year in Ohio, negotiating everything from internet bills to insurance premiums, and the emotional transformation from paycheck-to-paycheck lifestyle to feeling 'directionally correct.' They conclude with the realization that FI isn't just about money, it's about options. Whether you're a late starter, brand new or ten years into the journey; returning to the basics is how you stay grounded, stay motivated, and stay on course. ==================== DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS: MONARCH MONEY The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50 For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners SUPPORT THE SHOW 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.) 🌐ChooseFI 🌐Jackie's website FInomenalWoman.com 📕F.I.R.E. For Dummies 📘Money Letters 2 My Daughter 📈Jackie's Investment Club through BetterInvesting.org ⏰ Related Episodes The Godfather of FI Talks Fatherhood | JL Collins | 149 Stories, Hacks, & Tribes | Brad Barrett | 021 From Poverty to Wealth and Early Retirement | Jackie Cummings Koski | 007 If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.
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    1 Std. und 15 Min.
  • These New Rules Will Change The Way You Think About 529 Plans | Patricia Roberts | 193

    These New Rules Will Change The Way You Think About 529 Plans | Patricia Roberts | 193
    Feb 1 2026
    529 plan expert Patricia Roberts blows up the myth that 'it's too late' and '529s are just for rich people with toddlers and Ivy League dreams'. She is author of the book 'Route 529' and shares some big changes with 529 plans that make them an incredibly flexible savings vehicle for more than just college. In this episode we cover: How state tax deductions, credits and 'parity states' work for contributionsThe shockingly long list of qualified uses including trade schools, apprenticeships, non-degree credentials, K–12 tuition, tutoring, test prep and even student loan repayment Busting the 'use it or lose it' fear and the new option to rollover left over funds to a Roth IRAHow to juggle retirement vs. college savingsAdvanced strategies to create generational education wealth DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS: MONARCH MONEY The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50 For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners SUPPORT THE SHOW 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.) 🌐 Gift of College College Countdown 📕 Route 529: A Parent's Guide to Saving for College and Career Training with 529 Plans Morningstar 529 Ratings: The Best Plans of 2025 What You Can Pay for With a 529 Plan ⏰ Related Episodes The College Discount Game You Need To Know Before Choosing A School | Ron Lieber | 191 Stop Paying for College and Use These High-Return Scholarship Hacks Instead | Chris Corinthian | 189 Banishing The Burden of Student Loan Debt | Travis Hornsby | 122 If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.
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    1 Std. und 18 Min.
  • Why Your Financial Plan Will Fail (It's Not the Math) | Dan Haylett | 192

    Why Your Financial Plan Will Fail (It's Not the Math) | Dan Haylett | 192
    Jan 25 2026
    Dan Haylett gives us a late-starter masterclass on why retirement is a human problem long before it's a math problem. Dan is a UK financial planner, creator of 'Humans vs Retirement' podcast, and author of 'The Retirement You Didn't See Coming'. He walks us through how that outdated 'retire from work and fade away' script clashes with modern 50- and 60-somethings who still have health, curiosity, and huge ambitions. In this episode he also: Reframes risk as the possibility of dying with plenty of money but too few memoriesUnpacks why spreadsheets never quite make us feel safeLays out his three-phase map of the second half of life DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS: MONARCH MONEY The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50 ALLOY The Alloy Market offers a seamless and efficient way to sell your gold, silver, and platinum jewelry, regardless of its condition. They are committed to transparency and fairness, ensuring you get the best possible value for your items. Use this special Link and enter code CUTOFI15 to get a $15 bonus when you sell items over $199 (limited time offer). For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners SUPPORT THE SHOW 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.) 🌐 Humans vs Retirement Website & Podcast 📕 The Retirement You Didn't See Coming ⏰ Related Episodes What Would 'Your Money' Look Like In a Simple Sketch? | Carl Richards | 170 The Father of Financial Life Planning (Part 1) | George Kinder | 140 The Three Kinder Questions (Part 2) | George Kinder | 141 Hard & Soft Sides of Retirement | Fritz Gilbert | 019 If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.
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    1 Std. und 14 Min.
  • The College Discount Game You Need To Know Before Choosing A School | Ron Lieber | 191

    The College Discount Game You Need To Know Before Choosing A School | Ron Lieber | 191
    Jan 18 2026
    The cost of college is skyrocketing! To make sure you're not paying those sticker prices, we brought in New York Times 'Your Money' columnist, Ron Lieber. He is also author of 'The Price You Pay for College' and joins the show for a brutally honest walkthrough of what is actually going on behind the scenes. In this episode he breaks down: List price vs. cost of attendanceWhy most families don't pay rack rateHow to read a school's 'Common Data Set'Merit vs. need-based aidHow net price calculators and pre-reads can keep you from falling in love with a school you can't afford DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS: MONARCH MONEY The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50 ALLOY The Alloy Market offers a seamless and efficient way to sell your gold, silver, and platinum jewelry, regardless of its condition. They are committed to transparency and fairness, ensuring you get the best possible value for your items. Use this special Link and enter code CUTOFI15 to get a $15 bonus when you sell items over $199 (limited time offer). For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners SUPPORT THE SHOW 📩 Sign up for our newsletter 🌐 Visit Catching Up to FI website 🔗Connect with us ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.) 📕 Books by Ron Lieber 🌐 Merit Aid Course (with link to free merit aid checklist) Ron's New York Times Profile Niche (for comparing colleges) Saving For College (Compare 529 Plans) ⏰ Related Episodes Stop Paying for College and Use These High-Return Scholarship Hacks Instead | Chris Corinthian | 189 Banishing The Burden of Student Loan Debt | Travis Hornsby | 122 The New World of 529 College Savings | Patricia Roberts (Coming Soon) If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you! 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.
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    1 Std. und 21 Min.