Catching Up to FI: Financial Independence for Late Starters

What if the biggest risk in your portfolio isn't a crash, a recession, or even inflation, but the very human urge to believe that whatever just worked will work forever? Bill and Jackie sit down with Ben Carlson of A Wealth of Common Sense and Animal Spirits for a market-history masterclass that somehow manages to be equal parts calming, nerdy, and deeply practical. This one is for anyone who's ever stared at their portfolio, read one scary headline too many, and wondered whether simplicity still works. Ben's answer is basically yes—but only if you understand the risks, respect your own behavior, and build a portfolio you can actually stick with. This episode covers: Ben Carlson's "Bob" thought experiment and why even terrible market timing can still work out over the long run Why dollar cost averaging often beats waiting for the perfect entry point The psychology of lump-sum investing versus spreading money out over time What inflation looked like before World War II versus in the modern era How to think about inflation through a personal-finance lens, not just an investing lens Why housing, transportation, income growth, and stocks are major inflation defenses What Japan's lost decades teach us about home-country bias and international diversification Why diversification matters even more in retirement because of sequence-of-returns risk How to think about bonds, cash, duration, and risk tolerance in a more nuanced way . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined.  Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start  Covers everything from basics to advanced strategies in one guide  Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties  📕 Get Your Copy  (currently 40% off on Amazon)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW A Wealth of Common Sense Animal Spirits Podcast Risk and Reward: How to handle market volatility and build long-term wealth The Compound Youtube . ⏰ Related Episodes  The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201 Hanging On In a Yo-Yo Economy | Sam Stovall | 147  How to Bake a Cake: An Asset Allocation Mashup | Rick Ferri & Paul Merriman | 134  "The Risk Parity Paradox" an Exercise in Simple Complexity? | Frank Vasquez | 124   . 📌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.

7/12/26 • 71:07

What if "legacy" looks completely different when there are no kids in the picture and that difference actually unlocks a freer, more intentional version of FI? In this thoughtful crossover between Childfree Life by Design and Catching Up to FI, Dr. Jay and Bill sit down for the kind of conversation most money media skips: what happens after you hit the number and realize the bigger question is no longer "Can I retire?" but "What am I retiring to?" It's philosophical, personal, a little messy in the best way, and exactly the kind of episode that reminds listeners that FI is not the finish line. It's the moment when the real design work begins. This episode covers: The "fog of FI" and the identity shift that can come after reaching financial independence The childfree midlife crisis and why "now what?" hits harder than many expect Legacy beyond lineage and how childfree people often redefine impact Why it is more important to know what you are retiring to than what you are retiring from The tension between purpose, freedom, and drifting after hitting major goals Health span, lifespan, and why time becomes more valuable once money pressure drops How giving, service, and creativity can become the next chapter after FI Why books, podcasts, and numbers alone cannot answer life-design questions The difference between being rich on paper and living a truly wealthy life Why underspending and over-optimizing can become their own retirement risks . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined.  Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start  Covers everything from basics to advanced strategies in one guide  Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties  📕 Get Your Copy  (currently 40% off on Amazon)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Childfree Wealth https://childfreewealth.com/ . ⏰ Related Episodes  Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 . 📌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.

7/8/26 • 44:24

Bill jumps into a last-minute solo conversation with Rebecca Herbst of Yield and Spread for a surprisingly energizing deep dive into generosity, guilt, and what happens after the finish line of financial independence. Rebecca shares how hitting FI at 32 did not lead to endless victory-lap bliss so much as an identity jolt: if money is a tool, then what is it actually for? This episode covers:  Why Rebecca felt guilt, not just freedom, after reaching FI at 32 How giving can be framed as money, time, or skills—not just writing checks Why generosity is a habit and a muscle, especially for lifelong savers The surprisingly small impact that a 1% giving rate can have on your FI timeline How "effective giving" applies investing-style thinking to charitable impact The difference between reactive emotional giving and proactive intentional giving Tax-smart giving tools like appreciated securities, donor-advised funds, and QCDs Why the FI community may be uniquely positioned to normalize bold generosity How giving can become part of a "life portfolio," not just a side project References & Resources Mentioned . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined.  Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start  Covers everything from basics to advanced strategies in one guide  Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties  📕 Get Your Copy  (currently 40% off on Amazon)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Yield and Spread FI Service Corps   ⏰ Related Episodes  Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209 A Donor-Advised Fund For You (Daffy): Democratizing Philanthropy for Everyone | Adam Nash | 200 Contrarian Tax Planning Tips | Cody Garrett & Sean Mullaney | 179 . 📌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.

7/5/26 • 90:35

What if the person inspiring the room didn't come from a polished finance background at all, but from payday loans, being unbanked, a credit score in the 500s, and the kind of rock bottom most FI stories rarely admit out loud? In this on-location episode from Madison, WI, Jackie sits down with Afra Smith, founder of The Melanin Project and creator of the Wealth Empowerment Conference, for a conversation that is as honest as it gets. She's a late-starter and shares how depression, financial chaos, and a painful career setback forced her to finally confront what wasn't working. She shares how one financial coach, one budget, and one decision to stop waiting for someone else to rescue her changed the direction of her life. From there, she built something much bigger than a comeback story. It's now a growing movement centered on financial wellness, lived experience, and giving people the tools to rebuild from where they actually are. Her raw truth is proof that your hardest chapter does not have to be your final one. This episode covers:  Afra's journey from payday loans, ChexSystems, and depression to financial stability The career disappointment that became her wake-up call How one financial coach and a basic budget started her turnaround Why financial struggles in underserved communities are often deeper than "just spend less" The origin of The Melanin Project and the Wealth Empowerment Conference  Why lived experience and emotional honesty matter in financial education  The link between mental health, physical health, and wealth-building How Afra built a meaningful community event while still working a full-time job Why consumption habits and appearances can distort how we judge wealth and value  What it looks like to turn pain into service and purpose . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined.  Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start  Covers everything from basics to advanced strategies in one guide  Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties  📕 Get Your Copy  (currently 40% off on Amazon)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW The Melanin Project  TrueStage  CLIMB USA (Bob Wynn)  Madison Gas and Electric Company  Summit Credit Union   ⏰ Related Episodes  From Poverty to Wealth and Early Retirement | Jackie Cummings Koski | 007 We Found Them! Past Guests At The Women of FI Weekend | Kim H. and Lisa B. | 218   . 📌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.

6/28/26 • 26:31

What if the smartest legacy move isn't leaving your kids a pile of money someday, but using your wealth right now to help them buy time, build habits, and change their future while you're still here to watch it happen? We sit down with Allen Mueller of 7 Saturdays Financial for a practical, deeply useful conversation about gifting to family with intention. The thread running through all of it is simple: money is not just for accumulating. It's for strengthening the people and values you care about most. This episode covers: Why gifting during your lifetime can be more impactful than leaving a larger inheritance later The difference between a tax threshold and a paperwork threshold for gifts How the annual gift exclusion really works Why many retirees underspend and unintentionally miss chances to help family now Smart ways to fund kids' and grandkids' futures through 529s, custodial Roths, and brokerage accounts How to think about gifting for college, healthcare, and home down payments Why "skin in the game" still matters when helping younger family members How appreciated shares can be gifted downstream or upstream for tax advantages Why wisdom and stewardship matter more than simply transferring money How FI can turn parents and grandparents into real-time wealth builders for the next generation . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined.  Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start  Covers everything from basics to advanced strategies in one guide  Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties 📕 Get Your Copy  (currently 40% off on Amazon)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW 7 Saturdays Financial Allen's LinkedIn  . ⏰ Related Episodes Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209  These New Rules Will Change The Way You Think About 529 Plans | Patricia Roberts | 193    . 📌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.

6/21/26 • 63:53

What if the smartest move on your road to FI isn't buying a bigger house, but shrinking the footprint, clearing the clutter, and finally designing a life that actually fits? In this episode, we sit down with Sarah Susanka, the architect behind the bestselling "Not So Big House" movement. We talk about what happens when you stop building for appearances and start building for how you really live. Sarah shares how growing up in England, then landing in car-centric suburban Los Angeles made her question why Americans kept buying "hamburger bun but no hamburger" houses full of unused rooms.   This episode covers: Sarah Susanka's origin story and how suburbia pushed her toward architecture  The difference between building bigger and building better  Why unused rooms are the housing version of lifestyle bloat - How right-sizing a home parallels right-sizing a life  The design power of light, ceiling height, flow, and multi-use space  How small architectural moves can create huge changes in mood and function  Why old thought patterns can clutter a life just like unused rooms clutter a house  The connection between beauty, sustainability, and building things that last  How Bill used Sarah's ideas in his own home design and life redesign  Why intentional design matters even more for late starters making a reset spaces. . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined.  Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start  Covers everything from basics to advanced strategies in one guide  Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties  👉🏽 https://a.co/d/01umGgeh  (currently 40% off on Amazon)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Sarah's Website Not So Big Design Principles for House & Life with Sarah Susanka Sarah TedX talk 📗The Not So Big House: A Blueprint for the Way We Really Live The New Urbanism The Not So Big Bungalow   . ⏰ Related Episodes How Clutter Steals Your Time (And How to Get It Back) | Rose Lounsbury | 188   . 📌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.

6/14/26 • 63:20

What if the fastest way to understand women's financial power isn't another lecture, but a trivia game that quietly reveals how recent, fragile, and still unfinished so much of women's economic progress really is? In this special "Sheconomy" quiz-show episode, Jackie and Bill join Janine Firpo and financial planner Sarah-Catherine Gutierrez for a lively game show. They move from Equal Pay Day and credit-card rights to why women often outperform men as investors, why female-led companies and firms still get shut out, and what could happen if women intentionally shifted even a slice of their wealth toward their values. The tone is playful, but the message is serious: money is power, and women stepping into that power changes families, businesses, markets, and maybe the whole economy. This episode covers: The surprising timeline of women's financial rights in the US What Equal Pay Day reveals about how far women still have to go Why women often outperform men as investors  How overconfidence and overtrading hurt returns Why women-led businesses still receive a tiny share of venture capital The rise of advice-only and flat-fee financial planning models What values-aligned and ESG investing actually mean Why women's money choices can reshape markets and communities How much wealth women are expected to control in the coming years The collective impact women could have by shifting capital intentionally . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined.  Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start  Covers everything from basics to advanced strategies in one guide  Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties  👉🏽 https://a.co/d/01umGgeh  (currently 40% off on Amazon)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Our Sheconomy  . ⏰ Related Episodes Vote Your Money: Values Aligned Investing | Janine Firpo | 139  The Power of Cash Flow Planning | Sarah-Catherine Gutierrez | 016   . 📌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.

6/10/26 • 96:29

What happens when women in the financial independence community finally get a room of their own and use it not just to talk numbers, but to unpack the invisible stuff they've been carrying for years? In this on-location episode, Jackie takes us inside the Women of FI annual weekend in Maryland. This was a rare women-centered FI retreat that blends case studies, life design, laughter, and vulnerability. She catches up with two familiar voices from past episodes, Kim Hunter-Borst and Lisa B. to hear what retirement, sabbaticals, and post-FI life actually look like in motion, not just on paper. Other attendees also share why a women-only space hits differently: less posturing, more honesty, more room to talk about emotional labor, caregiving, identity, and the inner work that often gets skipped in mixed-money spaces. This episode covers:  What happened at the Women of FI annual women's weekend in Maryland  Why women-centered FI spaces create a different kind of openness and trust  Kim Hunter-Borst's vision for building a smaller, more vulnerable, more intentional retreat  The 2026 theme of "release" and what women said they were ready to put down  A retirement update from Kim after leaving full-time work  A follow-up from Lisa B. on quitting her job, taking a summer break, and what happened next  Why women said they needed space for both the "outer" and "inner" work of FI  How attendees are thinking about Coast FI, sabbaticals, community, and post-FI life . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== F.I.R.E. For Dummies Did you know that co-host Jackie Cummings Koski, CFP®, AFC® is also author of "F.I.R.E. For Dummies"? This is the perfect guide for anyone looking to move from the basics of their finances to reaching F.I.R.E. (Financial Independence, Retire Early) and enjoying the time freedom it creates. Even if you feel behind on your finances, the steps in this book will help you catch up sooner than you ever imagined.  Learn from someone who actually achieved F.I.R.E. in her 40s even after getting a late start  Covers everything from basics to advanced strategies in one guide  Practical solutions for early retirement obstacles like health insurance and early withdrawal penalties  👉🏽 https://a.co/d/01umGgeh  (currently 40% off on Amazon)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW   Women Of FI  WE Wealth Collective Facebook Group  EconoMe Conference https://economeconference.com CampFI  FinTalks Events . ⏰ Related Episodes Drowning in Debt at 48, Retired at 58: Here's How She Did It! | Kim Hunter-Borst | 181 Case Study: The Real Numbers That Told Her She Could Quit her Job, Now! | Lisa B | 161 The Power of Cash Flow Planning | Sarah-Catherine Gutierrez | 016   . 📌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.

6/7/26 • 30:47

What if "one more year" isn't a failure of courage. What if it's a messy, human, sometimes wise transition between the life you built and the life you're finally ready to choose? In this spontaneous, unusually raw episode, Bill, Jackie, and Patrick crack open the emotional side of financial independence. They go beyond the surface of the hesitation, identity shift, grief, relief, and weird freedom that can show up when the math says you're done but your nervous system is still catching up. Bill shares what it feels like to downshift after unexpectedly reaching FI, why he's enjoying work more now that he doesn't need it, and how a heartbreaking night in the ER sharpened his thinking about what really counts. Jackie reflects on her own two-year "one more year" phase and why she no longer sees it as a mistake so much as a cushion she needed. Patrick adds the planner's lens: if a choice still serves your life, it may not be "one more year" syndrome at all. This episode is a heartfelt reminder that the real work isn't just reaching the number but learning how to let go when the time comes. This episode covers: Why "one more year syndrome" may not actually be a bad thing The emotional transition from being FI on paper to actually changing your life Bill's intentional downshift and how FI gave him leverage at work Jackie's two-year hesitation and why she now sees it with more grace How fear, identity, purpose, and burnout all shape retirement timing  Why working after FI can still make sense if it serves your life The difference between choosing one more year and drifting into it unconsciously How tragedy and loss can change the way you think about time Why the second chapter of life requires more than just good math How late starters can prepare emotionally, not just financially, for freedom . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== STUDENT LOAN PLANNER Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup    For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Catching Up to FI Facebook Community Jackie's FIRE Letter . ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 From Poverty to Wealth and Early Retirement | Jackie Cummings Koski | 007 Our Team is Growing: Welcome Patrick! | Patrick McDonnal | 136 The Three Kinder Questions (Part 2) | George Kinder | 141 The pURPOSE Code | Jordan Grumet | 115 Hard & Soft Sides of Retirement | Fritz Gilbert | 019 . 📌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.

5/31/26 • 61:02

What if the real danger in retirement isn't running out of money, but spending so cautiously that you accidentally work too long, live too small, and die with a portfolio that never got a chance to do its job? In part two with Aubrey Williams, we go deeper into the "fog of FI" (that weird, anxious place where the spreadsheet says you're free, but your nervous system absolutely does not believe it). This episode covers: Why the 4% rule can make FI people overwork and underspend How future income streams like Social Security can move your FI date forward Why flexible spending is more realistic than flat, inflation-adjusted withdrawals How risk-based guardrails help you know when to cut or increase spending Why many FI people need more help increasing spending than reducing it How personal inflation can differ from CPI and affect retirement planning Why historical analysis may be more useful than Monte Carlo for some FI decisions How small amounts of income in retirement can meaningfully reduce portfolio pressure Why engineers and analytical types often need better data to trust they're "done" How Bill is using these ideas to finally get clearer about leaving work sooner . S U P P O R T    T H E    S H O W 📩 Sign up for our newsletter https://catchinguptofi.com/contact-us/#newsletter  🌐 Visit Catching Up to FI website  https://catchinguptofi.com 👥 Connect with us https://linktr.ee/cutfi ☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"  https://www.buymeacoffee.com/catchinguptofi 🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question https://catchinguptofi.com/contact-us/#voicemails   ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== STUDENT LOAN PLANNER Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup    For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Open Path Financial Aubrey's EconoMe Talk (2026): Coming soon! Income Lab FIREproof (Lauren Boland) Projection Lab  Open Source Guardrails Simulation (Roger Cost) . ⏰ Related Episodes Part 1: Why Your Brain is Hardwired to Keep You Working (and How to Fix It) | Aubrey Williams | 214 A Richer Retirement: The 4.7% Rule | Bill Bengen | 169 Sequence of Returns Risk: What Every Retiree Needs to Know | Karsten Jeske | 106    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.

5/24/26 • 51:38

What if the biggest difference between someone who starts at 22 and someone who starts at 50 isn't intelligence or income, but simply the moment they finally decide, nobody's coming to save me? In this crossover episode, Bill joins Joel on "How to Money" to tell the brutally honest and surprisingly hopeful truth. He shares his story of becoming financially independent after a 20-year sleepwalk through lifestyle inflation, doctor money mistakes, and zero real financial plan. It's candid, practical, and exactly the kind of episode that makes you stop saying "I'm behind" and start asking "What's my next move?"   This episode covers: Bill's late-starter journey from paycheck-to-paycheck doctor to financially independent at 60 How "rich doctor syndrome" and lifestyle inflation can keep high earners broke Why debt, overspending, and delayed gratification derailed his early money life The wake-up call that came from burnout, a malpractice lawsuit, and turning 50 How downsizing, geo-arbitrage, and a higher savings rate changed everything Why savings rate matters more than most people realize for late starters How to think about debt payoff versus investing when you feel behind Why college funding, generational wealth, and retirement planning are all connected How Bill thinks about using a financial advisor after a long DIY phase Why financial independence is really about buying back time, autonomy, and health . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 🆕Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup    For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW How To Money  The White Coat Investor George Kinder  William Bernstein  . ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 Flashback to Episode 1: 'A Boat Named YOLO' | Bill Yount | 197 . 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.

5/20/26 • 63:26

What if the thing keeping you from Financial Independence (FI) isn't your income, your portfolio, or your math. It's probably the quiet belief that you still need "one more year" when you actually don't. Our guest on this episode is Aubrey Williams, a former particle physicist, radar-tech leader, debt-slayer, and now advice-only financial planner. In this conversation, he flips some of the FI community's favorite assumptions on their head. This is the first of a 2-part episode with Aubrey so be sure to follow the podcast to be notified of the second part of this fascinating conversation. This episode covers: How Aubrey rebuilt after divorce and $90,000 of debt Why savings rate is nonlinear and more powerful than most people realize How a higher savings rate can erase working years faster than expected Why our brains are wired for survival, not modern investing and retirement decisions How to build evidence that you can safely spend instead of just hoard Why living smaller can sometimes create more freedom and more joy How Aubrey reached FI in high-cost Santa Barbara without leaving California Why the FI community itself often knows more than the average advisor The difference between fee-based, fee-only, flat-fee, and hourly advice Why Aubrey believes many FI people are still working too long . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== STUDENT LOAN PLANNER Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup    For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Open Path Financial Aubrey's EconoMe Talk (2026): Coming soon! . ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 Enoughness: Your Life or Your Money | Vicki Robin | 95 . 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.

5/17/26 • 59:21

You've worked twice as hard to catch up on your path to financial independence, so why leave your legacy to chance? To help keep your FI plan from going up in smoke we sit down with estate planning and small business attorney, Allison Harrison. It's a fast, funny and slightly alarming deep dive into estate planning for normal people who assume they're "not rich enough" to need one. This episode covers: Why your FI plan is incomplete without basic estate planning  The real cost, delay, and public exposure that can come with probate Why many people think they need a trust when they actually don't  When a trust does make sense, especially for control and complex family situations  The simplest ways to avoid probate using beneficiaries and transfer-on-death designations  Why healthcare and financial powers of attorney matter just as much as a will Estate-planning blind spots for small-business owners and side hustlers The role of umbrella insurance, LLCs, and business agreements in protecting your assets Why digital accounts, passwords, and two-factor authentication are now part of estate planning What parents of newly minted 18-year-olds need to handle before college or adulthood begins . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== STUDENT LOAN PLANNER Big changes with student loans in 2026! Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup    For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Allison's EconoMe Talk (2026) -Coming soon- ALH Law Group See Us Mob Podcast ALH Law Group Youtube Free Estate Planning Guides, Infographics and More (no email required) Safe Sendoff (Legal Planning for Young Adults)  . ⏰ Related Episodes Attorney Spilling all the Legal Tea on Estate Planning | Jenny Rozelle | 121 . 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.

5/10/26 • 69:17

What do you do when your accountant brain knows the numbers, your life blows up anyway, and the answer turns out to be halfway around the world in a weird little movement called FIRE? We head to New Zealand to talk with Bronwyn Candish, a chartered accountant, community builder, and one of the clearest Kiwi voices in financial independence movement. She talks to us about starting over after divorce, rebuilding from the middle, and discovering that "doing money right" has a lot less to do with credentials than with courage, alignment, and actually taking action. This episode covers: Growing up with scarcity in New Zealand and how that shaped Bronwyn's money mindset Why being an accountant did not automatically make her good with money Lifestyle creep, overbuying on housing, and drifting into paycheck-to-paycheck living Divorce as a financial wake-up call in her late 30s How Bronwyn found FIRE through a random article and went deep down the rabbit hole The role of KiwiSaver, housing, and DIY culture in the New Zealand version of FI  Why community and accountability matter so much on the journey How Bronwyn turned her accounting practice into a FIRE-adjacent coaching space The creation of Black Friday and the growth of the Kiwi FIRE community  What it looks like to be "mid-journey" and still deeply love the path . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 🆕Big changes with student loans in 2026. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off 'Catching Up to FI' discount, it's $495. 👉🏼 Be sure to use this link: studentloanplanner.com/catchingup    For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW KiwiFI and Black FI Day website Sheppard & Ormsby PocketSmith Personal Finance Software . ⏰ Related Episodes Borderless FI: The Happy KiwiSaver | Ruth Henderson | 165 Borderless FI: Australian Paramedic Healing Her Own Trauma | Tasch Rogers | 143 Indiana Jones and an Extraordinary Life with the Donegans | Alan and Katie Donegan | 079 Borderless FI: Thunder Down Under | Late Starter Fire | 004 . 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.

5/3/26 • 57:28

What if the biggest shift in your FI journey isn't hitting the number—but finally realizing you need a life plan, a tax plan, and maybe even a fiduciary teammate to help you spend it? Bill steps into the guest chair with Morningstar's Christine Benz for a thoughtful, surprisingly candid conversation about going from financially illiterate "rich doctor syndrome" to fully conscious wealth stewardship. He walks through the entire arc. But this episode goes deeper than a standard "how I retired" story. This episode covers:  ➡️ Bill's path from paycheck-to-paycheck physician to financially independent late starter ➡️ How childhood money scripts and "rich doctor syndrome" shaped his early financial mistakes  ➡️ Why the Great Financial Crisis and burnout became a wake-up call ➡️ What changed when Bill moved from financial consumer to conscious wealth steward ➡️ Why accumulation can be DIY—but decumulation often gets more complex  ➡️ How Bill searched for a fiduciary, flat-fee, life-planning-oriented advisor ➡️ Why risk parity appealed to him for retirement and sequence-of-returns protection  ➡️ The role of a modern advisor as behavioral buffer, tax strategist, and cognitive-risk safeguard ➡️ Why FI gave Bill leverage to redesign work instead of just quit cold turkey  ➡️ How Bill is thinking about legacy, living giving, and helping the next generation now, not just later . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial.   👉🏼 Be sure to use this link to get started:  Go.boldin.com/catchingup   Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course   Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW The Long View podcast  The White Coat Investor George Kinder  William Bernstein  . ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196 Flashback to Episode 1: 'A Boat Named YOLO' | Bill Yount | 197 Retirement Remix: Crafting Financial Futures with Purpose | Christine Benz | 117 . 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.

4/29/26 • 64:30

What happens when the two co-hosts stop being polite, start being honest, and publicly debate the money moves they still don't agree on? We throw open the doors on four of our favorite friction points: Simple index-fund investing versus "modest complexity"  Whether high school personal finance classes are actually helping  What to make of the new 530A Trump accounts  Taking Social Security at 62 versus waiting   The fun here is that neither of us is playing a character. Jackie comes in swinging for simplicity, practical execution, and "please stop overcomplicating this for normal people," while Bill makes the case for curiosity, customization, and not sleepwalking through important financial choices. Along the way, we swap real stories about helping kids with 401(k)s, seeing bad default investments in the wild, what personal finance education gets wrong, and why Social Security advice may be more nuanced than the "always wait until 70" crowd admits. It's a reminder that thoughtful disagreement can sharpen your own plan faster than blindly copying someone else's. . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial.   👉🏼 Be sure to use this link to get started:  Go.boldin.com/catchingup   Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course   Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Check your social security estimates Mike Piper's Open Social Security Calculator  Next Gen Personal Finance Trump Accounts . ⏰ Related Episodes Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205 These New Rules Will Change The Way You Think About 529 Plans | Patricia Roberts | 193  Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072 Social Security Made Simple | Mike Piper | 054 . 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.

4/26/26 • 64:51

What if the real reason family wealth disappears by the third generation has almost nothing to do with investing, and everything to do with what parents fail to teach at home? We sit down with Dr. Julia Myers, founder of Generational Wisdom, for a conversation that goes way past trusts, spreadsheets, and "someday" estate plans. Julia shares the medical crisis that abruptly ended her pharmacy career, the mindset shift that followed, and why she now believes legacy is not what you leave to your kids, but what you leave IN them. Together we unpack the three silent killers of generational wealth: no skills, no goals, no expectations, and explore what it looks like to raise kids who understand money and values, before the world teaches them. If you've ever wondered how to build wealth without accidentally raising entitlement, or how to recover from your own money story before passing it on, this episode is a gold mine. This episode covers Why 70–90% of family wealth disappears by the third generation Julia's shift from pharmacist to generational wisdom coach after a life-changing health crisis The three biggest reasons generational wealth gets lost Why "wealth without wisdom is wasted" How to build a family constitution around values, not just money  The difference between leaving wealth to your kids versus leaving legacy in them How to talk to kids about money, giving, enough, and expectations Why late starters can still change their family's financial story Practical ways to make values visible in daily family life . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial.   👉🏼 Be sure to use this link to get started:  Go.boldin.com/catchingup   Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course   Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW Charity: Hope International 🌐 JuliaMyers.com  Julia's Youtube Julia's TEDx Talk Say This, Not That (free guide) Free Audiobook "Wealthy and Well Known"   . ⏰ Related Episodes Enoughness: Your Life or Your Money | Vicki Robin | 95   Doña Quixote, Life Energy, and The Coming of Aging | Vicki Robin | 94 . 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.

4/19/26 • 60:30

APRIL IS FINANCIAL LITERACY MONTH! What do you get when two late starters hand the mic to two twenty-somethings and let the money questions fly? In this unusually fun follow-up to the University of Tennessee classroom visit, we bring Dr. Karen DeLong and two of her students, Emilie and Britton, onto the podcast to tackle the real questions young adults ask when money stops being theoretical and starts getting personal. Emilie – Majoring in Finance and International Business with a minor in Agricultural Business and will be pursuing a career in Wealth Management. Britton – Interning with Wells Fargo in their Investment Banking - Commercial Real Estate division and will be pursuing a career in that post grad. . This episode covers The real money questions college students are asking before graduation Why Roth IRAs are such a powerful early-start tool How to think about saving for retirement versus nearer-term goals What happens to your 401(k) when you switch jobs Why savings rate matters more than most young adults realize The balance between being responsible and being too frugal How parents, professors, and mentors shape money mindset Why financial literacy needs to be practical, not just theoretical What late starters can teach young adults before they make the same mistakes . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial.   👉🏼 Be sure to use this link to get started:  Go.boldin.com/catchingup   Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course   Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW   🌐 Dr. Karen DeLong  Farm Credit Mid-America 📘 If You Can: How Millennials Can Get Rich Slowly (Bill Bernstein) 📕 The Simple Path to Wealth- Updated 2025 (JL Collins) 📗 Your Money or Your Life (Vicki Robin & Joe Dominguez) 📙F.I.R.E. For Dummies (Jackie Cummings Koski)  📘Money Letters 2 My Daughter (Jackie Cummings Koski) . ⏰ Related Episodes I Have a PhD in Business but Never Had a Personal Finance Class | Dr. Karen DeLong | 206 Financial Literacy 101: Live Inside the Classroom at University of Tennessee | Bill & Jackie | 207 . 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.

4/12/26 • 70:03

APRIL IS FINANCIAL LITERACY MONTH! What happens when you hand a room full of almost-graduates a microphone, a few $2 bills, and permission to ask the money questions most adults still avoid? In this special on-the-road episode, we take you inside the financial literacy presentation at the University of Tennessee to share a few highlights of our recent talk. It's energetic, imperfect, and deeply encouraging. Financial literacy doesn't have to be stiff or scary. Sometimes it just looks like showing up, telling the truth about your mistakes, and helping the next person get a much earlier start than you did. This episode covers:  ➡️ Highlights from Bill and Jackie's live financial literacy presentation at UT Knoxville  ➡️ Why young adults need practical money education before entering the workforce ➡️ The difference between being rich and being wealthy ➡️ Why savings rate matters so much for financial independence  ➡️ How to think about 401(k)s, employer match, vesting, and job changes ➡️ Why index funds and simple investing often beat picking individual stocks ➡️ Jackie's $2 bill story and how tiny saving habits can shape a lifetime  ➡️ Bill's "rich doctor syndrome" story and the danger of lifestyle inflation ➡️ How listeners can adapt this presentation for their own school, church, or community . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial.   👉🏼 Be sure to use this link to get started:  Go.boldin.com/catchingup   Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course   Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW:    🌐 Dr. Karen DeLong  Farm Credit Mid-America BetterInvesting.org  📘 If You Can: How Millennials Can Get Rich Slowly (free digital download) 📄 Copy of Our Presentation Slides to UT Students    ⏰ Related Episodes  I Have a PhD in Business but Never Had a Personal Finance Class | Dr. Karen DeLong | 206 Questions from Students (coming in April) . 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.

4/8/26 • 45:20

APRIL IS FINANCIAL LITERACY MONTH! What if one passionate professor, one classroom, and a few brave money questions could change hundreds of financial lives before graduation? We head to Knoxville for a special Financial Literacy Month episode with Dr. Karen DeLong, the University of Tennessee professor quietly doing the work most schools still don't: making sure students leave campus with more than a degree. Karen shares how three advanced degrees somehow included zero personal-finance education and how that gap pushed her to build an annual money session for her students. Bill and Jackie reflect on what it was like to teach these soon-to-be graduates and how any late starter can become a powerful financial literacy advocate in their own little corner of the world.   This episode covers: ➡️ Why Dr. Karen DeLong started bringing personal finance into her classroom ➡️ How someone can earn multiple degrees and still never take a money class ➡️ Why college students are hungry for practical money conversations ➡️ The kinds of personal finance questions students are asking before graduation ➡️ How Bill and Jackie prepare for live financial literacy teaching sessions ➡️ Why financial literacy fits into almost any curriculum, not just finance classes ➡️ How Farm Credit Mid-America helped support this student enrichment work ➡️ Why late starters can still become mentors and financial literacy advocates ➡️ A preview of the student follow-up episode answering unanswered questions . === 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 . ===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS=== 📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial.   👉🏼 Be sure to use this link to get started:  Go.boldin.com/catchingup   Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course   Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)   For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners . RESOURCES MENTIONED ON THE SHOW   🌐 Dr. Karen DeLong  Farm Credit Mid-America . ⏰ Related Episodes Financial Literacy 101: Live Inside the Classroom at University of Tennessee | Bill & Jackie | 207 Questions from Students (coming in April)   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.

4/5/26 • 36:20

April is Financial Literacy Month and we're starting a little early! That's because we are so excited to launch a new project called "The Great 401(k) Cleanup." What if the easiest way to boost your retirement odds this year isn't reducing your spending or a side hustle, but cleaning up that messy, confusing 401(k) you've been ignoring? We are using Financial Literacy Month to launch a full-on 401(k) intervention with a step-by-step guide including: Access From Home  Contributions  Beneficiaries  Investments  Rate of Return  What's Next    401(k)s and similar workplace plans like the TSP, 403(b), and 457 have become the backbone of retirement for most Americans. Yet they are often confusing and complicated to the average employee. No wonder so many accounts get neglected and become messy over time. The good news is that 2026 can be the year you clean it all up. This friendly and straightforward guide was created independent of any employer or plan provider, and will help you get going. By the time you're done you'll better understand your 401(k) and feel more empowered to use it as a real tool to build wealth and support your money goals. This episode covers:  ➡️ How to clean up a messy 401(k) in less than an hour ➡️ Why year-to-date returns can mislead and longer time frames matter more  ➡️ How contribution rate and savings rate shape your retirement timeline ➡️ Employer match, vesting schedules, and why "free money" still confuses people ➡️ Target date funds and simple one- to three-fund strategies  ➡️ How to spot low-cost index funds inside an ugly 401(k) menu ➡️ What to do with old 401(k)s when you change jobs ➡️ How AI can help decode plan documents and confusing fund lists ➡️ Why forgotten 401(k)s now total a jaw-dropping $2.1 trillion   ====================   DOWNLOAD GUIDE & EDITABLE CHECKLIST 📄 Cleaning up your 401(k) in less than an hour (complete guide with references) 📄 Cleaning up your 401(k) in less than an hour- Editable Checklist (download first)   ====================   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     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.

3/29/26 • 62:41

What if the best retirement advice didn't come from a spreadsheet—but from a real retiree saying, "I wish I'd done it sooner"? Jackie crosses over to "REAL Retirees: Uncut" for a refreshingly candid, walk through of what six years of early retirement have actually looked like. She also shares her top five reasons to retire early, from time freedom and better mental health to the surprising new opportunities that open up when your job no longer runs your calendar. And because this is still Catching Up to FI, she closes with a message straight to late starters: most people wake up later than they wanted, but that doesn't mean they're doomed. It means they need a new frame and a little grace. This episode covers:  ➡️ Jackie's real-life retirement story, six years in ➡️ Retiring at 49 after corporate life  ➡️ Building a nest egg using FIRE math and the 4% rule ➡️ Living off brokerage assets, Roth contributions, and a 72(t) strategy before 59½ ➡️ ACA health insurance subsidies and managing income in early retirement ➡️ Why Jackie kept her mortgage and doesn't regret it ➡️ Her top five reasons to retire early ➡️ The hidden superpowers late starters already have  ➡️ Why retirement success is really about freedom, health, and impact   ====================   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.)  🌐REAL Retirees: Uncut http://www.youtube.com/@REALRetireesUncut 🌐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 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.

3/25/26 • 49:05

What if you were already financially independent at 40… and didn't realize it until a random pension search and a couple of podcasts blew the whole thing open? This was Jaylynn's "Surprise FI" and he joins the show to take us blow by blow. He gives us look back to his childhood of money orders, loving parents, and "value over flash" shaped him. He shares how he went from thinking the stock market was gambling to maxing out a 401(k), building a brokerage account, and accidentally discovering he had already hit FI in his forties. But this isn't just a "run the numbers and quit" story. Jaylynn talks through Surprise FI, staying in a job he loved until COVID burnout changed the equation, retiring at 44, managing ACA subsidies, planning Roth conversions and a future 72(t). He's now using time freedom to become the dad his son would later call his "best friend." He leaves us with the reminder that progress beats perfection—especially for late starters.  This episode covers: How Jaylynn's parents taught him value, bills, and stretching money without calling it "financial literacy" Why he thought investing was gambling after watching Trading Places The coworker moment that made him realize he was already an investor through his 401(k) A rare private-company benefits setup: automatic 401(k) contributions, pension, and relocation packages How he discovered the FIRE movement by researching pension payout options "Surprise FI" at age 40 using the 4% rule and liquid assets only Why he kept working after hitting FI—and what changed in 2020 Retiring at 44 with a mortgage, a tax strategy, and 15 years of runway Using ACA subsidies, Roth conversions, and a future 72(t) to bridge the early-retirement years Why the real wealth turned out to be time with his kids, not just a portfolio balance   ====================   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:    ChooseFI   BiggerPockets Money  Jill On Money  The Retirement Answer Man      ⏰ Related Episodes 72(t) Expert Tells All: No More Secrets About Early Withdrawals (Part 1) | Bill Stecker | 131 Cashing in on 72(t): The Goldmine of Early Retirement Rules (Part2) | Bill Stecker | 133   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.

3/22/26 • 75:31

Today we're putting AI (Artificial Intelligence) to the test with AI money expert Jeffrey Trull. He's founder of the blog and newsletter, Money Meets AI where he shares tested prompts for your money. He joins us to sort the genuinely useful from the wildly overhyped when it comes to AI. We expand our conversation into prompts, privacy, hallucinations, portfolio questions, Google vs. ChatGPT, paid vs. free tools, and where AI can actually save real time for DIYers. Along the way, Bill wrestles with the tradeoff between efficiency and original thought, Jackie pushes the "AI as thought partner" framing, and Jeffrey stresses that it's great for lower-risk questions but terrible as your all-knowing financial planner.  This episode covers: Where AI is genuinely useful for DIY personal finance Why prompts matter, but perfection is overrated Using AI to review insurance, contracts, and 401(k) plan docs Google vs. ChatGPT vs. Claude for money questions Paid vs. free AI tools and when subscriptions are worth it AI "hallucinations" and how to fact-check outputs Privacy concerns when uploading financial documents Why AI should be a thought partner, not your financial planner Agentic AI, AI shopping assistants, and what may be coming next   ====================   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.) 🌐 Money Meets AI Top 5 Prompts for the Money Math You've Been Avoiding    ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196   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.

3/15/26 • 62:44

What if the guy who literally wrote the book on asset allocation told you your biggest risk isn't the market…it's the person in your bathroom mirror? Neurologist-turned-market-historian William (Bill) Bernstein joins us for a fascinating conversation about his unlikely path from photochemistry to medicine to becoming the quiet godfather of Boglehead-style investing. He shares what shaped his "simple but not easy" philosophy, why he thinks all of investing is "half math, half Shakespeare," and how a homemade website in the 1990s turned into "The Intelligent Asset Allocator" and a second career. This episode covers: ✅ How a frustrated young scientist became a neurologist, then a financial theorist and writer ✅ Early investing mistakes (Palladium futures, hot funds, overconfidence) and what finally clicked ✅ The five hurdles from If You Can and why history and psychology matter as much as math  ✅ What makes a true bubble: social buzz, career-changing speculators, hostility to skeptics, wild predictions ✅ Predictions vs forecasts, and how Bill "called" the dot-com bubble and GFC without betting the farm ✅ His current mix: modest small/value tilts, cash/T-bills for sanity, and a TIPS ladder for 30 years of expenses ✅ Why a TIPS ladder feels different from a TIPS fund and why most investors still won't use one ✅ The 30-years-working / 30-years-retired "toy model" and why it implies 20–25%+ savings rates ✅ Teaching kids about money via your own behavior, crappy college jobs, and tiny three-fund portfolios ✅ A sober view of FIRE as a way out of the cubicle and into meaningful work—not a 36-year-old beach fantasy ====================   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.) 🌐 Efficient Frontier (Bernstein's website) 🌐 The John C. Bogle Center for Financial Literacy 📘If You Can: How Millennials Can Get Rich Slowly (free digital download) 📗 Your Money and Your Brain (Jason Zweig) https://a.co/d/07bgnfz1   ⏰ Related Episodes The $1,000 Gift From Jonathan Clements To 18-Year-Olds | Bill Bernstein & Christine Benz | 160     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.

3/8/26 • 58:05

What if your giving plan felt as intentional and optimized as your FI plan, and just as easy to automate? In walks Daffy, the new and modern donor-advised fund that is democratizing giving! Adam Nash, co-founder and CEO of Daffy, joins us today to explain how donor-advised funds (DAFs) went from stuffy tools for the ultra-wealthy to something you can open on your phone. Daffy is a fast-growing fintech platform and community for charitable giving, made for everyday people. Adam shares the pandemic-era "why now" behind Daffy, how traditional donor-advised funds quietly skim high AUM fees while setting eye-watering minimums, and walks through Daffy's flat-fee, app-first model.    This episode also covers:  ✅ What donor-advised funds are and why they've been hidden from most everyday givers  ✅ DAFs for tax optimization (bunching, appreciated stock, estate planning)  ✅ How to turn giving into a family and workplace culture (campaigns, matching, gift links)  ✅ Why Adam sees a DAF as a simple "charitable 401(k)" or mini family foundation without the lawyers, board meetings, or overhead, built to help you be more generous   ==========   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.)   ➡️ Join Bill or Jackie on :Daffy and receive an extra $25 bonus for charity in your new account  🌐 :Daffy (The Donor-Advised Fund For You™) ▶️ :Daffy on YouTube  📄The One Big Beautiful Bill Act (OBBBA) is Telling Donors One Thing: Get a Donor-Advised Fund  Donor-Advised Fund fee comparison calculator   Stock vs. Cash Donation Calculator      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.

3/1/26 • 74:37

What happens when a "late-starter" ER doc finally hits FI at 60, then must figure out how to actually spend the money without blowing it—or hoarding it forever? Bill joins Mindy and Scott on the BiggerPockets Money podcast to walk through his full "caught up to FI" debrief. Here his decade-long sprint from single-digit savings to 40%, taking his money back from a private bank, and the 60th-birthday retirement-readiness check that came back with a 100% success rate. From there, they dig into his move from a simple three-fund portfolio to a risk-parity setup, why he hired a flat-fee planner after years as a DIY investor, and how he's using FI to buy back time and jump-start his kids' wealth with Roth IRAs, HSAs, and tax-savvy living gifts. This episode covers:  ➡️ Going from "rich but broke doctor" to FI in about 10 years ➡️ Boosting a savings rate from single digits to ~40% without feeling deprived ➡️ Shifting from a three-fund portfolio to a risk-parity decumulation strategy ➡️ Using flat-fee, advice-only planner instead of 1% AUM ➡️ Order of withdrawals: taxable, pre-tax, Roth, plus asset location ➡️ Modeling taxes, RMDs, and Social Security timing in real life ➡️ Building a "3-1-1" spending plan for needs, comfort, and luxury/giving ➡️ Helping adult kids fill Roth IRAs and HSAs as part of generational wealth ➡️ Weighing when to actually leave medicine once money is no longer the boss   ==============================   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.) 🌐 BiggerPockets Money  BiggerPockets Money Youtube    ⏰ Related Episodes Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196  Flashback to Episode 1: 'A Boat Named YOLO' | Bill Yount | 197     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.

2/25/26 • 51:48

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.

2/22/26 • 59:07

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    ====================   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     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.

2/18/26 • 50:34

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 vulnerably 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's real superpower was boosting his savings rate up to ~40% in his early 50s using Mr. Money Mustache's 'shockingly simple math' to accept a 10 to 15-year timeline.   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' Saving Our Retirement on Humble Dollar 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.

2/15/26 • 72:18