Catching Up to FI

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  How to Retire at 40: Her Debt-Crushing Path to Financial Independence | Bernadette Joy | 228 26.07.2026 1ч 10мин

  What if crushing your money goals has less to do with finding the perfect formula—and more to do with getting lovingly bullied into taking action today? Bill and Jackie sit down with Bernadette Joy, a first-generation Filipino American who paid off $300,000 of debt in three years, reached her first million, and eventually built a multimillion-dollar portfolio. Bernadette also explains why she believes traditional financial literacy is dead, walks through her C-R-U-S-H framework, and reveals why the final "H" evolved from hustle to healing your money wounds. This episode covers How Bernadette paid off $300,000 of debt and reached her first million The $100-a-day strategy that made an intimidating goal feel actionable Why generating more income only works when you keep and invest the difference How she resisted lifestyle creep while building a seven-figure business Why her paid-off home mattered more emotionally than optimizing every return Her argument that financial literacy should become financial fluency and freedom The five-part C-R-U-SH framework for organizing money and designing an independent life The $1-per-use rule for spending intentionally without guilt How unsubscribing, reducing drama, and creating a peace plan support financial 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=== 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 Crush Your Money Goals Website  📕 CRUSH Your Money Goals Bernadette Joy's free retirement checklist and newsletter  2026 Plutus Impact Summit  2026 Plutus Awarsds    ⏰ Related Episodes  Live Talk from the Plutus Awards: Bill's Inspiring Message to Late Starters   . 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.  
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  Bonus: Is Your School's 403(b) On The Naughty List? Here's What To Do About It | Dan Otter | 227 22.07.2026 31мин

  What if the smartest way to fix teacher retirement is not patching the broken 403(b) machine, but quietly building an exit ramp to something better? In this bonus conversation, Bill, Jackie, and Dan Otter keep pulling the thread on the teacher-retirement mess and land on a surprisingly practical answer: the 457(b) may be the cleaner, simpler, more flexible plan that schools should be leaning into. Dan also highlights the new audio series Learned by Being Burned, Carl Fisch's 50-state teacher-retirement books, and several states that are getting it right. They end with a reminder that fixing a broken system starts with people who care enough to push back. This episode covers: Why auto-enrollment and employer matches are still rare in most teacher 403(b) plans How multi-vendor 403(b)s make even simple plan improvements harder than they should be The difference between individual and group 403(b) contracts, and why that matters How state-run 457 plans can simplify choices and lower costs for educators The role of unions, districts, and state policy in either helping or hurting teachers Real examples of school districts and states that are getting retirement plans right How teachers can organize coworkers, use advocacy tools, and pressure districts or states to improve plans . === 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===   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 403bwise 457bwiser https://457bwiser.org/ Learned by Being Burned (Special) Podcast Series) Man with the (Better Retirement) Plan (#262)  403bwise and 457bwiser Facebook Group  Banned by the NTSA  Request a Dan and Scott Presentation  Teach And Retire Rich  Meridian Wealth Management  Fisch Financial (Karl Fisch) . ⏰ Related Episodes Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205 The Wealthy Custodian Part 2: From Janitor to Millionaire | Jeff York | 076 The Wealthy Custodian Part 1: A Blue Collar Guide to Financial Freedom | Jeff York | 074 Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072   . 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.  
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  How K-12 Teachers Can Beat the Broken 403(b) System | Dan Otter & Scott Dauenhauer | 226 19.07.2026 1ч 12мин

  What if the most dangerous thing in a teacher's retirement plan isn't market volatility, it's the nice guy with free sandwiches and a terrible annuity contract? Jackie and Bill are joined by Dan Otter and Scott Dauenhauer of 403bwise, the duo who have spent decades exposing how badly K-12 educators get treated in the 403(b) world. What starts as a conversation about confusing vendor lists and a messy system, quickly turns into something bigger. This episode covers Why the K-12 403(b) system is fundamentally broken for many educators How Dan and Scott came together through the early 403bwise movement Why sales reps were able to roam campuses and sell high-cost products to teachers How 403(b)s became a multi-vendor mess while 401(k)s evolved under stronger fiduciary oversight Why newer teacher pension tiers are weaker and make supplemental retirement saving more important How bad 403(b) vendors can cost teachers hundreds of thousands of dollars over a career Why the 457(b) is increasingly the better option for many educators How state-run 457(b) plans can offer lower fees, simpler choices, and more retirement flexibility How teachers and school employees can advocate for better plans in their own districts . === 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===   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 . === 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===   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 403bwise 457bwiser https://457bwiser.org/ Learned by Being Burned (Special) Podcast Series) Man with the (Better Retirement) Plan (#262)  403bwise and 457bwiser Facebook Group  Banned by the NTSA  Request a Dan and Scott Presentation  Teach And Retire Rich  Meridian Wealth Management  . ⏰ Related Episodes Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205 The Wealthy Custodian Part 2: From Janitor to Millionaire | Jeff York | 076 The Wealthy Custodian Part 1: A Blue Collar Guide to Financial Freedom | Jeff York | 074 Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072 . 📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.
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  Risk & Reward: Stress Testing the Long Term Buy and Hold Strategy | Ben Carlson | 225 12.07.2026 1ч 11мин

  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.
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  You Hit The Number, Now What? | Childfree Life By Design Crossover | 224 08.07.2026 44мин

  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.
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  FIlanthropy: Radical Impact Giving Without Risking Your Retirement | Rebecca Herbst | 223 05.07.2026 1ч 30мин

  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.
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  Unbanked, Buried In Payday Loans & A 500 Credit Score: This Late-starter Overcame It All! | Afra Smith | 222 28.06.2026 26мин

  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.
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  Intergenerational Wealth: Strategies to Help Your Family NOW (Not Later) | Allen Mueller | 221 21.06.2026 1ч 3мин

  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.
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  Not So Big Life Design: The Architecture of Wealth | Sarah Susanka | 220 14.06.2026 1ч 3мин

  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.
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  Shocking Truths About Women's Financial History You Need to Know | Our Sheconomy Gameshow | 219 10.06.2026 1ч 36мин

  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.
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  We Found Them! Past Guests At The Women of FI Weekend | Kim H. and Lisa B. | 218 07.06.2026 30мин

  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.
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  Why "One More Year" Isn't Always a Mistake | Bill, Jackie, Patrick | 217 31.05.2026 1ч 1мин

  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.
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  How to Retire Sooner and Spend More: Risk-Based Guardrails Explained | Aubrey Williams | 216 24.05.2026 51мин

  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.
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  Why You Should Stop Beating Yourself Up for Starting Late | "How To Money" Crossover | 215 20.05.2026 1ч 3мин

  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.
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  Why Your Brain is Hardwired to Keep You Working (and How to Fix It) | Aubrey Williams | 214 17.05.2026 59мин

  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.
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  Your FIRE Plan is Screwed Without An Estate Plan! | Allison Harrison | 213 10.05.2026 1ч 9мин

  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.
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  Borderless FI: Starting Over At 37 After Divorce | Bronwyn Candish | 212 03.05.2026 57мин

  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.
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  The Fog of FI: Overcoming the Fear of Quitting Your Job | "The Long View" Crossover | 211 29.04.2026 1ч 4мин

  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.
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  Hot Takes & Money Debates: Social Security at 62, New Trump Accounts, & more! | Bill & Jackie | 210 26.04.2026 1ч 4мин

  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.
• 
  Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209 19.04.2026 1ч

  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.