Why "One More Year" Isn’t Always a Mistake | Bill, Jackie, Patrick | 217
Catching Up to FI: Financial Independence for Late Starters
Release Date: 05/31/2026
More Bonds, James, Bonds: Rethinking Your BND Strategy (Part 2) | Frank Vasquez | Episode 230
Catching Up to FI: Financial Independence for Late Starters
What if the safest-looking retirement portfolio is actually protecting you from the wrong disaster? In part two of Bill’s bond marathon with Frank Vasquez, the conversation moves from Bond 101 into the question that really matters: what role should fixed income play once you stop accumulating and start living from your portfolio? Frank explains why bonds should be chosen for a specific job, why a total bond fund may be trying to do too many things at once, and why retirement planning should prepare for a bad decade. The ultimate takeaway is reassuring: bonds are complicated, but most people...
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Are Bonds Dead?: Fixed Income Fundamentals (Part 1) | Frank Vasquez | Episode 229
Catching Up to FI: Financial Independence for Late Starters
What if bonds aren't dead at all—and we've just spent the last decade misunderstanding what job they were hired to do? Bill welcomes back Frank Vasquez, the hotdog-named engineer-lawyer-DIY investor behind Risk Parity Radio, for part one of a lively fixed-income deep dive. Starting with the basics, Frank explains what a bond actually is, why owning one makes you the lender rather than the shareholder, and how bonds can provide income, stability, or diversification depending on the type and duration. They work through the very real risks hiding behind the phrase "safe investment." Along the...
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How to Retire at 40: Her Debt-Crushing Path to Financial Independence | Bernadette Joy | 228
Catching Up to FI: Financial Independence for Late Starters
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...
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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
Catching Up to FI: Financial Independence for Late Starters
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...
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How K-12 Teachers Can Beat the Broken 403(b) System | Dan Otter & Scott Dauenhauer | 226
Catching Up to FI: Financial Independence for Late Starters
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...
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Risk & Reward: Stress Testing the Long Term Buy and Hold Strategy | Ben Carlson | 225
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...
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You Hit The Number, Now What? | Childfree Life By Design Crossover | 224
Catching Up to FI: Financial Independence for Late Starters
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...
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FIlanthropy: Radical Impact Giving Without Risking Your Retirement | Rebecca Herbst | 223
Catching Up to FI: Financial Independence for Late Starters
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...
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Unbanked, Buried In Payday Loans & A 500 Credit Score: This Late-starter Overcame It All! | Afra Smith | 222
Catching Up to FI: Financial Independence for Late Starters
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...
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Intergenerational Wealth: Strategies to Help Your Family NOW (Not Later) | Allen Mueller | 221
Catching Up to FI: Financial Independence for Late Starters
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...
info_outlineWhat 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
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