Catching Up to FI

Dana Anspach, CFP® and founder of Sensible Money, returns to explain why retirement isn't one long, predictable chapter, it's a series of distinct phases with different financial and emotional needs. Using the framework from her new book, Living Off Your Acorns, Dana walks Bill and Jackie through the pre-go, go-go, slow-go, and no-go years.

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What if getting to FI has less to do with avoiding mistakes and more to do with surviving them without setting too much money on fire? Bill joins Doug Cunnington of Mile High FI for a refreshingly imperfect look at the financial decisions they wish they could redo. Between them: credit card debt, lifestyle inflation, whole life insurance, expensive advisors, an underwater dream house, a foreclosure, selling stocks at exactly the wrong time, and the very FI-specific problem of eventually becoming too good at saving. But this isn't just a financial confession booth. Bill and Doug compare what actually...

Erin Moriarity, the plain-English force behind Erin Talks Money, joins Bill and Jackie to unpack why retirement planning gets easier when we stop worshipping giant portfolio numbers and start thinking in income, spending, and real life. Erin traces her path from buying Campbell Soup stock at eight with her investing grandmother to earning the best 34 cents of her life on YouTube. She eventually grew the massive financial education platform we know today. Then the conversation moves into the stuff retirees actually worry about: whether late starters can still catch up, how Social Security may change, why the 4% rule gets...

What if the smartest financial planning move isn't a 100-page plan, but one question that makes you stop and say, "Wait... I can do that?" In this crossover with the AICPA Personal Financial Planning Podcast, Jackie puts on her professional hat for two conversations about the small ideas that can create much bigger financial wins. First, she and host Cary Sinnett unpack five high-impact planning opportunities involving 529s, 72(t)s, HSAs, charitable giving, and forgotten retirement accounts. Then they zoom out to the bigger question: why financial literacy, not products or strategies, is the foundation for better decisions and...

Need to figure out health insurance on your own? It's a little scary if you don't get it through an employer and too young for Medicare, but there are lots of options. In Part 2 with health insurance broker, Lyndia Cunningham, Bill and Jackie put early-retirement healthcare planning to the test with three very different case studies. Jackie rewinds to age 49 and walks through the decisions she faced before leaving work, including ACA subsidies and income planning. Bill brings a high-income household with no employer benefits and explains how stumbling into Tennessee Farm Bureau coverage slashed his monthly premiums by...

What if the biggest thing standing between you and early retirement isn't your savings... it's your health insurance? Bill and Jackie welcome Lyndia Cunningham of Move Health to tackle the healthcare headache that keeps so many Americans working until 65. From COBRA and short-term medical plans to faith-based health sharing and the Affordable Care Act, Lyndia walks through the options that could change your retirement timeline. Throw in retroactive COBRA, Medicaid, college health plans and direct primary care, and suddenly the path to healthcare freedom looks a lot less mysterious.

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Exposed! We go behind the scenes with industry experts and disrupters in the retail car-buying market, Ray and Zach Shefska. They are the powerful father-son team behind CarEdge, a car-buying platform that's fighting fiercely for transparency. Ray brings 43 years of dealership experience and Zach brings the modern tech (like AI agents) and viral moments when he exposes dealers misbehaving. Together, they reveal how dealerships really make money, including things like dealer fees, financing, and often unnecessary ad-ons. Don't miss this breakdown of smart ways for you to research, shop, avoid games some dealers play, and get the fairest price...

What if the biggest retirement risk isn't running out of money, but being too afraid to spend the money you worked decades to build? Personal finance icon Jean Chatzky joins Bill and Jackie to tackle the psychology and math behind turning a lifetime of savings into a Forever Paycheck. Jean shares her own late-start reset after losing her father, getting divorced, and getting fired within a single year. She then explains why retirees often happily spend Social Security and pensions while fiercely protecting their investment balances. Together they explore Jean's tools that can create both security and permission to...

What happens when you finally reach financial independence and your brain responds with, "Great, now what?" In this special crossover from ChooseFI, Ginger turns the microphone on Bill and digs into the part of financial independence that spreadsheets rarely prepare us for. He shares how a lawsuit and burnout woke him up financially at 50 and how he and his wife flipped from single-digit saving to intentional wealth building. Bill also explains why reaching FI at 60 created a whole new problem: actually giving himself permission to leave work.

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A 72(t) plan is little-known IRS provision which gives you a perfectly legal way to access your retirement money before 59½ without the 10% penalty. In this second half of the 2-part episode, Jackie brings back Mr. 72t, William (Bill) Stecker, CPA and founder of 72tcalc.com. This episode takes on the practical half of their deep dive into 72(t) plans as they move from theory to execution. Jackie puts her own plan on screen to let Bill do what he does best... audit it! He scrutinizes her $240k starting balance, $15k annual withdrawals, plan timeline, and the surprising fact that h...

You won't find a more comprehensive resource on the topic of 72(t) plans and substantially equal periodic payments (SEPP). This little-known IRS provision gives you a perfectly legal way to access your retirement money before 59½ without the 10% penalty… and almost nobody in finance wants to touch it! So, Jackie brings back the one expert that lives and breathes 72(t)s, William (Bill) Stecker, CPA and founder of 72tcalc.com. Bill picks up where he left off when he last appeared on the show in 2025. He further explains the nuances of 72(t) plans and how to avoid common mistakes. Hear how...

What happens when one of investing's original disruptors buys one of the industry's newest disruptors? Barry Ritholtz thinks investors may be the biggest winners and Bill and Jackie dig into why. This special breaking-news is an excerpt from an upcoming Catching Up to FI episode, recorded on 8/26/26. Barry reacts to Vanguard's newly announced agreement to acquire Altruist, the fast-growing technology and custody platform built for independent financial advisors. Barry also gives an important disclosure: he's an Altruist investor, so yes, he has a dog in this fight. From there, he explains why combining Vanguard's enormous scale with Altruist's technology...

What if that old pension you barely think about is secretly one of the most valuable assets in your retirement plan? Bill and Jackie welcome back financial planner and educator, Andy Panko for a deep dive into the increasingly rare (but far from extinct) world of pensions. They explore plans from private and government employers and why a seemingly small monthly check can dramatically change the work the rest of your portfolio has to do.

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After Rishi Vamdatt's conversation with Bill and Jackie, his parents Renu and Raag step out from behind the scenes to share how their son became the 16-year-old financial educator behind Easy Peasy Finance. They believe raising a financially savvy kid has less to do with giving money lectures and more to do with letting them swipe the credit card at the grocery store and ask "what happens next"? Their approach was surprisingly simple: money was never taboo, questions were always welcome, and Rishi was allowed to follow his curiosity rather than being scheduled into oblivion. For late-starting parents, the...

What if the person explaining money to your kids has already been doing it for more than half his life, and passed the CFP exam before he could legally vote? Bill and Jackie sit down with 16-year-old Rishi Vamdatt, founder of Easy Peasy Finance. Rishi started learning about money at six, investing at seven, and teaching personal finance on YouTube at eight. But this isn't just a story about an unusually motivated teenager. Rishi offers a surprisingly universal lesson: money gets easier when we strip away the jargon, practice with real dollars, automate the basics, and start where we...

This is Part 2 of a 2-part Episode. Be sure to catch Part 1 that aired last week (August 2nd).

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...

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 way, they visit th...

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.

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How Bernadette paid off $300,000 of de...

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...

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.

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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 yo...

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...

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?

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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...

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.

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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.<...

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...

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...

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...

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).

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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?"

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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.

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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.

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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.

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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.

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➡️ Bill's path from paycheck-to-paycheck physician to financially independent late starter

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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:

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...

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...

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 Well...

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.<...

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...