PodcastsBusinessCatching Up to FI

Catching Up to FI

Bill Yount & Jackie Cummings Koski
Catching Up to FI
Latest episode

219 episodes

  • Catching Up to FI

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

    07/06/2026 | 30 mins.
    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.
  • Catching Up to FI

    Why "One More Year" Isn't Always a Mistake |Bill, Jackie, Patrick | 217

    31/05/2026 | 1h 1 mins.
    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.
  • Catching Up to FI

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

    24/05/2026 | 51 mins.
    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.
  • Catching Up to FI

    Why You Should Stop Beating Yourself Up for Starting Late | "How To Money" Crossover | 215

    20/05/2026 | 1h 3 mins.
    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.
  • Catching Up to FI

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

    17/05/2026 | 59 mins.
    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.
More Business podcasts
About Catching Up to FI
A mindset, money, and life podcast for late starters catching up to Financial Independence.
Podcast website

Listen to Catching Up to FI, She's On The Money and many other podcasts from around the world with the radio.net app

Get the free radio.net app

  • Stations and podcasts to bookmark
  • Stream via Wi-Fi or Bluetooth
  • Supports Carplay & Android Auto
  • Many other app features