Catching Up to FI

Don't miss this special 3-year anniversary of 'Catching Up to FI' as Bill marks the moment by doing something he's been helping everyone else do for years: officially 'coming out' as financially independent (FI)! It is hard to believe that the show has been around for 3 years, 196 episodes, 20k Facebook Community members, 1.4M audio downloads and 300k views on YouTube. Is this real?
 
Today we celebrate Bill's journey from Episode #1: 'A Boat Named Yolo', to officially reaching FI, but feels more like the 'The Fog of FI'. During this interview, Jackie gets Bill to open up and vulnerably share details of his wake-up call at 50: burned out, sued, house-poor after a disastrous renovation and de-risking at the bottom of the Great Recession, and still living paycheck to paycheck despite a 'rich doctor' income. He walks through discovering FI via blogs and books, taking a full year to reclaim his money from private bankers and whole life policies (he's naming names!). Bill's real superpower was boosting his savings rate up to ~40% in his early 50s using Mr. Money Mustache's 'shockingly simple math' to accept a 10 to 15-year timeline.
 
Fast-forward to 60 and a retirement-readiness check with a flat-fee, advice-only planner: after three years of expense tracking in Monarch Money, a comprehensive plan, and stress-testing with risk-parity portfolios, Bill gets the verdict every late starter dreams of, 'you could retire tomorrow'— and feels weirdly flat. We also dig into the emotional side: the identity crisis of possibly leaving medicine, using newfound leverage to negotiate work on his own terms, the choice to glide out over several years instead of cliff-retiring, and the shift from building wealth to giving with warm hands, mentoring younger docs, and helping his adult sons lay foundations he never had.
 
We close with Bill's hard-earned advice: 
➡️ Reverse-engineer your life from your tombstone
➡️ Focus on health span as fiercely as net worth
➡️ Stop over-identifying with your job or your number
➡️ Remember that for late starters, the real win is feeling less alone while you build a life you won't regret.
 
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DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS:
 
MONARCH MONEY

The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50
 
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners 
 
SUPPORT  THE  SHOW
📩 Sign up for our newsletter
🌐 Visit Catching Up to FI website 
🔗Connect with us
☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 
🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question

 
 
RESOURCES MENTIONED ON THE SHOW:
📄 Bill's 'Letter of Gratitude' and 'Financial Life Policy Statement'
Saving Our Retirement on Humble Dollar
Bill's Financial Planner:  Bryan Minogue CFP®, CFA (Kardinal Financial)
 
⏰ Related Episodes
A Boat Named YOLO | Bill Yount | 001
The Power of Cash Flow Planning | Sarah-Catherine Gutierrez | 016
The Father of Financial Life Planning (Part 1) | George Kinder | 140
 
If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!
 
 
📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Do you want to own your time, work less, and live more? What if the point isn't maxing out every account forever, but designing a week you don't want to escape from? This is the Coast FI life built by our guest today, Andy Hill. He shares the steps you can take to put your family first and escape the 9-5 grind: for good! He takes us through the full arc: starting married life at –$50K net worth, killing the debt in a year with budget parties, saving 40–50% to hit around $500K in investments by forty, then realizing that number was enough for Coast FI. With all that, he realized that what he really wanted was time. 
 
Andy is an award-winning blogger, podcaster, and family finance coach behind Marriage, Kids, and Money. He's also author of the new book 'Own Your Time: 10 Financial Steps to Put Your Family First and Escape the Corporate Grind', which walks readers through simple, yet highly effective steps families can take to achieve family financial independence. It also features real-life examples of couples who've conquered these family financial independence milestones and found better lives for themselves because of it.
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DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS:
 
MONARCH MONEY

The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50
 
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners 
 
SUPPORT  THE  SHOW
📩 Sign up for our newsletter
🌐 Visit Catching Up to FI website 
🔗Connect with us
☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 
🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question

 
 
RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)
🌐 Marriage Kids and Money
📕 Own Your Time: 10 Financial Steps to Put Your Family First and Escape the Corporate Grind
 
⏰ Related Episodes
Generosity and Smart Spending: A Family Affair | Andy Hill | 103
 
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.

Strap in, because Jackie joins Brad Barrett for a crossover episode on the ChooseFI podcast, home of the world's largest FI community! Together, they rewind all the way back to 2017, when Jackie first stumbled onto ChooseFI… and everything changed. She recounts her journey to reaching early retirement by December 2019, and using that freedom to go back to school, get her CFP, and write 'F.I.R.E. for Dummies'. Then the two of them dive deep into the fundamentals and break down what financial independence really means. They explain why even ten dollars a month can spark a lifelong investing habit, and how Jackie's first investment club taught her the power of community and compounding. They decode 401(k)s, demystify fund selection, and spotlight the quiet villain of investing: expense ratios.
 
The episode widens from there: debt payoff strategies, designing a modest but deeply rich life on $40–45K a year in Ohio, negotiating everything from internet bills to insurance premiums, and the emotional transformation from paycheck-to-paycheck lifestyle to feeling 'directionally correct.' They conclude with the realization that FI isn't just about money, it's about options. Whether you're a late starter, brand new or ten years into the journey; returning to the basics is how you stay grounded, stay motivated, and stay on course.
 
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DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS:
 
MONARCH MONEY

The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50
 
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners 
 
SUPPORT  THE  SHOW
📩 Sign up for our newsletter
🌐 Visit Catching Up to FI website 
🔗Connect with us
☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 
🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question

 
 
RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)
🌐ChooseFI 
🌐Jackie's website FInomenalWoman.com
📕F.I.R.E. For Dummies  
📘Money Letters 2 My Daughter  
📈Jackie's Investment Club through BetterInvesting.org
 
⏰ Related Episodes
The Godfather of FI Talks Fatherhood | JL Collins | 149
Stories, Hacks, & Tribes | Brad Barrett | 021
From Poverty to Wealth and Early Retirement | Jackie Cummings Koski | 007
 
 
If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!
 
 
📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

529 plan expert Patricia Roberts blows up the myth that 'it's too late' and '529s are just for rich people with toddlers and Ivy League dreams'. She is author of the book 'Route 529' and shares some big changes with 529 plans that make them an incredibly flexible savings vehicle for more than just college. In this episode we cover:
How state tax deductions, credits and 'parity states' work for contributions
The shockingly long list of qualified uses including trade schools, apprenticeships, non-degree credentials, K–12 tuition, tutoring, test prep and even student loan repayment 
Busting the 'use it or lose it' fear and the new option to rollover left over funds to a Roth IRA
How to juggle retirement vs. college savings
Advanced strategies to create generational education wealth
 
 

DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS:
 
MONARCH MONEY

The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50
 
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners 
 
SUPPORT  THE  SHOW
📩 Sign up for our newsletter
🌐 Visit Catching Up to FI website 
🔗Connect with us
☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 
🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question

 
 
RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)
🌐 Gift of College
College Countdown
📕 Route 529: A Parent's Guide to Saving for College and Career Training with 529 Plans
Morningstar 529 Ratings: The Best Plans of 2025
What You Can Pay for With a 529 Plan
 
⏰ Related Episodes
The College Discount Game You Need To Know Before Choosing A School | Ron Lieber | 191
Stop Paying for College and Use These High-Return Scholarship Hacks Instead | Chris Corinthian | 189
Banishing The Burden of Student Loan Debt | Travis Hornsby | 122 
 
 
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.

Dan Haylett gives us a late-starter masterclass on why retirement is a human problem long before it's a math problem. Dan is a UK financial planner, creator of 'Humans vs Retirement' podcast, and author of 'The Retirement You Didn't See Coming'.  He walks us through how that outdated 'retire from work and fade away' script clashes with modern 50- and 60-somethings who still have health, curiosity, and huge ambitions. In this episode he also:
Reframes risk as the possibility of dying with plenty of money but too few memories
Unpacks why spreadsheets never quite make us feel safe
Lays out his three-phase map of the second half of life
 
 

DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS:
 
MONARCH MONEY

The modern way to manage money! Monarch will change the way you organize your financial life. Track, budget, plan, and do more with your money – together. Get 50% off the first year using this link and entering code: CATCHINGUP50
 
ALLOY

The Alloy Market offers a seamless and efficient way to sell your gold, silver, and platinum jewelry, regardless of its condition. They are committed to transparency and fairness, ensuring you get the best possible value for your items. Use this special Link and enter code CUTOFI15 to get a $15 bonus when you sell items over $199 (limited time offer). 
 
For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners 
 
SUPPORT  THE  SHOW
📩 Sign up for our newsletter
🌐 Visit Catching Up to FI website 
🔗Connect with us
☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 
🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question

 
 
RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)
🌐 Humans vs Retirement Website & Podcast
📕 The Retirement You Didn't See Coming
 
⏰ Related Episodes
What Would 'Your Money' Look Like In a Simple Sketch? | Carl Richards | 170
The Father of Financial Life Planning (Part 1) | George Kinder | 140
The Three Kinder Questions (Part 2) | George Kinder | 141
Hard & Soft Sides of Retirement | Fritz Gilbert | 019
 
 
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.