Catching Up to FI

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
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☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee" 
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===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
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RESOURCES MENTIONED ON THE SHOW
Catching Up to FI Facebook Community
Jackie's FIRE Letter
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⏰ 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
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📌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.

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
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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)
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⏰ 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.

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.

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.

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.