Catching Up to FI

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 behavior, and build a portfolio you can actually stick with.
This episode covers:
Ben Carlson's "Bob" thought experiment and why even terrible market timing can still work out over the long run
Why dollar cost averaging often beats waiting for the perfect entry point
The psychology of lump-sum investing versus spreading money out over time
What inflation looked like before World War II versus in the modern era
How to think about inflation through a personal-finance lens, not just an investing lens
Why housing, transportation, income growth, and stocks are major inflation defenses
What Japan's lost decades teach us about home-country bias and international diversification
Why diversification matters even more in retirement because of sequence-of-returns risk
How to think about bonds, cash, duration, and risk tolerance in a more nuanced way
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🌐 Visit Catching Up to FI website 
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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===
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 
📕 Get Your Copy  (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
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RESOURCES MENTIONED ON THE SHOW
A Wealth of Common Sense
Animal Spirits Podcast
Risk and Reward: How to handle market volatility and build long-term wealth
The Compound Youtube
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⏰ Related Episodes 
The 5 Investing Hurdles You Can't Ignore | Bill Bernstein | 201
Hanging On In a Yo-Yo Economy | Sam Stovall | 147 
How to Bake a Cake: An Asset Allocation Mashup | Rick Ferri & Paul Merriman | 134 
"The Risk Parity Paradox" an Exercise in Simple Complexity? | Frank Vasquez | 124
 
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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 "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 the finish line. It's the moment when the real design work begins.
This episode covers:
The "fog of FI" and the identity shift that can come after reaching financial independence
The childfree midlife crisis and why "now what?" hits harder than many expect
Legacy beyond lineage and how childfree people often redefine impact
Why it is more important to know what you are retiring to than what you are retiring from
The tension between purpose, freedom, and drifting after hitting major goals
Health span, lifespan, and why time becomes more valuable once money pressure drops
How giving, service, and creativity can become the next chapter after FI
Why books, podcasts, and numbers alone cannot answer life-design questions
The difference between being rich on paper and living a truly wealthy life
Why underspending and over-optimizing can become their own retirement risks
.
=== 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 
📕 Get Your Copy  (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
Childfree Wealth https://childfreewealth.com/
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⏰ Related Episodes 
Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196
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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.

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 lifelong savers
The surprisingly small impact that a 1% giving rate can have on your FI timeline
How "effective giving" applies investing-style thinking to charitable impact
The difference between reactive emotional giving and proactive intentional giving
Tax-smart giving tools like appreciated securities, donor-advised funds, and QCDs
Why the FI community may be uniquely positioned to normalize bold generosity
How giving can become part of a "life portfolio," not just a side project
References & Resources Mentioned
.
=== 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 
📕 Get Your Copy  (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
Yield and Spread
FI Service Corps
 
⏰ Related Episodes 
Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209
A Donor-Advised Fund For You (Daffy): Democratizing Philanthropy for Everyone | Adam Nash | 200
Contrarian Tax Planning Tips | Cody Garrett & Sean Mullaney | 179
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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 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 how one financial coach, one budget, and one decision to stop waiting for someone else to rescue her changed the direction of her life. From there, she built something much bigger than a comeback story. It's now a growing movement centered on financial wellness, lived experience, and giving people the tools to rebuild from where they actually are. Her raw truth is proof that your hardest chapter does not have to be your final one.
This episode covers: 
Afra's journey from payday loans, ChexSystems, and depression to financial stability
The career disappointment that became her wake-up call
How one financial coach and a basic budget started her turnaround
Why financial struggles in underserved communities are often deeper than "just spend less"
The origin of The Melanin Project and the Wealth Empowerment Conference 
Why lived experience and emotional honesty matter in financial education 
The link between mental health, physical health, and wealth-building
How Afra built a meaningful community event while still working a full-time job
Why consumption habits and appearances can distort how we judge wealth and value 
What it looks like to turn pain into service and purpose
.
=== 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 
📕 Get Your Copy  (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
The Melanin Project 
TrueStage 
CLIMB USA (Bob Wynn) 
Madison Gas and Electric Company 
Summit Credit Union
 
⏰ Related Episodes 
From Poverty to Wealth and Early Retirement | Jackie Cummings Koski | 007
We Found Them! Past Guests At The Women of FI Weekend | Kim H. and Lisa B. | 218
 
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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 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 larger inheritance later
The difference between a tax threshold and a paperwork threshold for gifts
How the annual gift exclusion really works
Why many retirees underspend and unintentionally miss chances to help family now
Smart ways to fund kids' and grandkids' futures through 529s, custodial Roths, and brokerage accounts
How to think about gifting for college, healthcare, and home down payments
Why "skin in the game" still matters when helping younger family members
How appreciated shares can be gifted downstream or upstream for tax advantages
Why wisdom and stewardship matter more than simply transferring money
How FI can turn parents and grandparents into real-time wealth builders for the next generation
.
=== 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
📕 Get Your Copy  (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
7 Saturdays Financial
Allen's LinkedIn 
.

⏰ Related Episodes
Why 90% of Families Lose Their Wealth (and How to Stop the Cycle) | Julia Myers | 209 
These New Rules Will Change The Way You Think About 529 Plans | Patricia Roberts | 193 
 
.
📌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.