Catching Up to FI

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.

This episode covers

1. Why the K-12 403(b) system is fundamentally broken for many educators
2. How Dan and Scott came together through the early 403bwise movement
3. Why sales reps were able to roam campuses and sell high-cost products to teachers
4. How 403(b)s became a multi-vendor mess while 401(k)s evolved under stronger fiduciary oversight
5. Why newer teacher pension tiers are weaker and make supplemental retirement saving more important
6. How bad 403(b) vendors can cost teachers hundreds of thousands of dollars over a career
7. Why the 457(b) is increasingly the better option for many educators
8. How state-run 457(b) plans can offer lower fees, simpler choices, and more retirement flexibility
9. How teachers and school employees can advocate for better plans in their own districts

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===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS===

Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course

Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)

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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=== SUPPORT THE SHOW ===

📩 Sign up for our newsletter

🌐 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"

🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question

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===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS===

Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course

Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)

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

403bwise

457bwiser https://457bwiser.org/

Learned by Being Burned (Special) Podcast Series)

Man with the (Better Retirement) Plan (#262)

403bwise and 457bwiser Facebook Group

Banned by the NTSA

Request a Dan and Scott Presentation

Teach And Retire Rich

Meridian Wealth Management

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⏰ Related Episodes

Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205

The Wealthy Custodian Part 2: From Janitor to Millionaire | Jeff York | 076

The Wealthy Custodian Part 1: A Blue Collar Guide to Financial Freedom | Jeff York | 074

Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072

.

📌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 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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=== SUPPORT THE SHOW ===

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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"

🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question

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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

.

📌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:

1. The "fog of FI" and the identity shift that can come after reaching financial independence
2. The childfree midlife crisis and why "now what?" hits harder than many expect
3. Legacy beyond lineage and how childfree people often redefine impact
4. Why it is more important to know what you are retiring to than what you are retiring from
5. The tension between purpose, freedom, and drifting after hitting major goals
6. Health span, lifespan, and why time becomes more valuable once money pressure drops
7. How giving, service, and creativity can become the next chapter after FI
8. Why books, podcasts, and numbers alone cannot answer life-design questions
9. The difference between being rich on paper and living a truly wealthy life
10. Why underspending and over-optimizing can become their own retirement risks

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=== 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

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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

.

RESOURCES MENTIONED ON THE SHOW

Childfree Wealth https://childfreewealth.com/

.

⏰ Related Episodes

Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196

.

📌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:

1. Why Rebecca felt guilt, not just freedom, after reaching FI at 32
2. How giving can be framed as money, time, or skills—not just writing checks
3. Why generosity is a habit and a muscle, especially for lifelong savers
4. The surprisingly small impact that a 1% giving rate can have on your FI timeline
5. How "effective giving" applies investing-style thinking to charitable impact
6. The difference between reactive emotional giving and proactive intentional giving
7. Tax-smart giving tools like appreciated securities, donor-advised funds, and QCDs
8. Why the FI community may be uniquely positioned to normalize bold generosity
9. How giving can become part of a "life portfolio," not just a side project
10. 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

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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

.

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

.

📌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:

1. Afra's journey from payday loans, ChexSystems, and depression to financial stability
2. The career disappointment that became her wake-up call
3. How one financial coach and a basic budget started her turnaround
4. Why financial struggles in underserved communities are often deeper than "just spend less"
5. The origin of The Melanin Project and the Wealth Empowerment Conference
6. Why lived experience and emotional honesty matter in financial education
7. The link between mental health, physical health, and wealth-building
8. How Afra built a meaningful community event while still working a full-time job
9. Why consumption habits and appearances can distort how we judge wealth and value
10. 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

.

📌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.

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.

This episode covers:

1. Sarah Susanka's origin story and how suburbia pushed her toward architecture
2. The difference between building bigger and building better
3. Why unused rooms are the housing version of lifestyle bloat - How right-sizing a home parallels right-sizing a life
4. The design power of light, ceiling height, flow, and multi-use space
5. How small architectural moves can create huge changes in mood and function
6. Why old thought patterns can clutter a life just like unused rooms clutter a house
7. The connection between beauty, sustainability, and building things that last
8. How Bill used Sarah's ideas in his own home design and life redesign
9. Why intentional design matters even more for late starters making a reset spaces.

.

=== 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

Sarah's Website

Not So Big Design Principles for House & Life with Sarah Susanka

Sarah TedX talk

📗The Not So Big House: A Blueprint for the Way We Really Live

The New Urbanism

The Not So Big Bungalow

.

⏰ Related Episodes

How Clutter Steals Your Time (And How to Get It Back) | Rose Lounsbury | 188

.

📌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 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. The tone is playful, but the message is serious: money is power, and women stepping into that power changes families, businesses, markets, and maybe the whole economy.

This episode covers:

1. The surprising timeline of women's financial rights in the US
2. What Equal Pay Day reveals about how far women still have to go
3. Why women often outperform men as investors
4. How overconfidence and overtrading hurt returns
5. Why women-led businesses still receive a tiny share of venture capital
6. The rise of advice-only and flat-fee financial planning models
7. What values-aligned and ESG investing actually mean
8. Why women's money choices can reshape markets and communities
9. How much wealth women are expected to control in the coming years
10. The collective impact women could have by shifting capital intentionally

.

=== 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

Our Sheconomy

. ⏰ Related Episodes

Vote Your Money: Values Aligned Investing | Janine Firpo | 139

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.

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:

1. What happened at the Women of FI annual women's weekend in Maryland
2. Why women-centered FI spaces create a different kind of openness and trust
3. Kim Hunter-Borst's vision for building a smaller, more vulnerable, more intentional retreat
4. The 2026 theme of "release" and what women said they were ready to put down
5. A retirement update from Kim after leaving full-time work
6. A follow-up from Lisa B. on quitting her job, taking a summer break, and what happened next
7. Why women said they needed space for both the "outer" and "inner" work of FI
8. 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.

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:

1. Why "one more year syndrome" may not actually be a bad thing
2. The emotional transition from being FI on paper to actually changing your life
3. Bill's intentional downshift and how FI gave him leverage at work
4. Jackie's two-year hesitation and why she now sees it with more grace
5. How fear, identity, purpose, and burnout all shape retirement timing
6. Why working after FI can still make sense if it serves your life
7. The difference between choosing one more year and drifting into it unconsciously
8. How tragedy and loss can change the way you think about time
9. Why the second chapter of life requires more than just good math
10. 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"

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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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📌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.