Catching Up to FI

What if crushing your money goals has less to do with finding the perfect formula—and more to do with getting lovingly bullied into taking action today? Bill and Jackie sit down with Bernadette Joy, a first-generation Filipino American who paid off $300,000 of debt in three years, reached her first million, and eventually built a multimillion-dollar portfolio. Bernadette also explains why she believes traditional financial literacy is dead, walks through her C-R-U-S-H framework, and reveals why the final "H" evolved from hustle to healing your money wounds.
This episode covers
How Bernadette paid off $300,000 of debt and reached her first million

The $100-a-day strategy that made an intimidating goal feel actionable

Why generating more income only works when you keep and invest the difference

How she resisted lifestyle creep while building a seven-figure business

Why her paid-off home mattered more emotionally than optimizing every return

Her argument that financial literacy should become financial fluency and freedom

The five-part C-R-U-SH framework for organizing money and designing an independent life

The $1-per-use rule for spending intentionally without guilt

How unsubscribing, reducing drama, and creating a peace plan support financial 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===
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
Crush Your Money Goals Website 
📕 CRUSH Your Money Goals
Bernadette Joy's free retirement checklist and newsletter 
2026 Plutus Impact Summit 
2026 Plutus Awarsds 
 
⏰ Related Episodes 
Live Talk from the Plutus Awards: Bill's Inspiring Message to Late Starters
 
.
📌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 way to fix teacher retirement is not patching the broken 403(b) machine, but quietly building an exit ramp to something better? In this bonus conversation, Bill, Jackie, and Dan Otter keep pulling the thread on the teacher-retirement mess and land on a surprisingly practical answer: the 457(b) may be the cleaner, simpler, more flexible plan that schools should be leaning into. Dan also highlights the new audio series Learned by Being Burned, Carl Fisch's 50-state teacher-retirement books, and several states that are getting it right. They end with a reminder that fixing a broken system starts with people who care enough to push back.
This episode covers:
Why auto-enrollment and employer matches are still rare in most teacher 403(b) plans

How multi-vendor 403(b)s make even simple plan improvements harder than they should be

The difference between individual and group 403(b) contracts, and why that matters

How state-run 457 plans can simplify choices and lower costs for educators

The role of unions, districts, and state policy in either helping or hurting teachers

Real examples of school districts and states that are getting retirement plans right

How teachers can organize coworkers, use advocacy tools, and pressure districts or states to improve plans

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


.
=== 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===
 
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
.
=== 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===
 
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
.
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 
.
⏰ 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
.
=== 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
A Wealth of Common Sense
Animal Spirits Podcast
Risk and Reward: How to handle market volatility and build long-term wealth
The Compound Youtube
.
⏰ 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:
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/
.
⏰ 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.