Catching Up to FI

APRIL IS FINANCIAL LITERACY MONTH!
What if one passionate professor, one classroom, and a few brave money questions could change hundreds of financial lives before graduation? We head to Knoxville for a special Financial Literacy Month episode with Dr. Karen DeLong, the University of Tennessee professor quietly doing the work most schools still don't: making sure students leave campus with more than a degree. Karen shares how three advanced degrees somehow included zero personal-finance education and how that gap pushed her to build an annual money session for her students. Bill and Jackie reflect on what it was like to teach these soon-to-be graduates and how any late starter can become a powerful financial literacy advocate in their own little corner of the world.
 
This episode covers:
➡️ Why Dr. Karen DeLong started bringing personal finance into her classroom
➡️ How someone can earn multiple degrees and still never take a money class
➡️ Why college students are hungry for practical money conversations
➡️ The kinds of personal finance questions students are asking before graduation
➡️ How Bill and Jackie prepare for live financial literacy teaching sessions
➡️ Why financial literacy fits into almost any curriculum, not just finance classes
➡️ How Farm Credit Mid-America helped support this student enrichment work
➡️ Why late starters can still become mentors and financial literacy advocates
➡️ A preview of the student follow-up episode answering unanswered questions
 
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===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS===
📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial.   👉🏼 Be sure to use this link to get started:  Go.boldin.com/catchingup
 
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

 
 
RESOURCES MENTIONED ON THE SHOW: 
 
🌐 Dr. Karen DeLong 
 
Farm Credit Mid-America
 
 
⏰ Related Episodes
 
Highlights from Bill and Jackie presenting at UT Knoxville (coming in April) 
 
Questions from Students (coming in April)
 
 
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.

April is Financial Literacy Month and we're starting a little early! That's because we are so excited to launch a new project called "The Great 401(k) Cleanup." What if the easiest way to boost your retirement odds this year isn't reducing your spending or a side hustle, but cleaning up that messy, confusing 401(k) you've been ignoring? We are using Financial Literacy Month to launch a full-on 401(k) intervention with a step-by-step guide including:
Access From Home 
Contributions 
Beneficiaries 
Investments 
Rate of Return 
What's Next 
 
401(k)s and similar workplace plans like the TSP, 403(b), and 457 have become the backbone of retirement for most Americans. Yet they are often confusing and complicated to the average employee. No wonder so many accounts get neglected and become messy over time. The good news is that 2026 can be the year you clean it all up. This friendly and straightforward guide was created independent of any employer or plan provider, and will help you get going. By the time you're done you'll better understand your 401(k) and feel more empowered to use it as a real tool to build wealth and support your money goals. This episode covers: 
➡️ How to clean up a messy 401(k) in less than an hour
➡️ Why year-to-date returns can mislead and longer time frames matter more 
➡️ How contribution rate and savings rate shape your retirement timeline
➡️ Employer match, vesting schedules, and why "free money" still confuses people
➡️ Target date funds and simple one- to three-fund strategies 
➡️ How to spot low-cost index funds inside an ugly 401(k) menu
➡️ What to do with old 401(k)s when you change jobs
➡️ How AI can help decode plan documents and confusing fund lists
➡️ Why forgotten 401(k)s now total a jaw-dropping $2.1 trillion
 
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DOWNLOAD GUIDE & EDITABLE CHECKLIST
📄 Cleaning up your 401(k) in less than an hour (complete guide with references)
📄 Cleaning up your 401(k) in less than an hour- Editable Checklist (download first)
 
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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

 
 
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 best retirement advice didn't come from a spreadsheet—but from a real retiree saying, "I wish I'd done it sooner"? Jackie crosses over to "REAL Retirees: Uncut" for a refreshingly candid, walk through of what six years of early retirement have actually looked like. She also shares her top five reasons to retire early, from time freedom and better mental health to the surprising new opportunities that open up when your job no longer runs your calendar. And because this is still Catching Up to FI, she closes with a message straight to late starters: most people wake up later than they wanted, but that doesn't mean they're doomed. It means they need a new frame and a little grace.
This episode covers: 
➡️ Jackie's real-life retirement story, six years in
➡️ Retiring at 49 after corporate life 
➡️ Building a nest egg using FIRE math and the 4% rule
➡️ Living off brokerage assets, Roth contributions, and a 72(t) strategy before 59½
➡️ ACA health insurance subsidies and managing income in early retirement
➡️ Why Jackie kept her mortgage and doesn't regret it
➡️ Her top five reasons to retire early
➡️ The hidden superpowers late starters already have 
➡️ Why retirement success is really about freedom, health, and impact
 
====================
 
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.)
 🌐REAL Retirees: Uncut http://www.youtube.com/@REALRetireesUncut
🌐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
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.

What if you were already financially independent at 40… and didn't realize it until a random pension search and a couple of podcasts blew the whole thing open? This was Jaylynn's "Surprise FI" and he joins the show to take us blow by blow. He gives us look back to his childhood of money orders, loving parents, and "value over flash" shaped him. He shares how he went from thinking the stock market was gambling to maxing out a 401(k), building a brokerage account, and accidentally discovering he had already hit FI in his forties. But this isn't just a "run the numbers and quit" story. Jaylynn talks through Surprise FI, staying in a job he loved until COVID burnout changed the equation, retiring at 44, managing ACA subsidies, planning Roth conversions and a future 72(t). He's now using time freedom to become the dad his son would later call his "best friend." He leaves us with the reminder that progress beats perfection—especially for late starters. 
This episode covers:
How Jaylynn's parents taught him value, bills, and stretching money without calling it "financial literacy"

Why he thought investing was gambling after watching Trading Places

The coworker moment that made him realize he was already an investor through his 401(k)

A rare private-company benefits setup: automatic 401(k) contributions, pension, and relocation packages

How he discovered the FIRE movement by researching pension payout options

"Surprise FI" at age 40 using the 4% rule and liquid assets only

Why he kept working after hitting FI—and what changed in 2020

Retiring at 44 with a mortgage, a tax strategy, and 15 years of runway

Using ACA subsidies, Roth conversions, and a future 72(t) to bridge the early-retirement years

Why the real wealth turned out to be time with his kids, not just a portfolio balance

 
====================
 
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: 
 
ChooseFI  
BiggerPockets Money 
Jill On Money 
The Retirement Answer Man 
 
 
⏰ Related Episodes
72(t) Expert Tells All: No More Secrets About Early Withdrawals (Part 1) | Bill Stecker | 131


Cashing in on 72(t): The Goldmine of Early Retirement Rules (Part2) | Bill Stecker | 133


 
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.

Today we're putting AI (Artificial Intelligence) to the test with AI money expert Jeffrey Trull. He's founder of the blog and newsletter, Money Meets AI where he shares tested prompts for your money. He joins us to sort the genuinely useful from the wildly overhyped when it comes to AI. We expand our conversation into prompts, privacy, hallucinations, portfolio questions, Google vs. ChatGPT, paid vs. free tools, and where AI can actually save real time for DIYers. Along the way, Bill wrestles with the tradeoff between efficiency and original thought, Jackie pushes the "AI as thought partner" framing, and Jeffrey stresses that it's great for lower-risk questions but terrible as your all-knowing financial planner. 
This episode covers:
Where AI is genuinely useful for DIY personal finance
Why prompts matter, but perfection is overrated
Using AI to review insurance, contracts, and 401(k) plan docs
Google vs. ChatGPT vs. Claude for money questions
Paid vs. free AI tools and when subscriptions are worth it
AI "hallucinations" and how to fact-check outputs
Privacy concerns when uploading financial documents
Why AI should be a thought partner, not your financial planner
Agentic AI, AI shopping assistants, and what may be coming next
 
====================
 
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.)
🌐 Money Meets AI
Top 5 Prompts for the Money Math You've Been Avoiding 
 
⏰ Related Episodes
Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196
 
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.