Catching Up to FI

Need to figure out health insurance on your own? It's a little scary if you don't get it through an employer and too young for Medicare, but there are lots of options. In Part 2 with health insurance broker, Lyndia Cunningham, Bill and Jackie put early-retirement healthcare planning to the test with three very different case studies. Jackie rewinds to age 49 and walks through the decisions she faced before leaving work, including ACA subsidies and income planning. Bill brings a high-income household with no employer benefits and explains how stumbling into Tennessee Farm Bureau coverage slashed his monthly premiums by thousands. Then listener Brooke explores whether health insurance really needs to be the golden handcuffs keeping her in a W-2 job.
This episode covers
How Jackie could have evaluated healthcare before retiring at 49
Why retirement timing and modified adjusted gross income can dramatically affect ACA costs 
Bronze versus Silver plans, cost-sharing reductions, and HSA eligibility
How to make sure an ACA plan actually includes the doctors you want to keep
What Jackie ultimately paid for healthcare after retiring
Why Bill chose Farm Bureau coverage instead of the ACA marketplace 
How medical underwriting and non-ACA major medical plans work
Health insurance options for adult children aging off a family plan 
How association plans, college health plans, and HSAs can expand your choices
Whether healthcare really needs to keep Brooke (or anyone else) tied to a job 
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This is the second part of a 2-part episode. Be sure to subscribe the show and catch part 1 (episode 239) from 9/27/26.
 
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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
Move Health 
Move Health YouTube 
Health Insurance for Early Retirees 
ACA Health Insurance Marketplace 
 
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⏰ Related Episodes
How to Get Health Insurance When You Retire Early | Lyndia Cunningham (Part 1) | 239
Mind Blowing ways to Maximize Your Health Savings Account (HSA) | Jeff York | 98
Maximizing HSAs Part 2: Devising Drawdowns, Badass Scenarios, Listener Questions | Jeff York | 99
 
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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 biggest thing standing between you and early retirement isn't your savings... it's your health insurance? Bill and Jackie welcome Lyndia Cunningham of Move Health to tackle the healthcare headache that keeps so many Americans working until 65. From COBRA and short-term medical plans to faith-based health sharing and the Affordable Care Act, Lyndia walks through the options that could change your retirement timeline. Throw in retroactive COBRA, Medicaid, college health plans and direct primary care, and suddenly the path to healthcare freedom looks a lot less mysterious.
This episode covers
The health insurance options available to early retirees before Medicare at 65
How COBRA, short-term medical insurance, Farm Bureau plans and healthcare-sharing programs compare
The important differences between ACA-compliant insurance and other types of coverage
How spouses, dependents and college students can access alternative coverage
Retroactive COBRA and planning for the transition out of employer-sponsored insurance
ACA essential health benefits, provider networks and out-of-state coverage limitations
How ACA premium subsidies interact with household income, Roth conversions and HSA contributions
Medicaid eligibility and the complications that can arise for early retirees and their families
Dental, vision, accident and critical illness coverage beyond a basic health insurance plan
How HSAs and direct primary care can fit into a broader retirement healthcare strategy
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This is the first part of a 2-part episode. Be sure to subscribe to the channel and catch part 2 next week (10/4/26).
.
=== 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
Move Health 
Move Health YouTube 
ACA Health Insurance Marketplace 
 
.
⏰ Related Episodes
Mind Blowing ways to Maximize Your Health Savings Account (HSA) | Jeff York | 98
Maximizing HSAs Part 2: Devising Drawdowns, Badass Scenarios, Listener Questions | Jeff York | 99
 
.
📌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.

Exposed! We go behind the scenes with industry experts and disrupters in the retail car-buying market, Ray and Zach Shefska. They are the powerful father-son team behind CarEdge, a car-buying platform that's fighting fiercely for transparency. Ray brings 43 years of dealership experience and Zach brings the modern tech (like AI agents) and viral moments when he exposes dealers misbehaving. Together, they reveal how dealerships really make money, including things like dealer fees, financing, and often unnecessary ad-ons. Don't miss this breakdown of smart ways for you to research, shop, avoid games some dealers play, and get the fairest price on your next car.
This episode covers
How dealerships use monthly payments to distract buyers from the total cost of a car
Why negotiating a vehicle can be especially difficult for women and minority buyers
Using AI agents to obtain and negotiate real dealer pricinng
The fees, add-ons, and protection packages buyers should question
Why "if it's taxable, it's negotiable" is one of Ray's favorite rules
How to get and compare a true out-the-door price
Why a pre-purchase inspection is critical when buying a used vehicle
The pros and cons of CarMax and Carvana
How pre-approved financing can protect you from dealer interest-rate markups
Cash versus financing, leasing and total cost of ownership
Ray's ultimate rule: buy what you need, not just what you want
 
.
=== 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
CarEdge (Research, Dealer Ratings, Car-buying Service)
CarEdge Podcast
CarEdge YouTube
CarEdge Live YouTube
Shady Car Dealers are Done! Fair Pricing Summit DC
Zach's AI Summit Talk
Ray's letters to his late wife Suzanne 
 
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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 biggest retirement risk isn't running out of money, but being too afraid to spend the money you worked decades to build? Personal finance icon Jean Chatzky joins Bill and Jackie to tackle the psychology and math behind turning a lifetime of savings into a Forever Paycheck. Jean shares her own late-start reset after losing her father, getting divorced, and getting fired within a single year. She then explains why retirees often happily spend Social Security and pensions while fiercely protecting their investment balances. Together they explore Jean's tools that can create both security and permission to spend. Jackie even runs her own numbers and discovers her forever-income gap might be surprisingly easy to fill. 
This episode covers 
Jean Chatzky's own financial reset after a series of major life changes at 40 
Why retirees can become surprisingly reluctant to spend their accumulated savings 
The "decumulation gap" and the psychology behind creating a retirement paycheck 
How to build a "moat budget" around essential expenses and important wants 
How risk tolerance and FOMO can shape your retirement-income strategy 
Why Jean changed her long-held opinion about annuities 
How home equity, insurance, HSAs, and other assets can become retirement resources 
Why late starters need forgiveness, benchmarks, and trusted guidance, not perfection
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=== SUPPORT  THE  SHOW ===
📩 Sign up for our newsletter
📺 Watch & Subscribe to our YouTube Channel
🌐 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 Forever Paycheck
Her Money
Her Money Podcast
Guaranteed Income: A License to Spend  (A research paper by David Blanchett and Michael Finke) 
 
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⏰ Related Episodes 
Are Pensions Really Dead? The Surprising Value of Modern Pensions | Andy Panko | 233
How To Build Your Own Paycheck: From Saver to Spender | Fritz Gilbert & Dana Anspach | 171 
 
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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 happens when you finally reach financial independence and your brain responds with, "Great, now what?" In this special crossover from ChooseFI, Ginger turns the microphone on Bill and digs into the part of financial independence that spreadsheets rarely prepare us for. He shares how a lawsuit and burnout woke him up financially at 50 and how he and his wife flipped from single-digit saving to intentional wealth building. Bill also explains why reaching FI at 60 created a whole new problem: actually giving himself permission to leave work.
This episode covers
Bill's financial wake-up call at age 50 and his "trifecta" of late-starter mistakes
How he and his wife moved from single-digit saving to a 30–40% savings rate
Working through regret, shame, anger, and scarcity after a late start
Why lifestyle downsizing felt more freeing than depriving
The "fog of FI" and why reaching your number does not automatically make retirement easy
One-more-year syndrome, professional identity, and creating a gradual glide path out of work
How FI gave Bill leverage to cut shifts, reduce night work, and reclaim his time
The advantages late starters still have despite missing decades of compounding
Why health, relationships, community, and purpose become more important after the math is solved
Bill's belief that relationships may compound even better than money
 
.
=== 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
ChooseFI
https://choosefi.com

⏰ 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.