Catching Up to FI

What if the biggest shift in your FI journey isn't hitting the number—but finally realizing you need a life plan, a tax plan, and maybe even a fiduciary teammate to help you spend it? Bill steps into the guest chair with Morningstar's Christine Benz for a thoughtful, surprisingly candid conversation about going from financially illiterate "rich doctor syndrome" to fully conscious wealth stewardship. He walks through the entire arc. But this episode goes deeper than a standard "how I retired" story.
This episode covers: 
➡️ Bill's path from paycheck-to-paycheck physician to financially independent late starter
➡️ How childhood money scripts and "rich doctor syndrome" shaped his early financial mistakes 
➡️ Why the Great Financial Crisis and burnout became a wake-up call
➡️ What changed when Bill moved from financial consumer to conscious wealth steward
➡️ Why accumulation can be DIY—but decumulation often gets more complex 
➡️ How Bill searched for a fiduciary, flat-fee, life-planning-oriented advisor
➡️ Why risk parity appealed to him for retirement and sequence-of-returns protection 
➡️ The role of a modern advisor as behavioral buffer, tax strategist, and cognitive-risk safeguard
➡️ Why FI gave Bill leverage to redesign work instead of just quit cold turkey 
➡️ How Bill is thinking about legacy, living giving, and helping the next generation now, not just later
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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

.
===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
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RESOURCES MENTIONED ON THE SHOW
The Long View podcast 
The White Coat Investor
George Kinder 
William Bernstein 
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⏰ Related Episodes
Founder of 'Catching Up to FI' Just Hit Financial Independence, Now What? | Bill Yount | 196
Flashback to Episode 1: 'A Boat Named YOLO' | Bill Yount | 197
Retirement Remix: Crafting Financial Futures with Purpose | Christine Benz | 117
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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 happens when the two co-hosts stop being polite, start being honest, and publicly debate the money moves they still don't agree on? We throw open the doors on four of our favorite friction points:
Simple index-fund investing versus "modest complexity" 
Whether high school personal finance classes are actually helping 
What to make of the new 530A Trump accounts 
Taking Social Security at 62 versus waiting
 
The fun here is that neither of us is playing a character. Jackie comes in swinging for simplicity, practical execution, and "please stop overcomplicating this for normal people," while Bill makes the case for curiosity, customization, and not sleepwalking through important financial choices. Along the way, we swap real stories about helping kids with 401(k)s, seeing bad default investments in the wild, what personal finance education gets wrong, and why Social Security advice may be more nuanced than the "always wait until 70" crowd admits. It's a reminder that thoughtful disagreement can sharpen your own plan faster than blindly copying someone else's.
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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

.
===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
.
RESOURCES MENTIONED ON THE SHOW
Check your social security estimates
Mike Piper's Open Social Security Calculator 
Next Gen Personal Finance
Trump Accounts
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⏰ Related Episodes
Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205
These New Rules Will Change The Way You Think About 529 Plans | Patricia Roberts | 193 
Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072
Social Security Made Simple | Mike Piper | 054
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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 real reason family wealth disappears by the third generation has almost nothing to do with investing, and everything to do with what parents fail to teach at home? We sit down with Dr. Julia Myers, founder of Generational Wisdom, for a conversation that goes way past trusts, spreadsheets, and "someday" estate plans. Julia shares the medical crisis that abruptly ended her pharmacy career, the mindset shift that followed, and why she now believes legacy is not what you leave to your kids, but what you leave IN them. Together we unpack the three silent killers of generational wealth: no skills, no goals, no expectations, and explore what it looks like to raise kids who understand money and values, before the world teaches them. If you've ever wondered how to build wealth without accidentally raising entitlement, or how to recover from your own money story before passing it on, this episode is a gold mine.
This episode covers
Why 70–90% of family wealth disappears by the third generation
Julia's shift from pharmacist to generational wisdom coach after a life-changing health crisis
The three biggest reasons generational wealth gets lost
Why "wealth without wisdom is wasted"
How to build a family constitution around values, not just money 
The difference between leaving wealth to your kids versus leaving legacy in them
How to talk to kids about money, giving, enough, and expectations
Why late starters can still change their family's financial story
Practical ways to make values visible in daily family 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===
📈 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
.
RESOURCES MENTIONED ON THE SHOW
Charity: Hope International
🌐 JuliaMyers.com 
Julia's Youtube
Say This, Not That (free guide)
Free Audiobook "Wealthy and Well Known" 
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⏰ Related Episodes
Enoughness: Your Life or Your Money | Vicki Robin | 95
 
Doña Quixote, Life Energy, and The Coming of Aging | Vicki Robin | 94
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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! What do you get when two late starters hand the mic to two twenty-somethings and let the money questions fly? In this unusually fun follow-up to the University of Tennessee classroom visit, we bring Dr. Karen DeLong and two of her students, Emilie and Britton, onto the podcast to tackle the real questions young adults ask when money stops being theoretical and starts getting personal.
Emilie – Majoring in Finance and International Business with a minor in Agricultural Business and will be pursuing a career in Wealth Management.
Britton – Interning with Wells Fargo in their Investment Banking - Commercial Real Estate division and will be pursuing a career in that post grad.
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This episode covers
The real money questions college students are asking before graduation
Why Roth IRAs are such a powerful early-start tool
How to think about saving for retirement versus nearer-term goals
What happens to your 401(k) when you switch jobs
Why savings rate matters more than most young adults realize
The balance between being responsible and being too frugal
How parents, professors, and mentors shape money mindset
Why financial literacy needs to be practical, not just theoretical
What late starters can teach young adults before they make the same mistakes
.
=== 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===
📈 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
.
RESOURCES MENTIONED ON THE SHOW
 
🌐 Dr. Karen DeLong 
Farm Credit Mid-America
📘 If You Can: How Millennials Can Get Rich Slowly (Bill Bernstein)
📕 The Simple Path to Wealth- Updated 2025 (JL Collins)
📗 Your Money or Your Life (Vicki Robin & Joe Dominguez)
📙F.I.R.E. For Dummies (Jackie Cummings Koski) 
📘Money Letters 2 My Daughter (Jackie Cummings Koski)
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⏰ Related Episodes
I Have a PhD in Business but Never Had a Personal Finance Class | Dr. Karen DeLong | 206
Financial Literacy 101: Live Inside the Classroom at University of Tennessee | Bill & Jackie | 207
.
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! What happens when you hand a room full of almost-graduates a microphone, a few $2 bills, and permission to ask the money questions most adults still avoid? In this special on-the-road episode, we take you inside the financial literacy presentation at the University of Tennessee to share a few highlights of our recent talk. It's energetic, imperfect, and deeply encouraging. Financial literacy doesn't have to be stiff or scary. Sometimes it just looks like showing up, telling the truth about your mistakes, and helping the next person get a much earlier start than you did.
This episode covers: 
➡️ Highlights from Bill and Jackie's live financial literacy presentation at UT Knoxville 
➡️ Why young adults need practical money education before entering the workforce
➡️ The difference between being rich and being wealthy
➡️ Why savings rate matters so much for financial independence 
➡️ How to think about 401(k)s, employer match, vesting, and job changes
➡️ Why index funds and simple investing often beat picking individual stocks
➡️ Jackie's $2 bill story and how tiny saving habits can shape a lifetime 
➡️ Bill's "rich doctor syndrome" story and the danger of lifestyle inflation
➡️ How listeners can adapt this presentation for their own school, church, or community
.
=== 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===
📈 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
.
RESOURCES MENTIONED ON THE SHOW: 
 
🌐 Dr. Karen DeLong 
Farm Credit Mid-America
BetterInvesting.org 
📘 If You Can: How Millennials Can Get Rich Slowly (free digital download)
📄 Copy of Our Presentation Slides to UT Students 
 
⏰ Related Episodes 
I Have a PhD in Business but Never Had a Personal Finance Class | Dr. Karen DeLong | 206
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.