Catching Up to FI

Latest Episodes:

What Would 'Your Money' Look Like In a Simple Sketch? | Carl Richards | 170 Sep 28, 2025

Show notes

Carl Richards is one of the leading voices when it comes to money and emotions. For over a decade, he was the creator of the Sketch Guy column in The New York Times, where his hand-drawn sketches made financial complexity surprisingly simple—and deeply emotional. He joins us to ask the question that instantly ties our brain in knots: 'What is money, really?' From there, he discusses:

Why we unknowingly organize life around money and work
Why 'enough' is a way of being (not a number)
How we keep handing money jobs it can't do—like self-worth, love, and happiness

Come for the doodles; leave with a gentler, saner way to align your calendar, your checkbook, and your life.

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RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)

🌐 BehaviorGap.com

📗 Your Money: Reimagining Wealth in Simple Sketches

📕 The Behavior Gap

📘 The One-Page Financial Plan

50 Fires Podcast

⏰ 'Catching Up to FI' Episodes

Enoughness: Your Life or Your Money | Vicki Robin | 95

Doña Quixote, Life Energy, and The Coming of Aging | Vicki Robin | 94

If you enjoyed this episode, please follow the show on your podcast player and leave us a rating or 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.

A Richer Retirement: The 4.7% Rule | Bill Bengen | 169 Sep 21, 2025

Show notes

We are welcoming back the man behind the most debated number in retirement, Bill Bengen- this time with a special appearance from his lovely wife, Barbara. We take a brief detour to hear their love story and how they met, before getting into his new book, 'A Richer Retirement: Supercharging the 4% Rule to Spend More and Enjoy More'. He joins us in this episode to:

Break down the primary goals of the book
Help you understand what's required to create and manage a successful personal retirement withdrawal plan
Step us through all the tools required to make your money last your entire lifetime

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

👉🏼 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

RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)

🌐 Bill Bengen

📘A Richer Retirement

Charts and Tables from 'A Richer Retirement'

⏰ 'Catching Up to FI' Episodes

Mr 4% is now Mr 5% | Bill Bengen | 111

How This Savvy Young Planner is Helping Retirees | Emma Von Weise | 168 Sep 14, 2025

Show notes

The average financial planner is about 56 years old, but 25-year-old Emma Von Weise got a running start learning about money as a teenager and is now one of the youngest CFP professionals in the US. She shares how she became money savvy so early and what influences impacted her the most. She isn't here to judge the rest of us who started late, but to help us make up for lost time—with humor, heart, and practical advice that meets you exactly where you are. In this episode, we discuss:

Emma's money story and early financial literacy
The spark that led to a career in financial planning at such a young age
Why she is an old soul that just loves working with retirees
Modern day Continuing-Care Retirement Communities

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

👉🏼 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

RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)

Charity: 3rd Decade

🌐 Focus Partners Wealth

Reached FIRE At 50👉🏻 And Here's Why He Still Keeps Climbing | Darrow Kirkpatrick | 167 Sep 07, 2025

Show notes

Darrow Kirkpatrick retired from a 29-year career in civil and software engineering in April 2011 at the age of 50 and started the blog 'Can I Retire Yet' that same year. The Blog was one of the first in the FIRE (Financial Independence, Retire Early) space and focuses on the personal finance needs of anyone who is thinking about retirement or early retirement. He joins us for a deeply human masterclass on retiring, drawing down without drama, and pursuing hard goals the slow, sane way. In this episode, Darrow shares with us:

The origins of his blog 'Can I Retire Yet?'
How a nervous breakdown derailed his career
His six-year, section-by-section completion of the Colorado Trail on forearm crutches
The inspiration behind his new book 'Two Sticks One Path'

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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

RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)

Charities:

National Alliance on Mental Illness

The Colorado Trail

🌐 Can I Retire Yet?

🌐Trail Memoir

📗 Two Sticks, One Path

📘 Can I Retire Yet?

📕 Retiring Sooner

Critique circle (Online Writing Workshop)

Lessons Learned from Writing a Book

Pralana- Personal Financial Modeling

⏰ 'Catching Up to FI' Episodes

The Powers of Starting Late, Retirement Calculators, and More | Chris Mamula | 086

Sustainable FIlosophy with Mr. Money Mustache | Pete Adeney | 073

===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 course or PFC investing course only

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

A Very Different Voice in Financial Planning | Jackie Cummings Koski | 166 Sep 03, 2025

Show notes

In this crossover episode, Jackie joins the 'Wicked Pissah Podcast', brought to you by the Financial Planning Association (FPA) of New England. She trades in the Sunday sweatshirt for her CFP® blazer but still stays true to openly sharing her fascinating money story and spreading financial literacy. They discuss:

The story behind her $2-bill savings habit
The divorce-day gut punch that pushed her from $20k to FI
Why she is so passionate about the 'Catching Up to FI' platform and late starters
How she demystifies FIRE for financial professionals
How she tackled the big skeptic questions about retiring early

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🌐 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.)

🌐Jackie's website FInomenalWoman.com

📕F.I.R.E. For Dummies

📘Money Letters 2 My Daughter

📈Jackie's Investment Club through BetterInvesting.org

🎙️Wicked Pissah Podcast

https://wickedpissahpodcast.libsyn.com/about

Jonathan Clements Getting Going on Savings Initiative

https://boglecenter.net/gettinggoing

⏰ 'Catching Up to FI' Episodes

From Poverty to Wealth and Early Retirement | Jackie Cummings Koski | 007

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

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

For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners

Borderless FI: The Happy KiwiSaver | Ruth Henderson | 165 Aug 31, 2025

Show notes

Ruth Henderson is the creator of 'The Happy Saver,' a beloved New Zealand blog and podcast that brings personal finance down to earth. She transitioned from part-time work to full-time content creation, sharing her journey toward early retirement with honesty, humor, and heart. In this episode we swap notes with her on the financial independence journey of Americans vs. Kiwis (New Zealanders). She also shares with us:

Her late starter journey to FI
What inspired her to create 'The Happy Saver' to help everyday Kiwis reach FI
A breakdown of New Zealand's surprisingly simple ecosystem including universal healthcare and pension
How KiwiSaver operates similarly to US employer-sponsored retirement plans

📩 Sign up for our newsletter (NEW!)

🌐 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===

👉🏼 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

RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)

🌐The Happy Saver

The Happy Saver Podcast

Rebel Finance School

Sorted

Sorted Smart Investor

Tell Your Story With A Book, Here's How | Azul Terronez | 164 Aug 24, 2025

Show notes

Azul Terronez went from being an unknown schoolteacher to a Wall Street Journal and USA Today bestselling author. He is co-founder and lead coach at "Authors Who Lead," a platform dedicated to empowering authors to share their stories. He turns our conversation with him into a courage clinic for would-be storytellers, late starters, and anyone who suspects their "zone of genius" is dying to be unleashed. He gives us the reframe that authorship isn't about words so much as the message beneath them.

=== PLUTUS AWARDS: ONLY ONE WEEK LEFT TO VOTE ===

We need your vote for the 2025 Plutus Awards! You can now vote for your hosts behind "Catching Up to FI" - Bill Yount & Jackie Cummings Koski. The deadline to vote is August 30th, 2025. Winners will be announced in October.

✅ WHAT IS THE PLUTUS AWARDS?

The Plutus Awards recognize excellence in independent financial content. That's the best podcasts, books, video channels, blogs, and more.

✅ VOTE

If you've gotten value from our content and think we are worthy of recognition, please support by casting your votes here > >> https://plutus.awardsplatform.com/. There's a short registration needed to vote and you'll be in and out in just a few minutes.

✅ CATEGORIES

Below are the categories we have been nominated for and we'd love your vote in each of them.

Catching Up to FI

Best New Personal Finance Content Creator - Audio
Content Creator of the Year: Audio
People's Choice: Audio
Best Financial Advisor Content/Jackie Cummings Koski, CFP
Plutus Storyteller Award
Best Traditional Retirement Content
Best Personal Finance Content for Underserved Communities
Best Personal Finance Content for Women

Other categories

Best New Personal Finance Content Creator - Written (F.I.R.E. for Dummies)
Best New Personal Finance Book (F.I.R.E. for Dummies)
Plutus Resilience Award (Jackie Cummings Koski)
Best Financial Independence or Retire Early Content (F.I.R.E. for Dummies)

📩 Sign up for our newsletter (NEW!)

🌐 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 ===

👉🏼 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

RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)

Charity: Grey Bears

🌐Authors Who Lead

Authors Who Lead podcast

📗 The Art of Apprenticeship: How to Hack Your Way into Any Industry, Land a Kick-Ass Mentor, and Make A Killing Doing What You Love

Born to Write, Scared to Start: A secret podcast for the ones who whisper, "I think I'm supposed to write a book."

Why I Coached My Son to Drop Out of University and Maybe You Should, Too

TEDx Talk: What makes a good teacher great?

EconoMe Conference Talk

Late Starter Real Numbers: 1.5 M ➜ 864 K — And Back Again | J. C. & Bev Webber | 163 Aug 17, 2025

Show notes

J.C. and Bev Webber's late-starter journey is proof that resilience + innovation can outrun even a Great Financial Crisis. J.C. gives us his real numbers and how he sprinted from a net worth of ~$120k (age 51) to $1.5M (age 57)—only to see it crash to ~$864k in early 2009. But that didn't derail their plans because he and his wife Bev still retired early and hit the road in their RV. You could say they reached FIRE (Financial Independence, Retire Early) before it was hot! In this episode they walk us through all the twists and turns, giving us the excruciating details that you rarely hear about, including:

J.C.'s brother-in-law bailing him out of credit-card debt by loaning him money
J.C.'s military service and using the GI Bill hack college
Ditching dead-end jobs for higher paying tech careers and eventually retiring from Apple
Weathering multiple divorces and proving that it doesn't have to ruin your finances
The unshakeable confidence in their human capital
Plans to live out their later years in Mexico

=== VOTE FOR US: PLUTUS AWARDS ===

We need your vote for the 2025 Plutus Awards! You can now vote for your hosts behind "Catching Up to FI" - Bill Yount & Jackie Cummings Koski.

✅ WHAT IS THE PLUTUS AWARDS?

The Plutus Awards recognize excellence in independent financial content. That's the best podcasts, books, video channels, blogs, and more.

✅ VOTE

✅ DEADLINE

The deadline to vote is August 30th, 2025. Winners will be announced in October.

✅ CATEGORIES

Below are the categories we have been nominated for and we'd love your vote in each of them.

Catching Up to FI

Best New Personal Finance Content Creator - Audio
Content Creator of the Year: Audio
People's Choice: Audio
Best Financial Advisor Content/Jackie Cummings Koski, CFP
Plutus Storyteller Award
Best Traditional Retirement Content
Best Personal Finance Content for Underserved Communities
Best Personal Finance Content for Women

Other categories

Best New Personal Finance Content Creator - Written (F.I.R.E. for Dummies)
Best New Personal Finance Book (F.I.R.E. for Dummies)
Plutus Resilience Award (Jackie Cummings Koski)
Best Financial Independence or Retire Early Content (F.I.R.E. for Dummies)

🌐 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

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:

🌐 J.C. and Bev's Trip Journal

Images of J.C.'s Spreadsheets and numbers

YNAB (You Need A Budget)

From Silent Majority to Visible Voices | Bill & Jackie | 162 Aug 13, 2025

Show notes

In this midweek episode, Bill and Jackie join the 'The Visible Voices' podcast, hosted by Dr. Resa E Lewiss. We highlight the voice of late starters and discuss:

The huge gap that 'Catching Up to FI' is filling and what we mean by the 'silent majority'
How shock, regret, and money-trauma can become fuel
Unique advantages you may have when beginning your financial independence journey later in life
Why micro-steps (Kaizen-style) beat grand gestures every time

=== VOTE FOR US: PLUTUS AWARDS ===

We need your vote for the 2025 Plutus Awards! You can now vote for your hosts behind "Catching Up to FI" - Bill Yount & Jackie Cummings Koski.

✅ WHAT IS THE PLUTUS AWARDS?

The Plutus Awards recognize excellence in independent financial content. That's the best podcasts, books, video channels, blogs, and more.

✅ VOTE

✅ DEADLINE

The deadline to vote is August 30th, 2025. Winners will be announced in October.

✅ CATEGORIES

Below are the categories we have been nominated for and we'd love your vote in each of them.

Catching Up to FI

Best New Personal Finance Content Creator - Audio
Content Creator of the Year: Audio
People's Choice: Audio
Best Financial Advisor Content/Jackie Cummings Koski, CFP
Plutus Storyteller Award
Best Traditional Retirement Content
Best Personal Finance Content for Underserved Communities
Best Personal Finance Content for Women

Other categories

Best New Personal Finance Content Creator - Written (F.I.R.E. for Dummies)
Best New Personal Finance Book (F.I.R.E. for Dummies)
Plutus Resilience Award (Jackie Cummings Koski)
Best Financial Independence or Retire Early Content (F.I.R.E. for Dummies)

🌐 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===

👉🏼 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

RESOURCES MENTIONED ON THE SHOW: (As an Amazon Associate, I earn from qualifying purchases.)

Charity:

🌐 'This Visible Voices' Podcast

Bill and Jackie's Episode on 'The Visible Voices' Podcast

📗 Micro Skills

Case Study: The Real Numbers That Told Her She Could Quit her Job, Now! | Lisa B | 161 Aug 10, 2025

Show notes

We ❤️ Case Studies! Nurse practitioner and mom of three, Lisa, opens up and shares what's in her wallet, and her heart. In this episode we dive into her fascinating late-starter story and financials. She was also this year's brave Case Study at the EconoMe conference and revealed all her numbers in front of a live audience to get crowd-sourced feedback in real time. What transpired afterwards was powerful- she quit her day job and handed in her clinical badge to enjoy a sabbatical she had been longing for! With a little help from some Boldin financial modeling and a Nectarine hourly planner, she made the leap and takes us through exactly how she did it.

=== VOTE FOR US: PLUTUS AWARDS ===

We need your vote for the 2025 Plutus Awards! You can now vote for your hosts behind "Catching Up to FI" - Bill Yount & Jackie Cummings Koski.

✅ WHAT IS THE PLUTUS AWARDS?

The Plutus Awards recognize excellence in independent financial content. That's the best podcasts, books, video channels, blogs, and more.

✅ VOTE

✅ DEADLINE

The deadline to vote is August 30th, 2025. Winners will be announced in October.

✅ CATEGORIES

Below are the categories we have been nominated for and we'd love your vote in each of them.

Catching Up to FI

Best New Personal Finance Content Creator - Audio
Content Creator of the Year: Audio
People's Choice: Audio
Best Financial Advisor Content/Jackie Cummings Koski, CFP
Plutus Storyteller Award
Best Traditional Retirement Content
Best Personal Finance Content for Underserved Communities
Best Personal Finance Content for Women

Other categories

Best New Personal Finance Content Creator - Written (F.I.R.E. for Dummies)
Best New Personal Finance Book (F.I.R.E. for Dummies)
Plutus Resilience Award (Jackie Cummings Koski)
Best Financial Independence or Retire Early Content (F.I.R.E. for Dummies)

🌐 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

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: Adelante Latina

🌐 Lisa's Blog

⏬ Catching Up to FI version of Case Study Template (Download and save a copy)

The Advisor Lisa used at Nectarine (John O'Callaghan, CFP®). Book your own session using this Nectarine Affilate Link: https://hellonectarine.com/r/cutfi

Fioneers 'Coast With Confidence' Course

https://thefioneers.com/coast-with-confidence-waitlist

⏰ 'Catching Up to FI' Episodes

Mini Retirements, Sabbaticals, Career Breaks- Yes Please! | Jillian Johnsrud | 153

The Godfather of FI Talks Fatherhood | JL Collins | 149

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

$1M Debt!: "One Dollar at a Time" | Naseema McElroy | 014

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