Jackie joins our friends to the north in Canada for a live taping of TD Direct Investing's 'Inside Investing', turning her late-starter playbook into a friendly masterclass for Canadians and Americans alike. Host Rob Moysey tees up her arc—divorce in her 30s with ~$20k in retirement savings, millionaire a decade later, retired at 49. Jackie fills in the human bits: purpose after FI, why 'precision is not required,' and how a BetterInvesting club cured her market fear. 

She also walks through: 

• The simple engine that did the work: Maxing out an employer retirement plan, Roth IRA, and HSA in low-cost index funds
• The math behind her Financial Independence target (25× annual expenses ≈ $1M on ~$40k/yr)
• How she kept joy in the journey while saving ~$3k/month

The kicker: despite five years of withdrawals in retirement, her net worth rose from $1.3M (Dec 2019) to ~$2.1M (July 2025). The message lands like a hug and a nudge—know your numbers, automate the boring stuff, and retire TO something.

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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

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.)

🌐Jackie's website FInomenalWoman.com 

📕F.I.R.E. For Dummies

📘Money Letters 2 My Daughter 

📈Jackie's Investment Club through BetterInvesting.org

📺 TD Direct Investing YouTube

⏰ ‘Catching Up to FI’ 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 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.

Today’s episode is something TRULY special— something that’s never happened before!

For the first time ever… we’re joined by two remarkable women who’ve lived alongside one of the most influential voices in the FI community, JL Collins. In this one-of-a-kind episode we introduce you to his wife, Jane Collins and daughter, Jessica Collins. This is their first-ever joint podcast appearance. We’re pulling back the curtain to hear their perspectives. What was it like living with someone so passionate about financial independence? How did his philosophy shape their lives, their choices, and their own views on wealth and freedom? This isn’t just a conversation about finance—it’s about family, legacy, and the ripple effects of good financial education in a household. You’re about to hear a side of the story that’s never been told before.

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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

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: 

CHARITY:  

savethechildren.org

https://www.anelder.org/

The Adopt-A-Nation-Elder Food Runs are the heart of the organizations program and community.  Twice a year they travel to the reservation in service to the Elders whose lives, culture and traditions they cherish. Because of the trust built between the Elders and their families, the staff and volunteers are allowed to travel to the Elders remote homelands and distribute assistance directly to the Elders in their communities. The Food Runs involve hundreds of volunteers transporting hundreds of thousand pounds of food and supplies to the most remote lands in the United State.

🌐JL Collins Blog 

https://jlcollinsnh.com 

📗 The Simple Path to Wealth (Revised & Expanded 2025 Edition & NYT Best Seller!) https://amzn.to/4kFGdTM 

📕 Pathfinders: Extraordinary Stories of People Like You on the Quest for Financial Independence—and How to Join Them

https://amzn.to/4kHHKbS 

📘 How I Lost Money in Real Estate Before It Was Fashionable: A Cautionary Tale

https://amzn.to/4dVJb3O 

⏰ ‘Catching Up to FI’ Episodes referenced

Pathfinders: Triumphs and Trials on the Road to Financial Independence | JL Collins | 070

   https://www.youtube.com/watch?v=-abgF8nW58c&t=1195s

Pathfinders: Stories of Success and Financial Independence | JL Collins | 069

   https://www.youtube.com/watch?v=m-iKa32_xI8&t=27s

F-You Money Part 1 & 2 | JL Collins | 023 & 024

  https://www.youtube.com/watch?v=00lWfkBTJ6g&t=29s

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.

If you're within ten years of retirement (early or traditional age) or just want to get a head start on going from being a saver to a spender, this episode is for you. Decumulation without drama—that’s the mission as retirement pros Dana Anspach (Sensible Money) and Fritz Gilbert (The Retirement Manifesto) join the show to turn “build-your-own paycheck” into a repeatable process. Dana lays out why drawdown is a hundred small decisions, not one big leap; and Fritz brings in the field notes. Together they demystify:

• Tax Pitfalls
• Timing Social Security
• Asset Allocation and Location
• Why Most Retirees Underspend

The big takeaway: document the plan, automate the paycheck, and give yourself permission to enjoy the “go-go” years—because money’s job is to fund a life, not gather dust. 

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🎙️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

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: Freedom for Fido

🌐The Retirement Manifesto

📘 Keys to a Successful Retirement

🌐 Sensible Money

Sensible Money YouTube 

📕 Control Your Retirement Destiny

📗 Social Security Sense

📄 Dana’s breakdown of OBBBA

📄 Retirement Red Zone: Rethinking Your Investment Strategy

⏰ ‘Catching Up to FI’ Episodes

Hard & Soft Sides of Retirement | Fritz Gilbert | 019

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.

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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🎙️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===

🆕Big changes with student loans in the new budget bill that just passed. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off ‘Catching Up to FI’ discount, it's $495.

👉🏼 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.)

🌐 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

https://directory.libsyn.com/episode/index/show/965474e8-0ed6-4527-a513-26a270f7ae31/id/32726312

Doña Quixote, Life Energy, and The Coming of Aging | Vicki Robin | 94 https://directory.libsyn.com/episode/index/show/965474e8-0ed6-4527-a513-26a270f7ae31/id/32726267

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.

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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☕ 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===

🆕Big changes with student loans in the new budget bill that just passed. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off ‘Catching Up to FI’ discount, it's $495.

👉🏼 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

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.

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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🔗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===

🆕Big changes with student loans in the new budget bill that just passed. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off ‘Catching Up to FI’ discount, it's $495.

👉🏼 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

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.

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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🔗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.)

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

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.

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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🔗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.)

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

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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

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

🆕Big changes with student loans in the new budget bill that just passed. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off ‘Catching Up to FI’ discount, it's $495.

👉🏼 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 

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.

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

1. Best New Personal Finance Content Creator - Audio
2. Content Creator of the Year: Audio
3. People's Choice: Audio
4. Best Financial Advisor Content/Jackie Cummings Koski, CFP
5. Plutus Storyteller Award
6. Best Traditional Retirement Content
7. Best Personal Finance Content for Underserved Communities
8. Best Personal Finance Content for Women

Other categories 

1. Best New Personal Finance Content Creator - Written (F.I.R.E. for Dummies)
2. Best New Personal Finance Book (F.I.R.E. for Dummies)
3. Plutus Resilience Award (Jackie Cummings Koski)
4. 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 ===

🆕Big changes with student loans in the new budget bill that just passed. Get help from the experts at Student Loan Planner, all CFP®, CFA and CSLP® professionals. They charge a one-time fee for their thorough review. Our listeners receive $100 off a 1:1 consult using the link below. Flat fee is normally $595, but after your $100 off ‘Catching Up to FI’ discount, it's $495.

👉🏼 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

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.