Catching Up to FI

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.   📩 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=== 📈 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.

In a groundbreaking episode, Jane Collins, a former dance teacher, and her daughter Jessica, a fitness entrepreneur and ex-tech sales pro, share their unique insights on financial independence. They reveal how growing up with JL Collins shaped their money habits, emphasizing the importance of experiences over material goods. Jessica recounts her youthful financial lessons and the challenge of delayed car ownership. They also discuss charitable values, early investing habits, and their family's dedication to debt-free living, illustrating how financial education fosters a legacy.

Dana Anspach, a CFP and founder of Sensible Money, and Fritz Gilbert, creator of The Retirement Manifesto, delve into the nuances of transitioning from saving to spending in retirement. They explore the intricacies of drawdown strategies and emphasize that success hinges on a hundred small financial decisions. Key discussions include managing taxes, understanding social security's impact, and avoiding common pitfalls that lead to underspending. Their big takeaway? Document your plan, automate cash flow, and enjoy life’s ‘go-go’ years.

Carl Richards, a CFP and visual artist known for his Sketch Guy column in The New York Times, delves into the emotional aspects of money. He reveals how we unintentionally structure our lives around finances, often sidelining health and relationships. Discussing the concept of 'enough,' he emphasizes it's about mindset, not a figure. The conversation explores how money can't fulfill our deeper needs like love or self-worth, and introduces his book, filled with sketches that foster meaningful discussions about finances and life.

In this enlightening discussion, Bill Bengen, a renowned retirement researcher and creator of the original 4% rule, shares insights from his new book, A Richer Retirement. Joined by his wife, Barbara, they reveal their love story before diving into essential strategies for managing a successful retirement withdrawal plan. Bill explains the evolution of the 4% rule to 4.7%, discusses the impact of valuation and inflation, and offers guidance for late starters on how to balance saving and enjoying life. A must-listen for future retirees!

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   📩 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: 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'   📩 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   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   📩 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   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   📩 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.)   🌐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 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 === 🆕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.