Dr. Daniel Crosby took a circuitous path to the world of money — starting as a psychologist and ending up as one of the most engaging voices in behavioral finance. He is Chief Behavioral Officer at Orion and author of The Soul of Wealth. Dr. Crosby goes beyond the math to the meaning: identity, autonomy, and why 'you don't really want to be rich, you want to be free.' He joins the show to talk us through:

• Reframing money as a tool for time freedom, relationships, and purpose—not status
• Using behavior science to close the gap between 'knowing' and 'doing'
• Downshifting lifestyle creep and designing guardrails
• Replacing 'I'll be happy when...', with habits, community, and a clear vision of your 'retirement cow'

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TheAlloyMarket.com offers a seamless and efficient way to sell your gold, silver, and platinum jewelry, regardless of its condition. They are committed to transparency and fairness, ensuring you get the best possible value for your items. Visit TheAlloyMarket.com and use referral code CUTOFI15 to get a $15 bonus when you sell items over $199 (limited time offer).

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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Charity: National Alliance on Mental Illness

🌐 Standard Deviations podcast

Orion

📗 The Soul of Wealth

⏰ 'Catching Up to FI' Episodes

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

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

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.

Sean 'FI Tax Guy' Mullaney and Cody 'Measure Twice' Garrett are two of the smartest financial planning pros who are best known for sharing their deep knowledge in the financial independence community and beyond. They join us today to break down tax planning in a way you may not have ever heard before. They don't agree with some of the conventional advice and make a case for the contrarian views they share in their new book, 'Tax Planning To and Through Early Retirement'. In this conversation, we dive into:

1. Top year-end tax tips for later starters
2. Affordable Care Act (ACA) premium tax credits
3. Drawdown principles
4. Moving through the 5 phases of retirement
5. How a little tax awareness can go a long way

This discussion is intended to be for general educational purposes and is not tax, legal, or investment advice for any individual. Bill, Jackie, and the Catching Up to FI podcast do not endorse Sean Mullaney, Mullaney Financial & Tax, Inc. and their services.

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🆕NEW PARTNER: Alloy

TheAlloyMarket.com offers a seamless and efficient way to sell your gold, silver, and platinum jewelry, regardless of its condition. They are committed to transparency and fairness, ensuring you get the best possible value for your items. Visit TheAlloyMarket.com and use referral code CUTOFI15 to get a $15 bonus when you sell items over $199 (limited time offer).

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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📘 Tax Planning To and Through Early Retirement

--Cody Garrett

🌐 Measure Twice Money

🌐 Measure Twice Planners

📺 Measure Twice YouTube

--Sean Mullaney

🌐 FI Tax Guy

🌐 Mullaney Financial & Tax

📺 FI Tax Guy YouTube

📕 Solo 401(k): The Solopreneur's Retirement Account

📄 UBS Global Wealth Report 2025

⏰ 'Catching Up to FI' Episodes

Tactical Tips and Tripwires: The DIY Financial Planner's Guide | Cody Garrett | 112

Year End Tax Planning | Sean Mullaney | 045

Music Money Man | Cody Garrett | 035

Life & Taxes | Sean Mullaney | 013

72(t) Expert Tells All: No More Secrets About Early Withdrawals (Part 1) | Bill Stecker | 131

Cashing in on 72(t): The Goldmine of Early Retirement Rules (Part2) | Bill Stecker | 133

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.

Recorded live in Bali, at the FI Freedom Retreat (the 2nd one in 2025), Jackie teams up with Doc G from the Earn & Invest Podcast. They ask the spiciest FI question of all—not 'can I retire yet?' but 'should I?' Three very different journeys take the mic:

• Fara's 'accidental FIRE' at 47 and her boomerang back to a cause-driven job (then boomerang away again)
• Gene's post-quit LinkedIn relapse and the search for purpose without a W-2
• Rachel Richard's pivot from real estate and a viral brand (Money Honey Rachel) to doing the inner work, ditching external validation, and—surprise—catching the spark to write again.

Stay for the after-show hot seat where more attendees share their own takes on whether they'll ever 'work' again. Hear from Scott, Dave, Sophie, Selene, Justin, Kim, and Amy.

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TheAlloyMarket.com offers a seamless and efficient way to sell your gold, silver, and platinum jewelry, regardless of its condition. They are committed to transparency and fairness, ensuring you get the best possible value for your items. Visit TheAlloyMarket.com and use referral code CUTOFI15 to get a $15 bonus when you sell items over $199 (limited time offer).

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🌐 FI Freedom Retreats

Next Retreat: Sept 11 - 15, 2026

Earn and Invest Podcast

Rachel Richards- Money Honey Rachel

Scott On FIRE

⏰ 'Catching Up to FI' Episodes

International Educator, Bali FIRE | Amy Minkley | 137

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.

Our guest today is Beth Pinsker, CFP®-- seasoned financial journalist, MarketWatch columnist and author of the new book, My Mother's Money: A Guide to Financial Caregiving. She represents the sandwich generation and gives us tips, advice, and cautionary tales about her firsthand experience after finding herself caring for her mother and her finances. She explains that caregiving isn't just forms and bank calls—it's love, logistics, and a dash of stubborn grit. Beth also shares:

• The "death file" story that changed everything
• How to survive bank pushbacks on powers of attorney
• Why a tiny funeral policy became an act of love
• The must-do digital steps that make caregiving possible in a two-factor world

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

🆕NEW PARTNER: Alloy

TheAlloyMarket.com offers a seamless and efficient way to sell your gold, silver, and platinum jewelry, regardless of its condition. They are committed to transparency and fairness, ensuring you get the best possible value for your items. Visit TheAlloyMarket.com and use referral code CUTOFI15 to get a $15 bonus when you sell items over $199 (limited time offer).

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🌐 BethPinsker.com

📗 My Mother's Money: A Guide to Financial Caregiving

🗒️AARP Article: 5 Things I Learned From Managing My Mother's Money

⏰ 'Catching Up to FI' Episodes

Mom and Dad, We Need to Talk | Cameron Huddleston | 048

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

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.

50 people (now friends), 9 countries... all in one room, speaking the same language: Financial Independence! This is a special episode recorded live from in beautiful Bali, Indonesia at the FI Freedom Retreat. Australian blogger and podcaster, 'Captain FI', joins Jackie as guest co-host to share the FI stories of three of the extraordinary individuals we met at the retreat:

• Claire (Dubai via Ireland)- Restarting and living by the philosophy of 'trust your gut'
• Michael (Seattle)- Newly nomadic, choosing FI-enough over perfection
• Val (Hong Kong)- Taking a gap year that feels like several lifetimes

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🆕NEW PARTNER: Alloy

TheAlloyMarket.com offers a seamless and efficient way to sell your gold, silver, and platinum jewelry, regardless of its condition. They are committed to transparency and fairness, ensuring you get the best possible value for your items. Visit TheAlloyMarket.com and use referral code CUTOFI15 to a get $15 bonus when you sell items over $199 (limited time offer).

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Captain FI Blog

Captain FI Podcast

FI Freedom Retreats

Next Retreat: Sept 11 - 15, 2026

- UNITED STATES -

ChooseFI

Mr Money Mustache

BiggerPockets Money

Jillian Johnsrud

Mad Fientist

- INTERNATIONAL -

PKP Community Centre (Bali, Indonesia)

Firespark Australia

Lacey Filipich Ted Talk

Barefoot Investor (Scott Pape)

Strong Money Australia (Dave Gow)

Aussie Firebug

⏰ 'Catching Up to FI' Episodes

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

International Educator, Bali FIRE | Amy Minkley | 137

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

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.

Dr. Brad Klontz is a leading expert in financial psychology, professor, bestselling author, and, oh yeah — an internet influencer with millions of followers who tune in for his mix of straight talk and practical money wisdom. He joins Bill for a deep dive into why most money problems aren't math problems. Instead, they are about what's going on in our heads and in our habits. In this episode, Brad discusses:

1. Why smart people still make dumb money mistakes
2. The difference between poor and broke
3. The 4 money scripts (avoidance, worship, status, vigilance)
4. Why he argues that an internal locus of control is the ultimate wealth engine
5. A no-nonsense roadmap for breaking bad money patterns and building real financial freedom

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

🆕NEW PARTNER: Alloy

TheAlloyMarket.com offers a seamless and efficient way to sell your gold, silver, and platinum jewelry, regardless of its condition. They are committed to transparency and fairness, ensuring you get the best possible value for your items. Visit TheAlloyMarket.com and use referral code CUTOFI15 to a get $15 bonus when you sell items over $199 (limited time offer).

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.)

🌐 BradKlontz.com

🌐The Klontz Money Script Inventory

📕 Start Thinking Rich

📗 Financial Wisdom of Ebenezer Scrooge

📷 Brad's Facebook

📷 Brad's TikTok

📷 Brad's InstaGram

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.

On July 4th, 2025 an 870-page tax bill called the 'One Big Beautiful Bill Act' (OBBBA) was signed into to law. Some parts have been heavily discussed and others not so much. So we dug around ourselves and pulled out some hidden messages you may have missed that could have major implications to your FI (Financial Independence) journey.

👉🏽 Updates to 2017 'Tax Cuts and Jobs Act' Makes permanent the lowered individual tax brackets established by the Tax Cuts and Jobs Act and keeps the larger standard deduction in place. Also makes permanent the higher lifetime estate gift tax exemption and increases it to $15 million for single & $30 million for married couples in 2026 (indexed to Inflation).

👉🏽 Updates to 2021 'American Rescue Plan' Expiration of the Enhanced ACA premium subsidies (not directly in the bill, it's just not being extended). The lowered premiums will expire and revert back to pre-covid levels. The Subsidy Cliff will be back in play starting 1/1/26. This is a major part of the negotiation with the current federal government shutdown so may be subject to change.

We cover these topics in the new law:

1. Increased Standard Deduction
2. Extra Senior Deduction
3. SALT (State And Local Tax) Deduction Cap Raised
4. Changes with HSA (Health Savings Account) qualifications
5. Child Tax Credit, Dependent Care FSAs, & Dependent Tax Credit
6. Introduction of Child Savings Accounts
7. 529 College Savings Plan Enhancements
8. Deduction for Charitable Contributions Deduction (even if you take the standard deduction)
9. New Temporary Deductions (2025–2028), Even for those who don't itemize
10. Overhaul of Student Loans

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

🆕NEW PARTNER: Alloy

TheAlloyMarket.com offers a seamless and efficient way to sell your gold, silver, and platinum jewelry, regardless of its condition. They are committed to transparency and fairness, ensuring you get the best possible value for your items. Visit TheAlloyMarket.com and use referral code CUTOFI15 to a get $15 bonus when you sell items over $199 (limited time offer).

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.)

🌐Full Text of the Bill signed into law on 7/4/25

Newsletter with OBBBA Tax Law Toolkit Includes additional content from trusted resources & experts)

IRS Factsheet for OBBBA

Key Elements: 'One Big Beautiful Bill Act' from CFP Board

Newsletter with OBBBA Tax Law Toolkit (Includes additional content from trusted resources and experts)

⏰ 'Catching Up to FI' Episodes

Banishing The Burden of Student Loan Debt | Travis Hornsby | 122

A Hero's Journey: Krista & Ed, The Mother of All Case Studies! | Krista and Ed Kim | 97

Millennial Revolution is in The House! | Kristy Shen, Bryce Leung & Little Matchstick | 93

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.

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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📈 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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===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.