The worst tax stories aren't about criminals, they're about ordinary people doing what they thought was allowed and stepping into a trap. Bri Conn, CFP® reads a string of real-world cautionary tales while Maddy Roche reacts and Dr. Jay Zigmont, CFP® explains what actually went wrong, from the influencer myth that your whole life becomes a write-off, to the unpaid tax bill that can revoke your passport at the airport, to the rent your unmarried partner pays you that the IRS counts as income. The throughline is one every Childfree person building a life outside the standard script needs to hear: the tax code has sharp edges around staying single, filing unmarried, and living abroad, and ignorance of the rules is the one excuse the IRS will never accept.
In This Episode, You'll Learn:
- Why "I post about my life, so my life is a write-off" is a myth, how the IRS separates a real business with a profit motive from a hobby, and what actually happens when you never show a profit
- How unpaid taxes can get your passport revoked, why the IRS can lien your home or garnish wages after the fact, and why a payment plan keeps you current and protected
- Why chasing a lower tax bill by moving states or obsessing over brackets can cost you far more in happiness than it saves, and how to weigh the real tradeoffs
- Why getting legally married often works against Childfree couples on taxes and student loans, and how filing unmarried, gift-tax limits, and estate-tax cliffs quietly reshape the math
- How an ordinary foreign bank account can trigger FBAR reporting and life-altering penalties, and why your CPA and financial planner can only protect you if you tell them everything
Episode Hosts:
Bri Conn, CFP® is a Childfree Wealth Specialist® at Childfree Wealth® and Customer Experience Manager at Childfree Trust®. She specializes in financial management, life design, and estate planning, with particular focus on LGBTQ+ individuals and couples, drawing on her own early financial challenges and recovery to fuel her work in personal finance education.
Dr. Jay Zigmont, CFP® is the Founder of Childfree Wealth®, a life and financial planning firm dedicated to helping Childfree and permanently Childless people, and Childfree Trust®, the first of its kind next of kin representation service for Childfree people. He is also the author of The Childfree Guide to Life and Money.
Maddy Roche is the Chief Growth Officer at Childfree Trust®, where she leads all sales, marketing, and partnership initiatives and brings sharp insight to estate planning, LGBTQ+ legacy considerations, and Childfree financial decision making.
About Childfree Insights:
Childfree Insights delivers education for financial and estate planning without children. It supports people with no kids in making informed decisions about retirement, legacy planning, beneficiaries, and long-term care. Home of Childfree Wealth® and Childfree Trust®.
Connect with Us:
Ready to work on building better financial habits? Connect with our financial planning team at childfreewealth.com or learn more about estate planning at childfreetrust.com.
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Disclaimer: This podcast is for educational & entertainment purposes. Please consult your advisor before implementing any ideas heard on this podcast.
