Episode 185

full
Published on:

17th Dec 2025

End-of-Life & Estate Planning With Your Parents (In A Compassionate Way) | E185 Tess Waresmith

Talking about end-of-life planning is one of the hardest conversations we’ll ever have, but also one of the most important. Whether you’re pursuing financial independence or already work-optional, someone in your life will eventually rely on you to make decisions on their behalf. And without clarity, that responsibility becomes emotionally heavy, financially stressful, and often filled with guesswork.

In this episode, Financial Educator Tess Waresmith (Wealth With Tess) walks us through how to approach these conversations with compassion and confidence. Tess has navigated caregiving and loss firsthand, including the passing of her stepfather and aunt. She brings a personal and practical approach to preparing families for the future.

You’ll learn how to make these conversations feel less overwhelming, how to use Tess’s 3-Layer Talk Framework to guide your discussion, and which estate-planning essentials every FI-minded person should have squared away. More than anything, this episode will help you strengthen connections, reduce uncertainty, and create peace of mind for yourself and the people you love.

Key Takeaways:

  • How to start end-of-life conversations in a way that feels natural, not heavy
  • The 3-Layer Talk Framework for discussing logistics, values, and legacy
  • Essential estate-planning documents every family needs (Will, POA, Healthcare Directive)
  • Questions that help uncover a loved one’s hopes, fears, stories, and wishes
  • Why acknowledging mortality can lead to more intentional spending, saving, and FI planning

Other Episodes You’ll Love:

3 Hidden Traps That Make FIRE Feel Empty | E182 Jordan Grumet

How to Negotiate Your Medical Bills | E161 Dr. Virgie Bright Ellington

Does My FIRE Number Account for Inflation? | E140 Jesse Cramer


Guest Summary:

Tess Waresmith is a financial educator, speaker, and the creator of Wealth With Tess, where she teaches women how to build confidence with money and investing. Through her workshops, courses, and content, she shares clear, compassionate financial guidance to help women reduce stress and prioritize what truly matters.

Instagram: https://www.instagram.com/wealthwithtess/

Talking About Death: https://www.moneyconfidentclub.com/talkdeath

Deathly Yours Workbook ($60 off with code FIMINDED):

https://www.moneyconfidentclub.com/offers/BkfzyzKV?coupon_code=FIMINDED


Connect With Justin

Email me at Justin@FIMinded.com or connect with me on LinkedIn.


Support FI Minded

Want to hear more? Follow FI Minded on your favorite podcast player.

Like this episode? Share it with a friend pursuing financial independence.

Love the show? Say thanks by leaving a positive review.

Next Episode All Episodes Previous Episode

Listen for free

Show artwork for FI Minded - Financial Independence Without the Extremes

About the Podcast

FI Minded - Financial Independence Without the Extremes
Achieve Financial Independence & Have Fun Doing It
Pursuing financial freedom, a work-optional lifestyle, or early retirement often leads to the same questions: “one more year,” “do I have enough?” “what does life actually look like after this?”

FI Minded helps you think like someone who’s already financially independent so you can make smarter decisions about how you work, spend, and live.

From Coast FI and Slow FI to lifestyle design, career transitions, healthcare, and self-employment, each episode explores the real decisions behind building a flexible, work-optional life…without burnout, over-optimization, or missing out along the way.

We cover:
* Smarter ways to reach financial independence (without burnout)
* Designing a flexible, work-optional lifestyle
* Coast FI, Slow FI, and enjoying your time along the way
* What life actually looks like after FI (and how to prepare for it)
* The tradeoffs behind big money decisions

Make progress toward financial independence while actually living your life.

Some of our past guests include Carl Jensen (1500 Days), Jeremy Schneider (Personal Finance Club), Nick Loper (Side Hustle Show), Andrew Giancola (The Personal Finance Podcast), Jordan Grumet (Earn & Invest), Rachael Camp (Work Optional), Jillian Johnsrud (Retire Often), Sean Mullaney (FI Tax Guy), Jill Sirianni (Frugal Friends), Jackie Cummings-Koski (Catching Up to FI), Joel Larsgaard (How to Money), Cody Garrett (Measure Twice), Jesse Cramer (Personal Finance for Long-Term Investors), Jess (The Fioneers), Chris Hutchins (All The Hacks), Diania Merriam (EconoMe), Andy Hill (Marriage Kids Money), Fritz Gilbert (Retirement Manifesto), and and others helping you rethink how to approach financial independence.
Support This Show