Nobody wants to picture the version of later life where their mind or body stops cooperating, so most people file long-term care under "deal with it later." Jesse Vickey built a whole company on the belief that later is exactly the wrong time to start. The founder of Long Term What? joins Bri Conn, CFP® to make one of the most avoided money conversations feel clear and even a little hopeful, walking through what long-term care actually is, the four ways people pay for it, and why roughly 70 percent of adults will need it while the average long-term care bill already runs about $129,000 a year. For Childfree adults especially, who can't assume an adult child will step in as the default caregiver, the planning window and the health that lets you qualify for coverage are everything. The throughline is one Jesse comes back to again and again: the best time to plan is while you're still healthy enough to have all your options open.

In This Episode, You'll Learn:

  • What long-term care actually means, the two triggers insurers use to define it, and why 70 percent of adults will need care while costs climb around 5 percent a year
  • The four ways people pay for long-term care, from relying on family to Medicaid to insurance to self-funding, and how to think through which fits your life
  • Why insurance can act as a psychological "permission slip" to actually accept care, when self-funders often deny it to themselves to preserve their savings
  • Why a health pre-screen before you formally apply is critical, how a single recorded decline can follow you across insurers, and why your healthy window is the time to act
  • What to look for in a policy, from benefit length and cash versus reimbursement to rate-increase risk and the new coverage that finally follows you abroad

Episode Guest:

Jesse Vickey is the founder of Long Term What?, a company built on the belief that long-term care is one of the biggest untold stories in America. After graduating from Duke and beginning his career on Wall Street, he left banking to found two mission-driven companies, one using humor to teach college graduates the life skills school never covered, and another connecting busy families with in-home meal prep. Through Long Term What?, he now helps people cut through the confusion of long-term care, learn their options, talk with their families, and build a plan, guiding them through insurance when it's the right fit.

Connect with Jesse Vickey:

Website: longtermwhat.com
 YouTube: Long Term What?

Episode Host:

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.

About Childfree Insights:

Childfree Insights focuses on planning for solo aging and later life without children. It offers trusted education on financial planning, estate planning, and building support systems for people aging independently. 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.

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