The Death Readiness Podcast: Not your dad’s estate planning podcast

What Really Happens with DIY Wills and other Lessons from the Bench


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Jill talks with Judge Andra Hedrick, the first female probate court judge in Davidson County, Tennessee, to pull back the curtain on what really happens when DIY wills, internet forms, and quick-fix estate plans land in probate court. They discuss the rise of homemade documents, the conflicts they leave behind, and what families should know about probate, guardianships, and conservatorships. Judge Hedrick also shares insights on how the court works day-to-day, including what happens when families show up without a lawyer and why making your wishes clear is the best way to protect your loved ones.

What We Discussed:

What Probate Actually Means

  • Why a will has no legal effect until it is admitted to probate.
  • How the petition process works and what “pro se” (representing yourself) looks like in court.

Beyond Wills: Other Roles of Probate Court

  • Guardianships for minors inheriting money.
  • Emancipation proceedings for minors entering contracts (like young entertainers).
  • Conservatorships for adults with disabilities or cognitive decline, and the conflicts that arise when family members disagree.

Challenges in Court

  • Families surprised by estate outcomes that don’t match verbal promises.
  • The risks of vague or conflicting instructions from a deceased loved one.

The Rise of DIY and Internet Wills

  • Why homemade wills often create confusion and costly cleanup.
  • Missing provisions (like residuary clauses) that cause unintended gaps.
  • Examples of ambiguous language and why precision matters.
  • Why fixing problems after death is far more expensive than doing it right from the start.

Inside the Courtroom

  • Open access to the public and how hearings can often be observed (sometimes even via Zoom).
  • Court culture and expectations around dress, conduct, and participation.
  • Judge Hedrick’s perspective on keeping the court accessible to all.

Resources & Links

  • Parent Prep Plan – If you’re worried your parents may try the DIY will route, Jill can help walk them through the estate planning process with the right attorney and keep things moving forward: Parent Prep Plan — Death Readiness

Connect with Jill:

  • Website: DeathReadiness.com
  • Email: [email protected]
  • Subscribe to receive news and updates.
  • Love this episode? Please rate and review in the Apple podcasts app!
  • Submit a question for Tuesday Triage

Did you enjoy this episode? Share it with someone you care about.

This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy.

 

Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents.

 

Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state. 

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The Death Readiness Podcast: Not your dad’s estate planning podcastBy Jill Mastroianni - Estate Planning & Probate Consultant for Women

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