Jill on Money with Jill Schlesinger

Episode Summary: Estate Planning for My Parents

Date: October 27, 2025
Host: Jill Schlesinger
Guest Caller: Michael (from California)

Overview

This episode centers on a listener, Michael, seeking guidance for helping his aging parents with estate planning. Jill and her producer Mark walk Michael through crucial steps, share actionable advice, and discuss the emotional and practical challenges families face when tackling estate and future care decisions for elderly parents. The conversation highlights real-life hurdles, best practices for family communication, and key legal/financial moves everyone should consider in similar situations.

Key Discussion Points & Insights

1. Opening the Conversation with Parents

• Michael’s Dilemma: His parents are in their mid-70s with minimal estate planning in place. His mother’s health is declining, prompting urgent dialogue about their financial affairs and future care.
• Resistance: Michael describes resistance and discomfort from his parents about discussing money and mortality.
  • Quote:

    “Yes, yes and yes. Yeah, all the above.” (Michael, 03:30)
    On whether there was resistance to having these tough conversations.

• Family Dynamics: Michael is the youngest of three children; one sister has passed away, leaving minor children. This adds complexity to inheritance and guardianship concerns.

2. Understanding the Parents’ Financial Picture

• Assets & Income:
  • House paid off, worth $300k–$350k.
  • Investments: Father alludes to $500k, but exact asset allocation is unclear.
  • Monthly income: Around $5,600 from Social Security and a small pension.
  • Expenses: Lower than income; mainly insurance, taxes, basic needs.
• Bank Accounts & Titles:
  Michael is uncovering whether accounts are jointly or individually owned.

  “Do they have other money in other accounts? Possibly.” (Michael, 07:08)

3. Estate Planning Basics and Legal Guidance

• No Wills in Place:
  The parents haven’t written a will, at least not in the past 30 years.

  “I assumed they had one from 30 years ago... but they both said no.” (Michael, 07:26)

• Engaging an Estate Attorney:
  The family is reconnecting with an attorney who handled the grandmother’s estate, which will help structure and clarify their plans.
• Preparation for Attorney Meeting:
  Jill emphasizes bringing all financial documents—account statements, insurance policies, home deed, mortgage documents, etc.—to the first attorney meeting.
  • Advice:

    “You’ve got to bring an account statement for every account you have, every investment account, every retirement account, every bank account, you need to bring a copy of your insurance policies...” (Mark, 08:35)

• Physical Presence:
  Encourages at least one child to attend the meeting with parents, as it helps with understanding and accountability.
  • Quote:

    “It’s like going to the doctor with them.” (Mark, 08:17)

4. Special Considerations: Loan to Family & Guardianship

• Mother Holds a Mortgage:
  Michael’s mom holds the mortgage for his deceased sister’s husband and children, with about $100,000 outstanding.
  • Situation: This creates complexities if his mother passes or if she needs the capital for care.
  • Quote:

    “If something happened to your mother right now, I’m not sure what happens to that mortgage.” (Mark, 11:10)

• Guardianship:
  The deceased sister’s kids are minors and live with their father; the family relationship is good, but inheritance and trust structures need careful attention.

5. Housing Decisions & Future Care

• Staying vs. Moving vs. Renting:
  The siblings are encouraging their parents to sell their longstanding house for easier living arrangements, possibly renting to simplify.
  • Emotional Barriers: Resistance to the physical move/downsizing and sorting through decades of belongings.
    • Quote:

      “For years now, my mom said, I can’t imagine packing this house up and moving. And we said, you’re not the one doing it. We’ll be doing it.” (Michael, 06:34)

  • Financial Upside: Selling would free up $300k+, providing more liquidity if care is needed.
  • Renting Considered: For flexibility and to avoid the burdens of homeownership in older age.
    • Logic:

      “If they rent something in their area…there’s things that they wouldn’t have to deal with—upkeep of house, property taxes, homeowner’s insurance. It might be [worth it].” (Mark, 14:20)

6. Long-Term Care Planning

• The risk is that increasing care needs may deplete investments rapidly, so more liquidity (via sale of the house) and clear documentation (via estate planning) are crucial.

7. Family Communication and Guilt-Tripping

• Addressing Guilt & Avoidance: Jill and Mark encourage Michael to communicate frankly about the family’s loss and the need to avoid future chaos by planning now.
  • Quote:

    “It’s going to be horrible when something bad happens. Let’s tidy up what we can now.” (Jill, 17:37) “We’ll be able to focus on just feeling grief as opposed to freaking out about money.” (Mark, 17:39)

Notable Quotes & Memorable Moments

• On the emotional difficulty:

  “Oh, we’re here for dinner. Let’s talk about your death.” (Mark, 03:32)

• On avoiding family drama:

  “The horribleness will be with us. And we’ll be able to focus on just feeling grief as opposed to freaking out about money.” (Jill & Mark, 17:37–17:43)

• Encouragement to listeners:

  “Every situation is very fraught when it comes to estate planning. I understand that. So let us know how we can help you out.” (Jill, 18:25)

Timestamps for Key Segments

• [02:50] Michael introduces his family’s estate planning predicament.
• [03:30] Discussion of parental resistance and broaching difficult topics.
• [04:33] Sibling dynamics and impact of sister’s passing.
• [05:07–06:29] Assessing parents’ assets, monthly income, and expenses.
• [07:26] Confirmation that no wills exist; beginning steps.
• [08:35] Preparing for the estate attorney—what to bring and why.
• [11:07] Details about the intra-family mortgage.
• [13:09] Sibling cooperation and possibility of helping with future care.
• [14:20] Pros and cons of renting versus buying for aging parents.
• [17:37] Addressing emotional labor and family obligations; importance of planning now.

Conclusion & Action Steps

• Michael is proactive and following the optimal order:

  1. Start estate planning with legal counsel.
  2. Collect all financial and legal documents.
  3. Address housing and liquidity for potential care needs.
  4. Maintain open, honest family communication.
  5. Follow up with Jill after attorney meeting for tailored next steps.

• Listener advice: Have these conversations sooner rather than later. Bring in professionals, stay organized, involve your siblings, and “tidy up” logistics so you can focus on each other—not just the money—when difficulty strikes.

This detailed breakdown offers listeners a roadmap for navigating sensitive estate planning topics, highlights the emotional realities involved, and distills practical wisdom from Jill and her team.