HerMoney with Jean Chatzky

EP 499: Estate Planning Is an Act of Love: Here’s How to Start
Date: October 29, 2025
Guest: Heather Winston, Certified Financial Planner, Assistant Vice President, Principal Financial Group

Overview

In this episode, Jean Chatzky and guest Heather Winston break down the essentials of estate planning. They aim to dispel the myth that estate planning is only for the wealthy and make a compelling case for why every adult—regardless of net worth—should have a plan in place. Through compassionate discussion, practical advice, and personal anecdotes, they demystify key documents, highlight common pitfalls, and underline that planning your legacy is an act of love.

Main Discussion Points & Insights

1. Why Estate Planning Is for Everyone

• Estate planning isn’t just for the rich. Everyone has a legacy—possessions, family, values—that deserves protection and clarity.
• Estate planning is about aligning your values, intentions, and beliefs with your actions for the future.
  • Quote: “Clarity is kindness, right? If you can clearly outline your wishes, you’re preventing confusion. You’re preventing conflict among your loved ones.” — Heather Winston (01:14)

2. Essential Documents for Every Adult

• Four key legal documents everyone should have:
  • Will: Designates guardians for minors, allocates assets.
  • Healthcare Proxy/Power of Attorney for Healthcare: Names someone to make medical decisions if you cannot.
  • Financial Power of Attorney: Assigns someone to handle financial affairs if you become incapacitated.
  • Living Will/Advance Directive: Clearly communicates end-of-life medical preferences.
• Start estate planning at adulthood (age 18), especially regarding healthcare proxies.
  • Quote: “Truly figuring out who is someone that they not only trust, but they respect, that will advocate for their best interest…” — Heather Winston (10:49)

Notable Segment

• Importance of a Will for Parents:
  • “A will is the only document that allows you to name guardians for minor children. So as soon as you’re a parent, that becomes an absolute necessity.” — Jean Chatzky (08:25)

3. Special Considerations for Different Family Situations

• Blended Families: Update wills and beneficiary designations after major life changes (e.g., remarriage, divorce).
  • Consider trusts such as Qualified Terminal Interest Property (QTIP) trusts to balance care for new spouses and children from prior relationships.
  • Quote: “The more clearly you can articulate [asset distribution]…the better you can avoid potential conflict among family members.” — Heather Winston (15:41)
• Single Parents:
  • Naming guardians and establishing trusts for children’s care and financial management is critical.
• Single People Without Obvious Heirs:
  • It’s normal to struggle with whom to name as a decision-maker; professional trustees are an option.

4. Beneficiary Designations Trump Wills

• Always keep beneficiary forms updated for life insurance, retirement accounts, etc.
  • Beneficiary designations override wills.
  • "Beneficiaries trump wills. So you can say something in your will, but if you say it in a beneficiary designation, whoever you said…is going to get that money or get that property. So you have to get that right.” — Jean Chatzky (19:14)

5. What If You Don’t Have a Lot of Financial Assets?

• Future planning is just as much about instructions and clarity as it is about money.
  • Quote: “Leaving instruction is quite possibly one of the most crucial things that any of us can do. Clarity is kindness.” — Heather Winston (25:16)
• Even simple information—funeral preferences, account locations, or favorite stories—should be documented for loved ones.

Memorable Moment

• Jean shares a story about her stepfather leaving a detailed “manual” for after his passing, even specifying what food to order at shiva.
  • “It was just…it was so appreciated at a time when none of us could think straight. And so I think it’s a gift when you leave instructions.” — Jean Chatzky (26:17)

Important Advice Segments & Timestamps

Having the Conversation

• How to start estate planning conversations with family:
  • Use empathy. Normalize the conversation as an act of love, not morbidity.
  • Don’t force a single heavy conversation; spread it out if needed.
  • Anecdote: Heather recalls her father bringing up estate planning unexpectedly at a public birthday lunch—suggests choosing private, emotionally supportive settings instead. (30:07)
  • Quote: “Try to do it privately. Try to recognize signs…It’s okay to break apart the conversation and…revisit it regularly.” — Heather Winston (31:21)
  • Jean’s insight: “The first time I talked to one of my parents about this…it was just so hard. But the next time it was a little easier.” (32:23)

Choosing Executors & Proxies

• Critical to select (and inform!) the right people, and they don’t all need to be the same person.
  • Courts or medical staff may otherwise appoint someone who may not know your wishes.
  • Digital assets are often overlooked—provide instructions and passwords.
  • Quote: “If you don’t name an executor…the courts are going to appoint someone. If you don’t name a healthcare proxy, typically the medical professionals do that…It can be really expensive [and] time consuming.” — Heather Winston (33:23)

Legacy Beyond Money

Ethical Wills & Legacy Letters

• Consider writing a legacy letter or ethical will—a document or collection of notes, letters, or thoughts passing down values, advice, and family stories alongside assets.
  • “It’s really about what do you want to pass down…about your life and your history and what you were thinking in varying moments. And it can be simple, it can be clean and easy.” — Heather Winston (39:11)
  • Heather recounts a client who left thoughts daily in a bucket, comforting family and providing insight after their passing.

Notable Quotes

• “Clarity is kindness, right? If you can clearly outline your wishes, you’re preventing confusion.” — Heather Winston (01:14; echoed at 25:16)
• “A will is the only document that allows you to name guardians for minor children. So as soon as you’re a parent, that becomes an absolute necessity.” — Jean Chatzky (08:25)
• “Beneficiaries trump wills…So you have to get that right.” — Jean Chatzky (19:14)
• “Leaving instruction is quite possibly one of the most crucial things that any of us can do.” — Heather Winston (25:16)
• “Try to do it privately. Try to recognize signs…It’s okay to break apart the conversation and…revisit it regularly.” — Heather Winston (31:21)
• “It’s a gift when you leave instructions.” — Jean Chatzky (26:17)
• “Writing a legacy letter…opens up having that very clear intention present in the moment when you’re no longer here to tell us all those great stories and all those great memories.” — Heather Winston (40:54)

Key Takeaways

• Estate planning is for everyone, regardless of asset level.
• Act early—even young adults need basic documents.
• Update beneficiary designations and documents after major life changes.
• Good planning avoids family conflict and confusion.
• Instructions and legacy letters can be as important as financial documents.
• Approach estate talks with empathy, clarity, and kindness—it's about love, not just legalities.

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