• Skip to main content
  • Skip to footer

Windsor Wealth Management LLC

Investment service in Topsfield, Massachusetts

  • Home
  • About
    • Disclosure
  • Our Difference
  • Services & Fees
    • When to Hire a Financial Advisor
    • FAQ’s
  • Blog
  • Retirement Checklist
  • Contact

3 Later-in-Life Conversations; Important Decisions as Life Changes

October 28, 2025 by David Bunker

With the holiday season approaching, many of us are looking forward to favorite traditions like gathering for a big family dinner, watching a classic movie or relaxing by the fire together.

It’s also an ideal time to discuss how important decisions should be handled as your life changes.

Of course, these conversations are not always easy.

In fact, a new Fidelity study on later-in-life conversations found that as families age, they actually talk less about the topics that matter most.1

Even among financially prepared households, discussions often stall when it comes to three critical issues:

#1—Decision-Making and Change of Control: Who steps in if you can’t make financial or medical decisions?

#2—Dependence and Dependent Living: What’s the plan if living independently becomes difficult?

#3—Thinking Ahead for a Health Incident: Do loved ones know your wishes and how to access important information?

Fidelity’s research shows these conversations drop sharply around age 70, just when they become most urgent.

Also, nearly nine in ten baby boomers say at least one emotional barrier keeps them from talking about later-life issues, including not feeling prepared or not knowing how to start.

According to the study, baby boomers rank thinking ahead for a health incident as one of their most relevant topics. Yet, it’s the topic they’re most unwilling to talk about.



And while many describe their family communication as “open,” two-thirds admit they aren’t actually discussing the topics they consider most relevant.

The study also found that families who have active, ongoing conversations report more confidence that their plans will unfold smoothly, and feel closer as a result.

If you haven’t revisited your plan for these situations, now is the time.

We’re happy to help you:

  • Review or update your powers of attorney and health-care directives.
  • Clarify who makes what decisions and where key documents are stored.
  • Model how long-term care or a sudden health event could affect your finances.

[RELATED]: Longevity plays a major role in how long your plan needs to work for you. We discuss this and two other key considerations in our post, 3 Critical Retirement Planning Dynamics.

Let’s make sure your financial plan reflects both your wishes for care and decision-making.

Sincerely,

–David Bunker, Financial Advisor & Licensed Fiduciary

P.S., In case you missed it, check out our latest blog post: 5 Financial Moves to Make Before Year-End


Before You Go

Get help optimizing your retirement income. Download our FREE “Prolonging Retirement Income” checklist.

Also, receive help retiring to the life you want, schedule a complimentary financial planning consultation.


This communication was prepared with financial writer Sharron Senter’s assistance, based on interviews with David Bunker, a financial advisor and licensed fiduciary.


Source:

1: Fidelity, Later-in-Life Conversations Study, https://www.fidelity.com/bin-public/600_Fidelity_Institutional/fidelityinstitutional/Application/AP168302/family/TGP_LIL_Report_FCFE_FINAL.pdf


Filed Under: Estate Planning, Financial Planning, Retirement Planning, Windsor Insights, Windsor Money Minute

Footer

Amplify Your Retirement Income

"Prolonging Retirement Income" Checklist
Please enable JavaScript in your browser to complete this form.
Name *
Loading

Windsor Insights

A Key Trend Worth Watching & Your Portfolio

There’s been no shortage of noise lately about an “AI bubble.” Yet, the data suggests we’re seeing a structural shift in how the economy … [Read More...] about A Key Trend Worth Watching & Your Portfolio

More Posts from this Category

  • Home
  • About
  • Testimonials
  • Contact

Windsor Wealth Management, LLC · 27 Main Street · Topsfield, MA 01983 · (978)887-6940 · WindsorWM.com · Email Us

Investment Advisory Services offered through Bay Colony Advisors, an SEC Registered Investment Advisor

Disclosure
Form ADV Part 2A – Disclosure Brochure
Form ADV Part 3: Relationship Summary Bay Colony Advisory Group, Inc.

Copyright © 2026 · Website Design · Admin

Copy written by financial services writer Sharron Senter