Windsor Wealth Management LLC

Investment service in Topsfield, Massachusetts

Estate Planning

5 Financial Tasks to Tackle Before Fall

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As summer winds down, it’s a good time to take a few minutes to review your finances before the busy fall season begins.

Here are five areas worth checking now.

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#1—Plan for Age 18

If your child or grandchild is turning 18 or heading off to college, make sure they have the legal documents that allow you to help them if there’s a medical emergency.

Overall, it’s a good idea to have:

  • HIPAA Authorization
  • Medical Power of Attorney
  • Living Will
  • Durable Power of Attorney

Related Post: Turning Age 18 Legalities & Grandchild College Planning

Also, if your student is living on or off campus, consider whether renter’s insurance makes sense. Replacing specialized computer equipment can be costly. The same goes for e-bikes, which many students use to get around campus and can cost thousands to replace.

Note: While your homeowners policy may cover some losses in a dorm, e-bikes and high-value tech often require special endorsements or separate policies.

Finally, if you’re using a 529 plan, coordinate your withdrawals carefully. Using the same education expenses for both a 529 withdrawal and an education tax credit can lead to unexpected tax consequences.

Fidelity does a nice job explaining it here: How to spend from a 529 college plan1

#2—Get Ready for Open Enrollment (Medicare & Employer)

Open enrollment season is just around the corner.

Medicare’s Annual Enrollment Period runs from October 15—December 7, and many employers hold open enrollment in the fall.

Before finalizing your benefits, consider the following:

Health Insurance Coverage: Compare plan costs, deductibles, provider networks and out-of-pocket maximums to determine whether your current plan is still the best fit.

Prescription Drug Coverage: Make sure your medications are still covered and compare costs if your prescriptions or health needs have changed.

Health Savings Account (HSA) Contributions: If you’re eligible for an HSA, review your contribution amount during open enrollment. HSAs offer triple tax advantages, including tax-deductible contributions, tax-deferred growth and tax-free withdrawals for qualified medical expenses.

Flexible Spending Accounts (FSAs): Estimate next year’s eligible healthcare or dependent care expenses so you can elect an appropriate contribution amount.

Life and Disability Insurance: Review your coverage after major life events (e.g., birth, divorce or marriage). If your employer allows you to increase coverage without a medical exam during open enrollment, consider whether additional protection makes sense before your health changes.

Retirement Plan Contributions: Increase your contribution rate if you’re receiving a raise or bonus. Also, make sure you’re contributing enough to receive your full employer match.

Are you turning age 65 soon?

Your Medicare initial enrollment timeline is different from the annual enrollment period.

Most people can enroll in Medicare beginning three months before the month you turn 65 and continuing for three months afterward.

However, if you’re still covered by an employer health plan, different rules may apply.

Give us a call before you enroll, so we can help you sort through your options.

RESOURCE: Here’s our detailed Medicare guide describing initial enrollment timelines, premiums and deductibles for 2026.

#3—Review Your Taxes and Retirement Savings

Now is a great time to see whether you’re on track.

Review your paycheck withholdings to help avoid an unexpected tax bill or an unnecessarily large refund next spring. Also, check your retirement plan contributions to see if you’re on pace to maximize your 401(k), 403(b), etc. before year-end.

Keep in mind, if you’re age 50 or older and make catch-up contributions, be aware that recent law changes may require higher earners to make catch-up contributions on a Roth (after-tax) basis.

#4—Update Your Homeowners Insurance

Have you remodeled your kitchen, finished a basement or added a garage?

Major home improvements can increase the cost to rebuild your home. If you’ve completed significant renovations, review your homeowners insurance to help ensure your coverage keeps pace with your home’s current value.

Also, if you’ve added a pool, consider adding an umbrella policy.

#5—Plan Ahead for Holiday Spending

It may feel early, but the holiday shopping season will be here before you know it.

Therefore, take a few minutes now to decide how much you want to spend on gifts, travel and entertaining.

Setting a budget early can help reduce financial stress and prevent overspending later in the year.

If you have any questions, please reach out.

–David Bunker, Financial Advisor & Licensed Fiduciary

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.com, How to spend from a 529 college plan, https://www.fidelity.com/learning-center/personal-finance/college-planning/college-529-spending

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

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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