Windsor Wealth Management LLC

Investment service in Topsfield, Massachusetts

Financial Planning

Markets Don’t Send Invitations When the Best Days Arrive

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One of the most valuable things you can have during uncertain markets is perspective.

Yet when headlines intensify, it’s only human to consider moving to cash until things settle down. This feeling is often magnified if you’re approaching retirement or have recently transitioned into it.

The challenge?

Markets don’t send invitations when the best days arrive.

In fact, some of the biggest gains usually happen right when things feel the most uncertain.

Fidelity shared a chart that illustrates this clearly:

Imagine a $10,000 investment in the S&P 500 back in 1988. That initial amount surpasses $522,000 by 2024, provided you never walked away.

However, missing just the five best market days over that same 37-year period slashes the ending value by roughly 37%.

Find the chart sources and specifications at Fidelity.com1

These few great days are nearly impossible to predict.

What’s more, they often occur shortly after a decline.

Key Goal

Ultimately, our goal is to help you have the resources to live your best retirement life, exactly how you’ve pictured it. Sticking to a disciplined, long-term strategy instead of reacting to headlines is a key component.

For more context behind these numbers, Fidelity breaks it down in this article: 6 reasons why you should consider investing right now.

Reach out with any questions.

–David Bunker, Financial Advisor & Licensed Fiduciary

P.S. In case you missed it, I recently shared my perspectives on the Middle East conflict and what it could mean for your portfolio. Read the post.

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, 6 reasons why you should consider investing right now, https://www.fidelity.com/learning-center/wealth-management-insights/reasons-to-invest-now

The 3-Year “Buffer Strategy” for Portfolios

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When reviewing retirement projections, it’s easy to focus on average annual returns.

In reality, retirement outcomes are shaped less by averages and more by the timing of these returns—a concept known as sequence of returns risk.

EXAMPLE: How Identical Savings Lead to Different Futures

The chart below shows two couples, each starting retirement with $2.5 million and withdrawing $100,000 per year. Over 25 years, they earn the same average return.

The difference, however, is the order in which these returns occur:

Couple A: Experiences a market downturn in the first years of retirement.

Couple B: Experiences the same downturn much later.

A market downturn hits harder when you’ve just retired.

When withdrawals coincide with losses, you’re forced to sell more assets to generate the same income. This shrinks your portfolio and reduces its ability to recover because you have less capital working for you when the market rebounds.

Conversely, declines occurring later in retirement are often easier to absorb.

At this stage, your portfolio has already done the “heavy lifting,” plus it’s continued to grow, creating a financial buffer that helps your savings survive future market turbulence.

Finally, by the time a later downturn hits, your portfolio doesn’t need to support as many future years of income.

Same average returns. Very different outcomes.

RELATED: In case you missed it, we published a new post: How to Make the Decision to Retire. Market behavior is one of several key factors to consider.

Managing Sequence of Returns Risk

Windsor Wealth Management helps you address this risk by setting aside two to four years of income in a conservative investment account. This “buffer” remains stable while still providing modest growth.

It allows retirement spending to continue uninterrupted during market downturns, giving the rest of your portfolio time to recover.

For Example:

If your annual spending is $90,000, we may earmark $270,000 to cover the first three years of retirement.

This upfront reserve helps protect your lifestyle by reducing the need to sell investments when markets are volatile.

Key Action: It’s critical to plan for the “when” of your retirement to help ensure there’s enough time to set these funds aside. (Ready to retire? Reach out as soon as possible.)

Generally speaking, average returns don’t retire people.

Cash flow timing does.

–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.

How to Make the Decision to Retire

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Many people assume retirement is a single decision:

“I’m done. I’m retiring.”

In reality, retirement works best as a process, not a one-time leap.

The desire to retire often starts with a feeling: burnout, a personal milestone (e.g., reaching a specific age, becoming a grandparent, paying off a mortgage) or a realization that time matters more than it used to, especially after losing someone close.

The real question isn’t: Can I afford to retire?

Instead, it’s: How do I want this next chapter to look, and what financial options do I have?

Thoughtful financial planning makes a meaningful difference at this juncture.

Retirement Is a Series of Choices

Some people retire all at once.

Others work a few more years, shift to part-time or gradually step back (e.g., reduce from five days to three or cut back responsibilities while keeping key projects).

Some claim Social Security early. Others delay.

Interestingly, some people can look at the same financial data and make completely different decisions, because confidence, lifestyle and comfort matter just as much as the math.

Overall, approaching retirement as a process allows you to test different paths before committing to one.

Why Timing Matters More Than Most People Realize

Retirement outcomes aren’t shaped by a single decision.

Instead, they’re shaped by when decisions are made and how they interact with one another.

A few examples we routinely see:

Markets: Retiring just before or during a market downturn can put added pressure on your portfolio early, when withdrawals begin and flexibility is lowest. If markets decline in these early years, selling investments at lower values can permanently reduce how long your portfolio lasts, even if markets recover later. This is why Windsor Wealth Management focuses on proactive income planning and portfolio guardrails designed to help reduce this risk.

Taxes: The order and timing of withdrawals (taxable, tax-deferred and tax-free accounts) can quietly increase or reduce lifetime tax exposure.

Healthcare and Medicare Costs: The years before Medicare, Medicare enrollment and ongoing healthcare expenses all affect retirement cash flow.

In some cases, income that seems reasonable on paper can trigger higher Medicare premiums if certain thresholds are crossed, aka Income-Related Monthly Adjustment Amount (IRMAA). We explain this “income cliff effect” in our post: Medicare: The $1 Mistake that Costs $3,500

Social Security Timing: While delaying benefits increases income (roughly 8% per year after full retirement age until age 70), the “right” decision depends on longevity risk, health considerations, caregiving needs, portfolio size and tax strategy.

Looking at these factors in isolation can be misleading.

Seeing them together across multiple scenarios helps clarify what’s realistic, what’s flexible and where risks truly lie. It turns uncertainty into clarity by highlighting which decisions matter most while changes are still possible.

The Emotional Side of Retirement Matters

Retirement isn’t just a financial transition; it’s a deeply personal one.

While you’ve likely focused on the “math” for years, many retirees are surprised by how much they miss the structure of a career. Some even feel a loss of identity.

That’s why it’s helpful to think not only about what you’re retiring from, but what you’re retiring to.

To help visualize this journey, watch Dr. Riley Moynes’ TED Talk.1 He explains four distinct psychological phases you’ll likely experience:

#1—The Vacation Phase: The initial excitement of total freedom.

#2—Feeling Lost: Realizing the “honeymoon” is over and missing your old routine.

#3—Experimentation: Trying new activities to find a new sense of purpose.

#4—Reinvention: Successfully creating a fulfilling new identity.

Ultimately, retirement is less about reaching a final destination and more about having the flexibility to evolve along the way. Part of this evolution involves overcoming one of retirement’s greatest challenges: the loss of social connection.

The Harvard Study of Adult Development (one of the longest-running studies on human happiness) highlights that our relationships are the strongest predictor of health and longevity.2

Income Confidence Is Not a Magic Savings Number

A common misconception is that retirement decisions hinge on reaching a single savings target.

In reality, confidence comes from understanding income; specifically, how much is coming in, where it’s coming from and how long it’s likely to last under different conditions. This is one of our core roles: helping you understand how much you can comfortably spend.

This answer is shaped by three key forces:

  • How long you live.
  • When you claim Social Security.
  • How retirement spending changes over time.

We’ve explored these dynamics in more detail here: 3 Critical Retirement Planning Dynamics

Spending With Purpose and Without Regret

Once income is clearly defined, the challenge for many retirees shifts from Can I afford to retire? to How do I spend confidently?

However, this shift isn’t just financial. Moving from a lifetime of saving to relying on your money for income can be a real psychological adjustment—even when the numbers say you’re ready.

That’s why a well-structured financial plan creates guardrails that help turn income into a reliable “retirement paycheck,” reducing the temptation to question every spending decision or react emotionally to market swings.

For Example:

Rather than wondering when or how much to withdraw, our retired clients typically receive predictable, recurring income deposited directly into their checking account each month.

This usually includes Social Security and other reliable income sources, combined with a coordinated monthly “paycheck” from their portfolio—designed around individual income needs and adjusted as conditions change.

If you’d like to see how confident retirement spending actually works in practice, read our post: 3 Steps To Help Your Money Outlive—You. It features a realistic example of a couple who began retirement with $2 million in savings and—after 30 years of steady spending—actually had $2.6 million remaining (more than what they started with).

Is Retirement on Your Mind?

If you’re starting to think about retirement or questioning whether now is the right time, we’re always happy to talk through your options.

In general, it’s helpful to start retirement conversations as early as 10 years out. Doing so creates more options.

For Example:

  • Adjusting how you save (e.g., shifting from a traditional 401(k) to a Roth 401(k)), allowing more control over when and how taxable income shows up in retirement.
  • Building cash reserves to support early retirement years, so you’re not forced to sell investments during a market downturn.
  • Modifying Social Security timing, by modeling multiple claiming scenarios to see how different choices affect income, taxes and long-term outcomes.
  • Planning for healthcare coverage before Medicare begins, while being mindful of potential IRMAA surcharges.

If your retirement is fast approaching, be sure to read: Planning Your Final Days of Work Before Retiring, which includes a short video with a practical tip on preparing for the transition.

In general, most retirement decisions don’t need to be rushed or permanent. However, a few carry lasting consequences if made too quickly.

Approaching retirement as an ongoing process gives you time to explore options, understand trade-offs and move forward with confidence, knowing your plan can adapt as life evolves.

–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.

Sources:        

1: 4 Phases of Retirement…and the Psychological Challenges, https://www.ted.com/talks/dr_riley_moynes_the_4_phases_of_retirement

2: Good genes are nice, but joy is better. https://news.harvard.edu/gazette/story/2017/04/over-nearly-80-years-harvard-study-has-been-showing-how-to-live-a-healthy-and-happy-life/

2026 Tax Planning Resources & Key Financial Data

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Happy New Year!

As a new tax season begins, we’ve pulled together updates and resources you may find helpful to reference throughout the year.

Today, we discuss:

  • The SALT deduction increase and why more families will likely itemize taxes this year.
  • The new senior “bonus” deduction for individuals aged 65 and up.
  • A catch-up curveball impacting high earners.
  • The new $1,000 charitable deduction, even if you don’t itemize.
  • Why early-year QCDs create a “double” impact.
  • Deductions impacted by filing status.
  • 2025 withholdings and strategically positioning yourself for 2026.
  • Why January is a great time to adjust retirement contributions.
  • Required Minimum Distributions (RMDs).
  • Key financial facts for the 2025 and 2026 tax years, including standard deductions, retirement contribution limits, Social Security taxation, Medicare premiums and more. (2 handy handouts)

Reassess Itemizing Under the Expanded SALT Deduction

As a result of the One Big Beautiful Bill Act (OBBBA), the state and local tax (SALT) deduction cap has quadrupled to $40,000. For many, this makes itemizing a viable option again, offering potentially greater savings than the standard deduction.

(Note: This higher cap begins to phase down for households with a modified adjusted gross income (MAGI) over $500,000, eventually returning to the $10,000 limit for those earning over $600,000.)

If you:

  • Pay High State & Local Taxes
  • Own Your Home
  • Make Regular Charitable Contributions
  • Pay Mortgage Interest

…then itemizing may be a savings option for you.

EXAMPLE: See a side-by-side comparison of the standard deduction versus the new $40,000 SALT cap for married couples filing jointly in our recent post: 2025 Tax Changes: One Big Beautiful Bill Act (OBBBA)

Leverage the New Senior “Bonus” Deduction

Given the new OBBBA laws, those aged 65 and older can claim a new $6,000 senior bonus deduction ($12,000 for married couples).

This temporary benefit starts in 2025 and expires after December 31, 2028.

The full deduction is available to single filers with a MAGI up to $75,000 and married couples up to $150,000. It gradually phases out after, and is completely eliminated at incomes of $175,000 (single) and $250,000 (married).

This H&R Block article discusses the deduction in detail: New $6,000 deduction for seniors.1

Navigate the SECURE 2.0 Catch-Up Curveball

There’s a new twist for building your retirement nest egg starting in 2026.

If you earned more than $150,000 last year, the IRS now requires your “catch-up” contributions to be made as Roth (after-tax) instead of pre-tax.

While you won’t get the upfront tax break, the payoff is that this money will be tax-free when you retire, including any growth.

Finally, don’t forget about the “Super Catch-Up.” If you’re aged 60, 61, 62 or 63, you’ve hit a special four-year window that allows you to contribute a much higher limit of $11,250 to your 401(k) for tax year 2025.

RESOURCE: For a deep dive, Schwab has a great guide titled: Catch-Up Contributions 2025 and 2026. It breaks down these numbers and the new Roth requirement in detail.2

Claim the New $1,000 Charitable Deduction (No Itemizing Required)

You can deduct up to $1,000 (single filers) or $2,000 (married couples filing jointly) for cash donations to qualified charities, even if you take the standard deduction, starting in tax year 2026.

For tax purposes, “cash” includes donations made by check, credit card or electronic transfer—not property (e.g., clothing, furniture) or securities.

Accelerate Impact with Earlier QCDs

Qualified Charitable Distributions (QCDs) are an efficient way to manage RMD-related taxes.

By donating directly from your IRA, you can reduce taxable income, satisfy RMD requirements and support causes you care about.

However, timing matters.

Because of how the IRS applies annual distribution ordering, any IRA withdrawals taken before a QCD count as taxable income and are applied toward your RMD first. That leaves less room for a tax-free QCD later in the year.

For Example:

If your total RMD for the year is $150,000 and you withdraw $150,000 for personal use in February, this entire amount is taxable. Even if you make a $25,000 donation to charity in October, you cannot “swap” the two; the February cash has already satisfied your RMD with taxable dollars.

Instead, by prioritizing QCDs earlier in the year, you help ensure these first dollars go directly to charity, rather than accidentally triggering taxable income through personal withdrawals.

This approach also helps avoid year-end processing delays and gets your charitable dollars working sooner.

Verify Your Filing Status

Life changes often drive tax outcomes.

Marriage, divorce, the loss of a spouse, or a dependent aging out could impact your:

  • Standard Deduction
  • Tax Brackets
  • Eligibility for Credits and Deductions

A solid understanding of your filing status is critical in order to optimize your tax situation.

Fine-Tune 2025 Withholdings for 2026

Your tax return doesn’t just close the books on 2025; it informs smarter decisions for 2026.

Reviewing withholdings now helps you:

  • Avoid Surprises Next April
  • Align Tax Payments with Actual Income
  • Adjust for Bonuses, Side Income and Retirement Distributions

Overall, reviewing your withholdings now is especially important if your 2025 income fluctuated more than expected.

Optimize Retirement Contributions Early

January is the ideal time to revisit retirement contributions.

Increasing them early spreads savings evenly across the year, reduces decision fatigue and helps keep your financial plan on track automatically.

At the same time, if your income came in higher than expected in 2025, confirm you didn’t exceed contribution limits. Remember, over-contributions can trigger avoidable penalties, but they’re much easier to fix when caught early.

Prepare for Required Minimum Distributions (RMDs)

If you take RMDs—or will for the first time—this deserves early attention.

Taking RMDs increases your taxable income, which can:

  • Push You into a Higher Tax Bracket
  • Increase Medicare Premiums
  • Trigger Social Security Benefits Taxation

Also, if this is your first RMD year, timing matters.

Delays can result in two RMDs landing in the same tax year, increasing taxable income.

Download 2025 & 2026 Key Financial Data (Handouts)

To make your life easier, we have two handy spreadsheets highlighting key numbers you’ll likely need throughout the year.

They include:

  • Standard Deductions by Filing Status
  • Retirement Plan Contribution Limits
  • Educational Credits and Deductions
  • Medicare-Related Thresholds
  • Health Savings Account (HSA) Limits*
  • Capital Gains and Dividend Tax Rates
  • Social Security Taxation Thresholds
  • Tax Deadlines

*When possible, max-out this contribution, given its triple tax benefit: tax-deductible contributions, tax-free growth, tax-free qualified withdrawals.

Here are the handouts:

2025 Key Financial Facts — What to Know This Tax Season

2026 Key Financial Facts — Planning Ahead

If you’d like hard copies, please let us know. We’re happy to mail them to you, or you’re welcome to stop in. We’d love to see you!

–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.

Sources:

1: H&R Block, New $6,000 deduction for seniors, hrblock.com/tax-center/irs/tax-law-and-policy/one-big-beautiful-bill-senior-tax-deduction

2: Charles Schwab, Catch-Up Contributions 2025 and 2026, https://www.schwab.com/learn/story/what-to-know-about-catch-up-contributions

Bay Colony Advisors, DBA Windsor Wealth Management, is not a Certified Public Accountant and does not provide tax, legal, or accounting advice. Any tax-related information provided is for general informational purposes only and should not be construed as legal or tax advice. Each individual’s tax situation is unique, and you should consult with your own tax, financial, or legal advisors before making any decisions. We strongly recommend seeking the advice of a qualified CPA or other professional for personalized tax advice.

Rate Cuts, Jobs, Growth: A Look at 2026

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As we wrap up 2025, we’re closing the books on a year that delivered strong markets and a few surprises along the way.

More importantly, the trends taking shape now will help guide the decisions we make together in 2026.

Today, we discuss:

  • How the markets performed in 2025.
  • Why the Fed is likely to cut rates again.
  • Where the job market is showing quiet signs of stress.
  • What GDP growth and corporate earnings suggest for 2026.

2025 Market Review: Better Than Average

It’s been another impressive year for the stock market.

Year-to-date, we’ve seen growth of about 16.5%, following a strong 24% gain in 2024.

For perspective, the market usually averages around 8% to 10% each year, so we’re well ahead of the curve.

The one major bump we faced was a steep (but short-lived) drop in April when new tariffs were announced. This created a lot of uncertainty. Companies that rely heavily on global suppliers, like Walmart, saw their stock dip instantly.

In anticipation of the tariffs first mentioned in February, Walmart’s stock had already begun its decline from a high of $105 per share. When the tariffs were officially announced in April, the stock dropped further from $89 to a low of $82 per share, but it bounced right back. It’s currently trading strong at $115 per share, driven by people looking for better deals and the company’s leadership in online shopping and delivery.1

The good news is that many companies have adapted to the new tariffs.

For example, Walmart has successfully shifted a great deal of its product sourcing from China to India and Southeast Asia, including Vietnam and Thailand.

Ultimately, the tariffs caused uncertainty, but the market bounced back strongly.

Let’s switch gears now, and talk about three financial projections and key themes for 2026…

#1—Continued Rate Cuts

The Fed has a tough job: they must balance keeping inflation near their 2% target (now about 2.8%) while also ensuring the job market stays strong.

This balance is currently fragile.

To counteract the current risks in the economy, the Fed will likely continue to cut interest rates both in December and in early 2026. These cuts aim to lower borrowing costs, give the job market a lift and restore consumer confidence.

As long as the job market doesn’t weaken too fast, these cuts should help maintain steady economic conditions throughout 2026.

Related: We took a closer look at the delicate balancing act of rate cuts in our recent post, Today’s Economy: What’s Actually Going On?

#2—Labor Market Fragility

A key risk to the economy right now is the pressure placed on jobs, with the primary labor market weakness being concentrated in job cuts at small businesses.

This development will likely continue in 2026.

Signs of this trend were apparent in the November 2025 ADP report, with Reuters reporting an unexpected decline in private payrolls. (ADP processes payroll for 1 in 6 workers in the U.S.)2

This data suggests that while big company layoffs make headlines, the real pressure is happening quietly: small businesses are cutting jobs and offering fewer openings.

Read the full Reuters article here: US private payrolls post largest drop in more than 2-1/2 years in November.3

This pressure can create a dangerous self-fulfilling prophecy, consisting of a three-part cycle:

  1. Small businesses cut jobs due to uncertainty.
  2. People who are worried about losing their jobs start spending less money.
  3. The consequent slowdown validates the initial fear, making the prophecy self-fulfilling.

Keep in mind, small businesses are the main source of new jobs.

According to the U.S. Small Business Administration Office of Advocacy, “The U.S. contains 36.2 million small businesses, which account for almost 46% of private sector employment [share of employees]. From March 2023 to March 2024, U.S. small businesses created approximately 9 out of every 10 net new jobs.”4

If this massive engine pulls back on hiring or starts laying off, the overall job market quickly loses its critical source of new growth.

Two Other Points to Consider:

  • The low 4.4% unemployment rate doesn’t yet reflect what’s happening on the ground. Small business layoffs usually take a few months to show up in data, and the recent government shutdown added an extra delay. We’ll see some clarity when the November jobs report is released in mid-December.
  • We’ve yet to see any broad, hard data (enough to say there’s a clear trend) reflecting the real labor efficiency gains that artificial intelligence (AI) is expected to create. Up until now, the evidence we do see is largely anecdotal.

#3—Moderate Economic Growth

Most analysts’ forecasts for 2026 show U.S. economic growth ranging from 1.8% to 3.2%.

Even at the low end, a growing economy generally makes things easier because there’s more “pie” to go around for everyone.

This projected growth is supported by strong corporate earnings and by the fact that the tariffs didn’t lead to the severe economic damage many feared back in April. Remember, market sentiment also drives growth.

Finally, the housing market could provide a significant lift to the economy.

If the Fed continues to cut rates in 2026, it should cause interest rates and mortgage rates to keep coming down—possibly falling into the 5% range (optimistic but plausible). This could encourage more people to buy homes.

When the housing market picks up, it creates a ripple effect across the entire economy: demand increases for repairs, furniture, appliances and other home improvement projects, which in turn boosts thousands of businesses.

Lastly, on the investment side, several major banks are forecasting a 10% to 12% return for the stock market next year. As always, these are just estimates, but they reflect a generally healthy outlook for corporate earnings and valuations as we head into 2026.

Sincerely,

–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.

Sources:

1: Nasdaq.com, Walmart Inc. Common Stock (WMT), nasdaq.com/market-activity/stocks/wmt/historical

2: adp.com

3: Reuters, US private payrolls post largest drop in more than 2-1/2 years in November, reuters.com/business/us-private-payrolls-unexpectedly-decrease-november-adp-says-2025-12-03

4: U.S. Small Business Administration Office of Advocacy, New Advocacy Report Shows the Number of Small Businesses in the U.S. Exceeds 36 million, advocacy.sba.gov/2025/06/30/new-advocacy-report-shows-the-number-of-small-businesses-in-the-u-s-exceeds-36-million

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

5 Financial Moves to Make Before Year-End

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Fall brings more than changing leaves. It’s also an ideal time to revisit your financial plan before the holiday rush begins.

By making a few smart updates now, you can take advantage of valuable year-end opportunities and set yourself up for a strong start to the new year.

Let’s look at five key moves to consider:

#1—Revisit Retirement Plan Contributions

Now’s a great time to revisit your retirement plan contributions.

Even a small bump can make a big difference down the road. Plus, if your employer offers a match, that’s essentially free money. Also, consider directing a portion of any bonus or raise to your retirement accounts.

And don’t forget the power of compounding—it’s what turns small, consistent contributions into meaningful long-term growth.

Learn more in our post: Maintaining Retirement Lifestyles: Compound Interest’s Role

#2—Review Major Life Changes

If you’ve experienced any major life event, please contact us as soon as possible, including:

Employment Changes: New job, raise or retirement coming up? Let’s review your benefits, income, health insurance and tax withholdings. If you’re retiring soon, we’ll also help you determine whether your life insurance is portable and if you still need it.

Family Changes: Marriage, divorce, a new child or caregiving responsibilities? These often require adjustments to estate plans and insurance coverage.

Selling, Buying or Inheriting: Transactions like selling a home or receiving an inheritance can impact your taxes. Be sure to review your 2025 withholdings and be prepared for any capital gains or losses.

#3—Recognize OBBBA Impact

Tax laws changed earlier this year with the introduction of the new One Big Beautiful Bill Act (OBBBA).

One key benefit (the Senior Bonus Deduction) is for those age 65 and older.1

It’s a new “bonus” deduction, including $6,000 for qualifying individuals and $12,000 for qualifying couples. This benefit is in addition to the standard deduction. It’s available to both itemizers and non-itemizers but begins to phase out once income exceeds $75,000 for individuals or $150,000 for couples. This bonus deduction is temporary, and is effective for tax years 2025-2028.

Here are two resources on our website describing key takeaways from OBBBA:

#1—2025 Tax Changes: One Big Beautiful Bill Act (OBBBA) (Includes a “SALT Deduction Savings Example” highlighting how the higher SALT deduction cap now allows many households to deduct more of their state and local taxes than in previous years—and how you may save more by itemizing rather than taking the standard deduction this year.)

#2—Key Financial Data spreadsheet (Includes updated 2025 tax brackets, standard deductions, child tax credit and more.)

If you’d like, we can run year-end tax modeling to show how these changes may affect you.

Our Holistiplan tax software helps us forecast your taxes, model different scenarios, and identify opportunities such as Roth conversions or itemizing under the new, higher SALT deduction cap.

#4—Prepare for Year-End Charitable Giving

If you’re planning to give before year-end, start now to maximize your impact and tax benefits.

Consider using some of the following tax-smart strategies. We’re happy to help you decide which ones fit best.

Appreciated Assets: Donating stocks or mutual funds that have grown in value enables you to deduct their fair market value and avoid capital gains tax.

Donor-Advised Funds (DAFs): Gain an immediate tax deduction by making a contribution now, and enjoy the flexibility of distributing the funds to your favorite charities over time. This is a powerful tool for managing multi-year giving.

[RESOURCE]: Fidelity does a great job explaining what DAFs are, and you can take a quick quiz to see if this resource may work for you (or call us).2

Matching Gifts: Ask your employer if they’ll match your donation.

Qualified Charitable Distributions (QCDs): If you’re 70½ or older, you can donate directly from your IRA to help reduce Required Minimum Distributions (RMDs).

#5— Manage Income to Avoid Future Medicare Surcharges

When managing your 2025 taxes, it’s important to keep IRMAA (Income-Related Monthly Adjustment Amount) for Medicare on your radar.

IRMAA surcharges are based on your modified adjusted gross income (MAGI) from two years prior, meaning your 2025 income will determine what you pay for Medicare premiums in 2027.

Strategic tax planning can help you stay below key IRMAA thresholds by managing income sources such as Roth conversions, capital gains and RMDs. Timing these activities (especially toward year-end) can help reduce future surcharges and keep your overall retirement healthcare costs in check.

Medicare Resources Available on Our Website:

Will I avoid IRMAA surcharges on Medicare Parts B & D?

Medicare Premiums and Deductibles for 2025

BONUS MOVES: Other Tax & Retirement Savings Strategies

  • Roth Accounts: Consider whether shifting from a traditional 401(k) or IRA to a Roth option makes sense given your tax outlook. Remember, withdrawals in retirement from Roth accounts are tax-free, creating flexibility later on (e.g., reducing taxable income in years when you draw more from other sources).
  • Health Savings Account (HSA): If you’re eligible, consider maxing out your contributions. HSAs offer a triple tax advantage; specifically, contributions are tax-deductible, grow tax-deferred and can be withdrawn tax-free for qualified medical expenses. For example, a family contributing the 2025 maximum of $8,550 could reduce taxable income by that same amount, and individuals age 55 and older can add an extra $1,000 catch-up contribution. To qualify for an HSA, you must be enrolled in a High Deductible Health Plan (HDHP).
  • Tax-Loss Harvesting: Even with markets trending higher, we continue to look for tax-loss harvesting opportunities where appropriate to help offset gains and improve your after-tax returns. Keep in mind, if you have other accounts that we don’t manage, be sure to coordinate with us so you achieve maximum impact.

Quick Reminder

Many of the federal energy home improvement credits expire on Dec. 31, 2025. If you’re planning to replace your front door, add better attic insulation or similar, consider doing it now to take advantage of the credits.

Please reach out with any questions.

–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.

Sources:

1: IRS.gov, One, Big, Beautiful Bill Act: Tax deductions for working Americans and seniors, https://www.irs.gov/newsroom/one-big-beautiful-bill-act-tax-deductions-for-working-americans-and-seniors

2: Fidelity, What is a donor-advised fund (DAF)?, https://www.fidelitycharitable.org/guidance/philanthropy/what-is-a-donor-advised-fund.html

Bay Colony Advisors, DBA Windsor Wealth Management, is not a Certified Public Accountant and does not provide tax, legal, or accounting advice. Any tax-related information provided is for general informational purposes only and should not be construed as legal or tax advice. Each individual’s tax situation is unique, and you should consult with your own tax, financial, or legal advisors before making any decisions. We strongly recommend seeking the advice of a qualified CPA or other professional for personalized tax advice.

Clear Thinking: Are You Defining the Right Problem?

by

Ever made a decision you later second-guessed?

Shane Parrish’s book, Clear Thinking: Turning Ordinary Moments into Extraordinary Results, tackles this head-on.1

Clear thinking and decision-making are incredibly relevant for successful retirement planning.

While Clear Thinking had many great ideas, one in particular really stuck out.

Parrish suggests a two-session approach to decision-making, whether it’s for business or personal matters:

First, define the problem, and then, solve it.

Why?

In general, we’re taught how to solve problems, but rarely how to define them well. And a poorly defined problem often leads to poor decisions, no matter how clever the solution, according to Parrish.

Let’s apply this concept to retirement planning…

3 Retirement Planning Examples: Identifying the “Real” Problem

Here’s how separating the problem from solving it may look like:

Example #1

Let’s say you’re deciding whether to downsize your home or keep it as a base for the grandkids.

Instead of jumping to “What should I do?”—start by asking: What problem am I really trying to solve?

Is it cash flow? Simplicity? Travel flexibility? Family legacy?

Once the problem is clearly defined, you’re better equipped to make a thoughtful, regret-free decision.

Example #2

Let’s say you’re considering whether to buy a second home in another state.

Instead of jumping straight to “Can I afford this?” or “Is now the right time?”—start by asking: What problem am I really trying to solve?

Is it about escaping winter weather? Being closer to family? Creating new memories? Diversifying lifestyle assets?

By defining the why, you might uncover simpler alternatives or confirm it’s truly worth the tradeoffs. Clarity on your real goal helps you evaluate options more effectively.

Example #3

Let’s say you’re debating whether to help an adult child with a major expense, like a home down payment or launching a business.

Instead of going straight to “Should I give them the money or not?”—pause and ask: What problem am I really trying to solve?

Is it about providing opportunity? Keeping family close? Reducing future estate taxes? Easing your own guilt or anxiety?

Once you clarify your core motivation, it’s easier to assess if financial support is the right tool or if there’s a better way to support your goals and theirs. Separating emotional pressure from the actual problem leads to clarity.

Mental Time Travel

Another powerful insight from the book encourages us to slow down and consider the perspective of our future selves, a form of ‘mental time travel’ that can lead to better decisions.

To travel forward in time ask yourself:

“What would future me wish I had done?”

“How will this decision feel in 10 days, 10 months or 10 years?”

These questions help you avoid impulsive or rushed choices, a real risk when retirement brings a flood of new freedoms and decisions.

High Stakes vs Low Stakes

Parrish recommends spending more time on decision-making when the stakes are high, and less time where they’re low.

Said differently, when the cost of a mistake is high and irreversible, move slow. When the cost of a mistake is low and easily reversible, move fast.

Examples:

High Stakes “Irreversible” Decisions (e.g., when to take Social Security or whether to sell a business) deserve careful thought and deliberate planning.

Low Stakes “Reversible” Decisions (e.g., which airline credit card to use or whether to try a new budgeting app) are best handled quickly, saving time and mental energy.

[Related Resource]: Download our handy budgeting worksheet.

Retirement Decision-Making Checklist

Before making final retirement planning decisions, ask yourself these questions:

  • What problem am I really trying to solve?
  • What does success look like and what would I regret?
  • What assumptions am I making?
  • What could go wrong? Have I planned for it?
  • Is there a way to split this decision into smaller, more manageable parts?
  • Am I being reactive, or thinking clearly and long term?
  • What would future me wish I had done?
  • What are the hidden opportunity costs?
  • If you say yes, what are you saying no to (and vice-versa)?
  • And then what?

Diving Deeper: What Could Go Wrong?

If markets experience a prolonged downturn, a job loss occurs or family needs change, how is your financial plan impacted?

Parrish urges us to prepare for setbacks before they happen.

We couldn’t agree more!

In our world, that might mean:

  • Estimating a spouse’s death impact on Social Security benefits.
  • Keeping income sources diversified.
  • Preparing for income disruption (e.g., disability).
  • Running “what-if” simulations to stress test your plan.
  • Setting aside a buffer for unexpected expenses.
  • Updating insurance coverage regularly for adequate protection.

These kinds of safeguards allow you to spend confidently, knowing your retirement can weather a few storms.

Retirement planning and financial well-being thrive on clear thinking.

We recently wrote more about this mindset in our articles:

> How to Spend Confidently Without Regret in Retirement

> 3 Steps To Help Your Money Outlive—You (Describes the financial guardrails we use to stress test your retirement portfolio.)

As an aside, we spend a tremendous amount of time asking: What could go wrong, and have I planned for that?

This approach is key to managing uncertainty within your portfolio.

–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: Amazon: Clear Thinking: Turning Ordinary Moments into Extraordinary Results, https://www.amazon.com/Clear-Thinking-Turning-Ordinary-Extraordinary/dp/0593086112