Windsor Wealth Management LLC

Investment service in Topsfield, Massachusetts

Windsor Insights

Mid-Year Review: Small life changes can have big financial impacts

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Welcome to summer!

Longer days, warmer weather and a fresh mid-year perspective.

June is the perfect time to take stock of what’s changed in your life, and what might be just around the corner.

Even small life shifts can carry big financial implications, which is why a mid-year review can be so valuable.

What’s changed in your world?

Today’s discussion includes:

  • Reviewing your life changes that may warrant a financial plan update.
  • A checklist to help stretch your retirement income.
  • Tips for backing up and protecting essential documents.

Mid-Year Review: What’s changed?

Life can throw us curveballs and priorities can shift, so let’s make sure your financial plan is still aligned with what you want to achieve.

Give us a call if any of the following applies to you:

Job or Income Changes: A new role, early-retirement offer, added income stream, selling a business? These changes typically affect taxes, benefits (e.g., Medicare IRMAA penalty) and investing strategies. There are, however, financial moves we can often make to offset downside ramifications.

[Related Resource]: Planning Your Final Days of Work Before Retiring

Family Milestones: Marriage, divorce, birth, death, aging parents or adult children with new special needs may require estate or insurance updates.

Health: A recent diagnosis or nearing age 65? Let’s make sure your healthcare plans are in place. Also, if you want to learn more about long-term care insurance, contact us. We’re happy to discuss the pros, cons and costs. Keep in mind, we don’t sell insurance. However, we have long-standing relationships with insurance specialists.

Large Purchases, Sales or Windfalls: Selling a home, funding college or receiving an inheritance? Planning ahead can help reduce financial surprises.

Retirement Approaching: If retirement is just a few years away, it’s time to solidify your plans. A smart Social Security strategy and a well-timed savings withdrawal plan can often extend the life of your retirement funds. We’ll also help you establish a two-to-four-year financial safety net and structure your withdrawals to minimize taxes. For a closer look at our approach, check out: How To Spend Confidently & Without Regret in Retirement.

Prolonging Retirement Income (Checklist)

Whether you’re already retired or planning to be soon, this checklist can help you identify steps that may extend your savings. It’s a great resource to review annually.

[Download the checklist]

Are Your Essential Documents Backed Up and Safe?

If there were a house fire tomorrow, would you have what you need? A simple fire-safe box can help you protect the basics, including:

  • Birth Certificates
  • Digital Account Logins
  • Emergency Contact List
  • Estate Documents
  • Home Inventory Photos/Video (for insurance claims)
  • IDs & Passports
  • Insurance Policies
  • Key Warranties (e.g., new roof, solar panels, windows, etc.)
  • Loan Documents
  • Social Security Cards
  • Spare Emergency Cash
  • Vehicle Titles

Digital Vault

Our clients have access to a secure digital vault.

It’s a private, encrypted space where you can store digital copies of key documents, including those listed above but also scans of: credit cards, divorce decrees, marriage certificates, property records and more. The vault is accessible anytime, from anywhere, securely.

Fire-Safe Boxes for Important Items

To help protect your important documents, look for a fire-safe box with a UL 72 or ETL certification, a 120-minute fire rating and water resistance.

Underwriters Laboratories (UL) and Electrical Testing Laboratories (ETL) are Nationally Recognized Testing Laboratories. They independently test products to stringent safety and performance standards.1

Important: Your protection-rating needs may vary. For example, if you’re looking for a safe that protects digital media or is burglary resistant, these require different UL classes.

American Security has some helpful articles regarding safes, including Why Safe Ratings Matter.2

–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: Osha.gov, Current List of NRTLs: https://www.osha.gov/nationally-recognized-testing-laboratory-program/current-list-of-nrtls

2: American Security, Why Safe Ratings Matter: https://americansecuritysafes.com/why-safe-ratings-matter

Top 2025 Summer Travel Spots & Average Costs

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Summer is officially here—and for many of us, that means travel plans are heating up.

More than 2 in 5 Americans (44%) plan to take a vacation this summer that involves a flight or hotel stay, with an average trip cost of $3,861, according to NerdWallet’s annual summer travel survey.

That’s about 117 million Americans, spending roughly $452 billion on flights and hotels this summer.1

Where’s everyone going?

Seattle is the top domestic destination for Americans, and Cancun leads internationally, according to travel insurance provider Allianz Partners. Most are staying closer to home, with 71% of itineraries booked for U.S. travel and 29% for international trips.2

Overall, Americans are headed to both big cities and relaxed beach towns.

Source: Allianz Partners

Top 10 Domestic Locations

Ranked by popularity, the top domestic destinations for summer 2025 are: Seattle; Orlando; New York; Honolulu; Kahului, Hawaii; Boston; Portland, Oregon; Las Vegas; Los Angeles; and Anchorage, Alaska.

Internationally, the top destinations include:

Cancun; San Jose del Cabo, Mexico; London; Punta Cana, Dominican Republic; Montego Bay, Jamaica; Calgary, Canada; Oranjestad, Aruba; Paris; Puerto Vallarta, Mexico; and Dublin, according to Allianz Partners.

It’s always interesting to see the trends.

Remember, before booking, check travel advisories on the CDC Travelers’ Health3, TSA.gov4 and U.S. Department of State5 websites.

–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: Nerd Wallet: 2025 Summer Travel Report, https://www.nerdwallet.com/article/travel/2025-summer-travel-report

2: Allianz Partners: Beaches and Big Cities Remain the Top Travel Destination for American Summer Travelers, https://www.allianzworldwidepartners.com/usa/media-center/press-releases/Beaches-and-big-cities-remain-the-top-travel-destination-for-American-summer-vacations.html

3: CDC Travelers’ Health: https://wwwnc.cdc.gov/travel

4: Transportation Security Administration: https://www.tsa.gov

5: U.S. Department of State: https://travel.state.gov/content/travel/en/traveladvisories/traveladvisories.html/

Planning Your Final Days of Work Before Retiring

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The Calm After the Work Is Do

Today, we:

  • Discuss eight actions to take before you give retirement notice to your employer.
  • Provide a detailed checklist of essential pre-retirement tasks.

As you start thinking seriously about your final days of work before retirement—whether that’s at age 62, 67 or another time—there are a few key actions that help things go more smoothly.

Now, let’s look at eight actions to take before your last day of work:

#1—Retire to Something, Not Just from Work

Retirement isn’t just about leaving your job.

It’s about building a life you want to live. Whether that means a part-time job, volunteering, spending time with the grandkids or finally joining “that” gym—it’s important to have a purpose.

Beyond what you’ll be “doing” in retirement, it’s equally important to understand how you might feel and how your health could be impacted by this major transition.

Quick Tip by Dave Bunker, Watch the Video Now >

#2—Understand the Emotional Shift and Health Impact

The first year of retirement can bring a surprising health risk: stress-related heart issues spike.

The transition from earning and saving to drawing down what you’ve built is a big emotional adjustment.

Background:

Harvard School of Public Health researchers looked at rates of heart attack and stroke among men and women in the U.S. Health and Retirement Study. Among 5,422 participants, those who had retired were 40% more likely to have had a heart attack or stroke than those who were still working.1

The increase was more pronounced during the first year after retirement, before leveling off. Overall, research on retirement’s health effects is mixed.2

Our Recommendation…

Retirement isn’t a one-time event; rather, it’s a transition.

Many retirees experience changes in identity, routine and social connection. That’s why it’s important to prepare not just financially, but emotionally as well.

To better understand the emotional journey, check out this helpful TED Talk: 4 Phases of Retirement…and the Psychological Challenges.3 The four phases include: Vacation, Feeling Lost, Trial and Error, and Reinvent and Rewire.

#3—Clean Up and Consolidate Your Financial Life

Now is the time to tidy up your financial accounts, including:

  • Review and possibly consolidate old 401(k)s or other workplace plans into an IRA. While some 401(k)s are worth keeping, IRAs usually offer more flexible withdrawal options and simplify things for your heirs.
  • Open any needed accounts before your final day to avoid delays. For instance, give us a call about a month before you retire so we can help you set up the IRA account you’ll use to roll over your 401(k), 403(b) or similar.
  • If you’re receiving a pension, let’s analyze your options (lump sum vs. monthly annuity, single life vs. joint life, etc.) using our Income Lab modeling tool. Keep in mind, most pension decisions need to be made at least 60 days before retirement. Also, if you’re taking a lump sum, put it into an IRA. If you leave it in your brokerage, you’ll pay taxes on ordinary income. 

TIP: If you’re receiving a bonus or cashing out unused vacation time, it may impact your taxes or final 401(k) contributions. Therefore, timing your retirement date matters. Also, hold off rolling over your 401(k) into your IRA until your final contribution, unused vacation time, bonus, etc. hit.

#4—Secure Healthcare Coverage

Are you eligible for Medicare (typically at age 65)? Or will you need COBRA or private insurance? Will you want Medicare Advantage?

While pondering the latter, you’ll also want to revisit your healthcare proxy, powers of attorney and estate documents.

Important: If you’re 63 or older, let’s analyze your income to avoid triggering IRMAA surcharges (Income Related Monthly Adjustment Amount) on Medicare premiums. Being just one dollar over can cost you thousands.

We’ve written more about how this can happen here: Medicare: The $1 Mistake That Costs $3,500.

Free Medicare Counseling Resources:

#5—Plan Your Retirement Paycheck

We’ll help you set up a retirement income stream that feels like a paycheck.

Resource: Read our detailed blog post about how we help you create your monthly retirement paycheck.8

#6—Watch for Tax Triggers & Withholdings

Be sure to double-check your tax withholding rates for Social Security and pension income. Common options include 7%, 10%, 12%, 22% and higher.

Many retirees forget to set withholdings on these payments, which can lead to surprises at tax time. Alternatively, you can opt to pay quarterly estimated taxes.

As a general rule, use a 20% withholding rate as a starting point. It may need adjusting, but it offers a solid baseline.

Remember, while you’ll no longer pay into Social Security or Medicare, you’ll still owe taxes on retirement income.

Finally, if you’ve had a one-time income event, it’s important we run a tax analysis together.

For Example:

If your total income was $200,000, but $80,000 came from a one-time bonus, we’ll want to explore whether that bonus can be excluded when calculating your Medicare IRMAA.

Lastly, consider if there is anything else you should be doing right now, e.g., taking capital gains.

#7—Decide What Insurance to Keep (and What to Let Go)

As your needs change, it’s smart to review any life or long-term care insurance policies.

Key questions to ask yourself include:

  • Is your life insurance portable?
  • Do you still need it?
  • Should we evaluate or add long-term care coverage?

#8—Finalize Your Budget

A budget is a living, breathing document; it’s never truly final. Still, it’s important to think about how your spending patterns will shift in retirement.

For example, retirement may mean:

  • Less spending on commuting, work clothes or lunches out, but more on travel, healthcare, hobbies or RV maintenance.
  • Mortgage payments disappearing, but insurance or family support costs rising.
  • Savings on payroll taxes, but higher utility bills from being home more.
  • Dropping life insurance premiums, but adding Medicare costs, prescriptions or home repairs.

Resource: Download our handy budgeting worksheet.9

Understanding these trade-offs now helps set realistic expectations and keeps your retirement income plan on track.10

RESOURCE: Retiring Checklist

To help you think through additional retirement considerations, here’s a detailed checklist: What issues should I consider before I retire?11

Within the above checklist are links to other checklists and flowcharts that help answer the following questions:

  • Will I Avoid IRMAA Surcharges on Medicare Part B & Part D?
  • What Issues Should I Consider When Purchasing Long-Term Care Insurance?
  • Should I Consider Doing A Roth Conversion?
  • What Issues Should I Consider When Establishing My Charitable Giving Strategy?
  • What Issues Should I Consider Before I Update My Estate Plan?
  • Am I Eligible for Social Security Benefits If I Have Been Divorced?
  • Am I Eligible For Social Security Benefits As A Surviving Spouse?
  • Can I Make A Deductible Contribution To My HSA?

Next Steps

If you’d like an updated look at your retirement income and tax projections, give us a call. We’re happy to revisit the numbers as often as you need, regardless of how close or far off your retirement may be.

–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: Harvard Health Blog, Is retirement good for health or bad for it? https://www.health.harvard.edu/blog/is-retirement-good-for-health-or-bad-for-it-201212105625

2: National Library of Medicine, Transition to retirement and risk of cardiovascular disease: Prospective analysis of the US Health and Retirement Study https://pmc.ncbi.nlm.nih.gov/articles/PMC3367095/

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

4: Mass.gov, Serving the Health Insurance Needs of Everyone (SHINE) Program, https://www.mass.gov/info-details/serving-the-health-insurance-needs-of-everyone-shine-program

5: New Hampshire DHHS, Aging and Disability Resource Centers, https://www.dhhs.nh.gov/programs-services/adult-aging-care/aging-and-disability-resource-centers

6: Fidelity, We are Fidelity Medicare Services, https://medicare.fidelity.com/about-us/

7: Fidelity, Learn about Medicare, https://medicare.fidelity.com/learning-center/

8: Windsor Wealth Management, How To Spend Confidently & Without Regret in Retirement, https://windsorwm.com/how-to-spend-confidently-without-regret-in-retirement/

9: Windsor Wealth Management, Budgeting Worksheet, https://windsorwm.com/wp-content/uploads/2023/10/Budget-Worksheet.xlsx

10: Windsor Wealth Management, 3 Steps to Help Your Money Outlive–You, https://windsorwm.com/3-steps-to-help-your-money-outlive-you/

11: Windsor Wealth Management, What Issues Should I Consider Before I Retire, https://windsorwm.com/wp-content/uploads/2025/05/What-Issues-Should-I-Consider-Before-I-Retire-2025.pdf

Is market news scaring you? Here’s the bigger picture.

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Could the financial news headlines be more daunting?

Trade uncertainty and its economic ripple effects are behind most of these headlines. (Read our post for the “real” impact of tariffs.)

However, a crucial point often absent in media coverage is the historical link between market volatility and long-term portfolio growth.

For Example:

The below chart depicts the growth of one dollar from 1926 till 2024. The red lines highlight 20%+ market drops.

As you’ll see, time after time the market bounces back—even higher.

Your Financial Plan

We’ve built your financial plan to navigate market volatility.

Candidly, if you want long-term portfolio growth, then the price you pay is short-term volatility.

Unsurprisingly, we’ve seen this recent volatility before, i.e., during Covid. And, we bounced back from that—even higher!

Uncertainty drives volatility.

No one knows when the volatility will end. Nevertheless, we’re confidently buying valuable companies on sale.

I encourage you to stay the course and maintain your financial plan.

Reach out with any concerns or questions.

–David Bunker, Financial Advisor & Licensed Fiduciary

P.S. Thank you to everyone who requested a copy of Bill Perkins’ “Die With Zero.” I was thrilled by the response following last month’s email, How To Spend Confidently & Without Regret in Retirement, where we discussed the book. I still have a few copies available, so please let me know if you’d like one.

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.

Home Energy Audits and Energy Tax Credits

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Is your home leaking money?

Wealth isn’t just about accumulation; it’s about being intentional with your resources.

Optimizing your home’s energy efficiency is a prime example.

Just as we seek to help maximize your financial returns, you can maximize your home’s comfort and value, while also leveraging energy credits to lower your taxes.

Are your cooling and heating systems energy efficient?

Our goal today, is to help you:

– Discover hidden savings via a professional home energy audit.

– Reduce taxes by leveraging energy credits.

– Understand two key 2025 energy tax credit changes.

– Increase awareness of energy-efficiency scams.

Useful Home Energy Audits

A good energy audit includes a detailed report of where your home is losing energy, and what you can do to fix it.  

The first step, is finding a certified energy auditor. Specifically, a professional who’ll provide you unbiased information and isn’t selling products.

Finding a Reputable Auditor

The U.S. Department of Energy recognizes about 10 home energy auditor qualified certification programs for the Energy Efficient Home Improvement Credit.

To find certified professionals near you, try the Building Performance Institute (BPI) locator. Keep in mind, BPI is just one locator option.

Ideally, select an auditor that doesn’t perform repairs. This helps ensure less bias results.

Related…

Mass Save® is a collaboration of Massachusetts utilities that offer home energy assessments (at no cost), rebates and incentives to help you reduce your energy costs.

Incentive Example:

The Mass Save HEAT Loan offers 0% financing for eligible energy-efficient upgrades. Starting January 1, 2025, you can finance up to $25,000. The financing covers a range of improvements, including insulation, heat pumps, batteries and more.

Most states offer energy-efficiency programs, supported by state, utility and federal incentives, including New Hampshire.

Therefore, before upgrading any cooling or heating system, or replacing any appliance, be sure to check for available rebates and incentives.

Pinpointing where your home loses the most energy will help you prioritize repairs and maximize IRS home energy credits.

Resource: Here’s a helpful chart listing what to expect an auditor to have for tools, (e.g., combustion analyzer, infrared camera, digital probe thermometer, etc.) and what the audit entails.

Finally, watch out for unsolicited “free” energy audit offers. Some companies use these to push you into buying things you don’t need. Always double check who the auditor works for and get a few different opinions before agreeing to any work or signing on the dotted line.

Home Energy Tax Credits & Key 2025 Changes

The Energy Efficient Home Improvement Credit is available for qualifying home improvements made from January 1, 2023 through 2032. To qualify for these credits, generally the improvements must be for your primary residence and use only new materials and systems.

2 Key Changes:

There have been two key changes to the program starting in 2025, including:

#1—Energy-efficient products eligible for the credit need to be manufactured by “qualified” manufacturers.

The IRS is establishing a program to certify manufacturers whose products meet specific energy efficiency standards. This requirement helps ensure the products receiving tax credits are genuinely contributing to energy savings.

#2—When claiming the credit, you must provide the Product Identification Number (PIN) for the qualifying items on your tax return.

Basically, the PIN is a unique ID the IRS uses to ensure the product meets standards, comes from a legit company and matches your credit claim.

Watch Out for Energy-Efficiency Scams

The number of U.S. solar installations is expected to double by 2030, according to the Solar Energy Industries Association®.

Therefore, it’s not surprising we’re seeing increases in solar scams.

The U.S. Treasury describes popular solar scams in their article, Consumer Solar Awareness. (It also talks about buying vs. leasing solar power systems.)

The article highlights several scam tactics, including:

– Sales pitches saying, “This is a government program” to make you think a solar installation is free or government-endorsed.

– Promises of free solar panels and limited-time offers and other pressure tactics urging you to sign up without examining the details.

– Promises of tax credits even though you owe no taxes or promises that the government will send you a tax rebate check in the mail.

Overall, solar panels may be a good option to lower your energy costs, but take your time when evaluating your options.

Buyer Beware: In general, if something is unsolicited, creates a sense of urgency, demands immediate or unusual payment, or sounds too good to be true—assume it’s a scam.

[Related]: Since the weather is getting warmer, watch out for paving scams.

Helpful Tips: No matter if you’re buying a new home or an appliance, be sure to look for the Energy Star mark. Keep in mind, the Energy Star isn’t always the only requirement for tax credits. But, it’s a good indicator of energy efficiency and, therefore, a good place to start.

Finally, don’t forget about Consumer Reports, a nonprofit organization that provides unbiased testing and ratings of products and services, (e.g., new A/C, refrigerator, smart thermostat, etc.). You can often access their reports online for free with most library memberships.

–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.

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.

How To Spend Confidently & Without Regret in Retirement

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Let’s challenge conventional wealth accumulation wisdom…

Our team recently read the book, Die With Zero: Getting All You Can From Your Money by Bill Perkins. It’s an easy-to-read personal finance book that challenges current retirement norms.

(We have extra copies—feel free to stop by and pick one up. We’d love to meet you!)

Creating memories or leaving an inheritance: when is the right time to give?

Today, we discuss how to:

  • Get all you can from your money, (i.e., highlight ideas from the book Die With Zero).
  • Spend confidently and without regret in retirement.
  • Decide the right time to give—now or later—using sophisticated money modeling.

Get All You Can From Your Money

Bill Perkins’ “Die With Zero” overall argument is:

When preparing for retirement, people often save too much and spend too little, ultimately missing out on meaningful life experiences.

Perkins argues money should be spent strategically for fulfillment, not just left behind.

Before going any further, let’s be clear…

We’re not encouraging you to be financially irresponsible. Absolutely not!

But, Perkins is definitely onto something—especially when you combine his ideas with strategic financial planning.

Here are some of his key points:

Maximize Life Experiences: Instead of focusing solely on accumulating wealth for retirement or your heirs, think about how you can use your money to create meaningful experiences while you’re able to enjoy them.

Time-Bucket Your Life: Your life has different stages, and each one comes with unique opportunities. Be intentional about how you allocate your money so you can make the most of every phase—especially while you’re healthy.

Invest in Experiences Early: The best time to create lasting memories isn’t “someday”—it’s now. Enjoying experiences earlier in life helps you feel more fulfilled.

Avoid Over Saving: Too many people work longer than they need to and save more than they’ll ever spend. The result? They leave behind wealth they never got to enjoy themselves.

Optimize Giving: If you plan to leave money to loved ones or charities, consider giving earlier rather than waiting until after you’re gone. Your generosity could have a much bigger impact now.

[Related Blog Post]: One of the best times to use Qualified Charitable Distributions (QCDs) is early in the year. Learn why in our post, 2025 Tax Planning Resources & Key Financial Data Spreadsheet.

Plan for a Declining Health Curve: Your ability to travel, explore and be active won’t last forever. That’s why it’s important to strike a balance between financial security and truly living while you can.

Perkins’ ideas sound reasonable. In reality, though, most require detailed financial planning.

This is where we come in…

Spend Confidently and Without Regret in Retirement

Many retirees worry about spending their money, i.e., What if the market takes a downturn? What if I outlive my savings?

While these concerns are natural, a well-structured financial plan helps you be intentional with your spending and feel secure knowing your money will outlive you.

Our role is to guide you through this process with a clear four-step approach:

Step #1—Determine Your Retirement Spending Capacity & Create a Tax-Efficient Withdrawal Plan

Everyone’s financial situation is unique, with different levels of savings, income sources and comfort with risk. We take a personalized approach to managing your investments—balancing growth with stability while ensuring you can spend confidently in retirement.

A key part of this strategy is minimizing taxes on your withdrawals so you keep more of what you’ve saved. We do this by carefully selecting which accounts to withdraw from first—whether taxable, tax-deferred or tax-free—based on your income needs and current tax rates.

This approach helps extend the life of your portfolio, allowing your investments to continue growing even as you draw from them.

Overall, it’s our job to tell you how much you can afford to spend in retirement. A primary tool we use to help you is advanced software (aka Income Lab) that includes sophisticated money modeling guardrails.

Resource: We discussed money modeling guardrails in a recent post: 3 Steps To Help Your Money Outlive—You.

Step #2—Create a Monthly Paycheck for You

One of the biggest adjustments in retirement is transitioning from a regular paycheck to drawing from multiple income sources.

Most of our clients rely on a mix of Social Security, pensions, part-time work and investment withdrawals for their retirement income.

Some also have additional income streams, e.g., rental properties, royalties, payments from seller financing, etc.

Understanding how these income sources interact is essential for confident retirement spending.

That’s why we focus on transforming your various income streams into a tax-efficient monthly paycheck.

Simple Example:

Imagine your annual withdrawal plan from investments is $84,000 (excluding Social Security, pensions and other income sources). Each month on the 15th, we’ll deposit $7,000 from your investment portfolio into your checking account, ensuring you receive a steady stream of income.

This way, you can enjoy a sense of stability, knowing a $7,000 “paycheck” will arrive in your account every month.

Step #3—Put Aside Two-to-Four Years of Safety Net

To help ensure you can weather market fluctuations without disrupting your lifestyle, we set aside two-to-four years’ worth of income needs in a conservative investment account (that still grows).

For example, if you plan to spend $84,000 per year, we earmark $252,000 to cover the first three years of retirement.

This portion of your portfolio is stable, meaning that even if the market declines, your ability to meet your spending needs remain intact. Meanwhile, the rest of your investments continue growing for the future.

Step #4—Perform Annual Audits & Make Smart Adjustments

Each year, we reassess your portfolio balance versus your spending and market conditions.

If the market performed well, we “refill” the amount spent from the safety net.

However, if the market had a down year, we hold off on refilling and use the second year’s reserve instead.

Since market recoveries typically take six to 18 months, this approach helps protect your long-term investments.

Audit: Keeping Spending on Track

As part of the audit, we discuss your spending target. Again, let’s say it’s $84,000. If you end up spending more, perhaps $98,000, it may not be an issue if the market was strong. However, if higher spending becomes a pattern, we’ll flag it and have a conversation about sustainability.

Retirement should be about enjoying life, not worrying about money.

By following a plan that balances stability with flexibility, you can confidently spend with the knowledge that your financial future is secure.

Decide the Right Time to Give—Now or Later

Imagine sharing your wealth with loved ones now—without stressing about your future finances.

How does Windsor Wealth Management help you decide whether to give money now (especially if your loved ones could really use it), or wait?

We typically present two scenarios:

Scenario One: You hold onto your money and pass it on after you’re gone.

Scenario Two: You gift, say, $5,000 to each grandchild now and see the impact on your financial plan.

Most of the time, the effect from early giving is minimal.

Using our real-time software modeling, we run the numbers so you can see the difference.

For example, perhaps instead of spending $12,000 per month, you adjust to $11,500.

This way, you can give—now—with confidence.

Final Thoughts

Bill Perkins offers some good insights, encouraging people to make the most of their wealth during their lifetime.

Keep in mind, his perspective comes from the lens of a successful (and wealthy) hedge fund manager and entrepreneur.

Ultimately, as with all things in life, balance is key—enjoying your wealth while ensuring financial security for the long run.

–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.

Our Response to Recent Market Volatility

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The stock market’s recent volatility can feel unsettling, but we remain confident in our strategy.

That said, it’s natural to feel rattled—or even tempted to move to cash—when markets drop, especially with the media constantly promoting this approach during market swings.

However, history shows that some of the best market days happen right after the worst ones.

As an example, see the chart below highlighting: Staying invested yields a 10.4% gain, while missing the 60 best days results in a -3.7% loss.

When Visibility Is Low, Strategy Matters More Than Ever

Background

The stock market has been volatile the past few days, down about 8.2% from a recent high in early February.

For perspective, the market dropped 8.5% between July 16 and its low on August 5, 2024, but rebounded by August 30, surpassing its July 16 level.

In general, market recoveries tend to be quick. The average time to recovery is three months from a 5%-10% downturn and eight months from a 10%-20% correction, according to Invesco research.

Let’s take a look at two key factors causing the current fluctuations:

#1—Tariffs

President Trump recently imposed new tariffs on Canada, Mexico and China, escalating trade tensions and contributing to market uncertainty. After a 30-day pause, he implemented 25% duties on Canadian and Mexican imports, along with a second round of 10% duties on Chinese goods, bringing total tariffs on China to 20%. (Then, just two days after, Trump issued some exemptions for Mexico and Canada goods. The situation is highly fluid.)

The media often frames this as a “trade war” or even an “act of war,” but we urge you not to get caught up in the rhetoric.

FACTS: Clarifying Misconceptions & Highlighting Opportunity

Tariffs existed well before income taxes in the U.S.

In fact, they were the primary source of federal revenue for much of U.S. history before the income tax was introduced in 1913.

While tariffs continue to generate revenue today, they’re a very small portion of the federal budget compared to income taxes. (To learn just how small, read our post: The Economy, Tariffs & Consumer Sentiment.)

This historical perspective can help put recent tariff activity in context, i.e., rather than viewing them as unprecedented or catastrophic, it’s helpful to remember that tariffs have long been an economic policy tool.

Tariff activity may cause short-term market fluctuations. However, it’s not inherently a signal of economic collapse—despite media hype.

Finally, past volatility—whatever the cause (e.g., inflation, pandemic, tariffs, war, etc.)—has been an opportunity to buy great companies at a discount.

#2—Broad Economic Uncertainty

There’s a general sense of economic uncertainty driven by multiple factors, including geopolitical tensions, inflation concerns, interest rate policies and the new administration’s actions.

In just the last few weeks, Trump has signed nearly 100 executive orders targeting key areas, e.g., immigration, energy, federal workforce policies, trade, etc.

This activity and uncertainty fuels market fluctuations as investors react to shifting economic conditions. Markets tend to be sensitive to uncertainty, and volatility often follows when investors struggle to predict how these factors will play out.

Our Recommendations

Keeping a long-term perspective can help ease concerns about volatility and uncertainty.

In fact, staying invested through the ups and downs is key to long-term success.

Keep in mind:

-Each day, we rebalance 20 to 30 client portfolios to help maintain diversification and manage volatility. We also ensure your portfolio has the right mix of cash and bonds to navigate market fluctuations. Every decision is tailored to your unique risk tolerance and retirement timeline.

-Market swings often present opportunities, and have historically been an opportunity to buy good companies on sale.

Maintain Your Long-Term Financial Plan (Chart)

As we mentioned earlier, it’s natural to feel the urge to move to cash when markets drop. But doing so could mean missing out on some of the best market rebounds.

Consider these market facts from the below chart covering 1/3/05-12/31/24:

  • Seven of the 10 best days occurred within two weeks of the 10 worst days.
  • Six of the seven best days happened right after the worst days.
  • The second-worst day of 2020 (March 12) was immediately followed by the second-best day of the year.

Market downturns are often followed by strong recoveries. Staying invested helps ensure you don’t miss those critical days.

Of course, no one knows the future—but history offers a clear lesson.

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.

S&P 500 Shifts From Home Runs to Singles and Doubles

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For the past few years, the Magnificent 7 have dominated market earnings growth, at one point soaring nearly 60%. (see chart)

However, this pace is unsustainable.

As expected, the Mag 7’s (Apple, Microsoft, Amazon, Nvidia, Tesla, Alphabet and Meta) earnings growth is slowing. It’s now projected around 20%, still a strong gain.

Meanwhile, the rest of the S&P 500 is growing steadily.

This is a welcome sign, since diversification helps manage risk, (i.e., instead of home runs, the market’s delivering singles and doubles—small, steady gains that add up over time).

Let’s face it, home runs are great.

But, a well-rounded team—built on singles, doubles and solid defense—wins more games.

The same goes for diversification in investing.

What’s causing the shift?

Steady economic growth is helping drive the broader earnings, including a GDP around 2.5-2.7% and low unemployment. AI also remains a key growth driver.

It’s encouraging to see more companies contributing to earnings growth.

Granted, the right side of the chart (gray shaded area) is an estimate, but if these trends hold, we’re likely looking at a more balanced market in the coming months.

PS: If you missed it, we previously shared a detailed update on the economy: The Economy, Tariffs & Consumer Sentiment.

–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.