• Skip to main content
  • Skip to footer

Windsor Wealth Management LLC

Investment service in Topsfield, Massachusetts

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

Market Highs & Mid-Year Review (5 key items)

June 23, 2026 by David Bunker

It’s hard to believe we’re almost halfway through the year, making it a good time to review your financial situation.

Before we look at what’s changed in your life, let’s talk about what’s happening on Wall Street.

Image source: ChatGPT

The S&P 500 posted gains for the last nine straight weeks.

To put this in perspective, a nine-week winning streak has only happened 10 other times since 1945.

Overall, the index is up roughly 11% year-to-date (27% over the last 12 months).

For context, this follows three consecutive years of growth: 26.3% in 2023, 25.0% in 2024 and 17.9% in 2025.


There are several key reasons for this positive momentum, including:

AI Infrastructure: Companies providing the hardware for AI are delivering strong financial results. For example, Dell Technologies saw its share value increase by about 74% in recent weeks following a surge in demand for AI-optimized servers.

Strong Corporate Earnings: First-quarter earnings exceeded expectations, with 84% of large U.S. companies reporting stronger-than-expected profits. Overall earnings are growing at 13–14%—well above the historical average of 6–8%.

[Related Reading]: 3 Key Portfolio Maneuvers & New Market Highs

Geopolitical Resilience and Lower Oil Prices: While ongoing conflicts in the Middle East have caused volatility, recent optimism surrounding ceasefire discussions has kept oil prices relatively stable (about $91 a barrel). This is a significant drop from the $112 a barrel earlier this spring.

Ironically, this positive data can make some feel uneasy.

After all, when stocks continue climbing, it’s easy to start wondering when the next correction will arrive.

In fact, you may find yourself questioning whether it’s time to take some money off the table.

It’s a natural reaction.

But, this famous quote offers an important reminder:


Now, unless your name is Peter Lynch (even he admitted he couldn’t predict the future) market timing is a losing game.

That’s why we focus on what we can control: monitoring your portfolio, managing risk and executing your long-term plan.

[Related Deep Dive]: For an in-depth look at the economy and markets, checkout Capital Group’s 2026 Outlook. It covers the challenge of high valuations and the debate over whether we’re experiencing an AI bubble.


MID-YEAR REVIEW

Life doesn’t stand still (e.g., jobs change, families grow and retirement gets closer).

Even positive changes can create financial implications that are easier to address when we plan ahead.

Therefore, if any of the following applies to you, reach out as soon as possible:

Employment

Have you or your spouse changed jobs, accepted an early retirement package, started consulting work, or added a new income source?

These changes can affect taxes, benefits, Medicare premiums and retirement planning opportunities.

Family

Has your family dynamic changed due to marriage, divorce, a birth, a death, aging parents or a child who needs additional support?

These events often warrant a review of your estate plan, beneficiaries and insurance coverage.

Health

Has anyone in your family experienced a serious illness? Or are you approaching age 65 and preparing for Medicare?

These are important planning milestones that can impact both your finances and healthcare decisions.

Large Purchases, Sales or Inheritance

Are you buying or selling a home? Paying for college? Planning a major renovation or vacation? Selling a business? Receiving an inheritance?

Planning ahead can help reduce tax surprises and help ensure these decisions fit within your overall financial strategy.

Retirement

If you’re considering retirement within the next few years, don’t wait until your last day of work to start planning. Decisions involving Social Security, healthcare coverage, retirement account withdrawals and tax planning are often easier to optimize before you leave your employer.

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


Overall, ask yourself two simple questions:

#1—Has anything changed in my life?

#2—Am I planning a major event or expense in the next few years?

Remember, small changes today can have a meaningful long-term impact.

If something has changed, or you’re simply wondering whether it matters, 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.


Filed Under: Economy, Financial Planning, Investments, Retirement Planning, Windsor Insights

Footer

Amplify Your Retirement Income

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

Windsor Insights

Tax Planning During Your 50s & 60s

There are certain moments in life when tax planning becomes especially important. If you're in your 50s or 60s, this is one of them. Retirement … [Read More...] about Tax Planning During Your 50s & 60s

More Posts from this Category

  • Home
  • About
  • Testimonials
  • Contact

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

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

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

Copyright © 2026 · Website Design · Admin

Copy written by financial services writer Sharron Senter