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Blog

Gary Cowles | Mar 27, 2026

When the Headlines Keep Changing, Your Strategy Shouldn’t

Investments
Finance
Risk Management

It rarely starts calmly.

A headline breaks. Markets react. Another update follows—then another. Before long, the story feels like it’s shifting by the hour.

And

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Gary Cowles | Mar 6, 2026

A More Flexible Way to Think About Retirement

Retirement
Finance
Lifestyle
Risk Management

Many retirement plans are built on a quiet assumption: that spending stays roughly the same from year one to year thirty.

It sounds reasonable. But research

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Toddler standing at the bottom of a stone staircase
Gary Cowles | Feb 27, 2026

Investment Strategy: Where You Are Now vs. Where You're Headed

Investments
A gap analysis can help you see if you’re still on track to pursue your financial goals.
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Ten key accounting calculator on a soft yellow desk
Gary Cowles | Feb 20, 2026

Organization Tips to Help Take Time off Taxes

Tax Planning
Feel overwhelmed by tax documents? Staying organized may help reduce your tax season stress.
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Gary Cowles | Feb 10, 2026

Tax Planning vs. Tax Preparation: They're Not the Same Thing

Tax Planning
Finance
Retirement
Investments

Many people think about taxes once a year — when April rolls around and it's time to file.

By then, the year is already in the rearview mirror. The decisions

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Man sitting on a park bench and working on a laptop
Gary Cowles | Feb 2, 2026

Financial FAQs

Finance
Retirement
From retirement savings to living abroad, here are some of our commonly asked questions.
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Gary Cowles | Jan 30, 2026

Tax Planning vs. Tax Preparation: They're Not the Same Thing

Tax Planning
Retirement
Finance

Many people think about taxes once a year — when April rolls around and it's time to file.

By then, the year is already in the rearview mirror. The decisions

Read More
Parent reading a book to their newborn child
Gary Cowles | Jan 23, 2026

What does "Wealth" Mean to You?

Finance
Lifestyle
A clear understanding of what wealth looks like to you may help you build a financial strategy.
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Woman sitting on a rock looking out at lake. In the distance is a large mountain range
Gary Cowles | Jan 16, 2026

It's Never Too Late to Save for Retirement

Retirement
If you’re in your 50s and haven’t done much to save for retirement, you still have time.
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Gary Cowles | Jan 6, 2026

5 Financial Crossroads That Could Reshape Your Future

Finance
Retirement
Family
Tax Planning
Risk Management

You know how life tends to throw in a few plot twists?

They don't ask if you're ready. They just show up—with potential financial consequences tagging along.

A

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Gary Cowles | Dec 15, 2025

What 2025 Taught Us About Staying the Course

Investments
Finance
Risk Management
Retirement

Some years pass quietly. 2025 wasn't one of them.

Between market swings, geopolitical shocks, and a news cycle that never seemed to pause, this year tested

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Gary Cowles | Dec 8, 2025

Common Retirement Regrets—And Proactive Moves to Consider

Retirement
Finance
Savings
Risk Management
Insurance
Health
Family
Estate Planning

Many people don’t regret being retired. They regret how they got there.1

“I wish I had saved earlier.”

“I didn’t think long-term care would matter.”

“I should’ve

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Contact

gary.cowles@the-cowles-group.com
Phone: 978-999-5461
Fax: 603-965-4539

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124 Main Street, Unit 2
Rockport, MA 01966

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