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Best of Chatham - 2025 Best of Chatham - 2024

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Blog

Michael Whitman | Jun 5, 2026

Business Succession Planning: Built to Last vs. Built to Transfer

Finance
Retirement
Estate Planning
Family
Investments

Many business owners spend decades building something that works. The team. The reputation. The customers who keep coming back.

Then comes a quieter assumption

Read More
Michael Whitman | May 30, 2026

Checking Your Portfolio Isn't the Same as Reviewing It

Investments
Retirement
Tax Planning
Risk Management
Estate Planning

Nearly half of investors check their portfolio at least once a day.1

Many of them aren't reviewing anything.

They're refreshing a number. Watching it move

Read More
Michael Whitman | May 7, 2026

The Estate Plan That Looks Complete on Paper

Estate Planning
Tax Planning
Real Estate
Property
Family
Retirement
Risk Management
Finance
Investments

Many estate planning failures aren't dramatic. There's no missing will, no family feud, no document anyone forgot to sign.

The plan is right there in the drawer

Read More
Michael Whitman | Apr 9, 2026

What $100 Invested in 1928 Would Be Worth Today

Investments
Finance
Savings
Retirement
Risk Management

Many people think the biggest risk with money is losing it. A bad investment. A market crash. A bet that doesn't pay off.

But what if the most expensive

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Toddler standing at the bottom of a stone staircase
Michael Whitman | Apr 2, 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.
Read More
Ten key accounting calculator on a soft yellow desk
Michael Whitman | Mar 31, 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.
Read More
Michael Whitman | Mar 28, 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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Supreme Court of USA Building
Michael Whitman | Mar 10, 2026

Context on the Tariff Ruling

Finance
Market Update
Tariffs were struck down, reinstated under a different authority, then increased again. It felt abrupt. It felt messy.
Read More
Michael Whitman | 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

Read More
Michael Whitman | Feb 11, 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

Read More
Michael Whitman | 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
Michael Whitman | 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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