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Education

Kimsey Hollifield | Nov 5, 2026

Tax Season Has Two Dates. Many People Only Show Up for One.

Tax Planning
Retirement
Finance
Savings

Ask people when “tax season” is, and many will say spring.

That’s when the documents get gathered, the appointment gets booked, and the return gets filed. It’s

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Kimsey Hollifield | Nov 3, 2026

Are You Giving on Purpose — or Just in December?

Finance
Tax Planning
Estate Planning
Investments
Family

You know the season. Envelopes in the mailbox, messages in your inbox, and a cashier asking if you'd like to round up for a good cause.

And somewhere between

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Kimsey Hollifield | Oct 26, 2026

Financial Impersonation Scams: What to Watch For

Privacy
Risk Management
Finance
Savings
Family

Many people picture a scam as something obviously off: a strange email, a robotic voice, a too-good-to-be-true offer.

The more dangerous version sounds like

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Kimsey Hollifield | Oct 19, 2026

Trump Accounts: Giving the Next Generation a Head Start

blog

Trump Accounts: Giving the Next Generation a Head Start

 
Kimsey Hollifield
Sep 28, 2026
 
A few weeks ago, I was thinking about something I wish I had understood
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Kimsey Hollifield | Oct 7, 2026

Six Estate Planning Assumptions Worth a Second Look

Estate Planning
Family
Insurance
Retirement
Tax Planning

It's easy to set estate planning aside once you've done a version of it. You sign the paperwork. You name a beneficiary. You mentally close the file.

The only

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Kimsey Hollifield | Sep 11, 2026

More Than a Number: The Four Risks That Shape Your Retirement

Retirement
Risk Management
Health
Investments
Finance

Many people can tell you their portfolio balance. Far fewer can tell you what else determines whether their retirement actually works.

That's understandable. The

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Kimsey Hollifield | Sep 8, 2026

Retirement Isn't Just About How Much You Save. It's About When.

Retirement
Risk Management
Investments
Finance
Savings

You can do everything right on paper — save diligently, spend reasonably, stay invested for the long haul — and still land in a very different retirement than

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Kimsey Hollifield | Aug 27, 2026

Permission to Spend in Retirement: A Skill Rarely Taught

Retirement
Lifestyle
Finance
Savings
Family

For decades, you trained one financial muscle: save, invest, don't touch it. Then retirement arrives and asks you to do the opposite.

Nobody teaches that part

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Kimsey Hollifield | Aug 5, 2026

What to Do With Your Next Dollar: A Financial Order of Operations

Finance
Savings
Investments
Retirement
Risk Management

What do you do when you earn well and have generally dialed in the fundamentals: save, invest, reduce debt, stay protected? The challenge was never knowing what

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Kimsey Hollifield | Jul 17, 2026

Trump Accounts: What Parents and Grandparents Should Know

Education
Savings
Family
Tax Planning
Finance
Investments

Trump Accounts have been in headlines for months. Few of those headlines explain them the same way.

Depending on the article, they sound like a college fund, a

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Kimsey Hollifield | Jul 2, 2026

How Retirement Has Changed Over the Last 75 Years (And What It Means for Your Plan)

Retirement
Lifestyle
Finance

Retirement used to mean a short, quiet final chapter. For many people today, it's something else entirely.

For much of the last century, retirement followed a

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Kimsey Hollifield | Jun 17, 2026

Long-Term Care: Considering the Benefits of Insurance for Your Future

Education
Long-Term Care
Retirement Planning
From traditional policies to hybrid options, choosing the right long-term care coverage takes some research. This guide breaks down your options and what to
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