Real Money Pros
Articles
Dive deeper into retirement planning and other topics.
Tax Strategies Investors Often Miss During Market Downturns
Market downturns usually trigger the same reaction. People look at their accounts, see things down, and immediately shift into defense mode—cut risk, wait it out, or just hope things recover. That instinct makes sense. But for investors with more substantial portfolios, that’s only part of the picture. What often gets missed is that volatility doesn’t…
1099 Reporting Issues That May Cause You to Pay More Tax Than Necessary
With the federal filing deadline for 2025 individual returns set for April 15, 2026, many taxpayers are doing what they do every year: gathering 1099s, uploading PDFs, and assuming the forms tell the whole story. Often, they do. But when retirement-account transactions are involved, that assumption can sometimes lead to confusion about how those transactions…
When Federal Tax Changes Create State-Level Confusion
Every tax season presents its own set of challenges. But occasionally, the difficulty isn’t in the forms themselves — it’s in the uncertainty surrounding the rules. This year, that uncertainty stems from the gap between federal tax changes and how individual states choose to respond to them. Recent federal legislation introduced new deductions and adjustments…
Why a Smart Tax Move Can Increase Your Medicare Bill
We talk about it all the time… Roth conversions are one of the most powerful tax-planning tools available in retirement. They can reduce future Required Minimum Distributions (RMDs), create tax-free income later, and give retirees more control over their long-term tax picture. But there’s a planning detail many people overlook — one that can lead…
Hidden Fees: What Your Advisor Really Costs
If you’ve ever stared at your investment statement and thought, “Okay… so what am I actually paying?” — You’re asking the right kinds of questions. On our most recent Real Money Pros radio show, we got a call from Brian in California that perfectly captures what millions of investors are wondering right now. He said…
Retirement Taxes: Why People Get Hit With “Underpayment Penalties” (and How to Avoid Them)
If you worked a typical W-2 job most of your career, there’s a good chance you never once thought about “estimated taxes.” And honestly, that makes sense. When you’re working, taxes are handled automatically. Every paycheck has federal and state withholding built in, the IRS gets their cut throughout the year, and you’re free to…
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