Real Money Pros
Articles
Dive deeper into retirement planning and other topics.
A Retirement Projection Is Not a Retirement Plan
Retirement calculators have become one of the most common tools investors use to gauge their readiness for retirement. Enter a few assumptions, estimate future spending, click a button, and receive a probability of success. For many people, that number becomes a source of confidence. If the projection says the plan works, retirement feels achievable. If…
Stock Compensation Tax Planning: RSUs, Stock Options & ESPP Mistakes
For many high earners, stock compensation feels like a sign that things are going well. And often, it is. Restricted stock units. Employee stock purchase plans. Stock options. These benefits can be powerful wealth-building tools — particularly for executives, key employees, and professionals at thriving companies. But they can also introduce a level of financial…
The Disconnect Between Portfolio Growth and Real Income
There’s a shift that tends to happen when markets perform well. It doesn’t feel like a problem. In most cases, it feels like progress. Account values rise and your account statements look better. The quiet concern that used to sit in the background—Am I going to be okay?—starts to fade. And as that concern fades,…
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…
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