How to Stay Ahead of Taxes and Avoid Penalties episode artwork

EPISODE · Jan 22, 2026 · 21 MIN

How to Stay Ahead of Taxes and Avoid Penalties

from Real Personal Finance · host Scott Frank

Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning.— Taxes tend to fade into the background until something feels off, like a larger bill than expected, a penalty you didn’t see coming or a moment where you wonder whether you handled the year correctly or just got lucky.In this episode of Real Personal Finance, Scott and Nick talk about how the tax system actually works and why the idea of making one payment on April 15 simply won’t cut it. For example, did you know there’s a pay-as-you-go structure? Or that different types of income can change your tax reality? Scott and Nick go through salaried employees, executives with bonuses or stock compensation, small business owners, and retirees whose income has started to shift.When you understand what the IRS is looking for and how to build a simple system around it, taxes can stop being a surprise and become something you can manage with less stress throughout the year.Ready to learn more? Scott Frank on LinkedIn Stone Steps Financial Nick Covyeau on LinkedInSwell FinancialLeave us a question! Money can be confusing, but it doesn’t have to be. When you’re able to understand the complexities, you can make better decisions to improve your daily life. Connect with us at Stone Steps Financial.

Episode metadata supplied by the publisher feed · Published Jan 22, 2026

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Curious about your retirement savings? Our How Much Do I Need To Retire? quiz gives you an idea of where you stand and a starting point to think about your long-term planning. — Taxes tend to fade into the background until something feels off, like a larger bill than expected, a penalty you didn’t see coming or a moment where you wonder whether you handled the year correctly or just got lucky. In this episode of Real Personal Finance, Scott and Nick talk about how the tax system actuall...

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How to Stay Ahead of Taxes and Avoid Penalties

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