EPISODE · Feb 21, 2026 · 14 MIN
Self-Employed Estimated Tax Pitfalls
from Resilience and Resolve with Lance Drury · host resilienceandresolve
Episode Summary: Attorney Lance Drury explains the common mistakes self-employed individuals make with estimated taxes—and how to avoid them. From commission-based income to quarterly tax rules, he breaks down how late or missed payments can spiral into IRS debt and penalties. He also shares practical steps to stay compliant, protect income, and avoid long-term tax trouble. Key Timestamps: 00:00: Understanding estimated tax requirements for self-employed individuals 01:30: How commission-based earners fall behind on taxes 03:00: Missed payments, bad timing, and lack of planning 05:00: How IRS calculates late fees and interest 06:30: Using a separate account for quarterly taxes 08:00: Realtors and other commission-based workers 09:30: What to do if you’ve missed or underpaid 11:00: Lance’s three-step plan to protect clients 13:30: Where to start if you’re already behind About the Show: Resilience and Resolve features Lance Drury helps individuals and small business owners fight back when the IRS comes calling. With over 20 years of experience, Attorney Lance Drury shares expert strategies to protect assets, prevent tax problems, and build financial peace of mind.
What this episode covers
Attorney Lance Drury explains the common mistakes self-employed individuals make with estimated taxes—and how to avoid them. From commission-based income to quarterly tax rules, he breaks down how late or missed payments can spiral into IRS debt and penalties. He also shares practical steps to stay compliant, protect income, and avoid long-term tax trouble.
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Self-Employed Estimated Tax Pitfalls
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