Tax Planning for People Who’ve Already Fallen Behind

Episode Summary: In this episode, Lance breaks down what to do when you’re already behind on your taxes and feel buried by IRS debt. Instead of focusing on theory or prevention, he explains how to create a real plan for recovery — even if you owe money or haven’t filed in years. From becoming compliant to avoiding the most common mistakes self-employed individuals make, Lance walks through the exact steps to get back on track and stay there. What You’ll Learn in This Episode: Why compliance is the first step toward any IRS negotiation. The biggest mistake self-employed people make when trying to fix tax debt. How estimated tax payments can actually reduce what you owe. Why paying monthly is smarter than waiting for quarterly deadlines. How the Offer in Compromise really works (and who qualifies). Practical habits to avoid falling behind again — and how to stay compliant long term. Key Timestamps: 00:00 – Introduction: Tax planning when you’re already in trouble. 01:10 – The first step to recovery — becoming IRS compliant. 03:25 – The most common mistake self-employed people make when repaying tax debt. 05:40 – How estimated tax payments help you pay less overall. 07:50 – Why monthly payments beat quarterly deadlines. 09:30 – Understanding the Offer in Compromise — and why most people don’t qualify. 12:45 – Smart tax habits that prevent future debt. 14:30 – Final advice for anyone currently struggling with the IRS. About the Show: Resilience and Resolve with Lance Drury provides practical legal insights into IRS matters, tax law, and financial defense strategies. Each episode explores timely and complex tax issues with real-world examples and expert analysis from Lance Drury and his experienced legal team.