Self-Employed Success
Gig Workers. Freelancers. Consultants. IRS Problems Solved.
Self-employment makes IRS problems harder — variable income, quarterly estimates, and SFRs that ignore every business expense. These are the taxpayers who got back on track.
Free Self-Employed Evaluation
Self-employed taxpayers have unique resolution opportunities. Find out yours.
New York Freelance Designer — 6 Years Unfiled, $187K Resolved
Situation
Freelance graphic designer with highly variable income. Filed nothing for 6 years after a divorce. IRS assessed $187K via SFRs with no business expenses applied. Revenue officer threatening levy.
IRS Debt
$187,000 (SFR assessments)
Strategy
Filed all 6 years of returns with accurate Schedule C filings capturing all business expenses — equipment, software subscriptions, home office, health insurance, and SE retirement contributions. Corrected liability was approximately $94K. Set up streamlined IA on the corrected balance.
Outcome
Corrected liability: $94K — a 50% reduction. IA approved at $1,305/month. Revenue officer case closed. Active compliance plan established for estimated tax payments going forward.
Key Lesson
Self-employed taxpayers have the most to gain from filing accurate returns. The IRS's SFR gives a 1099 recipient the standard deduction and personal exemption — that's it. No business expenses. No home office. No SE health insurance deduction. No retirement contributions. Filing corrects all of this.
Texas Rideshare Driver — $42K Corrected to $12K
Situation
Full-time rideshare and delivery driver. 3 years unfiled. IRS assessed $42K based on 1099-K gross receipts — treating every dollar of gross rideshare income as profit, with no mileage deduction.
IRS Debt
$42,000
Strategy
Filed accurate returns with the standard mileage deduction for all business miles driven. For rideshare drivers, mileage is typically the largest deduction — often reducing taxable income by 50-70%. Also captured phone, supplies, and platform fees.
Outcome
Corrected liability: approximately $12,000. Entered streamlined IA at $167/month. All 3 years now properly filed. Client tracks mileage automatically through an app to prevent future issues.
Key Lesson
For gig workers, the IRS's SFR is especially unfair — it treats all 1099-K income as pure profit. The standard mileage deduction alone typically reduces taxable income by more than half. Filing accurate returns is not optional for gig workers — it's the difference between a manageable tax bill and a catastrophic one.
Colorado Consultant — OIC Accepted at $8,500 on $95K
Situation
IT consultant who went through a prolonged period with almost no income while caring for an ill parent. 4 years of unpaid taxes while also dealing with personal medical debt. No significant assets — rented apartment, older car with a loan.
IRS Debt
$95,000
Strategy
Filed all missing returns to establish accurate liability. Then submitted OIC-DATC — Reasonable Collection Potential analysis showed approximately $8,000 in net equity (bank account + vehicle equity) and minimal monthly disposable income after IRS allowable expenses. Strong case for settlement because income was unlikely to increase (client was nearing retirement).
Outcome
OIC accepted at $8,500. Remaining $86,500 forgiven. 5-year compliance period in effect. Client now files quarterly estimated taxes and annual returns on time.
Key Lesson
A self-employed taxpayer with irregular income, limited assets, and genuine hardship is exactly the profile for an OIC. The IRS evaluates future earning potential — a consultant nearing retirement has less future income to collect than a 30-year-old with decades of earnings ahead.
Self-Employed? Behind on Taxes? You're Not Alone.
Self-employed taxpayers face unique IRS challenges — but also have unique resolution opportunities. Proper business deductions can dramatically change the numbers. Let us show you what's possible.