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April 22, 2026 · Jeffrey Joju

5 deductions sole proprietors miss every year

If you file a Schedule C and feel like you're paying more tax than you should, you're probably right. Here are five legitimate deductions that consistently get missed.

1. Home office (the simplified method counts)

You don't need a dedicated room — you need a dedicated space used regularly and exclusively for business. The simplified method gives you $5/sq ft, up to 300 sq ft, with no extra paperwork.

2. Health insurance premiums

Self-employed people can deduct premiums for themselves, their spouse, and dependents — even if they take the standard deduction. Most software won't surface this for you automatically.

3. Half of your self-employment tax

You pay both halves of Social Security and Medicare as a sole prop. The IRS lets you deduct the employer half. Roughly 7.65% of net earnings, deducted on Schedule 1.

4. Mileage (and not just client visits)

The IRS rate covers any business driving — coffee meetings, supply runs, post office trips. Track it from the start of the year. We use MileIQ and similar apps.

5. Continuing education

Courses, books, conferences, and certifications that maintain or improve skills required for your current business are deductible. New careers don't count — keep it adjacent.


Not sure which apply to you? Book a free consult and we'll do a 15-minute deduction audit on the house.

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