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Self-Employment Tax Questions & Answers
Freelancer taxes, 1099 income, quarterly estimated payments, and business expenses.
23 questions — IRS-sourced, AI-assisted answers
Self-Employment
Can I write off my gym membership as a self-employed personal trainer in 2025?
1.9k2 answersJul 11, 2025
Self-Employment
What business expenses can I deduct as a freelancer on Schedule C in 2025?
4.3k4 answersMay 30, 2025
Self-Employment
How do I pay quarterly estimated taxes as a self-employed person in 2025?
3.8k4 answersMar 25, 2025
Self-Employment
Can I deduct health insurance premiums if I am self-employed in 2025?
2.9k3 answersMay 12, 2025
Self-Employment
What tax deductions can Uber and Lyft drivers claim in 2025?
3.2k5 answersFeb 10, 2025
Self-Employment
How do DoorDash and Instacart delivery drivers file taxes in 2025?
2.6k3 answersFeb 28, 2025
Self-Employment
Do I have to pay taxes on Etsy and eBay sales in 2025?
2.8k3 answersJan 28, 2025
Self-Employment
How do I report freelance income from a 1099-NEC in 2025?
2.5k4 answersFeb 18, 2025
Self-Employment
When does a side hustle need to be reported on taxes in 2025?
2.3k3 answersMar 5, 2025
Self-Employment
What can YouTubers and content creators deduct on taxes in 2025?
1.9k4 answersMay 15, 2025
Self-Employment
How do I file taxes with multiple 1099 forms in 2025?
2.1k3 answersMar 10, 2025
Self-Employment
I got a 1099 from my internship. How do I file taxes on it in 2025?
1.6k3 answersMar 8, 2025
Self-Employment
Is crypto mining a business or hobby for tax purposes in 2025?
1.3k3 answersJul 12, 2025
Self-Employment
Is the 20% QBI deduction still available for my small business in 2025?
01 answerMar 15, 2026
Self-Employment
What are the estimated tax payment due dates for 2026 and how do I avoid the underpayment penalty?
01 answerMar 20, 2026
Self-Employment
I use Venmo and PayPal for side work — will I receive a Form 1099-K for 2025, and do I owe taxes?
8.4k5 answersMar 23, 2026
Self-Employment
What are the biggest IRS audit red flags for self-employed people filing Schedule C in 2025?
9.2k5 answersMar 24, 2026
Self-Employment
What is the 1099-K threshold for 2025 — will I get one from Venmo or PayPal for my side hustle?
8.9k7 answersMar 25, 2026
Self-Employment
What is the IRS standard mileage rate for 2025 and how do I deduct vehicle expenses?
01 answerMar 28, 2026
Self-Employment
Can I deduct health insurance premiums if I'm self-employed in 2025?
01 answerMar 28, 2026
Self-Employment
Do I need to pay quarterly estimated taxes as a gig worker in 2026?
01 answerMar 30, 2026
Self-Employment
How do I calculate my Q1 2026 estimated tax payment as a freelancer?
01 answerApr 3, 2026
Self-Employment
I received both a W-2 and 1099-NEC income this year. How do I file my taxes?
01 answerApr 5, 2026