tax-professional/references/common-writeoffs.md

Common Write-Offs People Miss

Frequently Overlooked Deductions

For W-2 Employees

• HSA contributions — Triple tax advantage (deductible, grows tax-free, withdraws tax-free for medical)
• Student loan interest — Even if someone else pays it (if you're the borrower)
• Job search expenses — In same field (but note: suspended 2018-2025 for W-2)
• State sales tax — Can elect to deduct sales tax instead of state income tax (Schedule A)

For Self-Employed / Side Hustlers

• Self-employment tax deduction — 50% of SE tax is above-the-line
• Health insurance premiums — 100% deductible above-the-line if SE
• Retirement contributions — SEP-IRA or Solo 401(k) are massive deductions
• Cell phone — Business use percentage
• Internet — Business use percentage
• Home office — Even a corner of a room counts if exclusively used
• Bank fees & merchant fees — PayPal, Stripe, bank account fees
• Continuing education — Must be in current field
• Business miles — Track EVERY trip. Apps: MileIQ, Everlance, manual log
• Startup costs — Up to $5,000 deductible in first year, amortize the rest

For Everyone

• Charitable mileage — 14¢/mile, most people forget
• Glasses and contacts — Medical expense (if itemizing and exceeding 7.5% AGI)
• Tax preparation fees — For Schedule C filers, business portion is deductible
• Moving expenses — Only for active-duty military (suspended for others 2018-2025)
• Gambling losses — Deductible up to amount of gambling winnings (must itemize)
• Casualty & theft losses — Only in federally declared disaster areas (2018-2025)

Investment-Related

• Investment advisory fees — Suspended for 2018-2025 (may return in 2026!)
• Margin interest — Deductible against investment income
• Capital loss harvesting — $3,000/year against ordinary income
• Worthless securities — Deduct full loss in year stock becomes worthless

AI & Tech Worker Specific

• Cloud computing costs — AWS, GCP, Azure for business/freelance
• API costs — OpenAI, Anthropic, etc. if used for business
• Domain names & hosting — Business websites
• SaaS subscriptions — Business tools (Notion, GitHub, Figma, etc.)
• Hardware — Laptops, monitors, keyboards, mice, webcams
• Conference tickets — Tech conferences, AI summits
• Online courses — Udemy, Coursera, etc. if work-related
• Books & publications — Technical books, O'Reilly subscription