Beyond the obvious laptop and software: the home office rules that aren't scary, the vehicle method most people pick wrong, the self-employed health insurance deduction, and the retirement moves that dwarf everything else.
Self-employed taxpayers overpay for two reasons: they miss legitimate deductions out of audit fear, and they waste energy on tiny ones while ignoring the four-figure levers. Here's the honest ranking.
A solo 401(k) lets you contribute up to $24,500 (2026) as 'employee' plus roughly 20% of net self-employment profit as 'employer' — potentially $70,000+ combined. Nothing else on this list comes close. A SEP-IRA is the simpler cousin (about 20% of net profit). Deadline nuance: solo 401(k) elective deferrals want the plan opened by December 31.
Premiums for you and your family deduct above the line — medical, dental, and part of long-term-care premiums — up to your business profit. S corp owners: the premiums must run through your W-2 to keep this one; it's a payroll-setup detail that quietly costs people thousands when missed.
Automatic on qualified profit if income is below the thresholds — but interacts with everything above (retirement contributions lower QBI while lowering tax; the net is still almost always positive). See our full QBI guide.
Deducted automatically above the line — listed here so you know it's already working.
A separate business bank account and card, books updated monthly (not in a January panic), receipts photographed the day they happen, and a mileage app. Deductions aren't found in April — they're recorded all year. If your books are behind, that's fixable fast (see our catch-up bookkeeping playbook), and every month of cleanup usually pays for itself in recovered deductions.
This guide is the hub — each of these covers one specific situation in detail:
Talk it through with a licensed US tax professional — we'll tell you honestly whether it applies to your situation.
Permanent QBI, permanent 21% corporate rate, bigger QSBS — the 2026 rules changed the entity math for good. A practical framework for choosing (or switching), with the real numbers.
Equity compensation creates the most expensive tax surprises we see — under-withheld RSUs, double-taxed ESPP shares, phantom AMT from ISOs. How each type is really taxed, and the moves that protect you.
The 20% pass-through deduction survived, permanently — with wider phase-in ranges and a new $400 minimum. Who qualifies, where the SSTB trap bites, and the levers that protect the deduction at high incomes.
