Plain-language guides for sole props, freelancers, and S-corp owners. Updated as the rules change.
1099s
Since 2020 the IRS split contractor pay (1099-NEC) from rent, royalties, and other payments (1099-MISC). Here's the decision tree.
May 3, 2026 · 5 min read
Operations
The smallest possible bookkeeping system that survives an audit, supports a clean Schedule C, and runs in under 30 minutes a month.
May 3, 2026 · 6 min read
Taxes
The two safe-harbor rules that shield you from the underpayment penalty — and the income threshold that flips you between them.
May 3, 2026 · 6 min read
Forms
Line-by-line through Form 8829 — Expenses for Business Use of Your Home — for sole props using the actual-expense method.
May 3, 2026 · 5 min read
Taxes
Two ways to deduct your home office. Simplified is fast and capped at $1,500. Actual is more work and often worth more. Here's how to pick.
May 3, 2026 · 5 min read
Filing
Step-by-step through TurboTax Self-Employed for sole props, with the gotchas that surprise first-time filers.
May 3, 2026 · 6 min read
Operations
Married freelancers commingling funds in a joint account: how to keep clean books, defend deductions, and avoid the worst-case audit narrative.
May 3, 2026 · 6 min read
Taxes
What the IRS actually wants in a mileage log: contemporaneous, four required fields, and the apps that survive an audit.
May 3, 2026 · 5 min read
Operations
Why sole props need a separate business bank account, how Plaid sees mixed accounts, and the cleanest way to split.
May 3, 2026 · 5 min read
Taxes
Why the IRS expects you to pay every three months, how to compute the four payments, and how to avoid the underpayment penalty.
May 3, 2026 · 5 min read
Entity
The IRS requires S-corp owner-employees to pay themselves a reasonable salary. Here's how the IRS defines 'reasonable' and how to defend your number.
May 3, 2026 · 5 min read
Records
The $75 rule, the per diem exception, and what counts as adequate substantiation when an auditor asks.
May 3, 2026 · 6 min read
Entity
The S-corp election cuts SE tax but costs you payroll, separate returns, and a reasonable salary. Here's the break-even math.
May 3, 2026 · 5 min read
Taxes
Every Schedule C line, what counts, and the receipts the IRS expects. Updated for 2026 returns.
May 3, 2026 · 6 min read
Taxes
How SE tax is actually computed — the 92.35% adjustment, the Social Security wage base, the Medicare surtax, and the half-deduction on Schedule 1.
May 3, 2026 · 5 min read
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