Self-Employment & 1099
Everything self-employed workers, freelancers, and 1099 contractors need to know about self-employment tax, quarterly payments, deductions, and business structure.
23 articles
How to Calculate Estimated Tax Payments
Who has to pay, how much (the 90%/100%/110% safe harbors), the annualized method for uneven income, a full worked example, and how to pay.
How to Fill Out a W-4
W-4 guidance by situation: single, married filing jointly, and dual-income couples — plus multiple jobs, dependents, and extra withholding done right.
Employer Payroll Taxes Explained: FICA, FUTA & SUTA
What employers actually owe on top of gross wages: 7.65% employer FICA, FUTA on the first $7,000, and state SUTA — with worked examples.
Self-Employed Health Insurance Deduction (Form 7206)
The SE health insurance deduction is above-the-line, capped by net SE profit and age-based LTC limits. See who qualifies and how Form 7206 works.
Self-Employment Tax Rate 2026: 15.3% Explained
The 2026 self-employment tax is 15.3% — 12.4% Social Security (capped at $184,500) plus 2.9% Medicare (uncapped). See the 92.35% rule and the half-SE-tax deduction.
How to Fill Out Form W-4 in 2026: Step-by-Step
A step-by-step guide to the 2026 Form W-4: filing status, the multiple-jobs box, dependent credits, deductions, and extra withholding done right.
Schedule K-1 Explained: How Partners, S-Corp Shareholders & Trust Beneficiaries Are Taxed
Walkthrough of K-1 (Forms 1065, 1120-S, 1041) — the boxes that drive your 1040, what each line means, basis tracking, at-risk and PAL limits.
§199A QBI Deduction 2026: 20% Pass-Through Deduction & the Specified Service Trade Phase-Out
How the §199A 20% qualified business income deduction works in 2026 — the taxable income thresholds, the SSTB (specified service trade) phase-out, and the W-2 wage/UBIA limit.
RSU Sell-to-Cover Explained: How Many Shares Disappear at Vest
Sell-to-cover withholds shares at vest to pay federal tax (typically 22% supplemental), Social Security, Medicare, and state. Why your net-share count is always less than you expected, the supplemental withholding gap, and when same-day-sale or cash withholding is the better choice.
Q2 Estimated Tax Due June 15 2026 — Safe Harbor, Form 1040-ES, and Penalties (IRS)
Complete guide to the Q2 2026 estimated tax payment due June 15: safe harbor rules (100%/110%/90%), Form 1040-ES vouchers vs EFTPS vs IRS Direct Pay, underpayment penalty math, and a worked freelancer example.
Estimated Tax Underpayment Penalty: How It's Calculated and How to Avoid It
The IRS charges an underpayment penalty when you don't pay enough tax throughout the year. Learn exactly how the safe harbor rules work, 2025 quarterly due dates, and the annualized income method for uneven earners.
RSU Tax Guide: How Restricted Stock Units Are Taxed at Vesting and Sale
Restricted stock units are taxed twice — once as ordinary income at vest, again as capital gains at sale. A complete guide to withholding, double-taxation traps, and the tax-smart way to manage your RSU grant.
1099 Filing Deadlines and Penalties 2026
1099-NEC is due January 31, 2026. Learn all 1099 filing deadlines, late filing penalties ($60–$310 per form), intentional disregard penalties, and how to avoid IRS enforcement.
LLC vs. S-Corp: Which Business Structure Saves More in Taxes?
Compare the tax implications of an LLC versus an S-Corp for self-employed individuals, including SE tax savings, reasonable salary requirements, and compliance costs.
Quarterly Estimated Tax Payments Explained
Who must pay estimated taxes, how the safe harbor rules work, how to avoid underpayment penalties, and the 2026 due dates for quarterly payments.
Self-Employment Tax: How It Works
Understand the 15.3% self-employment tax, how to deduct half of it, what Schedule SE requires, and how it differs from W-2 FICA withholding.
W-2 vs. 1099: Tax Differences Explained
Understand the key tax differences between W-2 employee income and 1099 independent contractor income — including self-employment tax, withholding, deductions, and benefits.
Home Office Deduction Guide: Who Qualifies and How to Calculate It
Learn who can claim the home office deduction, the difference between the simplified and regular methods, and what expenses qualify — including key rules for remote employees.
Side Hustle Tax Guide: How Gig Income Is Taxed in 2025
Learn how side income and gig work is taxed, including 1099-K reporting, estimated taxes, common deductions, and the hobby vs. business distinction.
1099 Freelancer Tax Guide: Everything You Need to Know for 2025
A complete guide to 1099 freelancer taxes in 2025: self-employment tax, quarterly payments, top deductions, and exactly how much to set aside so you never get blindsided at tax time.
Lottery and Gambling Tax Guide: How Winnings Are Taxed in 2025
How lottery winnings and gambling income are taxed at the federal and state level in 2025, including lump sum vs. annuity decisions, withholding rules, and how to deduct gambling losses.
Self-Employment Tax Guide: What Freelancers and 1099 Workers Need to Know
A complete guide to self-employment tax for freelancers and independent contractors, including the 15.3% SE tax rate, deductions, and quarterly estimated payment due dates.
Quarterly Estimated Tax Payments: Who Needs to Pay and How to Calculate
Learn who must make quarterly estimated tax payments, the 2026 due dates, how to calculate your payments, the safe harbor rule, and how to avoid underpayment penalties.