Freelancer Tax & Insurance Guides
Plain-English guides for 1099 earners, independent contractors, and self-employed professionals. Every figure is tied to the 2026 IRS inflation adjustments and shows the publication it came from.
New here? Start with these three.
How self-employment tax works explains the 15.3% you owe on top of income tax. Then see when quarterly payments are due so you avoid the underpayment penalty, and how to get health coverage without an employer plan.
Tax guides
Nineteen guides covering self-employment tax, quarterly estimates, deductions, retirement, and entity choice.
Self-Employment Tax: The Complete Guide
How the 15.3% Social Security and Medicare tax is calculated, what you can deduct against it, and the legitimate ways to lower it.
Run the numbersEstimate Your Self-Employment Tax
The number to type in, what the 15.3% result covers and leaves out, and how to turn one figure into four quarterly payments.
Record keepingHow to Track Business Expenses
The setup, the weekly routine, and the records that make every deduction on your return provable.
Record keepingHow to Track 1099 Income
One row per client payment, what to do with an unpaid invoice, and how much to hold back for tax.
1099 forms1099-NEC vs 1099-K
Who sends each 2026 form, the $2,000 and $20,000/200 thresholds, and why a 1099-K doesn't mean you owe more tax.
Tax planningComplete 2026 Quarterly Tax Guide
Deadlines, safe harbor rules, penalty math, and a step-by-step Form 1040-ES walkthrough.
Tax planningEstimated Tax Penalty and Safe Harbor
When the underpayment charge applies, how the 90% and 100%/110% safe harbors spare you, and the fix that reaches backward.
What changed2026 Tax Changes for Freelancers
What the OBBBA changed for QBI, bonus depreciation, and the Social Security wage base — and what stayed the same.
DeductionsFreelancer Tax Deductions Checklist
Every write-off a 1099 earner can claim, with the qualification rules and records you need for each.
DeductionsHome Office Deduction Guide
Simplified versus regular method, the IRS rules that decide eligibility, and worked calculation examples.
Tax strategyQBI Deduction Guide
How the Section 199A 20% deduction works, who qualifies, and how the 2026 income thresholds apply.
Tax strategyS-Corp Election Guide
Salary versus distribution, the breakeven income where an S-Corp pays off, and the filing requirements.
Entity choiceLLC for Freelancers
Whether forming an LLC actually saves you tax, the 2026 numbers, and the state fees that can make it cost you.
Tax basicsSchedule C Filing Guide
Line-by-line reporting of 1099 income and expenses, and how to pair it with Schedule SE.
EquipmentSection 179 & Bonus Depreciation
The 2026 limits, what qualifies, and how to write off equipment and vehicles in year one.
DeductionsBusiness Mileage Deduction
The 2026 two-rate year — 72.5¢ through June 30, 76¢ after — and how to choose your method.
RetirementSEP IRA vs Solo 401(k)
Contribution limits, Roth options, and which retirement plan wins at each income level.
RetirementHSA for the Self-Employed
The triple tax advantage, 2026 contribution limits, and how an HSA doubles as a retirement account.
RetirementSelf-Employed Retirement Contribution Limits
The 2026 dollar limit for every plan and age band, and the 20% calculation that turns net profit into a SEP IRA or Solo 401(k) contribution.
Tax guides by state
Six guides on how individual states tax self-employment income — rates, estimated payment deadlines, and filing thresholds, each sourced from the state's own tax agency.
Self-Employment Taxes by State
How the federal layer stays the same while the state layer changes, four steps to find the state that taxes you, and what to check in your own.
State taxCalifornia Self-Employment Tax
A graduated tax with a 12.3% top rate, a 1% surcharge above $1 million, and the $500 line that triggers estimated payments.
No income taxTexas Self-Employment Tax
No state income tax, no state return, and no state estimated payments — plus where the franchise tax does apply.
State taxNew Jersey Self-Employment Tax
A 10.75% top rate and one of the lowest filing thresholds in the country: $10,000 for a single filer.
Flat 5% rateMassachusetts Self-Employment Tax
A flat 5.00% rate, a 4% surtax on higher income, and a June 16 second installment that does not match the business calendar.
Plus city taxNew York Self-Employment Tax
A 10.9% top state rate, plus New York City and Yonkers layers, the MCTMT, and a $4,000 filing threshold.
Insurance guides
Eight guides on the coverage a freelancer actually needs, and what it costs.
Freelancer Insurance: What Coverage You Need
Which policies a freelancer actually needs, what each costs, and which one to buy first.
HealthComplete 2026 Health Insurance Guide
ACA marketplace changes, subsidy math, and how to pair coverage with an HSA.
SubsidiesACA Subsidies for the Self-Employed in 2026
Who still qualifies for a premium tax credit, the 2026 cliff, and how to lower your MAGI.
LiabilityComplete Freelancer Liability Guide
General versus professional liability, errors and omissions coverage, and average monthly costs.
DisabilityDisability Insurance Guide
Short-term versus long-term coverage, benefit caps, and how to size a policy to your income.
Workers' CompWorkers' Comp for the Self-Employed
When you must carry it, how the rule follows your business structure and state, and how the premium is deducted on Schedule C.
AutoCommercial Auto Insurance for the Self-Employed
When your personal policy stops covering business use — rideshare, delivery, and the Schedule C deduction.
AccidentOccupational Accident Insurance for the Self-Employed
The injury coverage that fills the gap when workers' comp does not reach you, and how the premium is taxed.
Run the numbers for your situation
Free self-employment tax calculator, quarterly estimator, and deduction finder. Everything runs in your browser — no sign-up and no data upload.
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