TaxStow.

Freelance taxes, in plain English

Fifteen guides on planning federal self-employment taxes — what to set aside, when to pay, what you can document, and how the rules actually read.

  1. 01How much should freelancers set aside for taxesA simple, adjustable framework — not a fixed percentage — for deciding how much of each freelance payment to hold back for taxes.planningself-employment taxestimated taxes9 min
  2. 02Quarterly estimated taxes explained for first-timersA first-timer's walkthrough of what quarterly estimated taxes are, when they're due in 2026, and how to work out what to pay.estimated taxesdeadlinesplanning8 min
  3. 03What happens if you miss a quarterly paymentWhat actually happens — and doesn't happen — if you miss an estimated tax deadline, plus practical steps to catch up.penaltiesestimated taxesdeadlines7 min
  4. 04The safe harbor rule, in plain EnglishA plain-English explanation of the safe harbor rule that can protect freelancers from an underpayment penalty, with a worked example.safe harborpenaltiesestimated taxes7 min
  5. 05Schedule C line by lineSchedule C reports your self-employment profit or loss to the IRS. Here's what each part of the form is asking for and where planning decisions actually happen.schedule-cfilingself-employment9 min
  6. 06Home office deduction: the two methods comparedThe home office deduction has two calculation methods with different recordkeeping burdens and different payoffs. Both require your workspace to meet the same use test.home-officedeductionsschedule-c8 min
  7. 071099-NEC vs 1099-K vs W-2Freelancers often receive a mix of 1099-NEC, 1099-K, and (for side W-2 jobs) W-2 forms. Here's what each one actually reports and why the forms don't define your tax obligation.1099filingincome-reporting7 min
  8. 08When a freelancer should form an S-corpElecting S-corp status is a facts-and-circumstances decision that trades potential self-employment tax savings for payroll obligations, added compliance costs, and IRS scrutiny of your compensation.s-corpbusiness-structureself-employment-tax9 min
  9. 09Deducting your car as a freelancerA planning overview of the two ways self-employed people can account for business vehicle use, and why commuting miles never qualify.deductionsvehiclerecordkeeping8 min
  10. 10Self-employed health insurance deductionThe self-employed health insurance deduction can lower taxable income for eligible freelancers, but it comes with specific eligibility rules and a cap tied to your business profit.health insurancedeductionsself-employment7 min
  11. 11SEP IRA vs solo 401(k)SEP IRAs and solo 401(k)s are both retirement plans built for the self-employed, but they differ in contribution structure, flexibility, and paperwork.retirementSEP IRAsolo 401(k)8 min
  12. 12Tracking expenses without accounting softwareYou don't need paid accounting software to track deductible expenses well — a consistent habit and a simple system will get most freelancers most of the way there.recordkeepingexpensestools7 min
  13. 13What to do if you got a 1099 you weren't expectingSteps for reviewing an unexpected 1099-NEC, 1099-K, or 1099-MISC: verify the amount, contact the payer if needed, and understand duplicate reporting.1099income reportingrecordkeeping7 min
  14. 14Freelancing in one state, clients in anotherExplains why client location generally doesn't drive state tax obligations for freelancers, why rules vary so much by state, and how to find authoritative answers.state taxesmulti-stateresidency6 min
  15. 15Your first year freelancing: a tax timelineA practical timeline of tax-related tasks and deadlines for a freelancer's first year in business, using 2026 estimated payment due dates.getting startedestimated taxesplanning8 min

Every guide cites its sources and shows the date it was last reviewed. Figures that change from year to year are labelled with the tax year they belong to.