Vocations · Professional Development

No surprise
in April.

Nobody withholds tax from freelance pay, so it comes due four times a year and lands hard if you forget. Enter each quarter’s income, expenses and payment; the page works out the self-employment tax, the safe-harbor payment and when the next one is due.

Start a tax yearWhat you get
$5one-time · every device you sign in on
Buy · $5

Included with the Caveat Academy pass and Whole-school licenses. Or get it in the Job search kit, $29 for 34 items.

Your tax year

The worked example is made up: a freelance designer three quarters into 2026 with $35,900 of profit, whose September payment came in $950 short. Saved on this device only.

Loading the tax year form. If nothing appears, turn on JavaScript.

What you get

Vocations · Professional Development$5

What you finish with
A record per tax year: filing status, last year’s total tax and whether AGI was over $150,000, the share set aside; income, expenses and estimated payments for each quarter; six record-keeping habits. Works out net profit, self-employment tax, the safe-harbor quarterly installment and the set-aside amount; flags quarters paid short, the next due date, profit above the Social Security wage base and a set-aside that looks too low.
Who it is for
Freelancers, gig workers, independent contractors and students with side income who receive 1099s instead of a paycheck.
Format
Browser organizer with a saved record per tax year. Prints the year’s summary for a tax preparer, every year in a table or a blank form; downloads a spreadsheet (.csv); exports and imports a file.
Access
$5 one-time, yours on every device you sign in on; the tool opens once you are signed in with it. Included with the Caveat Academy pass and Whole-school licenses. Also in the Job search kit ($29) and the Vocations Suite pass ($99), and 1 more bundle. Everything you type stays in this browser; nothing is sent to Caveat.
Where it lives
The Professional Development space in Caveat Vocations.
Support
Questions about access, an order or a correction: team@caveatacademic.com.

How to use it

  1. Enter last year’s total tax from your Form 1040.
  2. Add each quarter’s income and expenses as it ends.
  3. Pay at least the safe-harbor installment by each due date.
  4. Set aside your chosen share of every payment you receive.
  5. Bring the printout and your records to whoever prepares your return.

Start a tax year

Self-employment tax, step by step

Where the self-employment tax comes from$35,900Net profit: income minus expenses$33,154× 92.35%: the taxable base$5,073× 15.3%: 12.4% Social Security + 2.9% MedicareHalf of it is deducted from income on Schedule 1. Income tax comes on top.Self-employment taxNet profit$35,900income minus expenses× 92.35%$33,154the taxable base× 15.3%$5,073Social Security 12.4% + Medicare 2.9%Half is deductible. Income tax comes on top.
Above the year’s Social Security wage base, only the 2.9% Medicare part continues (and an extra 0.9% Medicare tax applies at higher incomes).

The safe harbor

You generally avoid the underpayment penalty if your withholding and estimated payments, paid on time, cover 100% of last year’s total tax (110% if last year’s AGI was over $150,000), or 90% of this year’s. Most freelancers use last year’s figure because it is known in April.

Due dates

Estimated payments for a tax year are due April 15, June 15 and September 15 of that year and January 15 of the next; a date that falls on a weekend or holiday moves to the next business day. Pay through IRS Direct Pay or your IRS online account.

Sources

  1. Internal Revenue Service. Form 1040-ES, Estimated Tax for Individuals, and Publication 505, Tax Withholding and Estimated Tax (irs.gov).
  2. Internal Revenue Service. Schedule SE and Self-Employment Tax (Social Security and Medicare Taxes) (irs.gov).
  3. Internal Revenue Service. Publication 463, Travel, Gift, and Car Expenses, and Publication 587, Business Use of Your Home (irs.gov).
  4. Internal Revenue Service. Publication 560, Retirement Plans for Small Business (irs.gov).

The worked example is made up. The page estimates self-employment tax only, not income tax, and is not tax advice; state estimated taxes are separate. Nothing you type is sent to Caveat. Support: team@caveatacademic.com.