Taxes8 min readBuilding

Quarterly Estimated Taxes: A Guide for Self-Employed and Side Hustlers

Learn when and how to pay estimated taxes to avoid penalties and surprises.

Quarterly tax calculations

When you're an employee, taxes are automatically withheld from your paycheck. But freelancers, contractors, and side hustlers? You're responsible for paying taxes yourself—four times a year.

Why Quarterly Payments?

The U.S. tax system is "pay as you go." The IRS wants money throughout the year, not just at tax time.

Who must pay quarterly:

  • Freelancers and independent contractors
  • Self-employed individuals
  • Gig workers (Uber, DoorDash, Etsy, etc.)
  • Anyone with significant investment income
  • Side hustlers with profitable businesses

Pro Tip

If you expect to owe $1,000+ in taxes for the year (beyond ), you likely need to make quarterly payments.

The Four Due Dates

QuarterIncome PeriodDue Date
Q1Jan 1 - Mar 31April 15
Q2Apr 1 - May 31June 15
Q3Jun 1 - Aug 31September 15
Q4Sep 1 - Dec 31January 15 (next year)

Watch Out

Notice Q2 covers only 2 months, and Q3 covers 3 months. The dates are quirky, so mark your calendar.

What Taxes You're Paying

Self-employment income faces multiple taxes:

Self-Employment Tax (15.3%)

  • 12.4% Social Security (on first $168,600 in 2024)
  • 2.9% Medicare
  • This replaces what employers normally pay

Federal Income Tax

  • Based on your
  • Typically 12-24% for most self-employed

State Income Tax

  • Varies by state (0-13%+)

Aisha started freelance graphic design and earned $40,000 her first year. She was shocked to owe $8,000+ at tax time: $5,652 in self-employment tax plus federal and state income taxes. The next year, she paid quarterly and avoided the painful lump sum.

How to Calculate Your Payments

Method 1: Safe Harbor (Easiest)

Pay 100% of last year's total tax liability, divided by 4. Even if you owe more, no penalties.

Example:

  • Last year's total tax: $8,000
  • Quarterly payment: $2,000

For high earners ($150,000+ AGI), the safe harbor is 110% of last year's tax.

Method 2: Current Year Estimate

Estimate this year's income and pay 90% of projected tax, divided by 4.

Example:

  • Expected self-employment income: $50,000
  • Estimated total tax: $10,000
  • Quarterly payment: $2,500

Method 3: Actual Income Method

Calculate tax on actual income each quarter. More accurate but more work.

Do This

Use the IRS Form 1040-ES worksheet or tax software to calculate your quarterly amount. Update estimates if income changes significantly.

The Self-Employment Tax Calculation

Self-employment tax is calculated on net self-employment income:

  1. Calculate net profit: Revenue minus business expenses
  2. Multiply by 92.35%: Only this portion is subject to SE tax
  3. Apply 15.3%: Calculate SE tax
  4. Divide by 4: Quarterly SE tax amount

Example:

StepCalculation
Quarterly net profit$10,000
× 92.35%$9,235
× 15.3% SE tax$1,413
+ Federal income tax (~22%)$2,200
= Quarterly payment~$3,613

How to Make Payments

Option 1: IRS Direct Pay (Free)

  • Go to irs.gov/payments
  • Select "Estimated Tax"
  • Pay from bank account
  • Get confirmation number

Option 2: EFTPS (Free)

  • Electronic Federal Tax Payment System
  • Requires enrollment at eftps.gov
  • Good for scheduled payments

Option 3: IRS2Go App

  • Mobile app for payments
  • Convenient for on-the-go

Option 4: Credit/Debit Card

  • Third-party processors
  • 1.87-1.99% fee for credit cards
  • Not usually worth it unless earning rewards

Quick Win

Set up automatic quarterly payments through EFTPS. Schedule them a few days before due dates so you never miss one.

State Estimated Taxes

Most states with income tax also require quarterly payments:

  • Due dates often match federal
  • Separate payment system per state
  • Calculate based on state tax rate

What Happens If You Don't Pay

The IRS charges an underpayment penalty:

  • Currently around 8% annual rate
  • Calculated daily on each missed quarter
  • Even one missed payment triggers penalties

Example: Miss $3,000 Q1 payment → ~$180 penalty by year end

The penalty isn't huge, but it adds up—and it's completely avoidable.

Special Situations

Side Hustle + Day Job

If you have W-2 income, you have options:

  1. Increase W-2 withholding to cover side hustle tax
  2. Make quarterly payments on side income only
  3. Combination of both

Do This

Adjust your W-4 at your day job to withhold extra. It's easier than quarterly payments if your side income is modest.

Variable Income

If income fluctuates wildly:

  • Use annualized income installment method
  • Pay more in high-earning quarters
  • Requires Form 2210 at tax time

First Year Self-Employed

No prior year to base safe harbor on. Estimate conservatively and adjust as you go.

Common Mistakes

Avoid This

  1. Forgetting state payments - Penalties apply there too
  2. Underestimating income - Be conservative in estimates
  3. Not tracking expenses - Reduces taxable income
  4. Waiting until Q4 - Pay as you earn, not at year end
  5. Ignoring payment confirmations - Save proof of payment

Setting Money Aside

For every dollar of self-employment income, set aside:

  • 25-30% for self-employment tax + federal income tax
  • Additional 5-10% if your state has income tax

Pro Tip

Open a separate savings account for taxes. Transfer your tax percentage immediately when you receive payment. Treat it as money that isn't yours.

Tracking for Tax Time

Keep records of:

  • All quarterly payments made (dates and amounts)
  • Confirmation numbers
  • Business income and expenses
  • Mileage logs if applicable

Your tax preparer (or software) will need this information to file accurately and claim credit for payments made.

Key Takeaways

  • 1Self-employed individuals and side hustlers must pay taxes quarterly
  • 2The safe harbor method—paying 100% of last year's tax—avoids penalties
  • 3Self-employment tax is 15.3% on top of regular income tax
  • 4Set aside 25-35% of self-employment income for taxes immediately
  • 5Missing quarterly payments triggers penalties around 8% annually