Quick Answer
No, you only owe estimated taxes starting with the quarter you earned freelance income. If you start in June, your first payment is Q2 (due June 15), not Q1. You won't owe penalties for quarters before you had self-employment income.
Best Answer
James Okafor, Self-Employment Tax Specialist
Best for people who just started freelancing and are confused about quarterly payment timing
When do estimated tax payments start?
You only owe estimated taxes for quarters when you actually earned freelance income. If you start freelancing in June, your first estimated tax payment is for Q2 (due June 15), not Q1. The IRS doesn't expect you to pay estimated taxes for periods when you had no self-employment income.
Example: Starting freelancing in June 2026
Let's say you land your first freelance client on June 1, 2026, and earn $3,000 in June:
Your Q2 payment would be roughly $459 (assuming 25% effective tax rate: $3,000 × 0.153 self-employment tax + federal/state income tax).
Quarterly due dates you need to know
How to calculate your first payment
For your first quarter with freelance income, estimate your total annual freelance profit and divide by 4. If you started in June and expect to earn $20,000 for the rest of the year:
1. Self-employment tax: $20,000 × 15.3% = $3,060
2. Income tax: Depends on your total income and tax bracket
3. Total quarterly payment: Roughly $1,500-2,000 (varies by situation)
Safe harbor rule protection
According to IRS Publication 505, you avoid underpayment penalties if you pay either:
Since this is your first year with freelance income, focus on the 90% rule.
Key factors that affect your payment
What you should do
1. Calculate your expected annual freelance profit
2. Use the quarterly estimator tool to determine your payment amount
3. Set up calendar reminders for remaining quarterly due dates
4. Consider increasing W-4 withholding if you have a day job to cover freelance taxes
Key takeaway: You only start owing estimated taxes the quarter you begin earning freelance income. Starting in June means your first payment is Q2 (due June 15), not Q1, and there's no penalty for the quarters before you freelanced.
Key Takeaway: You only owe estimated taxes starting with the quarter you earned freelance income, so June starters pay Q2 first with no penalties for Q1.
Quarterly estimated tax due dates and what income periods they cover
| Quarter | Income Period | Due Date | What to Include |
|---|---|---|---|
| Q1 | January - March | April 15 | All freelance income Jan-Mar |
| Q2 | April - June | June 15 | All freelance income Apr-Jun |
| Q3 | July - September | September 15 | All freelance income Jul-Sep |
| Q4 | October - December | January 15 (next year) | All freelance income Oct-Dec |
More Perspectives
James Okafor, Self-Employment Tax Specialist
Best for people adding freelance income to existing W-2 employment
Your W-2 withholding might cover you
If you're adding freelance income to a W-2 job, your existing payroll withholding might already cover your total tax liability. Many side hustlers don't need to make estimated payments at all — they can simply adjust their W-4 to increase withholding.
Example: $75,000 W-2 + $15,000 freelance income
Let's say you start a side hustle in June earning $2,500/month:
Instead of quarterly payments, you could increase your W-4 withholding by ~$215 per paycheck ($5,595 ÷ 26 pay periods) starting in June.
When to choose increased withholding vs. quarterly payments
Choose increased W-4 withholding if:
Choose quarterly payments if:
What you should do
Run the numbers both ways: either increase W-4 withholding to cover the extra tax, or start making quarterly payments for Q2. Most side hustlers find increased withholding simpler for their first year.
Key takeaway: Side hustlers can often cover freelance taxes by increasing W-4 withholding instead of making quarterly payments, especially if the freelance income is a smaller portion of total earnings.
Key Takeaway: Side hustlers can often increase W-4 withholding to cover freelance taxes instead of making quarterly payments, which is simpler for most people.
James Okafor, Self-Employment Tax Specialist
Best for people whose freelance income varies significantly by season or project
Uneven income requires different planning
If your freelance income varies dramatically by season (like tax preparation, holiday retail, or summer services), you don't have to make equal quarterly payments. The IRS allows you to match payments to actual quarterly income.
Annualized income installment method
According to IRS Form 2210, you can calculate each quarter's payment based on actual income earned that quarter, not projected annual income. This prevents overpaying early in the year when income is low.
Example: Summer landscaping business
Starting freelance landscaping in June with seasonal income:
This method requires more calculation but prevents cash flow problems from overpaying during slow periods.
Key takeaway: Seasonal freelancers can use the annualized income method to match quarterly payments to actual quarterly earnings rather than making equal payments year-round.
Key Takeaway: Seasonal freelancers can match quarterly payments to actual quarterly income using the annualized income method, preventing overpayment during slow periods.
Sources
- IRS Publication 505 — Tax Withholding and Estimated Tax
- IRS Form 2210 — Underpayment of Estimated Tax by Individuals, Estates, and Trusts
Reviewed by James Okafor, Self-Employment Tax Specialist on February 28, 2026
This content is for educational purposes only and is not a substitute for professional tax advice. Consult a qualified tax professional for advice specific to your situation.