If you made money outside a regular paycheck last year — gig work, side hustles, freelance clients, even reselling stuff online — there's a decent chance you owe the IRS a chunk of money right now.
The first estimated tax payment for 2025 was due April 15, and the second one lands on June 16.
Miss either, and the penalties start stacking up quietly in the background.
Here's the part that trips people up: unlike a W-2 job, nobody is withholding money from your Venmo, your Etsy shop, or your DoorDash earnings.
That means you're responsible for sending the IRS its cut four times a year.
Skip it, and you're not just paying the tax later — you're paying interest and a penalty on top.
You need to pay at least 90% of what you'll owe this year, or 100% of what you owed last year, whichever is smaller.
If you owed $6,000 last year and your income hasn't changed much, sending in roughly $1,500 per quarter keeps you out of trouble.
Pay too little, and the IRS charges interest that currently runs around 7% annually — not catastrophic, but not free either.
For 2025, the payment schedule is April 15, June 16, September 15, and January 15, 2026.
You can pay through IRS Direct Pay, your IRS online account, or by mailing a check with Form 1040-ES.
The IRS also has a free tool that calculates what you owe each quarter if you punch in your income and deductions.
One thing worth knowing: if you also have a regular job, you can often dodge the quarterly hassle entirely by bumping up your W-4 withholding.
Ask your employer for a new W-4 and add extra withholding on line 4(c).
The IRS treats withheld money as paid evenly throughout the year, which can wipe out an underpayment penalty even if you catch up late.
A lot of people got burned this spring because they picked up gig work in 2024 and didn't realize the tax bill doesn't come out of the app.
Uber, Etsy, and most platforms don't withhold anything for independent contractors.
Some now offer optional withholding, but you have to turn it on yourself.
If you're already behind, don't panic and don't ignore it.
The IRS offers payment plans starting with short-term options for under $100,000 in total debt.
Setting one up stops the penalty from growing and usually costs far less than people assume.
Ignoring a notice, on the other hand, is how a manageable bill turns into a lien.
Final Thoughts
The takeaway is boring but real: if money is coming in without taxes taken out, set aside roughly 25% to 30% the moment it hits your account.