If you’re self-employed, the IRS doesn’t want to wait until April to get paid. They want money four times a year — and if you skip it, they tack on penalties even if you pay your full bill on time.

Here’s how quarterly taxes actually work, without the jargon.

Who has to pay

You owe quarterly estimated taxes if you expect to owe at least $1,000 when you file. That covers nearly every freelancer, contractor, and small business owner who isn’t having taxes withheld from a paycheck.

The four deadlines

  • April 15 — covers Jan 1–Mar 31
  • June 15 — covers Apr 1–May 31
  • September 15 — covers Jun 1–Aug 31
  • January 15 — covers Sep 1–Dec 31 of the prior year

Yes, the periods are uneven. Yes, it’s annoying. Mark them in your calendar now.

How much to pay

The simplest method is the safe harbor rule: pay either 100% of last year’s total tax (110% if you earned over $150K), spread across four equal payments. Do that, and the IRS can’t penalize you regardless of how much you actually owe at year-end.

If your income is wildly different from last year, calculate 25–30% of each quarter’s net profit and send that in.

How to pay

Use IRS Direct Pay (free, takes two minutes) or the EFTPS system. Don’t mail checks unless you enjoy worrying about the postal service.

The habit that fixes everything

Open a separate “Tax” savings account. Every time a client payment hits, transfer 25–30% over. When the quarterly deadline arrives, the money is already sitting there. No scrambling, no penalties, no surprises.

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