Like a Root Canal, But You Can Prepare for It 

Ah, quarterly estimated taxes—the recurring nightmare of freelancers and business owners. Miss them and the IRS treats you like someone who skipped grandma’s birthday. Repeatedly.

Who has to pay quarterly taxes?

• Sole proprietors, partners, S-corps, freelancers—anyone with income not subject to withholding

When are they due?

• Typically April 15, June 15, September 15, and January 15. Mark your calendar with skulls if necessary.

Why do they matter?

• Avoid underpayment penalties

• Smooth out your tax payments across the year

• Reduce your spring tax shock (or at least brace for it)

Tips to stop dreading them:

• Set aside 25–30% of your income in a separate account

• Use tools like QuickBooks Self-Employed or Keeper Tax to auto-calculate your payments

• Pay online through the IRS Direct Pay Portal

✅ Funny Tip: Think of quarterly taxes as a subscription service to keep the IRS out of your DMs.