Estimated taxes: pay as you go, four times a year

Because no employer withholds tax for you anymore, the IRS wants its share throughout the year instead of one giant bill in April. If you expect to owe $1,000 or more, you generally make four estimated payments. It sounds like a chore, but it's the very thing that saves you from the April gut-punch.

Do this

1. If you expect to owe $1,000+ for the year, plan on quarterly estimated payments using Form 1040-ES.
2. Payments are roughly quarterly — typically mid-April, mid-June, mid-September, and mid-January. Confirm exact dates each year (they shift for weekends and holidays).
3. Use the safe harbor: pay at least 100% of last year's total tax (110% if higher income), or 90% of this year's, to avoid a penalty.
4. Pay online with IRS Direct Pay or EFTPS — free, fast, and you get a confirmation to keep.

Never miss a quarterly payment

• Estimate this year's profit and roughly what you'll owe (income tax + 15.3% SE tax)
• Divide into four and calendar all four due dates now
• Move each payment out of your 'taxes' savings the week it's due
• Pay via IRS Direct Pay or EFTPS and save the confirmation
• Lean on the safe harbor (100%/110% of last year) so you're never underpaid