Your money year has four dates that matter most as a self-employed tradesperson: quarterly estimated taxes due April 15, June 15, September 15, and the following January 15; the 1099-NEC and W-2 deadline in early February; and the December 31 cutoff to put equipment "in service" if you want to write it off this year. Miss the quarterly dates and you get penalties and interest. Miss December 31 and a truck you already paid for counts against next year's taxes instead of this one. Nobody hands a self-employed contractor a payslip with the tax already taken out, so you have to run the calendar yourself. Here is the whole year on one page.
The four quarterly estimated-tax dates
If you expect to owe $1,000 or more in tax for the year, the IRS wants it paid quarterly, not in one lump at filing. For 2026 the dates are:
- Q1: April 15, 2026 (covers January through March)
- Q2: June 15, 2026 (covers April and May)
- Q3: September 15, 2026 (covers June through August)
- Q4: January 15, 2027 (covers September through December)
Pay through IRS Direct Pay or EFTPS, and schedule them in advance so you never miss one. These payments cover both your income tax and your self-employment tax, which in 2026 is 15.3% on 92.35% of your net self-employment income up to the Social Security wage base (verify the current base at ssa.gov), plus 2.9% Medicare on everything above that. Half of your SE tax is deductible above the line.
The safe harbor that makes it penalty-proof
The simplest way to avoid an underpayment penalty is the safe harbor: pay at least 100% of last year's total tax (110% if your prior-year adjusted gross income was over $150,000), split into four equal payments. Do that and it does not matter if this year turns out much bigger, you are protected from the penalty either way.
Worked example (illustrative numbers): Say last year your total tax came to $16,000 and your AGI was under $150,000. Your safe-harbor target is $16,000. Divide by four and you pay $4,000 each quarter. Even if this year you clear far more and end up owing $24,000, you owe no underpayment penalty, because you hit the safe harbor. You still settle the extra $8,000 when you file, but with no penalty on top.
One catch: the Q1 payment on April 15 falls before you have filed the prior-year return, so you need last year's numbers to hand early in the year.
January and February: 1099s and W-2s
If you paid other people for work, you have filing duties at the start of the year.
- 1099-NEC for your subs. If you paid an unincorporated contractor more than the reporting threshold, you owe them a 1099-NEC. That threshold was $600 for 2025 payments and is rising to $2,000 for payments made in 2026, so verify the current figure at irs.gov. Collect a W-9 at the start of every relationship, not in a January scramble.
- The deadline. For 2025 payments, both furnishing 1099-NEC forms to your subs and filing them with the IRS is due February 2, 2026 (because January 31 fell on a Saturday). If you have employees, W-2s to them and the SSA are due the same day.
- Late filing bites. Penalties start around $60 per form and climb steeply the longer you wait, into the hundreds per form for willful failure. Verify the current tiers at irs.gov.
October to December: the equipment window
Section 179 lets you deduct the full purchase price of qualifying equipment in the year you place it in service, instead of depreciating it over several years. The 2026 limit runs into the millions ($2,560,000, with the phase-out only starting at $4,090,000), so the cap almost never binds a small contractor. Bonus depreciation is 100% in 2026 on top of that.
The rule that actually matters for you is the timing: the equipment must be placed in service by December 31. "Bought" is not enough, it has to be received and operational. Finance a work truck, trailer, or tools in November and put them to work, and you can take the deduction this year. Buy on January 2 and you wait a full year.
The honest caveat: a Section 179 deduction cannot push your business income below zero. So the smart move is to check your year-end profit with a CPA in October or November before you spend, rather than buying gear you do not need just to chase a write-off.
The year on one page
- January: review last year's books, prep 1099s and W-2s, Q4 estimated payment due the 15th.
- February: issue 1099-NECs and W-2s by the 2nd, start tax prep.
- March to April: file the return or an extension, pay Q1 by April 15.
- May to June: mid-year income check, pay Q2 by June 15, adjust if you are running ahead or behind.
- July to August: assess year-to-date profit, start thinking about equipment.
- September: pay Q3 by the 15th, begin year-end planning.
- October to November: equipment window, CPA check on Section 179 strategy and year-end profit.
- December: finalize equipment so it is in service by the 31st, close the books.
Why this calendar is your friend
Running it turns tax from a once-a-year panic into four predictable payments and two filing dates. It is also how you stay out of the penalty spiral covered in "I owe the IRS and can't pay," and it works best alongside setting money aside as you earn rather than finding it later (see How much tax to set aside). Surviving a genuinely slow season on saved cash is a separate problem, covered in Surviving the slow season.
Common questions
Do I have to pay taxes four times a year if I'm self-employed?
If you expect to owe $1,000 or more in tax for the year, yes: the IRS wants estimated tax paid quarterly rather than all at once. For 2026 the dates are April 15, June 15, September 15, and January 15, 2027. You pay through IRS Direct Pay or EFTPS. Skipping them does not make the tax go away, it just adds an underpayment penalty and interest on top.
How do I avoid an underpayment penalty on my estimated taxes?
The simplest way is the safe harbor: pay at least 100% of last year's total tax, split into four equal quarterly payments. If your prior-year adjusted gross income was over $150,000, the figure is 110%. Hit that and you avoid the penalty even if this year turns out to be a big one, though you still settle any remaining balance when you file. Verify the current thresholds at irs.gov.
When do I have to send 1099s to my subcontractors?
For payments you made in 2025, the deadline to furnish and file 1099-NEC forms is February 2, 2026. You owe a 1099-NEC to any unincorporated contractor you paid over the reporting threshold, which was $600 for 2025 payments and is rising to $2,000 for payments made in 2026, so verify the current figure at irs.gov. Collect a W-9 from every sub at the start, not in a January scramble.
What's the deadline to buy equipment for this year's tax deduction?
December 31, but with a catch: the equipment has to be placed in service, meaning received and actually operational, by year end, not merely ordered or paid for. Finance a work truck or tools in November and put them to work and you can write them off this year under Section 179; buy on January 2 and you wait a full year. Check your year-end profit with a CPA first, because the deduction cannot push your business income below zero.
What if I can't pay my estimated tax on time?
Pay what you can and file everything on time anyway, because the failure-to-file penalty is far larger than the failure-to-pay penalty. Paying something reduces the interest and penalties building on the balance, and the IRS offers installment agreements if you fall behind. The full playbook is in "I owe the IRS and can't pay." Never borrow from money you withheld from an employee's pay to cover the gap.
The honest bit
- All dates and dollar figures here are for the 2026 tax year and they move. Verify them at irs.gov and, for the Social Security wage base, ssa.gov.
- State income-tax deadlines, thresholds, and any state filing duties are separate from these federal ones and vary. Confirm yours in Working in Your State.
- This is general guidance, not tax advice. For a self-employed tradesperson, a CPA or enrolled agent usually saves more than they cost.
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