Welcome to The Write-Off!
I'm Tyler, an Enrolled Agent. What is an Enrolled agent? It is a tax professional licensed by the federal government to represent taxpayers before the IRS. I’ve been in the tax industry for almost a decade and my goal is to share my expertise and experience in plain English so self employed people and entrepreneurs know more about accounting and taxes. Every issue, I translate one tax or money topic into plain English so you, the self-employed, keep more of what you earn and never get blindsided by a deadline. No jargon, no fear-mongering. Just what to do and when.
Let's start with something on the clock.
The Main Thing: Your Q2 payment is due Monday, June 15
When you're self-employed, no employer withholds taxes for you. The IRS still wants its cut throughout the year. So you pay it yourself in four estimated installments. The second one for 2026 is due Monday, June 15, and it covers income you earned from April 1 through May 31.
Miss it, and the IRS charges an underpayment penalty. This is effectively interest that compounds from the due date until you pay. It's avoidable, and it's usually small relative to the stress of scrambling later.
Do you even need to pay? As a general rule, you're expected to make estimated payments if you'll owe at least $1,000 in tax for the year after subtracting withholding and credits. Most profitable self-employed people clear that bar easily.
How much to send (the safe-harbor shortcut)
You don't need to predict your full-year income perfectly. The IRS gives you a "safe harbor" — pay at least one of these across the year and you avoid the underpayment penalty even if you end up owing more at filing:
90% of this year's total tax, or
100% of last year's total tax (110% if your prior-year adjusted gross income was over $150,000).
The simplest approach for most people: take last year's total tax, apply the right percentage, divide by four, and send that each quarter. Predictable, and penalty-proof.
Remember self-employment tax. Your estimate isn't just income tax — it also includes self-employment tax of 15.3% (12.4% Social Security up to the annual wage cap, plus 2.9% Medicare) on your net self-employment earnings. Forgetting this is the #1 reason people underpay.
Do This Now
Pull last year's Form 1040 and find your total tax line.
Apply your safe-harbor percentage (100%, or 110% if prior-year AGI topped $150,000) and divide by four.
Pay online before June 15 at IRS Direct Pay (irs.gov/payments) or through your IRS Online Account — about five minutes, with instant confirmation. Prefer mail? Use a Form 1040-ES voucher, postmarked by the 15th.
On the Calendar — 2026 Estimated Tax Dates
Q1 — April 15, 2026 (passed)
Q2 — June 15, 2026 (Monday)
Q3 — September 15, 2026
Q4 — January 15, 2027
Note the periods are uneven — Q2 only covers two months. That quirk trips people up every year.
Quick Hits
Pay even if you can't pay it all. A partial payment shrinks the penalty base. Something beats nothing.
Had a big income jump this year? The prior-year safe harbor still protects you from penalties — even if you'll owe more at filing.
Set a recurring reminder now for September 15 and January 15. Future you will be grateful.
See you next week,
Tyler Rodriguez, EA
The Write-Off
The Write-Off. All Rights Reserved. The Write-Off is general educational information, not personalized tax advice. Your situation may differ. Please consult a tax professional about your specifics. The Write-Off ·
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