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Here’s exactly what to send, and how much.
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Good morning! Quick heads-up before anything else: your Q3 estimated tax payment is due September 15 — five days from now. If that payment isn’t already sitting in a separate account, this is your nudge. This week: how to get that payment right, what happens when a side hustle outgrows your day job’s withholding, and a Social Security myth we’re finally killing.
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🗓️ Your Q3 payment is due in 5 days: What it is, how to calculate it, and the penalty that shows up if you skip it.
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📈 What happens when your side income grows faster than your withholding: The day job used to cover you. Then the business started paying better than the day job.
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🔁 Self-employment tax vs. FICA — are you actually double-paying into Social Security?: Probably not. Here’s the form that’s already fixing it, and the one situation where you really can get money back.
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🛠️ Plus: Three built-in calculators — one per article — so you can run your own numbers instead of taking our word for it.
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Follow us for even more great tips, tricks, and deadline reminders.
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The Basics
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🗓️ Your Q3 payment is due in 5 days — here’s what to send
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The Quick & Bristly: Your third-quarter estimated tax payment is due September 15 — five days from today. If you expect to owe $1,000 or more in tax for the year after subtracting withholding and credits, this is one of your four required payments, not optional. Miss it or underpay and you owe a penalty on top of the tax, calculated like interest, back to the date it was due.
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Nobody hands you a manual when you start a business. You find out about quarterly taxes the way most people find out about tax rules — after the fact, via a penalty notice. This week, you get the heads-up instead.
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Why September 15 matters right now
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The U.S. tax system is pay-as-you-go. Employees satisfy this through payroll withholding. Business owners don’t have a payroll department doing that for them, so the IRS requires estimated payments instead, four times a year — and the next one lands in five days.
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September 15, 2026 covers income earned June 1 through August 31 — that’s the payment due this week
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The full 2026 schedule is April 15, June 15, September 15, and January 15, 2027
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They’re not evenly spaced — that’s not a typo, that’s just how the IRS built the calendar decades ago and never fixed it
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You’re on the hook if you expect to owe at least $1,000 in tax for the year, after subtracting withholding and refundable credits
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Most sole proprietors, freelancers, and small LLC owners clear that bar without trying
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Knowing the date matters less than knowing the number. Here’s the fast way to get one.
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How to actually calculate the payment
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Most people use Form 1040-ES: estimate your annual net income, calculate the income tax and self-employment tax you’ll owe on it, then divide by four. Uneven income? The annualized income installment method lets you pay less in slow quarters and more in busy ones, matching payments to when the money shows up.
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The penalty, and the way around it
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Miss a payment or underpay and the IRS charges an underpayment penalty, calculated like interest on the shortfall from the date it was due.
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There’s a safe harbor that protects you from the penalty even if you underestimate:
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Pay at least 90% of what you’ll owe this year, or
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Pay 100% of what you owed last year (110% if last year’s AGI was over $150,000)
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Hit either number and you’re penalty-proof, even if your final bill is bigger than expected.
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🛠️ Try: The Quarterly Payment Calculator
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Before you send anything Monday, run the actual number. A guess that’s too low costs you a penalty; a guess that’s too high ties up cash you might need.
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Bookkeeping that doesn’t require an accounting degree
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The Deep Dive
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🔁 Self-employment tax vs. FICA — are you actually double-paying into Social Security?
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The Quick & Bristly: If you have a W-2 job and a side business, it’s reasonable to worry you’re paying Social Security tax twice — once through payroll withholding, once through self-employment tax. Mostly, you’re not: Schedule SE has a built-in worksheet that reduces your self-employment Social Security tax by wages you’ve already paid it on. The real double-pay scenario involves two W-2 jobs, not a job plus a business, and it has its own fix.
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This is one of the most common tax myths among business owners with a day job on the side. The worry: my employer withholds Social Security tax from my paycheck, and self-employment tax includes a Social Security component too. Am I paying into the same 12.4% twice?
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Mostly, no — and the form that prevents it is one almost nobody reads past line 4.
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The form that’s already handling it
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Schedule SE includes a section (lines 7 through 10) specifically for this situation:
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It takes the Social Security wage base for the year — $184,500 for 2026
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It subtracts any W-2 wages you already paid Social Security tax on
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Only the remainder gets hit with the 12.4% Social Security portion of self-employment tax
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If your day job wages already meet or exceed the wage base on their own, the Social Security portion of your self-employment tax on the business income drops to zero
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The form does this automatically. You don’t have to ask for it, and you don’t get to skip it.
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That’s the theory — here’s how to see it play out with your own numbers.
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Where the myth has a grain of truth
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The 2.9% Medicare portion has no wage base and no such reduction. It applies in full to every dollar of net self-employment earnings, regardless of what you already paid at your job. Medicare tax is never capped, for anyone.
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Where you actually can double-pay (and get it back)
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That takes two W-2 jobs, not a job plus a business.
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Each employer withholds Social Security independently, with no visibility into the other
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Combined wages over the wage base can push total withholding above the annual maximum
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Fix: a refundable credit on Schedule 3, line 11, when you file
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It’s a real credit, but it belongs to the multiple-employer situation, not the self-employment-plus-day-job one this article is about.
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The takeaway: self-employment tax already avoids true double-taxation on the Social Security side. It can’t fix the Medicare side, because that one was never capped.
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🛠️ Try: Social Security Double-Pay Checker
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Two employers, one overlooked refund. Plug in your numbers and see if you’re owed money back.
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