09/03/2026
Your paycheck isn't covering all your taxes anymore ๐จ
Once your income picture gets more complex, the IRS expects you to pay them directly throughout the year, not just at filing time.
These 3 income events are the most common triggers:
Side income or full self-employment. No employer means no automatic withholding. Self-employment tax can run as high as 15.3% on top of your regular income tax rate, and skipping quarterly payments can mean IRS underpayment penalties on your April return.
A big bonus or equity payout. Your employer withholds at a flat supplemental rate, which often falls short of your real tax bracket. That shortfall is yours to make up, ideally before year-end.
Capital gains from selling investments, property, or a business interest. Nothing is withheld on these transactions, but the IRS still expects payment, and they have a timeline in mind.
The good news: there's a safe harbor rule that shields you from penalties if you plan ahead.
The penalty for missing it isn't enormous. The missed planning window is.
If any of these situations sound familiar, reach out and let's figure out exactly where you stand.
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