DENISE STUBBS, CPA

If you’re self-employed, a freelancer, or own a small business, one of the most important tax deadlines of the year is coming up fast: June 15, 2026. This is your Q2 estimated tax payment deadline, covering income earned from April 1 through May 31. If you’ve been having a good year, or if you owed money last April, this payment matters more than you might think. Here’s what every self-employed person should understand before June 15. Why Estimated Taxes Exist W-2 employees h

Most people who work for an employer don't think much about taxes throughout the year because their employer handles it. Money comes out of each paycheck, gets sent to the IRS, and by tax time, things roughly even out. Simple. But the moment you add self-employment income, freelance work, rental income, investment gains, or significant side hustle money to the picture, that system breaks down. Nobody is withholding taxes on your behalf. That responsibility becomes yours.

It's mid-February and you're realizing you might not have everything together by April 15. Maybe you're missing a K-1 from a partnership. Maybe your bookkeeping is a mess and you need more time to sort it out. Maybe life happened and you just can't deal with taxes right now.

Fall Tax Deadlines You Don't Want to Miss