Welcome to Business of One, the biweekly read for people running the whole show, solo.
Each issue connects what’s happening in the world to what it means for your business and your wallet- the financial concepts worth knowing, what’s coming on the tax calendar, and what’s actually worth your attention online.
Good to have you here. Let’s get into it.
The Brief
What’s happening and what it means for your business
- Deadline coming: Q3 estimated taxes are due September 15, 2026. That’s two weeks out.
- Ask the accountant: Missed your first couple of quarterly payments this year? Here’s why it’s still worth paying in September.
- Tool we’re testing: Tired of reconstructing your mileage log from memory come tax time? We tried an app that tracks drives automatically.
- The number: 70- the percent of U.S. workers who have historically received a paid holiday on Labor Day.
The Big Idea
Labor Day Is for Employees. What About You?
Labor Day lands on September 7 this year, and if you’re running solo, it’s a strange kind of holiday. There’s no company-wide email announcing the office is closed, no coworker covering your inbox, and no one clocking out but you.
That’s not a complaint- it’s just the reality of being both the owner and the only employee. And it means the decision to truly take the day off is entirely yours to make, which is exactly why so many solo business owners don’t.
Here’s a different way to think about it: an unplanned day away from your business is useful information. If a single day off feels impossible- if clients would notice, invoices would stall, or nothing would move forward without you- that’s a sign of how much of the business currently lives in your head alone.
Treat the long weekend as a small test. Pick one task that only you currently know how to do, and see if you can hand it off, automate it, or at least write down the steps before Friday. You don’t have to fix everything by Monday. You just need to find the one thing that would break first, so you know what to work on next.
Ask the Accountant
Q: I’ve missed the first couple of quarterly payments for the year. Should I bother paying September’s?
A: Yes- paying now still helps, even though it may not undo the penalties on the payments you already missed.
The IRS assesses underpayment penalties separately for each quarter, based on how late and how large the shortfall was. But you don’t have to treat catching up as its own separate task. The simplest move is to pad your September payment, putting the extra toward what was missed for April and June. That said, any payment is better than none: it brings down the balance you’ll still owe when you file in April, and it lowers the risk of another penalty stacking on top of the first two..
A few things that can help:
- Pay what you can, even if it’s not the full amount: Partial payments reduce the balance the penalty is calculated on.
- Check if you qualify for safe harbor: If you pay at least 90% of this year’s tax bill, or 100-110% of last year’s, you may reduce or avoid penalties.
- Get ahead of January: The fourth quarterly payment is due January 15. Catching up now makes that one easier to hit on time.
Skipping a payment because you already missed a couple doesn’t save you money, it adds another quarter to the pile. Figure out what you owe before the September 15 deadline so you can make a plan to catch up.
Tool We’re Testing: MileIQ
With Q3 taxes on your mind, mileage is one of the easier deductions to lose track of- especially if you’re trying to reconstruct months of trips from memory right before a filing deadline. We’ve been testing MileIQ, an app that runs in the background on your phone, automatically logs each drive, and lets you swipe to mark it as business or personal.
It won’t tell you which trips actually qualify as deductible- that’s still a conversation for your accountant. But if your mileage log currently lives in your memory instead of anywhere your accountant can see it, this removes most of the friction of tracking it going forward.
Worth testing if: You drive for client meetings, errands, or other work-related trips regularly and don’t already have an automatic way to log the miles.
Around the Web
Your next watch: We broke down how to build your business credit
Your next read: If you haven’t chosen your favorite AI minion yet, a new one has entered the scene
Your next event: Have your own questions about quarterly taxes? Join us this Thursday, September 3rd for our free webinar: Tax Moves to Make Before September 15th
Member spotlight
Itzel Islas, Graphic Designer & Illustrator
Itzel built a business around color, culture, and community, creating logos, branding, murals, and workshops that help people and brands tell more vibrant stories. Like a lot of creative solopreneurs, the business side came second to the craft. Invoicing, taxes, and quarterly payments weren’t exactly part of the dream.
After joining Collective, Itzel got her S-Corp set up, her books in order, and her tax strategy dialed in, which meant less time stressing about money and more time doing the work she actually started the business to do.
Read Itzel’s full Faces of Collective highlight.
