You’re reading Business-of-One, the bi-weekly briefing for solo business owners moonlighting as their own finance team.
Every issue takes what’s moving in the economy and connects it to what it actually means for a one-person business.
Let’s get into today’s issue.
The Brief
What’s happening and what it means for your business
- Deadline ahead: October 15 closes out extended 2025 returns and is the last call to make a 2025 SEP-IRA contribution.
- Ask the accountant: Buy your own health insurance? Here’s why open enrollment (Nov 1-Jan 15) still matters for the self-employed.
- Tool we’re testing: An AI email add-on that sorts inbox noise from what truly needs a response.
- Around the web: ACA premiums are set to jump 15% in 2027, plus whether business credit card rewards are taxable.
The Big Idea
October 15 Is Closer Than It Looks
If you filed a tax extension back in April, October 15 is the date it’s been buying you time toward. It’s the final deadline to file your 2025 Form 1040 – and this year, it lands on a Thursday. Miss it, and the failure-to-file penalty your extension was holding off starts running: 5% of unpaid tax per month, up to 25%. If you owed money and didn’t pay it back in April, interest and the smaller failure-to-pay penalty have already been accruing since then regardless.
The date also carries a second deadline that’s easy to miss. If you have a SEP-IRA and filed an extension, October 15 is your last chance to make a 2025 contribution – up to 25% of net self-employment earnings (after the deduction for half your self-employment tax), capped at $70,000 for 2025. It’s one of the few retirement moves you can still make for a year that’s already over, so it’s worth a final look at your numbers before the window closes.
The practical step this week is to block off time to confirm your return is filed (or filing) and to decide whether a SEP contribution makes sense before the 15th. Waiting until the 14th leaves no room if your bookkeeping needs a cleanup first.
Ask the Accountant
Q: I buy my own health insurance since I don’t have an employer plan. Does open enrollment matter for someone self-employed?
A: Yes. Marketplace open enrollment typically runs from November 1 through January 15, and outside that window you generally can’t enroll in or change a marketplace plan unless you qualify for a special enrollment period, such as marriage, a new child, or losing other coverage. Missing it means being locked into your current plan or potentially going without coverage until the next window opens.
On the tax side, self-employed health insurance premiums are usually deductible above the line, meaning you don’t need to itemize to claim them. The deduction can’t exceed your net self-employment income, and it doesn’t apply for any month you were eligible for a subsidized plan through a spouse’s employer. If you’re weighing plans during open enrollment, it’s worth running the numbers with your accountant before you pick one.
Tool We’re Testing: SaneBox
With Q4 ramping up, inbox overwhelm becomes a real tax on a solo operator’s time. We’ve been testing SaneBox, an email add-on that layers onto your existing inbox and uses AI to sort low-priority messages into a separate folder, so your main inbox holds only what actually needs a response. It also handles snoozing, follow-up reminders, and sends a daily digest of everything it filtered out, so nothing gets permanently lost.
Worth testing if: You’re spending real time each morning triaging an inbox that’s more noise than signal, and you’d rather have that sorted automatically than build your own filter rules.
Around the Web
Your next watch: Are business credit card rewards taxable? We broke down the tax law.
Your next read: Not-so-great news for your wallet- ACA premiums are jumping 15% in 2027
Your next event: Collective will be at FRAK 2026 sharing insights on the rise in solopreneurship and how to set up your business for success
Member spotlight
Anita Barcsa, Photographer
San Francisco portrait photographer Anita Barcsa took a winding path here — fashion design, art history, personal chef work, martial arts, and street photography across the world before settling into her craft. A Hungarian native, she credits early hardship with building the resilience behind her entrepreneurial drive.
Professionally, Anita is the photographer behind Collective’s community spotlight portrait series. She’s also navigated major personal milestones as a self-employed business owner, including buying her first home during a high-interest-rate period, leaning on organized financials and Collective’s support to get through the process. Her advice to fellow self-employed people: don’t wait for the “perfect” moment to buy, and look into FHA loan options for lower down payments.
Read Anita’s full Faces of Collective highlight.
