You’re reading Business-of-One, the bi-weekly briefing for solo business owners pulling double duty as their own CFO.
Every issue takes what’s moving in the economy and connects it to what it 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
- Q4 kickoff: The year-end tax and cash-flow moves worth making before the holiday rush hits.
- The Deadline: October 15 is the extended filing deadline if you requested more time back in April.
- New tool: Our 2026-2027 tax deadline calendar, synced to Google Calendar, so deadlines show up before they sneak up on you.
- Around the web: Why the ACA subsidy cliff could cost self-employed households thousands next year.
The Big Idea
Q4 Is Showtime: What to Handle Before the Holiday Rush
Q4 started two weeks ago, and for a one-person business it’s rarely just “the last stretch.” If you sell a product, this is the run-up to the biggest shopping weeks of the year. If you sell a service, it’s the quarter where clients either rush to spend down their 2026 budget or go quiet until January. Either way, what you do with the next 11 weeks shapes your whole year’s numbers.
On the tax side, Q4 is when year-end moves have to happen, not just get planned. A Solo 401(k) has to be opened by December 31 even if you fund it in 2027. Equipment or software you buy and put into use before year-end can often be written off immediately instead of depreciated over several years. And if you’re weighing an S Corp election for next year, this is the window to speak with our team. That paperwork has deadlines too.
On the business side, now’s the time to get practical. If you hold inventory, check vendor lead times before shipping slows down in December. If you invoice clients, send a friendly nudge about any 2026 budget they’re sitting on before it resets to zero in January. And either way, sketch a rough cash-flow map for November and December so a slow week doesn’t catch you off guard.
Ask the Accountant
Q: I filed an extension back in April, but I still haven’t paid everything I owe for 2025. What should I do before October 15?
A: File anyway. The failure-to-file penalty (5% of unpaid tax per month, up to 25%) is far steeper than the failure-to-pay penalty (0.5% per month), so submitting your return and paying whatever you can afford is almost always cheaper than waiting until you have the full balance. Keep in mind interest has already been accruing on any unpaid 2025 tax since the original April deadline. The extension only bought you more time to file, not to pay.
Send what you’re able to with the return, then set up an IRS payment plan for the rest – short-term plans of 180 days or less typically don’t carry a setup fee, and online long-term plans carry a modest one. Interest will keep accruing on whatever’s left, but it’s small compared to what the late-filing penalty would cost you.
Your next tool: Tax Deadline Calendar
Our team built a calendar that maps every tax deadline through the end of 2027 – quarterly estimates, 1099 and W-2 filing dates, SEP-IRA and Solo 401(k) windows, S-corp election cutoffs, and more. Sync it straight to your Google Calendar and each deadline shows up with enough lead time to act on it.
Worth adding if: You’ve ever missed a deadline because it wasn’t on your radar until the week it was due, or your current system is a sticky note.
Around the Web
Your next watch: Worried about the possibility of an audit? Our team broke down how to prep your solo business finances.
Your next read: On the ACA subsidy cliff – how crossing a household income threshold ahead of November’s open enrollment can mean losing thousands in premium assistance.
Your next event: Collective and Solo Health team up to discuss what open enrollment means for solopreneurs and how it becomes a deductible business expense.
Member spotlight
Brian Liu, Art Director & Founder of DRMWKND
Brian Liu left a career shaping hospitality and lifestyle brands to launch DRMWKND, his San Diego-based design studio, in 2020. Five years later, the client roster spans hotels, wellness brands, and startups, built almost entirely through referrals.
Brian credits a tight circle of fellow founders, and his Collective team, for making the business side feel less isolating. His advice: find people who are genuinely good at the parts of running a business that aren’t your strength, so you can stay focused on your craft.
Read Brian’s full Faces of Collective highlight.
Have We Met?
We’re Collective, a back-office platform built exclusively for solo business owners. We handle business formation, bookkeeping, payroll, and taxes for thousands of one-person businesses across the U.S.
We started the Business-of-One weekly newsletter because the financial side of self-employment is complicated and most of the advice out there is written for companies with finance teams, not for people running the whole operation themselves. We’re here to change that. Know a solopreneur that needs to read it? Share the love.
