You’re reading Business-of-One, the twice-a-month briefing for solo business owners who don’t have a finance team- because they are the finance team.
Every issue takes what’s moving in the economy and connects it to what it actually means for a one-person business: the deadlines on your calendar, the concepts worth understanding, and the noise worth tuning out.
Let’s get into today’s issue.
The Brief
What’s happening and what it means for your business
- Deadline today: Q3 estimated taxes, plus extended S Corp and partnership returns, are due September 15.
- Ask the accountant: Realized an S Corp election could have saved you money this year? Here’s when it’s still possible to make it count retroactively.
- Tool we’re testing: A flat-fee financial planning membership that pairs you with a real CFP® with no AUM fees or product pitches.
- The number: $20,000- the new 1099-K reporting threshold (up from $600) that quietly kicked back in this year, thanks to a tax law most solopreneurs missed.
The Big Idea
The Tax Form You Might Not Get This Year (And How to Prepare)
Last year’s tax law overhaul, the One Big Beautiful Bill Act (OBBBA), quietly rewrote a couple of rules that hit solopreneurs directly, and one is becoming real this filing season.
Platforms like Etsy, eBay, Uber, and payment apps were on track to send a 1099-K to anyone who crossed $600 in a year. That threshold has reverted to $20,000 and 200 transactions- the original bar before it was lowered. That means far fewer 1099-Ks will land in your inbox this year, but the income behind them is still taxable whether or not a form ever arrives. It’s a paperwork change, not an income change.
The practical effect is that since fewer 1099-Ks will show up to remind you what you earned, it’s on you to track every platform payout, invoice, and client payment yourself. It’s worth five minutes today to check that your bookkeeping reflects this change before filing season hits.
Ask the Accountant
Q: I didn’t file my S Corp election by the deadline earlier this year. Is it too late to make it count for this tax year?
A: Not necessarily. The IRS allows late S Corp elections in certain cases, but whether yours qualifies depends on why you missed the window and how you’ve been operating since.
Normally, an S Corp election (Form 2553) has to be filed within two months and fifteen days of the start of the tax year you want it to apply to- March 15 for most calendar-year businesses. The exception is the IRS’s late-election relief process, which lets you request that the election apply retroactively to this year. A few things that matter:
- Reasonable cause is required: Simply forgetting isn’t enough on its own- you’ll need an explanation the IRS will accept, such as relying on a preparer who didn’t file it.
- Consistency matters: If you’ve been running payroll and filing as though the election was already active, that supports the request. If you haven’t, retroactive relief gets harder to justify.
- There’s still a deadline: Late-election relief is generally available up to three years and 75 days after the effective date you’re requesting- but the sooner you file, the cleaner the case.
Getting compliant with a retroactive election isn’t a DIY project. Reasonable cause must be documented and your compliance tool-kit in place. Set up a chat with our team at Collective.com before you file anything.
Tool We’re Testing: Facet
With Q3 estimated taxes behind you, it’s a good time to zoom out and ask whether your money has an actual plan behind it, not just a place to sit. We’ve been testing Facet, a flat-fee financial planning membership that pairs you with a team of CFP® professionals to help with investments, taxes, and benefits, without the AUM percentage fees or product-sale incentives that come with a lot of traditional advisors.
Worth testing if: You’ve got the quarterly taxes and bookkeeping under control but have never had an actual financial plan for retirement, benefits, or long-term goals.
Around the Web
Your next watch: We highlighted 6 solopreneurs running million dollar businesses as your gentle reminder that “you’ve got this.”
Your next read: Because ‘I’ll figure it out when I need to’ is not a retirement plan. Invest in your next skill before your business forces your hand.
Your next event: Have questions about your own S Corp timeline? Join us for our free webinar: Why S Corp Isn’t Out of Reach: How Solos Can Still Save in 2026
Member spotlight
Luke Stone, Independent studio founder
Luke built Studio Tahluk, an award-winning animation studio with a footprint in both Los Angeles and Melbourne, to spend his time doing what he loves: animating. From first-sketch concepts through storyboarding, production, and post, the studio has brought stories to life for television shows, music videos, commercials, and even an off-brand puppet musical.
After bringing in Collective to handle the back office, Luke got the paperwork and tax questions off his plate, freeing up the creative bandwidth to keep building.
Read Luke’s full Faces of Collective highlight.
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