It’s January. Tax season is here. 5 signs you’re already behind (from a small business accountant who's seen it all—and how to take action now).
- Karolyn & Bryan LaLonde
- 7 hours ago
- 3 min read
January isn’t too late.
Here’s how to shift from scramble to strategy.
It’s January.
If tax season feels like it’s barreling toward you and you’re not ready. You might be behind, but you’re not alone.
For many small business owners, the start of the year brings a hard look at the books, and some telltale signs that things didn’t stay as up-to-date as you hoped.
Here are five red flags you’re heading into tax season behind, and what you can do now to turn things around without the panic spiral.
🚩 1. “I haven’t finished last year’s books yet…”
Why it matters: If December’s not reconciled, chances are the rest of the year isn’t either, which means your numbers might be wrong (or incomplete) come tax time.
What it looks like: You meant to finish your books over the holiday break, but December's expenses are still sitting in your inbox. You’re not confident your Profit & Loss is accurate, and that makes everything else feel shaky.
Take action: Start with the most recent reconciled month and work backward. Use a simple tracker to note what’s complete. Need backup? We've designed our firm for exactly this kind of catch-up and bookkeeping support.
🚩 2. “Wait, do I owe 1099s to anyone?”
Why it matters: The January 31 deadline to send 1099s to contractors (and the IRS) creeps up fast. If you haven’t confirmed who needs one or whether you have W-9s on file, you’re behind.
What it looks like: You worked with a freelance designer, a part-time consultant, and a few contractors, but you can’t remember who got paid via Venmo, PayPal, or check.
You’re unsure who qualifies, and those W-9s? Maybe in your inbox. Maybe not.
Take action: Pull a contractor payments report from QuickBooks and check for vendors paid $600+ via cash, check, or bank transfer.
🚩 3. “My business changed a lot last year, but I haven’t updated my tax plan.”
Why it matters: Hired employees? Switched entity types? Started selling online? These changes could impact everything from deductions to deadlines.
What it looks like: You made big moves, maybe your first employee, maybe a shift to an S-Corp, but your tax advisor hasn’t asked about it yet. You’re relying on last year’s process, but your business isn’t the same.
Take action: Make a list of business changes from the past year. Even if you’re not sure what’s tax-relevant. If you think it's time to amp up up strategic support after an increase in your 2025 revenue, it might be time to consider a vCFO.
🚩 4. “I haven’t logged into QuickBooks in weeks… maybe months.”
Why it matters: If opening QuickBooks makes your stomach drop, there’s probably something broken, missing bank connections, duplicate transactions, or worse.
What it looks like: Your bank feeds disconnected months ago. You know there are duplicate charges. Logging in feels overwhelming, so you don't, hoping things will somehow resolve themselves.
Take action: Start with a 15-minute daily check-in to slowly re-engage. And if the mess is bigger than you can manage, find a trusted bookkeeper or accounting firm who can support you in a full clean-up with clarity and compassion.
🚩 5. “I have no idea what I owe or if I owe anything.”
Why it matters: January 15 is the final estimated payment for 2025 and it’s easy to miss if your income tracking isn’t solid.
What it looks like: You didn’t send in quarterly payments because you weren’t sure how much to pay. Now you’re unsure if you’re behind, ahead, or about to get hit with a surprise bill.
Take action: Pull a Profit & Loss report for 2025 and review your net income. If you need help calculating or submitting your estimated payment, we’ve got you.
📌 If any (or all) of these feel painfully true as you enter January and tax season, you might be behind, but you're not alone.
We see it all the time. It’s normal and honestly, it’s a milestone.
Outgrowing your DIY bookkeeping or having a year where you couldn’t stay as on top of things as you usually do?
That’s not failure.
It’s a sign your business is growing and shifting.
January is the time to ask for help from a trusted accountant who can help you clean up what’s behind, get you caught up, and make sure nothing gets missed this tax season.
Let’s talk about getting your books ready.
Stillwater Business Solutions is run by Karolyn and Bryan, a tech-savvy and community-focused team who believe bookkeeping should feel collaborative and empowering—not confusing. Whether you're looking to simplify your systems or get support you can trust, we're here when you're ready. No pressure. Just people-first accounting that fits your business.