There’s something about October that feels like a beginning. Maybe it’s the shift in weather, or the way the year suddenly feels finite. Whatever it is, October offers entrepreneurs something rare: a moment to breathe before the sprint to year-end begins.
While most business owners are still coasting through fall, the savvy ones are doing something different. They’re treating October like a dress rehearsal for January—cleaning up the mess, tightening the bolts, and setting themselves up for a stronger finish to the year.
If you’ve been putting off the “boring” parts of running your business, this is your permission slip to tackle them now. Not in December when you’re drowning in holiday chaos. Not in January when you’re trying to execute new plans. Right now, when you still have breathing room.
Here’s your October reset checklist.
1. Dust Off Your Financials
Let’s start with the most neglected part of most businesses: the books.
Don’t wait until January to discover missing receipts, miscategorized expenses, or invoices that never got sent. The longer you wait, the harder it becomes to remember what that random $347 charge was actually for, or which client that draft invoice was meant for.
Start with a basic financial audit. Reconcile all your bank and credit card accounts through September. Make sure every transaction is accounted for and properly categorized. It’s tedious work, but it’s also the foundation of every other decision you’ll make about your business.
Next, check your receivables. Make sure all invoices are sent and collected. Nothing kills cash flow faster than forgetting to actually bill for work you’ve already done. If you have outstanding invoices, now’s the time to follow up—before everyone disappears for the holidays.
Finally, verify that your payroll and contractor payments match your records. Discrepancies here can create serious tax headaches later, and they’re much easier to fix now than during tax season.
If you work with a bookkeeper or accountant, schedule a Q3 review meeting this month. Don’t wait until they’re buried in December deadlines. A calm, focused conversation in October is worth three frantic emails in January.
2. Revisit Contracts and Renewals
Here’s a money leak most entrepreneurs don’t notice: the quiet auto-renewals.
Fall is peak season for vendor and service contracts to automatically renew, often with subtle price increases tucked into the fine print. When was the last time you actually looked at what you’re paying for software subscriptions, insurance policies, or professional services?
Pull out your contracts—yes, all of them—and look for three things. First, hidden price increases that kick in at renewal. That $99/month software might be about to become $149/month, and if you’re not paying attention, you’ll only notice when your annual budget stops adding up.
Second, automatic renewal clauses that trap you for another year. Some contracts make it deliberately difficult to cancel, requiring 60 or 90 days’ notice. If you miss that window, you’re stuck paying for another full year of something you might not even need.
Third, services you no longer use. We’ve all been there: the marketing tool you tried once, the insurance policy that’s redundant now, the consultant retainer you forgot to cancel. These zombie expenses quietly drain your profit margin month after month.
Set a reminder on your calendar for next October to do this exercise again. Fifteen minutes of contract review each fall can save you thousands of dollars and countless headaches.
3. Audit Your Customer and Vendor Relationships (and Get Your W-9s)
October is the perfect time to take a hard look at who you’re doing business with—and whether those relationships still make sense. But there’s also a critical compliance task hiding in this review: getting your tax paperwork in order.
Start with your customer list. Not all revenue is created equal. Some clients pay on time, respect your boundaries, and are genuinely pleasant to work with. Others are perpetually late on payments, demand constant exceptions, and consume a disproportionate amount of your mental energy. Pull your client profitability report and ask yourself: Are there any customers I should fire?
It sounds harsh, but keeping problem clients is expensive. They don’t just cost you money—they cost you opportunity. The time you spend managing a difficult client is time you can’t spend serving good ones or growing your business. If someone consistently makes your life harder, October is the month to plan your exit strategy or renegotiate terms for next year.
On the flip side, look at your best clients. Are you showing them enough appreciation? A simple thank-you note, a surprise discount, or early access to a new service can go a long way. Your best customers are your biggest asset—make sure they know it.
Now do the same exercise with vendors and contractors—but add one crucial step: collect W-9 forms from everyone you’ve paid $600 or more this year. You’ll need these to issue 1099s in January, and trust me, chasing down tax forms during the holidays is nobody’s idea of fun. Do it now while you have time and leverage.
While you’re at it, evaluate whether you’re still getting value from everyone you’re paying. Are there suppliers who consistently underdeliver or create more work than they save? Just like with clients, vendor relationships need regular evaluation. Sometimes loyalty becomes inertia, and inertia becomes expensive.
This isn’t just about being organized—it’s about staying legally compliant. Getting your W-9s now means you won’t be scrambling to meet the January 31st 1099 deadline. And that vendor audit? It might reveal misclassified workers or contract terms that need updating before they become legal headaches. A little proactive cleanup in October can prevent expensive problems down the road.
4. Tighten Up Operations
While you’re in cleanup mode, tackle the small operational fixes that never feel urgent but always pay dividends.
If you have employees, update your employee handbook and HR policies. Employment laws change, your business evolves, and those outdated policies can create liability. A few hours of updates now can prevent expensive problems later.
Back up your critical data and client files. When was the last time you actually tested your backup system? Don’t wait for a catastrophic failure to find out your backups haven’t been working for six months. Make sure everything important is stored securely and redundantly.
Review your cybersecurity practices, especially before the holiday shopping season when cyber threats spike. Update passwords, enable two-factor authentication, train your team on phishing awareness, and make sure your payment systems are secure. Think of it as your business’s version of changing the smoke detector batteries—unglamorous but potentially lifesaving.
5. Reflect on What’s Working—and What’s Not
The October reset isn’t just about administrative cleanup. It’s also about strategic clarity.
Take an hour—just one hour—to honestly assess your business. What’s one product, service, or process you should stop doing? We all have something we’re hanging onto out of habit, guilt, or the sunk cost fallacy. Maybe it’s a service that’s more trouble than it’s worth, a client segment that drains your energy, or a marketing channel that’s never produced results. Give yourself permission to let it go.
Then ask the opposite question: What’s one thing that’s been quietly working well that deserves more focus? Often, our biggest opportunities aren’t new shiny objects but double-downs on what’s already proving successful. Maybe it’s a product that sells itself, a referral source you’ve been undervaluing, or a process that’s more efficient than you realized.
This kind of honest reflection is hard to do in the middle of execution. October gives you the space to think clearly before you start planning for next year.
Bottom Line
A few focused hours in October can make your December far less stressful and your January far more strategic. Instead of scrambling to close your books, renew contracts at the last minute, and wonder why you’re still paying for that thing you cancelled six months ago, you’ll start the new year with clean books, clear priorities, and a business that’s actually set up to execute on your plans.
The entrepreneurs who succeed aren’t necessarily the ones with the best ideas. They’re the ones who handle the boring stuff consistently, so they have the bandwidth to focus on what actually grows their business.
Don’t wait for January to get your house in order. Do it now, while you still have time to do it right.