September Kickoff: Setting Your Small Business Game Plan

Fall isn’t just football season, it’s business season, too. After a summer that may have been full of vacations, slower sales, or simply a different rhythm, September has a way of snapping everyone back into gear. Kids head back to school, sports return to TV, and small business owners start feeling the pressure of year-end coming fast.

If you don’t want tax season to feel like a desperate fourth-quarter scramble, now’s the time to review your playbook and call the right plays. September is the perfect moment to evaluate where your business stands, clean up messy processes, and make strategic moves before deadlines sneak up.

Here are some winning strategies, football-inspired, of course, to set your small business game plan for the rest of the year.

1. Check Your Scoreboard

Imagine watching a football game where no one bothers to check the score until the last two minutes. Chaos, right? That’s what it’s like to run a business without checking your financials until tax season.

September is the time to pull out your numbers and ask:

• How is revenue stacking up compared to your goals?
• Are expenses creeping higher than expected?
• Do you still have runway to make smart moves before December 31?

A mid-year (or technically, three-quarters-year) review gives you the visibility you need to adjust. If sales are higher than expected, you may need to think about putting aside more for taxes. If they’re lower, you might want to review your pricing strategy, cut unnecessary costs, or invest in marketing to finish the year strong.

Think of this as your halftime show, not just for entertainment, but to reset and come back strong.

2. Tighten Up Your Bookkeeping

Messy books are like fumbling the ball. It’s usually avoidable, but costly when it happens.

If your bookkeeping has been an afterthought this year, September is the time to catch up. Reconciling bank accounts, organizing receipts, and making sure your expenses are categorized correctly will save you headaches later. The last thing you want is to be buried under months of transactions when your tax professional asks for clean reports in January.

And here’s the truth: bookkeeping isn’t just about compliance. Accurate books help you see the field. They tell you where money is really going, which customers or products are most profitable, and whether your cash flow can handle that next big investment.

If you wouldn’t send your quarterback out without knowing the down and distance, why would you run your business without accurate numbers?

3. Plan for Tax Savings

Here’s where strategy comes into play. Taxes aren’t just about filling out forms, they’re about making proactive decisions that can save you money. September is a great time to explore your options because you still have a few months to implement changes before year-end.

Some areas to consider:

• Adjusting how you pay yourself: Depending on your business structure, there may be tax advantages to revisiting the balance between salary, draws, or distributions.
• Retirement contributions: Setting money aside for retirement doesn’t just help future you, it can lower your taxable income today. And if you want to set up a retirement plan for employees, starting in the fall gives you enough time to get it right before deadlines hit.
• Year-end purchases: If you know you’ll need new equipment, software, or other business assets soon, buying before December 31 may allow you to take deductions this year. Don’t wait until the last second, you want those purchases to be strategic, not rushed.
• Health benefits: If you’ve been thinking about offering health reimbursement arrangements or other benefits, now’s the time to evaluate. These programs can be tax-friendly for both you and your team.

Think of these as offensive plays, strategies that move the ball down the field and set you up to score when April comes around.

4. Play Defense Against Surprises

A strong defense is just as important as a flashy offense. In business, this means protecting yourself from the unexpected.

• Set aside money for taxes: Nothing feels worse than reaching April and realizing you don’t have cash to cover your tax bill. Treat your tax savings like a non-negotiable expense something you contribute to regularly.
• Double-check payroll systems: Payroll errors are like false starts; they cost time, money, and penalties. Make sure your payroll is accurate and compliant.
• Track contractors now: If you’ve paid independent contractors during the year, don’t wait until January to pull together names, addresses, and totals. Keeping this list current avoids a mad scramble later when 1099s are due.

Playing defense may not be glamorous, but it keeps you from getting blindsided. The IRS doesn’t hand out trophies, but they do hand out penalties—and avoiding them is a win in any business owner’s book.

5. Call in Coaching Support

Even the best teams need coaches. They see the whole field, adjust strategy, and help avoid costly mistakes. As a business owner, you don’t have to do it alone either.

Having a trusted advisor, whether that’s a tax professional, accountant, or financial consultant, can make all the difference. They can spot opportunities you might miss, warn you about pitfalls, and help you stay focused on what matters most: running and growing your business.

Think of them as your offensive coordinator: you’re still the quarterback, but they’re helping you make the right calls to get the ball into the end zone.

Bonus Play: Keep Your Eye on the Long Game

It’s easy to get caught up in the week-to-week grind of running a business, but September is also a good time to zoom out and think long-term. Where do you want your business to be next year? In five years? What investments will help you get there?

Like football, business isn’t just about winning one drive; it’s about building a season, and ideally a dynasty. Small, smart decisions now compound into big results later.

Wrapping It Up

September is more than just pumpkin spice and football—it’s your chance to regroup, refocus, and reset your business strategy.

• Check your scoreboard and know where you stand.
• Clean up your books so you’re working with real numbers.
• Put tax-saving strategies into play while you still have time.
• Protect yourself from surprises with a strong defense.
• Lean on advisors who can guide you through the complexity.

By treating September as your kickoff, you can head into the fourth quarter with confidence. Instead of scrambling in December or panicking in April, you’ll already be running your plays, controlling the clock, and moving steadily toward your goals.

Grab your coffee (or maybe a game-day snack), review your playbook, and get ready. Business season is here and you’re ready for a winning drive.

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