October Tax Planning: 7 Decisions Business Owners Should Start Reviewing Now

October is a good time to check your tax position, because you can still do something about it before December 31. You’ve got several months of real results by now, enough to estimate where the business will finish.

Wait until December and you’ll have less room to look at purchases, pay, or retirement contributions. Some of these also come with payroll requirements, eligibility rules, or deadlines that need attention well before the year ends.

I’d start with the numbers: current profit, expected expenses, cash on hand, and what you plan to do in the last few months. Then go through the seven decisions below with your CPA and figure out which ones apply to you.

1. Get a Realistic Estimate of Year-End Profit

Everything else depends on this one. How much will the business make by December 31?



Pull your year-to-date profit and loss statement and compare it with your original budget. Then update the forecast for the months that are left. If sales beat expectations, your taxable income may be higher than you planned for. If margins tightened or costs rose, it could come out lower.

Take a consulting firm that landed several big contracts over the summer. Revenue is ahead of plan, but the firm also brought on subcontractors to do the work. The owner needs to know how much profit those contracts are really producing before making decisions based on the higher sales.

With an updated forecast, your CPA can estimate taxable income and test how planned transactions would change it. Your books have to be current for this to work, since an outdated profit and loss statement gives you a projection you can’t trust.

2. Check Your Estimated Tax Payments

Once you have a believable income number, compare the tax you expect to owe with what you’ve already paid.

If withholding doesn’t cover all your income, you may need to make estimated payments. That can apply to self-employed people and owners of pass-through businesses, depending on their overall situation. C corporations generally have their own estimated payment rules.

A strong year can leave you owing more than you expected. Looking now gives your CPA time to decide whether your payment schedule still makes sense and whether you could face an underpayment penalty.



The IRS covers the general rules and exceptions in its estimated tax guidance. Federal and state rules both matter here, and the same approach won’t fit every business.

3. Look for Deductions While There’s Still Time

Go through your expenses and look for anything without paperwork behind it, like a subscription renewing on a card nobody checks or a contractor you paid by Venmo. Every expense needs the right category and a receipt you can find later. Your CPA can also check whether you qualify for credits or deductions you haven’t claimed.



Just don’t buy something only for the deduction. Spend $10,000 to save $2,500 in tax and you’re still out $7,500.

4. Think Through Planned Equipment Purchases

If you’re planning to buy equipment, machinery, computers, or other assets, talk to your CPA about timing before you place the order.

How a purchase is treated depends on the asset, how much you’ll use it for business, when it’s placed in service, and which rules apply. Some qualifying property may be eligible for accelerated deductions. Other assets have to be depreciated over several years.

Say a company is replacing aging equipment. It should compare the benefits of buying now with the cost of keeping the old equipment going, figure out how much cash the purchase takes, and make sure the asset can actually be in use before year-end.



Buying something in December doesn’t guarantee a deduction for the year, so check the requirements before you commit.

5. Review Your Own Pay and Payroll

If you work in your own company, your compensation deserves a separate look before the last payroll runs of the year.

S corporation owners who do work for the business have to be paid reasonable compensation for it before they take non-wage distributions. What counts as reasonable depends on the work you do and other facts. The company’s profit alone doesn’t decide it.

Look at your salary, your responsibilities, how much time you spend working in the business, and the distributions you’ve taken. Think about any bonuses and payroll changes you might need. 

Your CPA and payroll provider can tell you whether your pay needs adjusting and what has to be done before the year closes. 

6. Consider Retirement Contributions and Benefits

Retirement planning can help both your personal finances and the business’s tax picture, but your options depend on how the business is structured and which plan you use.

If you already have a plan, check what’s been contributed so far, how much more can be contributed under the applicable limits, and the rules for owners and employees. If you’re thinking about starting one, October is a smart time to talk, because some plans have setup, election, or funding requirements that need lead time.

For an owner weighing a SEP IRA, a Solo 401(k), or another qualified plan, the right fit depends on eligibility, employee coverage, pay, contribution limits, and timing. Don’t assume everything has to be funded by December 31, either. Deadlines differ by plan type and situation, and your CPA can sort out which apply to you.

7. Protect Your Cash While You Plan for Taxes

A tax move that drains your bank account isn’t a good one, even if it saves money on paper.



Before you commit to a purchase, a retirement contribution, or a bonus, check what you actually have. Add up your cash, then subtract what you owe suppliers, the next few payrolls, loan payments, and your tax bill. What’s left is what you can spend.

That number is often smaller than owners expect. A business can show strong profit and still be waiting 45 days on a big customer’s invoice. If you spend the cash first, payroll is the thing that suffers.

A cash-flow forecast makes this easier, since it shows when money comes in and when it goes out. Put it next to your projected profit and tax bill, and the moves you can afford now will be clear. The rest can wait until January.

Make the Last Months Count

The point of October planning is to find the decisions that still need attention while there’s time to think them through. Start with an updated forecast. Check your estimated payments, look at deductions, and talk with your CPA about big purchases, owner pay, retirement options, and cash needs.

That’s how we work at Straight Talk CPAs, with financial reporting, tax planning, and CFO advice in one conversation. Looking at your numbers before year-end helps us find tax savings without losing track of profit and cash flow.

Put the meeting on the calendar now. Bring your current financial reports and a list of what you expect to decide before December 31.

👉 Schedule a conversation