October Is the New January (for Tax Planning)

Many small business owners treat tax season as a January problem—but the smartest planning happens before the year ends. October is the new January when it comes to getting ahead on tax strategy.

By this point in the year, you have three quarters of financial data to work with. That gives you—and your tax advisor—enough information to estimate your year-end position with much greater accuracy. Waiting until January often means missed deductions, rushed decisions, or worse—surprise tax bills.

Start by reviewing your year-to-date profit. Are you ahead of where you were last year? If so, you may need to increase your estimated tax payments to avoid penalties. If income has dipped, you may be able to conserve cash by adjusting your next payment accordingly.

Next, evaluate major purchases or investments you’ve been postponing. Equipment, software, professional services, or vehicle expenses might qualify for accelerated depreciation or deductions—but only if they’re purchased and placed in service by December 31.

Also, consider your retirement contributions. If you haven’t set up a SEP IRA, solo 401(k), or other tax-advantaged plan, October gives you time to get organized and potentially reduce your tax liability while investing in your future.

Don’t forget about year-end bonuses, charitable contributions, or other planned expenses. Properly timed, these can have meaningful tax impacts.

This is also a good month to schedule a tax strategy session with your bookkeeper or CPA. A quick 30- to 60-minute review in October can reveal savings opportunities that simply won’t be available in January.

Lastly, if your books are behind or messy, use October to clean things up. Solid financials are essential for making accurate projections—and for avoiding stress when filing season arrives.

Good tax planning is proactive, not reactive. October gives you space to think clearly, act intentionally, and close the year from a position of control—not chaos.