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Tax StrategyFeb 20, 2026Β· 10 min read

Year-Round Tax Planning: The Entrepreneur's Guide

Local insights and strategies for business owners to optimize their tax position all year long.

Why April 15 Is Too Late to Start Planning

By the time tax season arrives, most of your tax liability for the prior year is already locked in. The decisions you make throughout the year β€” how you structure income, when you make purchases, how you pay yourself β€” determine your tax bill months before you file.

Q1: Set Your Structure and Baseline

The first quarter is the time to review your entity structure. Are you still filing as a sole proprietor when an S-Corp election would save you thousands in self-employment taxes? At revenue levels above Custom Consultation the answer is often yes.

Q2: Review Estimated Payments

Underpaying quarterly estimated taxes triggers penalties. Overpaying is an interest-free loan to the government. Use Q2 to reconcile your first quarter actuals against your estimates and adjust.

Q3: Make Strategic Purchases

If you're planning equipment purchases, Q3 is the time to pull them forward into the current year (or push them into next year) based on your projected income. Section 179 and bonus depreciation decisions should be made before December.

Q4: Maximize Retirement Contributions

401(k) contributions must be made by December 31. SEP-IRA contributions can be made until the filing deadline, but waiting until April means you've lost months of tax-advantaged growth.

Working With Ombsy Year-Round

Our tax planning service isn't a once-a-year transaction β€” it's an ongoing relationship. We check in quarterly, flag changes in tax law that affect you, and make sure you're positioned to pay the minimum legal amount every April.

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