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Key Takeaways Q4 is the only window where tax decisions still change real dollars owed.
Filing season reports history; Q4 is when proactive tax strategy actually happens.
Tax law revolves around December 31st deadlines, not April 15th filings.
Most people think “tax season” starts in January and ends on April 15th (or October 15th if you’re waiting for those K-1s). But that’s filing season. It’s simply the administrative deadline for reporting what has already happened.
For founders, high-earning professionals and practice owners, the real tax season — and the only window where decisions still move real dollars — is Q4, October through December.
Many smart, successful people procrastinate tax planning because they feel like they still have time, or they assume their CPA can “fix it” in the spring. This is a fundamental misunderstanding of how the tax code works. Tax law is built on deadlines, and the most important one is the end of the “Tax Year” — December 31st.
Q4 is when you can still sign plan documents, strategically move money, harvest investment losses and lock in actions that legally and permanently lower what you owe. This is the period for action. If you wait until spring, the work becomes more about reporting than planning. You’ll find yourself paying a tax bill based on situations you could have changed — but didn’t.
Related: I Run a Portfolio of High-Growth Companies — This Practice Makes It All Possible
Q4 is when real tax strategy happens
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