With the 2025 tax year coming to a close and a new tax landscape taking shape for 2026, business owners face a critical planning inflection point. Whether the TCJA was extended, modified, or allowed to sunset, the start of a new year requires a fresh assessment of tax strategies, entity structures, compensation arrangements, and investment plans. The businesses that thrive in a changing tax environment are those that plan proactively rather than react after the fact.
Reassessing Entity Structure
The relative advantage of different entity types depends on the tax rates in effect. If TCJA rates were extended, the current S corporation and pass-through entity advantages largely continue. If the TCJA expired and rates reverted to pre-2018 levels—with the loss of the Section 199A deduction—the calculus shifts. At higher individual rates without the 199A deduction, the C corporation's flat 21% rate becomes more competitive. Business owners should revisit the entity selection analysis with updated numbers.[1]
Compensation Planning
Changes in individual tax rates directly affect the optimal compensation strategy for owner-employees. S corporation shareholders must balance reasonable compensation (subject to employment taxes) with distributions (not subject to employment taxes). At higher rates, the value of tax-deferred retirement plan contributions increases. Deferred compensation arrangements may need to be reconsidered based on the relative rates in the year of deferral versus the expected rates in the year of payment.[2]
Estimated Tax Recalibration
Business owners must recalibrate their estimated tax payments for 2026 based on the new rate structure. If rates increased, the prior year safe harbor (110% of the prior year's tax for high-income taxpayers) provides protection against underpayment penalties while the new rates are being assessed. However, relying solely on the safe harbor may result in a large balance due at filing time if income is significantly higher or rates are significantly higher than the prior year.[3]
Estate Planning Updates
If the estate tax exemption dropped, individuals who did not use the enhanced exemption before the sunset need to revisit their estate plans. Trusts that were designed to hold the maximum exemption amount may need to be updated with new formula clauses. Credit shelter trust provisions should be reviewed to ensure they still operate correctly at the lower exemption level. Life insurance needs may have increased to cover the additional estate tax exposure.[4]
Action Items for January
The first month of 2026 should include a meeting with your tax advisor to review the new rate structure and its impact on your business, a review and update of estimated tax payments for the first quarter, a reassessment of retirement plan contribution strategies under the new limits, a review of your estate plan with your estate planning attorney, and an evaluation of whether your current entity structure remains optimal. The cost of delaying these reviews increases with each passing month as planning opportunities are lost and the risk of underpayment penalties grows.[5]