Bean: Turning tax season frustration into smart planning for executives and business owners

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For many executives and business owners, tax season can be frustrating. By the time April 15 arrives, most opportunities to reduce last year’s tax bill have already passed, potentially leaving sticker shock and a sense that it’s too late to positively impact your situation.

While tax season is largely a look in the rearview mirror, it can be a valuable opportunity to identify gaps, avoid repeating mistakes and position yourself more strategically for the years ahead. For high-income earners, especially those with multiple income streams or business ownership, the lessons learned now can meaningfully improve outcomes in 2026 and beyond.

Here are some common issues we see and ways to address them with proactive planning.

• The “Too Late” Trap — Many executives wait until tax season to focus on planning, only to discover that most levers were locked in months earlier. State and local tax (SALT) deductions, retirement deferrals, charitable strategies and income timing all require advance coordination. While recent and upcoming legislative changes may expand planning opportunities in 2026, they will not retroactively lower last year’s bill. Recognize that distinction and shift your mindset from frustration to preparation.
• Underestimating Taxes on Non-Wage Income — A frequent issue for high-income business owners and executives is insufficient withholding on income outside of a paycheck, such as bonuses, equity compensation, pass-through income or investment earnings. Employers typically withhold at flat supplemental rates, which may fall short for those in higher marginal brackets. Inaccurate and insufficient quarterly estimates can lead to underpayment penalties and unexpected balances due. One of the simplest ways to reduce tax-season surprises is to review projected income early in the year and align estimated payments accordingly.
• Missing Last-Minute Opportunities — While most strategies must be implemented well in advance, there are still a few meaningful moves available before filing. Health Savings Account (HSA) contributions, for example, can be made up to the tax filing deadline. High-income earners who qualify may also benefit from a Backdoor Roth conversion, making a nondeductible IRA contribution and converting it to a Roth to create future tax-free growth. These strategies do not eliminate last year’s tax bill, but they can improve long-term, after-tax outcomes.
• Powerful Tools for Business Owners — For business owners, retirement funding remains one of the most effective ways to reduce taxable income. SEP IRAs, solo 401(k)s, profit-sharing plans and cash balance plans can be funded up to the tax filing deadline (including extensions), depending on plan type and business structure. For owners who had a strong year but lack a formal retirement plan, these vehicles can provide immediate tax benefits while strengthening long-term financial security. Each option has different rules and limits, so make sure to get guidance from your tax professionals and financial advisors.
• The Communication Gap — One of the biggest stress points during tax season is when executives act as the middleperson between their CPA and financial advisor. Tax and investment professionals often speak different technical languages, and clients can be left translating concepts they should not have to interpret. Encouraging direct collaboration between advisors reduces errors, uncovers planning opportunities and makes tax season far less burdensome.
• Turning Insight Into Action — Rather than seeing tax season as a setback, it’s better to see it as a checkup. Understanding where deductions were missed, where estimates fell short or where communication and planning could have been stronger offers ideas for future improvement. For executives and business owners, the biggest payoff comes when tax decisions are made in the context of overall financial and long-term goals.

The most effective tax strategies are rarely about last-minute moves. They’re built through thoughtful, ongoing planning. By engaging advisors early and coordinating tax and investment decisions, executives and business owners can reduce surprises, increase flexibility and make better use of their income year after year with clarity and confidence.

Cody Bean is a Financial Planning Specialist for Arvest Wealth Management and can be reached at [email protected].