What to Do After You File Your Taxes
Filed your 2025 taxes? We explain how to turn your return into a smart 2026 tax strategy.
Most people treat the tax filing deadline as a finish line. At Windward, we see it as a starting point.
Your 2025 return is more than a record of what happened — it is a roadmap for what comes next. The income, deductions, and tax you paid are all signals. If you know how to read them, they tell you where to focus your planning for 2026.
Here are the six tax-planning conversations our team has with clients:
Step 1: Review Your Withholding and Estimated Tax Payments
Did you owe more than you expected when you filed? Or receive a refund that seemed larger than it should have been? Either result is a signal worth paying attention to.
Owing a significant balance — especially if it came with an underpayment penalty — means you need to increase what you are paying in throughout the year. A large refund means you overpaid and gave the government an interest-free loan.
April is a great time to fix this. If you receive a W-2, we can help you update your withholding with your employer. If you pay quarterly estimates, we can recalculate based on your estimated 2026 income. An adjustment now may prevent a much bigger surprise next spring.
Step 2: Identify Retirement Contribution Opportunities
Your 2025 return confirms your final income for the year, which tells us what you were eligible to contribute to retirement accounts — and whether you took full advantage of it.
If you did not max out your IRA or 401(k) last year, now is the time to set up a plan so that you can. For 2026, that might mean increasing your contribution rate, setting up automatic IRA contributions, or exploring catch-up contributions if you are 50 or older.
Retirement contributions are one of the most straightforward ways to reduce your taxable income. Every dollar contributed pre-tax lowers your 2026 tax bill — but only if the contributions get made.
Step 3: Review Your Charitable Giving Strategy
If you give to charity, your 2025 return tells us whether your approach is working from a tax standpoint — or whether there is a more tax efficient way to structure your giving.
Three strategies are worth considering:
Bunching means concentrating several years of giving into a single year so you can itemize and capture a larger deduction, then take the standard deduction in off years.
Donating long term appreciated securities lets you avoid capital gains tax while still deducting the full fair market value.
And a Donor-Advised Fund lets you make a contribution in a high-income year, take the deduction immediately, and distribute to your charities on your own timeline.
None of these require a large estate. They require a plan — and April is a good time to build one.
Step 4: Plan for Capital Gains
If you have a taxable brokerage account, any withdrawals or rebalancing in 2026 may trigger capital gains. And those gains can have consequences beyond just the tax line -- they can affect Medicare premiums, push you into a higher bracket, or interact with other income in unexpected ways.
Your 2025 return gives us the income baseline we need to model what additional gains would cost at different levels. If you have positions with embedded losses, those can be used to offset gains elsewhere. If you are planning a significant withdrawal, both the timing and the amount matter more than most people realize.
Getting ahead of this in April — while the year is still young — gives us room to plan around it.
Step 5: Plan for Required Minimum Distributions
If you are subject to Required Minimum Distributions — from your own retirement accounts or an inherited IRA — your 2025 return is a useful starting point for projecting what 2026 will look like.
RMDs are taxable income, and they do not come with much flexibility. But there is planning to be done around them. We can review whether having taxes withheld directly from your distribution makes sense, whether a Qualified Charitable Distribution could satisfy part of your RMD tax-free if you are charitably inclined, and how your RMD interacts with your other income for the year.
For clients navigating inherited IRA rules — which have changed significantly in recent years — this conversation is especially worth having early in the year.
Step 6: Evaluate Your Roth Conversion Opportunity
A Roth conversion moves money from a traditional IRA to a Roth IRA. You pay income taxes on the converted amount today, but future growth and withdrawals are tax-free. For the right client in the right year, it can be a valuable planning opportunity.
Clients who are retired but are not yet taking Social Security, or who are between retirement and the start of RMDs, often have a window where their taxable income may be lower than future years. That window is worth using intentionally — but it requires knowing where you stand.
Your freshly filed 2025 return tells us your income baseline and how much room may exist before crossing into the next income tax bracket. We model each conversion scenario individually. The goal is not to convert as much as possible — it is to convert the appropriate amount for your tax situation.
The Windward Approach
Our CPA heritage means the tax conversation never stops. We look at your return together, identify what the numbers are telling us, and build a strategy that carries forward into the year ahead. If you filed your 2025 return and have not yet had this conversation, now is the time.
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This content is provided by Windward Private Wealth Management Inc. (“Windward” or the “Firm”) for informational purposes only. Investing involves the risk of loss and investors should be prepared to bear potential losses. No portion of this blog is to be construed as a solicitation to buy or sell a security or the provision of personalized investment, tax or legal advice. Certain information contained in the individual blog posts will be derived from sources that Windward believes to be reliable; however, the Firm does not guarantee the accuracy or timeliness of such information and assumes no liability for any resulting damages.
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