By Tom Schiller, CPA, CFP®
Filing your taxes feels like the finish line. And in some ways it is. But for people who are serious about their financial picture, May is actually one of the most useful windows of the year. The numbers are fresh, the documents are in order, and you have a clearer view of where things stand than you will at almost any other point in the calendar.
The problem is that the majority of people close the folder, move on, and don’t revisit any of it until next April. By then, the window for real action has closed on several fronts. Here are seven moves to consider making now, while the information is still in front of you.
1. Start With What Your Return Is Actually Telling You
Most people look at one number when their taxes are done: what they owe or what they are getting back. But your return is a much richer document than that. It’s a detailed summary of your financial year, and if you read it carefully, it will often point you toward decisions worth making before December.
Before you file it away, ask yourself:
- Did my income increase or decrease significantly from last year?
- Does my savings rate and investment strategy still reflect where I am now?
- Did I have more capital gains than I expected?
- Did I miss any deductions I could have captured with better planning?
- Did my effective tax rate surprise me in either direction?
Your return is not just a report on last year, it’s one of the best inputs you have for planning this one.
2. Revisit Your Withholding
Withholding tends to be one of those things people set once and never revisit, even as their financial situation changes substantially from year to year.
If you received a large refund this year, you overpaid and gave the government an interest-free loan in the process. If you owed more than expected, you may have underpaid to the point of facing a penalty, and without an adjustment you will start next year already behind.
The fix is the same either way: update your W-4 to better reflect your actual tax liability. Getting that withholding number right means looking at the full picture, including side income, investment gains, and any significant life changes from the past year. This is a good conversation to have with your CPA now while the numbers are current.
3. Check Where You Stand on Retirement Contributions
The months right after tax season are one of the best times to evaluate whether your retirement contributions are keeping pace with your goals. You have a full picture of last year’s income, and you still have the better part of the year ahead to make adjustments.
Workplace Plans
If you received a raise recently but did not adjust your contribution rate, you may be leaving significant tax-advantaged space on the table. Increasing your deferral rate by even one or two percent now compounds by year-end.
IRAs
If you have not yet contributed to a traditional or Roth IRA for the prior tax year, you have until the federal filing deadline to do so. This is one of the few planning moves that lets you look backward once the calendar has already turned. Whether a traditional or Roth IRA makes more sense depends on your income level, current tax bracket, and expectations about where taxes are headed.
4. Update Your Cash-Flow Plan
Tax season has a way of surfacing changes that have not yet made it into your actual financial plan. A raise you received in the fall. A bonus that was larger than expected. A shift in business income. These are not unusual, but they do require a response.
Take what you learned from your return and run it forward. Does your monthly cash-flow plan still reflect your actual income, or is it based on what you were earning a year ago? Is your savings rate calibrated to what you actually want to accomplish this year? Are there spending categories that grew quietly in the background?
A cash-flow plan that is 12 months out of date is a best guess built on old information. Spending an hour updating it now typically reveals at least one thing to act on.
5. Think Through Equity Compensation and Benefits Timing
For executives and employees with equity-based compensation, the weeks right after tax season are one of the most consequential planning windows of the year. Your income picture for last year is clear, your expectations for this year are taking shape, and you still have time to make real decisions before the fourth quarter compresses your options.
Vesting schedules: Know what is vesting and when, and whether you will hold or sell.
Stock options: The timing of an exercise matters significantly. Exercising in a lower-income year can make a meaningful difference in what you ultimately keep.
Employee stock purchase plans: Review your enrollment and the upcoming offering period.
Benefits elections: HSA contributions, dependent care FSAs, and supplemental insurance deserve a fresh look before upcoming windows close.
Deferred compensation: If your employer offers a nonqualified plan, the election window for next year’s deferrals may arrive sooner than you expect.
6. Make Sure Your Advisors Are Working Together
This one tends to get skipped not because people think it’s unimportant, but because it requires coordination effort and there is never a perfect moment. Right after tax season is actually a very natural one.
Your CPA has just spent significant time with your financial data. Your attorney may have drafted documents that have not been reviewed since your situation last changed. Your insurance professional may not know about income or asset changes that affect your coverage. When these conversations happen in silos, things can fall through the cracks.
Some of the most common gaps that surface when advisory teams do not communicate:
- An investment strategy generating more taxable income than necessary
- Estate documents naming beneficiaries or trustees that no longer reflect current family dynamics
- Life insurance coverage that has not kept pace with the growth of an estate
- A tax-loss harvesting opportunity that passed because no one flagged it in time
At our client’s request, The Wealth Dimensions team spearheads communications with our clients’ CPAs, attorneys, and insurance professionals to confirm all planning is coordinated and fully implemented. You should not be the one holding all the threads together.
7. Put a Mid-Year Review on the Calendar
Life gets busy, the urgency of tax season fades, and suddenly it is October and nothing has been reviewed since April. Planning conversations that happen in July are almost always more useful than ones that happen in November. By mid-year you have real data for the first half of the year and still have six months to act on whatever surfaces.
A one-hour check-in with your advisor before summer ends is a small investment for the clarity it provides. Schedule it now, before everything else fills in around it, by calling (513) 554-6000 or visiting wealthdimensions.com.
Frequently Asked Questions
What financial planning steps should high-net-worth individuals take immediately after filing taxes?
After filing your tax return, you have a precise, up-to-date snapshot of your income and tax liability. This makes the post-tax season window the optimal time to update your cash-flow strategy, adjust your withholdings to prevent overpaying, and review asset location across your accounts. At Wealth Dimensions, we use this data to update your Financial Playbook, confirming your wealth strategies remain tied to the quality of life you are seeking to achieve.
How should corporate executives handle equity compensation planning after tax season?
For professionals with equity-based compensation, the period immediately following tax season provides a clear view of your baseline income for the year. This makes it the ideal time to plan for upcoming vesting schedules, manage concentrated stock positions, and evaluate stock options. By modeling the tax implications of these decisions in the spring or summer, you create significantly more flexibility than if you wait until the fourth quarter. At Wealth Dimensions, equity compensation planning is coordinated alongside your CPA and legal counsel so the investment, tax, and legal dimensions are all working together.
Why is it important for a financial advisor to coordinate with my CPA and estate attorney?
When financial professionals operate in silos, critical details often fall through the cracks: missed tax-loss harvesting opportunities, uncoordinated charitable giving, or estate documents that no longer reflect your actual wishes. At Wealth Dimensions, we spearhead communications directly with your CPA, attorney, and insurance professional to help verify all planning is coordinated and fully implemented. This interdisciplinary approach means your financial life is fully aligned, and you are not left playing quarterback between advisors who are not talking to each other.
About Tom
Tom Schiller, CPA, CFP®, is a Financial Advisor at Wealth Dimensions in Cincinnati, Ohio, where he specializes in holistic planning, wealth transfer, and tax minimization for high-net-worth individuals and business owners. Drawing on his extensive background at Plante Moran, he provides skilled guidance on investment strategies and planning for complex liquidity events.