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By Eric Croak · Updated April 7, 2026
Most serious tax planning happens well before filing season. By the time the New Year arrives, many of the key deadlines for tax timing strategies and deductions for the prior year have already passed.
But some opportunities remain.
For business owners and other affluent or high net worth households, there are still actions that can be taken before April 15—and sometimes before filing extension deadlines—that may improve the outcome of your tax return. Just as important, the filing process itself can reveal planning gaps, missed opportunities, or areas where coordination between advisors may not be fully aligned.
This article highlights several practical steps you can still consider now, while you and your advisors prepare to file your returns for tax year 2025, along with ideas that may help strengthen your tax planning for 2026 and beyond.
1) Confirm Your PTET Business Tax Election Was Filed. And Filed Correctly
If you own an S-corporation or partnership, your business may qualify for a state-level tax election that can significantly reduce your federal tax bill.
The strategy is known as the pass-through entity tax election (PTET). In simple terms, certain state income taxes are paid at the business level rather than by the individual owner. When structured properly, that payment may reduce the income passed through to owners and create a federal deduction that is not subject to the individual state and local tax (SALT) deduction cap.
PTET elections are state-specific. Not every state offers one (Ohio does), and the rules, deadlines, and entity requirements vary.
It is not always the right move. In some situations, taxpayers may be better off not making the election. But for many business owners paying substantial state income tax, it is an opportunity worth reviewing carefully.
As you prepare your 2025 return, two simple questions are worth asking your tax advisor:
- Was the PTET election filed for 2025?
- Did we analyze how the election interacts with my other deductions?
If the answer to either question is “no” or “I’m not sure,” it is worth reviewing before you file. This election can represent one of the most valuable—and frequently overlooked—tax planning opportunities available to business owners today
2) Take a Closer Look at Your SALT Deduction
The federal cap on state and local tax deductions (SALT) increased from $10,000 to $40,000 for 2025 under the One Big, Beautiful Bill Act passed last July.
For households paying significant state and local taxes, that change can create a meaningful deduction. But the benefit only applies if you itemize deductions rather than take the standard deduction.
There is another detail to be aware of. The $40,000 SALT deduction cap begins to phase out once household income exceeds $500,000, and at higher income levels the deduction can gradually shrink back toward the previous $10,000 limit.
In other words, the number on paper may not be the number you actually receive.
As your return is prepared, it is worth asking your tax advisor to calculate your actual SALT deduction for your 2025 tax return, based on your final income and filing position.
For many affluent households, this is a small detail that can quietly change the math of the entire return.
3) Review Your Tax-Loss Harvesting
If you had significant investment gains in 2025 but little or nothing in the way of losses to offset them, that’s worth discussing with your advisory team.
Tax-loss harvesting—selling losing positions to offset realized gains, while carefully observing wash-sale rules—can reduce your tax bill without meaningfully changing your long-term investment strategy.
Every brokerage account issues an IRS Form 1099-B each year listing every investment sale, including what was sold, when it was sold, and whether the result was a gain or a loss. Before meeting with your CPA, take a moment to review your 2025 Form 1099-B and look at the overall balance of gains and losses.
If your 1099-B shows substantial gains but minimal realized losses, it is reasonable to ask what tax-loss harvesting strategies were executed during the year, and whether a more consistent approach is built into your 2026 investment plan from the start of the year, rather than only toward the end.
In many cases, missed opportunities are not about the competence of any individual advisor. Tax-loss harvesting strategies are well understood by both investment managers and tax professionals. The issue is often coordination. When investment and tax planning operate in separate lanes, important information can fall between them. This dynamic is sometimes referred to as information siloing.
Closing that gap can make a meaningful difference. Periodic check-ins during the year—particularly during significant market moves—can help identify opportunities to realize tax losses at the right time while keeping your long-term investment strategy intact.
4) Move Retirement Funds Toward the Tax-Free Column (Roth Conversions)
If you have money in a traditional IRA or an old 401(k) from a previous employer, every dollar in those accounts will eventually be taxed as ordinary income when you withdraw it—at whatever tax rates exist at that time.
For households in higher tax brackets, that future tax exposure can become significant.
It’s not only the possibility of higher tax rates in the future. Large required minimum distributions (RMDs) can also create a cascade of secondary effects, including higher Medicare Part B and Part D premiums under IRMAA rules, higher marginal tax brackets, increased capital gains taxes, and exposure to the 3.8% Net Investment Income Tax.
This is more common than many people realize.
The key is addressing it early—often years before retirement.
One strategy many investors consider is a Roth conversion. The idea is straightforward: gradually move assets from tax-deferred accounts like traditional IRAs and 401(k)s into a Roth account, where future growth and withdrawals can be tax-free.
Converting a portion of those funds means paying some taxes today at known tax rates. In exchange, those assets can grow tax-free for the rest of your life, without future required minimum distributions.
For many affluent households, this trade-off can be a worthwhile long-term strategy.
Backdoor Roth Strategies
If you are eligible to make Roth IRA contributions, you have until April 15 to contribute up to $7,500 for the 2025 tax year, with additional catch-up contributions available for those age 50 and older.
However, many high-income households earn too much to contribute directly to a Roth IRA.
In those cases, a strategy often called a backdoor Roth contribution may still be available. This involves contributing to a traditional IRA—sometimes on a non-deductible basis—and later converting those funds into a Roth account.
When structured correctly, this approach can allow high-income earners to continue building assets in the tax-free Roth category.
Advanced Strategies for Business Owners
Business owners often have additional options.
For example, some retirement plans allow the addition of a Roth 401(k) feature, giving owners and employees the ability to make Roth contributions within a workplace plan.
For those seeking to contribute more than traditional retirement plans allow, it may also be worth exploring a qualified pension plan, such as a cash balance plan.
These strategies won’t affect the current filing season, but depending on your age, income, and business structure, they may allow you to shelter substantial income from taxes in future years.
5) Review Your Quarterly Estimated Tax Payments
Business owners typically make quarterly estimated tax payments throughout the year rather than settling their entire tax bill at filing. If those payments fall short, the IRS may assess an underpayment penalty—even if the full balance is paid by April.
To avoid that outcome, many tax advisors recommend following a common safe harbor rule, such as paying at least 100% of the prior year’s tax liability through estimated payments.
However, that guideline can break down if your income changes significantly.
If your 2025 income was meaningfully higher than in 2024—perhaps because of a business sale, a large distribution, or an unusually strong year—last year’s tax bill may no longer be a reliable benchmark.
One simple step can provide clarity. Ask your CPA or tax advisor to review your fourth quarter estimated tax payment and compare it to your projected liability for the year.
That quick check can provide an early signal of whether your quarterly tax payments need to be adjusted going forward.
6) Consider a Donor-Advised Fund to Maximize After-Tax Charitable Giving
If you made charitable contributions in 2025, it’s worth confirming whether those gifts actually reduced your federal tax bill.
For married couples filing jointly, the standard deduction for 2025 is $31,500. If your itemized deductions, including charitable gifts, did not exceed that amount, your donations may not have produced any additional federal tax benefit.
For some households, a different structure can be more effective: a donor-advised fund (DAF).
A donor-advised fund allows you to make a large charitable contribution in a single high-income year, take the tax deduction immediately (subject to AGI limits), and then distribute gifts to your chosen charities over time.
There can also be additional advantages when appreciated investments are involved.
If you contribute appreciated stock or other investments instead of cash, the capital gains tax that would normally be due on those assets is eliminated. At the same time, you may still receive a deduction for the full fair market value of the shares.
Your chosen charities ultimately receive the same support—but the structure can allow you to give more efficiently and retain more after taxes.
7) Update Beneficiaries and Fully Fund All Trust Accounts
If your trust documents, beneficiary designations, or account titling haven’t been reviewed in the past two to three years, there is a very high chance they no longer reflect your current financial situation. Failing to update them is a very common and expensive mistake.
Outdated beneficiary designations can send assets to the wrong person. Poor titling or structure choices can unintentionally reduce — or complicate — the step-up in basis your heirs might otherwise receive, increasing their future capital gains taxes.
Failing to update these documents or move assets into the name of the trusts is a very common mistake — and an expensive one.
8) Double-Check Your Strategic Gifting Strategy
Consistent annual gifting to children and grandchildren is one of the simplest and most effective wealth-transfer tools available, and most families who qualify for it aren’t using it at full capacity.
While the 2025 window for tax-free annual gifting — up to $19,000 per person, or $38,000 per couple — closed on December 31, 2025, preparing your tax return with your advisors is a good opportunity to confirm those gifts were made and documented correctly.
Conclusion
None of these actions, other than starting a donor-advised fund, requires setting up a new or complicated structure.
In most cases, it simply requires that you have someone on your team tasked with seeing the whole picture, coordinating the different expert team members, and making sure the parts are working together.
At Croak Capital, that’s the role we often play for our clients: We act as the central point of coordination across your entire advisory team. We help make sure the right professionals are aligned, the right strategies are executed, and nothing falls through the cracks.
If you’re not confident your current advisory structure is working that way, we’d welcome the conversation. We invite you to contact us for a no-obligation diagnostic of your full financial picture—designed to show you exactly what’s working, what isn’t, and what it may take to close the gap.
Click here to schedule a consultation and review.
Also Read:
What to Do After Selling a Business
How to Select the Perfect Financial Advisor
Dominating Tax Season: Strategic Wealth Tactics for Serious Business Owners