Mid-Year Tax Planning: What to Talk to Your CPA About Now

Most people only think about taxes in March or April, but by the time you're filing your return, the year's decisions are already locked in. March and April are the time for reporting what happened. Mid-year is different: it's when you still have room to act and build a strategy to minimize your tax bill by shifting income, accelerating deductions, or restructuring before December 31 closes the door.

Here is a concise list of items worth reviewing during your next conversation with your CPA.

For Individual Taxpayers

• Estimated tax payments — true these up against actual year-to-date income, not January's projection, to ensure you're not overpaying on your third and fourth estimated payments.
• Capital gains and loss harvesting — review your brokerage accounts for large capital gains so that they can be offset now before year-end selling pressure sets in.
• Roth conversions — decide now while there's time to spread the tax hit across years.
• Charitable giving strategy — consider donor-advised funds, appreciated stock gifts, qualified charitable distributions, and bunching donations to clear the new deduction floor.
• State and local tax strategy — the One Big Beautiful Bill increased the cap on state and local tax deductions through 2029. Paying next year's taxes before year-end could result in higher overall deductions over the next few years before the cap reverts back to $10,000.
• Other One Big Beautiful Bill provisions — the deductions for tips, overtime, and auto loan interest are all temporary (gone after 2028). Your CPA can advise you on how to best take advantage of these provisions.

For Business Owners

• Estimated tax payments — like individuals, if you make estimated payments, it's time to reassess based on actual year-to-date income.
• Entity structure — the Qualified Business Income deduction has been made permanent, which changes the long-term math for entity selection. Is S-Corp, LLC, or C-Corp still the right call at your current income level?
• Reasonable compensation — make sure your salary-to-distribution split can survive a look from the IRS.
• Retirement plan setup — whether you're considering a SEP-IRA, Solo 401(k), or a defined benefit plan, some of these must be established, not just funded, before year-end.
• Expanded childcare tax credit — the Employer-Provided Child Care Credit got a big upgrade with the One Big Beautiful Bill, with higher caps and more ways to qualify. If you're already helping employees or are considering offering this benefit, more of that spending is creditable on a dollar-for-dollar basis than ever before.
• Equipment purchases — Section 179 and 100% bonus depreciation are back, and timing matters. Are you trading in old equipment as part of the purchase? Depreciation recapture may apply. Talk to your CPA about purchases in advance to ensure that you structure purchases in a way that aligns with your tax strategy.

Why This Conversation Matters

Most of what shows up on a surprise tax bill isn't a mystery — it's a transaction nobody flagged in time. A large trade, a poorly thought-out strategy, or a missed plan deadline can all increase the amount due at filing time. Luckily, at mid-year there's still time to make a different choice. A 30-minute conversation now can be the difference between a tax season where you get predictable results and one built on damage control.