Most people don’t think about taxes until January — by then, most of the year’s opportunities to actually change the outcome are already gone.
That’s the problem with waiting. Tax filing season is about reporting what already happened. Tax planning season is happening right now — and it closes faster than most people realize.
We work with clients every summer who are surprised to learn how much is still on the table in July that won’t be come December. Here are the areas worth a second look before the window narrows.
1. Check Where You Sit in Your Tax Bracket
The One Big Beautiful Bill Act (OBBBA), signed into law July 4, 2025, kept federal income tax rates between 10% and 37% — but where you fall matters more than the rates themselves. What counts for planning purposes is your marginal rate: the rate that applies to your next dollar of income.
If you’re sitting close to the edge of a bracket, there’s often still time to manage that — for example, by accelerating certain deductible expenses before year-end.
2026 bracket thresholds (income above the 10% rate):
| Filing Status | 12% | 22% | 24% | 32% | 35% | 37% |
|---|---|---|---|---|---|---|
| Single | $12,401 | $50,401 | $105,701 | $201,776 | $256,226 | $640,601 |
| Head of Household | $17,701 | $67,451 | $105,701 | $201,776 | $256,226 | $640,601 |
| Married Filing Jointly | $24,801 | $100,801 | $211,401 | $403,551 | $512,451 | $768,701 |
| Married Filing Separately | Half of joint-filer amounts |
A quick gut check: has your income moved meaningfully since you last ran these numbers? If yes, it’s worth a closer look now — not in April.
One nuance worth knowing: the OBBBA kept the standard deduction high ($16,100 single / $24,150 head of household / $32,200 joint for 2026), which means itemizing only helps if your itemized total clears that bar. The law also reshuffled a few deductions — some got more generous (like state and local tax deductions), others got more limited (like charitable deductions) — and added a few brand-new ones available even if you don’t itemize: deductions for qualified tips, overtime, auto loan interest, and a new “senior” deduction for those 65+.
2. Medical Expenses: Timing Is Everything
Medical expenses are only deductible above 7.5% of your adjusted gross income (AGI) — which means when you incur them can matter as much as how much you spend.
Deductible expenses can include health insurance premiums, long-term care premiums, medical/dental services, prescription drugs, and even mileage for medical care.
- Close to the 7.5% floor? You may be able to bunch additional expenses into this year to clear it.
- Already well past the floor? Bunching more into 2026 maximizes the deduction.
- Nowhere close, or not itemizing this year? It may make more sense to defer discretionary expenses into 2027 instead.
(Your health always comes first — this is about timing elective or flexible expenses, not delaying anything medically necessary.)
3. Investment Gains and Losses: A Two-Way Street
Long-term capital gains rates weren’t touched by the OBBBA — they remain 0%, 15%, and 20% for investments held over a year. Short-term gains, by contrast, are taxed at your full ordinary-income rate, which can be significantly higher.
Long-term capital gains thresholds for 2026 (above the 0% rate):
| Filing Status | 15% Rate Begins | 20% Rate Begins |
|---|---|---|
| Single | $49,451 | $545,501 |
| Head of Household | $66,201 | $579,601 |
| Married Filing Jointly | $98,901 | $613,701 |
| Married Filing Separately | Half of joint-filer amounts |
If you’ve already realized — or expect to realize — significant gains this year, selling underperforming investments to generate offsetting losses is worth exploring. Just keep the wash-sale rule in mind: you’ll need to wait at least 31 days before repurchasing the same or a substantially identical investment.
Also worth checking: the 3.8% Net Investment Income Tax (NIIT), which can apply once modified AGI exceeds $200,000 (single/HOH) or $250,000 (joint). There are ways to manage exposure here by adjusting MAGI or net investment income.
The Real Question Isn’t “What Deductions Am I Missing?”
It’s this: when’s the last time you reviewed your tax strategy — not just your tax return?
A bonus, a business distribution, a Roth conversion, an investment sale — these rarely affect just one line of your return. They interact. And by the time everything lands on your 1040 in April, the moment to shape that outcome has already passed.
Midyear isn’t just a good time to check in. It’s really the last time.
If you’ve read this far, you already know whether this applies to you. Reach out — we’re happy to walk through what a midyear check would look like for your specific situation, no pressure, no obligation.