Originally published February 2015. Last updated March 2026.
Tax season doesn’t have to be stressful. A little organization up front saves time, money, and headaches when you sit down with your tax preparer.
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Gather Your Documents
Before meeting with your CPA or tax preparer, make sure you have:
- Income: W-2s from employers, 1099-MISC or 1099-NEC from freelance/contract work, 1099-INT/DIV from banks and brokerages, 1099-R from retirement distributions, SSA-1099 from Social Security
- Deductions: Mortgage interest (Form 1098), property tax statements, charitable donation receipts, medical expense records, state/local tax payments
- Business owners: Profit and loss statements, business expense receipts, 1099-K from payment processors, home office measurements
- Life changes: Social Security numbers for new dependents, marriage/divorce documents, records of home purchase or sale
Last-Minute Moves That Can Still Help
Even after December 31, you have options:
- IRA contributions: You can make 2025 IRA contributions until April 15, 2026. The limit is $7,000 ($8,000 if you’re 50+). This applies to both traditional (potentially deductible) and Roth IRAs.
- SEP IRA contributions: If you’re self-employed, you can set up and fund a SEP IRA until your tax filing deadline, including extensions. That’s potentially $70,000 in deductions.
- HSA contributions: Like IRAs, you can make prior-year HSA contributions until the tax filing deadline. The 2025 limits are $4,300 (individual) and $8,550 (family).
Commonly Missed Deductions
- Unreimbursed medical expenses above 7.5% of AGI
- Student loan interest (up to $2,500, even if you don’t itemize)
- Educator expenses ($300 for teachers who buy classroom supplies)
- State sales tax (especially useful in states with no income tax)
- Charitable mileage (14 cents per mile for charity-related driving)
- Energy-efficient home improvements (tax credits under the Inflation Reduction Act)
FAQ
Should I itemize or take the standard deduction?
The 2025 standard deduction is $15,000 (single) or $30,000 (married filing jointly). If your total itemized deductions exceed those amounts, itemize. If not, take the standard deduction. Most people take the standard deduction since the 2017 tax reform roughly doubled it.
When should I file?
As soon as you have all your documents. Filing early means an earlier refund and less risk of identity theft (someone filing a fraudulent return in your name). If you owe money, you can file early and schedule payment for April 15.
Is it worth hiring a tax professional?
If you have a straightforward W-2 and standard deduction, tax software may be enough. But if you’re self-employed, have investment income, own rental property, or are dealing with retirement distributions, a CPA or enrolled agent usually pays for themselves in tax savings.
Schedule a free 20-minute consultation to review your tax situation and retirement plan together.
R.L. Brown Wealth Management
106 W Vine St, Suite 300, Lexington, KY 40507
859.317.5889
