Tax Season Lessons: How to Make 2025 Smoother & Stress-Free

by Masa Yamazaki, 

CPWA® CEPA® CDFA® 


Many of us have just closed the tax chapter on 2024 (unless filing an extension). While it feels good to turn the page, now is the time to reflect on any pain we felt in the filing process and get organized for a more stress-free experience in 2025. Here are some key takeaways that could help improve your annual tax-time experience.

Establish your system NOW for gathering tax documents (W-2s, 1099s, investment statements, etc.) and keep them organized throughout the year. You can create a simple folder or use digital tools to store everything in one place. Keep track of potential deductions, like charitable donations, medical expenses, or home office costs if applicable. Using a simple spreadsheet or a tax software app can help you log these expenses throughout the year. This is far easier to do along the way than to try to piece together records after the fact.

If you received a large refund or owed money this tax season, it might be a good idea to adjust your tax withholding. You can update your W-4 with your employer to ensure the right amount is taken out of your paycheck each month to help you avoid surprises next year. If you’re self-employed or have additional sources of income that aren’t subject to tax withholding, consider setting aside money each month for your quarterly estimates. And you don’t have to leave that money in your checking account earning nothing. You might open a high interest savings account; earn some interest until you need the funds.

Finally, consider maxing out retirement plan contributions if you can. This may help reduce your taxable income and help you save for retirement. If you’re self-employed, many flexible retirement vehicles are available to meet your needs.

Here’s to an easier 2025 tax filing season!

Masa Yamazaki, CPWA® CEPA® CDFA® is a Principal at Oxler Private Wealth®, an independent, family owned and operated wealth advisory firm in Rye Brook and Manhattan, offering financial care to women and families. For a complimentary, no pressure conversation, please call (212) 785-2860 or visit www.oxlerpw.com. Oxler Private Wealth is a SEC-Registered Investment Adviser. Registration of an investment adviser does not imply any specific level of skill or training and does not constitute an endorsement of the firm by the Commission. Oxler Private Wealth does not provide tax or legal advice. The information presented is not a solicitation to buy or sell any securities or investment advisory services.