3 Strategies for a Smooth and Stress-Free Tax-Filing Season

October 28, 2024

Unlike other seasonal changes, “tax time” isn’t typically welcomed by small business owners. Why not shift your perspective? Rather than dread tax season and all it entails, consider it a challenge that can be easily managed with the right tools. For example:

1. Efficient Filing Options — You can choose to file 1099s, W-2s, and ACA forms a few different ways, depending on your business needs. The first approach is submitting paper forms – a traditional method used by employers with minimal filings. You can also use desktop software to input data and create the necessary forms. 

For employers filing an aggregate of 10 or more forms, it is required to file electronically, or e-file. When e-filing, you enter data online and the information is automatically processed and submitted to the IRS and SSA. You can even have recipient copies printed and mailed, making e-filing the most convenient method. Keep in mind that with e-filing, you can skip Form 1096 (or W-3) because the totals are automatically calculated and transmitted.

2. Prepare Necessary Information in Advance — Even if tax season is right around the corner, you still have time to organize specific details. For example, to properly file the 1099-MISC for contractors, freelancers, and consultants, you need a Form W-9. The W-9 captures the individual's legal name, address, and Taxpayer Identification Number (TIN). Ideally, have the contractor fill out this document before services are provided. Otherwise, request it immediately to avoid the last-minute rush for information.

3. File 1099-MISC Forms Early — The early bird gets the worm … and is less stressed, too. Instead of waiting until January, consider filing your 1099 forms now. You can proceed if an independent contractor has completed their work for the calendar year and you have the necessary information.

Leverage Tools for Successful Tax-Filing

Navigating your tax-filing responsibilities can be a breeze with the right tools. Office Depot has everything you need to help you file your forms accurately and on time – from paper tax forms and tax form envelopes to reliable tax and financial software and e-filing.


All content provided herein is for educational purposes only. The information should not be relied on as replacement for professional tax advice. It is provided “as is,” and neither the author nor Office Depot warrants the accuracy of the information provided, nor do they assume any responsibility for errors, omissions, or contrary interpretation of the subject matter herein.