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

October 1, 2022

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 options for filing — 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 typically used by employers with minimal filings. Beyond that, you can take advantage of desktop software to input data and create the necessary forms. 

And then there’s electronic filing, where you enter data online and the information is automatically processed and submitted to the IRS and SSA. You can also have recipient copies printed and mailed, which makes e-filing the most convenient method of filing. Keep in mind, too, that you can skip Form 1096 (or W-3.) with e-filing because the totals are automatically calculated and transmitted.

2) Time to collect necessary information — Although tax season is right around the corner, you still have a few weeks to line up certain details. To properly file the 1099-MISC for contractors, freelancers and consultants, for example, you need a Form W-9. The W-9 captures the individual’s legal name, address and Taxpayer Identification Number (TIN). Ideally, you should have the contractor fill out this document before services are provided. Otherwise, request it immediately to avoid the rush for information.

3) Opportunity to file 1099-MISC forms early — The early bird gets the worm … and is less stressed, too. Instead of waiting until January, try to begin filing your 1099 forms now. You can jump ahead if an independent contractor has completed their work for the calendar year and you have the necessary information.

Get Ahead of Your Tax-Filing Responsibilities

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