Freelancer Tax Prep: The First Five Steps

Tax season is already starting to get to a lot of us: it feels like there is so much to do and no time to do it in. Personally, I’m of the opinion that any project — taxes included — can be easier to do if you can break it down it easy steps. I’ve broken down tax season into several steps. The first five are here: you don’t need to sit down and do all of them in one go, but try knock out one or two over the weekend, and finish them up next week. It’s a matter of just getting things done.

  1. Fill out your W-9s. If you think you’ll need one on file with a particular client, check in with them and offer to send it. Personally, I filled out the .pdf version available on the IRS’ website on my computer and saved it on my desktop. Now, whenever I need to send out a W-9 to a company, I just print it out, sign it and send it off.
  2. Check which clients will owe you a 1099 form. I just run down my list of paid invoices and see who has paid me more than $600 in the last year. If you haven’t kept track of your income, this step could be harder: you’ll need to go back through your projects and determine what you were paid.
  3. Contact those clients who need to send you a 1099. A lot of companies may need some time to turn around a request, especially if you haven’t worked for them in the past few months. Plan to give them a little time.
  4. Figure out your business expenses. I know a lot of freelance writers rely on the shoebox method of tracking expenses — they stick all of their receipts in a shoebox — which can make this step a bit harder than the rest. Not doing it, however, can lose you the opportunity to write off deductions and generally save yourself from a hefty tax bill.
  5. Decide who will be doing your taxes. I’m of the opinion that, if your taxes aren’t unusually complicated, it’s worth doing them yourself. It can be expensive to hire someone and all of that. I know that plenty of freelancers have no interest in doing their own taxes, and that’s fine. But now is the time to make up your mind who is handling your paperwork — check them out, and generally decide whether you can work with them beyond just your tax return (don’t forget your quarterly payments!)


  1. Rena Sherwood   •  

    Wait a minute…you need to send the W-9 to the company and they send you the 1099 or they send you the W-9 and the 1099 back? Interesting post. Hope you are well.

  2. thursday   •     Author

    Sorry for the confusion, Rena — you send a W-9 to the company, and they send you the 1099.

Leave a Reply

Your email address will not be published. Required fields are marked *