Dealing with taxes as a freelance writer

Freelancer taxes

I’ll try to hit a few transparency targets around dealing with taxes as a freelance writer in this post. We probably need to begin with a little bit of personal backstory.

The background leading up to freelancing

I moved to Texas in July 2014 for a job at a B2B travel consortium company in Fort Worth. I lasted at that job around 17 months and got canned. The actual day of the firing was the same day as the Paris attacks; just figured I’d throw that in for some additional historical relevance.

That was November 2015. I had a small severance but no real plan. Seeing as how it was before the holidays, I pretty much spent the 2015 holiday season drinking and feeling sorry for myself. Always a fun time to be alive.

In January 2016, I had about four different sets of interviews for jobs. None of them really panned out. I got far on two of the four but didn’t get them. So around late January 2016, I needed some kind of plan. I didn’t want to go through some long, drawn-out hiring process to ultimately not get a job for some subjective reason like my hair.

At this time, I was making maybe $500 to $1,000/month on the side doing some writing projects. My wife had a full-time job, but $500/month on my side wasn’t enough. So I started cultivating some freelance clients and opportunities.

That job I got fired from, I had been making $72,000/year or so. I knew freelancing would be hard — “a hustle,” if you will — so I figured a good year would be about $45,000.

Here’s what happened on the taxes side

First off, I asked my therapist — yes — how this all works. He told me we needed to pay quarterly taxes, which is detailed a little bit in this blog post. The actual IRS guide to self-employed quarterly taxes is here, and the actual form you use is the 1040-ES, which can be paid online or via mail.

Now you know the forms and resources. Next step is figuring out what your percentage is. There are different approaches to this. I was thinking I’d make $45,000 or so; I ended up making about double that. (I got lucky in some spots.) When I initially asked one of my friends, he told me to slot 15-20 percent of every paycheck towards quarterly taxes. He had been paying them for years and making more than $45,000, so he seemed to know what he was discussing and I went with that. I dumped about 16 percent of every payment I got into an account for quarterly taxes.

There is a more scientific way to do it, detailed in this post. I’ll probably do that in coming years, but in the first year, I think just making sure you have the right systems is important.

Like what systems?

Freelancers get paid in different ways, obviously. In 2016, I was probably 80 percent PayPal. PayPal has accounting functionality within it, and it keeps records of everything you received via your account. Also: if you upgrade to PayPal for Business Payments, you can see less fees when you get paid. (50 cents vs. 2/3 percent, I believe.)

Even though I was mostly getting paid via PayPal, I set up a Google Sheets within my Google Drive where I recorded every payment. I listed:

  • Date
  • Who paid me
  • Exact amount
  • Source (PayPal, check, cash, etc.)

The quarterly tax deadline dates cut-off around March 31, May 31, August 31, and December 31. So after my last payment on those four dates, I left a blank row and bolded the next quarter, i.e. “Q3 starts here” or something.


Then I could easily scroll down from the beginning of Q3 to the end and Sheets would tell me what all the “exact amount” column added up to. I could multiply that by .16 (16 percent) and determine my payment.

You can also use Intuit business resources, and ultimately I organized and filed through TurboTax, which is an Intuit product. I’ll be the first to admit that I don’t fully understand taxes as well as I should, and TurboTax is good in that regard because it’s an extremely intuitive, guided product for the less-informed tax-filers.

So what happened?

Because I made more money than expected, I did have to pay the IRS for 2016. (I was hoping not to, but alas.) The good thing? I did better than expected. The other good thing? I learned a little bit in the process about how to file as a freelancer and some “hacks” and “tricks” along the way.

If you have any additional self-employed filing tips or hacks and want to leave ’em below, let me know. Meanwhile, it’s back to that proverbial hustle.

Ted Bauer


  1. Thanks for sharing Ted—this is great stuff.

    Very encouraging that you blasted past your target of $45k—like yourself, I have been doing some freelance SEO stuff on the side for some extra scratch over the past couple of years. I usually set aside 30% of my earnings in a savings account for quarterly taxes—I picked that trick up a few years back in a contracting gig for the City of New York and am glad I did—I would freak out if I had to dip into my savings/investments to pay taxes.

    Good call on using PayPal’s accounting functions to tally totals—I do the same thing and it’s very helpful.

    I am taking a break from writing for now to focus on part-time grad work but—I’m planning a relo later this year and would like to have the option to subsist off freelance income while searching for F/T work. As we both know, hiring processes are FUBAR; early interviews have produced head-scratching results. Had a first round interview at a nonprofit in my future home a few weeks back…nice conversation that lasted an hour. “Oh, we want to have someone start by the end of the month, so we’ll get back to you soon”. Radio silence since then. I’m used to it by now, but it doesn’t make the practice any less gross.

    I would love to pick your brain about best ideas for ID’ing potential clients and pitching to them—heck, I’d take $45k in a heartbeat from freelancing for a while until I found a good job fit—most of my work thus far has been through agencies, and though I’m grateful for them sending me work I’d love to cut out the middle man.

    I’m at plopcornblog@gmail.com if you feel so inclined 🙂



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