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Freelancing: It’s Complicated. NOT! President’s Post by Laura Stigler

09 Jun 2019 7:25 PM | Anonymous

Fresh off our Magical Mystery "Life in the Freelance Lane"* tour, I’m seeing a pattern in some of the questions we get asked. No matter where we present, from the American Writers Museum to Skokie Library to the Career Transitions Center of our most recent presentation at Next Door Chicago (a buzzing community hive located in Lincoln Park), budding (or even seasoned) freelancers are consistently inquiring: 1) “Do I need to set up an LLC?” 2) “Do I need a license to start my freelance writing business?” and 3) “Do I need a tax permit?”

Gonna be totally frank here. When I started out freelancing, none – and I mean none – of those questions ever crossed my mind. Under the heading of “Ignorance is Bliss,” I began my business simply by making cold calls, answering ads and joining IWOC. This was in 1989. Knock wood a million times, I’ve been working ever since. Yes, throughout the years there have been feasts and famines. But overall, the work has been steady. Apparently Ignorance has paid off, and freed me to just dive in and start earning a living doing what I love. Again, knock wood.

So for the record, let’s unpack each of the questions with as pithy an answer as I can muster.

1). “Do I need to set up my business as an LLC?” Disclaimer: I’m no lawyer. But from the way it was explained to me, LLC’s do have some advantages, such as:

  • You can set up a 401k, which you can even borrow against should the need arise.
  • It protects you against liability.
  • You can pursue giant clients, who sometimes like that protection.

Taking all that into consideration, here’s the most sensible advice I’ve heard from experts: START MAKING MONEY FIRST. I also have to say that unless you intend to engage in slander, lies and plagiarism, there ain’t a whole lot you can be sued for when you’re on assignment. But don’t quote me on any of this. Best to consult an attorney. (We have a great one right here in our midst: IWOC member Marci Rolnik Walker of Lawyers for the Creative Arts.)

2).“Do I need a license to start my freelance writing business?”Not unless you’re planning to also give Botox injections. Or sell booze. Or offer hair weaving services. That sort of thing. In other words, even if you’re getting paid for it, you don’t need a license to write.

3). “Do I need a tax permit?” Not quite sure what is meant by that. But the only thing related to taxes that I deal with is paying them quarterly, using the 1040-ES (Federal) and IL-1040-ES (State) forms you can download from online. You can also pay online. But I am not a CPA either. So my advice would be to talk to your trusty accountant to discuss your particular situation.

The bottom line is this: Freelance writing is probably one of the easiest businesses in the world to set up. Yes, you can chase your tail, make sure all your ducks are in a row, get sidetracked with articles and classes that will give you every imaginable and confusing – and even irrelevant “how-to.” Writers are infamous procrastinators, and sometimes, all these “to-dos” are nothing more than procrastination tactics.

To start working as a freelance writer, all you really need is your computer and a phone. Oh yes, and your talent. That’s it. You’re ready to hang out your shingle.

Now, as those experts advise: Just. Start!

- Laura Stigler

* "Life in the Freelance Lane: Business Basics for Freelance Writing Success" is presented regularly at various venues throughout Chicago and surrounding suburbs. Regular speakers are Jeff Steele and Laura Stigler, along with alternating presenters George Becht, Sally Chapralis and David Steinkraus. If you'd like to join our speakers roster or host a presentation at your venue, please contact or

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