Ask The Hustle: How Do I Start Freelance Writing?

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Sara Friedman
Sara Friedman

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A while back we invited you to slide into our DMs, and almost 300 of you wrote in with questions. We got some good ones, and we’re getting back to you here. This one’s from Valerie in Alameda, California:

Ask The Hustle

How do I start freelance writing? What kind of tax setup is needed? How do I find my first clients?

The desire for remote work and career flexibility has led to an increasing interest in freelancing. Paired with the rise of platforms such as Medium and Substack, launching a side hustle or a full-blown career in freelance writing seems more attainable than ever. 

But diving in can be trickier than you think. We sat down with Juliet Bennett Rylah, senior writer for The Hustle newsletter and a longtime freelancer, to learn how to launch a successful freelance career: 

  • Assemble your portfolio: If you’re not already a professional writer with a portfolio of clips, the best way to get started is by putting pen to paper (or, rather, fingers to keyboard). 

    Bennett Rylah suggests creating a blog (or using Substack, Medium, or another writing platform) where you can begin writing articles. 

    Once you have some links to your name, create a portfolio or website where you can aggregate and showcase your work. WordPress and Squarespace are common options, but you can use whatever feels most intuitive.

    You can also include any multimedia work, such as photography, illustration, or video, if you have it. These types of talents could make you more appealing to publications.

  • Pitch, pitch, pitch: Once you have some published articles and a site to store them on, you’re ready to get pitchin’. 

    Bennett Rylah says it’s helpful to pitch stories you’re genuinely interested in and have some prior knowledge of. 

    If you’re a foodie, you could pitch stories to niche food publications. If your day job is in marketing, you could pitch stories to a marketing blog or a business site.  

    Many editors will let you know how they want to receive pitches, listing instructions on their Twitter profiles or websites (the norm is pitching via email).

    When writing up an email, introduce yourself, link to your portfolio, and highlight articles you’ve written that relate to the story you’re pitching. Then, spell out the story you want to write and how you would go about it (if you already have a contact or research, include that).

    “Keep it short, because editors are receiving countless pitches a day,” says Bennett Rylah.

    And don’t let fear get in the way: “The worst thing that can happen is that you don’t get a reply or they say no,” she says.

  • Build your network: Connections will get you everywhere. Bennett Rylah suggests following editors who work for outlets you're interested in on Twitter as they often post calls for articles or ways to pitch.

    Simply type in “editor” on LinkedIn and Twitter to begin the search. Other helpful sites include Media Bistro, a job board dedicated to creative positions, and Study Hall, a paid weekly newsletter with calls for pitches from editors across publications.

    Tip: Once you land a gig, show your editor how reliable you are by handing in clean copy before or on deadline. You’d be surprised how rare reliable, talented freelancers are, and a job well done can mean more future business.

  • Figure out finances: Working for yourself can mean a much more complicated tax season. Clients will commonly give you W2 or W9 forms after you’ve completed and been paid for an assignment. Come tax time, the taxes you owe can pile up quickly.

    If you plan on freelancing frequently and have it in the budget, consider bringing in a professional during tax season to sort everything out.

    But how do you know you’re being paid enough for your work in the first place?

    Bennett Rylah says a good rule of thumb is to not accept less than 10 cents per word for freelance work, with the gold standard being $1 per word (though she says that’s difficult to earn).

  • Bottom line: Price isn’t the only thing at play. Take into account what you can gain from every assignment, and see if the hassle (and the taxes) are worth the money and the byline.

    Freelancing isn’t easy, especially if you want to go all-in, but once you build up a steady roster of clients, it can be a freeing and exciting career. 

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