The Most Frequently Asked Freelance Writing Questions

Some times I get questions from aspiring writers about how to make it as a writer. I thought this post would be helpful to share the most frequently asked questions I get and answer them here.

1. Can I make money as a writer?

Yes. I do make my living from freelance writing and editing. Would I say that I make as much as I did when I worked full-time? No. But I’m much happier. I get to control my own schedule, work on a variety of projects, and have time for my own personal projects. If you are aiming to make $100,000 a year your first year freelancing, I would say that’s probably not realistic unless you worked all the time. If your main goal is to make lots of money, freelance writing may not be the career for you. I also recommend this very detailed blog post—the ultimate guide to setting up a freelance business—from freelancer Jennifer Armstrong. Armstrong’s website also has a ton of posts about the realities of being a freelance writer.

2. How do I get started in writing?

I highly recommend taking classes whether online or in-person. Through a class, you’ll have a solid deadline, meet your peers, and work with a professional who has been through the freelancing world. I’ve taken great freelance writing classes through Mediabistro and UPOD Academy. Paula Derrow is a fantastic personal essays teacher. Check out her website to see when she’s teaching. She also privately consults as an editor, if you want to work more one-on-one.

3. How do I make the transition to full-time freelancing?

I worked as a magazine editor full-time while slowly building a portfolio of clips and networking with editors. When I felt like I was ready to switch over to freelance, I had a list of contacts that I could reach out to and pitch. Through past coworkers who knew my work and liked me, I got more contacts and work from them. I must admit, it still felt scary to dive into the waters of not getting a steady paycheck every two weeks, but a year or so later, I’m loving it. I’m a deadline-oriented and schedule-type person so I structure my work day similar to my previous 9-to-5 jobs.

4. How do I write a pitch?

This one is tricky. The best way to write a pitch is to take a class and learn. While it’s easy to shoot off an email to an editor you just met, you’ll do much better if you research the publication and tailor your idea to that particular magazine or website. David Hochman, the founder of UPOD Academy, says it best: Why should we care about this story?

5. Should I write for free when starting out?

When I first started out, I wrote a few pieces for free. I wish I hadn’t. It’s understandable when you’re green that you take on free work to get a byline. It’s up to you, but don’t work for free forever or if you do, make sure you get something out of it more than just a byline.


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