Guide to Becoming a Freelance Writer
By: Francesca Di Meglio
Tags: Writing, Blogging, Entrepreneurship, Careers, Freelance

Find out how to become your own boss, work from home, and earn a living from someone who has been a freelance writer for nearly two decades.

My plan always was to become a freelance writer. First, I was going to work on staff at different publications as a writer and editor. However, I ended up changing course 7 years earlier than I had anticipated. Sometimes, life makes these kinds of decisions for you.

At the time, I had injured my knee and ended up needing to work from home with flexibility to go to doctor’s appointments and regular physical therapy. It took two years and three surgeries to correct my knee. By the end of the ordeal, I was a full-fledged freelance writer and there was no turning back.

You can do it, too. Ideally, you have cultivated experience and a network of editors through full-time work first. But nowadays you don’t necessarily need that on your resume to successfully launch a freelance writing career.

Read and Write Like Your Life Depends on It

To be successful at freelance writing, you need to read voraciously. Ideally, you are keeping up with current events, especially in the area of your expertise. I set up Google alerts, read new relevant books as they are released, and read mainstream newspapers, including The New York Times, the Washington Post, and the Wall Street Journal.

Don’t stop there. News magazines and websites, such as Slate or Buzzfeed, could be relevant to the beats you cover, too. Google to your heart’s content to stay informed and brainstorm ideas. The point is that you have to know what’s happening in the world and make connections to it in your writing.

Then, you have to write often. Writing is all about practice, after all. Be unafraid to edit and revise. Rewrite and cut entire paragraphs. Look at the publications for which you are writing or pitching and figure out the formula for their stories. Try to convert your writing to their format whenever pitching to them.

Become an Expert

While I was working on staff at Ladies’ Home Journal and then Bloomberg Businessweek, I covered a few different beats. I wrote stories about family travel and relationships for LHJ, and I wrote about higher education with a focus on business schools for BW.

During my tenure at those places, I learned everything I could about those topics. I developed a network of sources, who could answer questions and provide comments for stories I write. In addition, I learned to follow organizations that focus on these areas.

Since I left LHJ, I have used my knowledge to write stories for travel publications, and I even was the Newlyweds expert for About.com for more than a few years. My work at BW has proven to be even more fruitful. I have worked on short-term and long-term writing and editing projects related to universities and business schools for the last two decades as a result of that experience.

Maybe you have a hobby or passion. Learn as much as you can about it. Talk to people in that industry or world. Once you have enough knowledge, where you can contribute thought leadership, begin sharing your ideas.

Start a Blog

One of the easiest ways to start getting noticed is to self-publish a blog. You can actually create your own website using services, such as GoDaddy. Or you could write regularly right here on Medium and other social media platforms, such as LinkedIn.

You’ll have the most success if you write well about that one topic in which you’ve become an expert. My website and blog is about family travel with a bent toward Italy. My family comes from Italy, I’m fluent in the language, and before Covid-19, I traveled there often. In addition, my previous experience as assistant editor of travel for Ladies’ Home Journal and the book I wrote about traveling with kids in my home state of New Jersey made this topic a good fit.

I also include relevant articles about parenting and creating memories for your family even if you can’t afford a lavish vacation or can’t go anywhere now because of the pandemic. I spend some time on LinkedIn, on the other hand, focused on management education and universities and colleges. I sometimes publish stories with that kind of information on LinkedIn. While stories and articles published in outside publications and websites are better clips when pitching stories to clients, these blog entries can still show your range and expertise.

Get Your Work Out on Social Media

Promote everything you write on social media platforms. Even if you start out writing to your friends and family only, you will eventually grow your audience. The key, as I understand it, is to regularly post, preferably throughout the day. You can schedule posts to make it easier. Honestly, I’m still working on this.

Ideally, you will create a dialogue with readers, so you have to block out time to respond to their messages. This won’t happen overnight, but eventually, if you’re persistent you will get some readers to respond. You might even get hundreds or, dare I say it, thousands. You may also send newsletters via email, which alert readers of new content and your presence online.

Reach Out to Your Network

If you’re like me, you have been cultivating a network of editors and other writers. You keep in touch with them and can reach out for advice or to pitch story ideas. My network has helped me get regular work, which allows me to pay the bills. Those in my network give me feedback and advice. Some of them serve as mentors to me.

As you develop your network, you should stay in touch. Send emails, make calls, and set up meetings. It should not be a purely transactional relationship, nor should you only be getting in touch with your contacts when you need something. Of course, whenever help is provided, be sure to show gratitude. Send thank you cards and express your thanks verbally.

Make sure the relationship is a two-way street. In other words, return the favors by putting those helping you in touch with others who can help them. Share potential jobs with other freelance writers. Provide feedback when called upon and so on.

Pitch Stories and Look for Work

This is the part of the guide where I diverge from most other freelance writers. Many of them suggest pitching stories all the time, at least one a day. You will mostly get rejected, so you need to increase your odds by increasing quantity. I’m sure that does work for some writers. Maybe you will be among them.

However, I’m not the pitching type. I have almost never gotten a story from cold pitching an editor. I was successful at selling a couple of stories to publications for Italian Americans. Other than that, I have always been rejected.

Instead, I turn to those with whom I’ve developed relationships and see if there is any kind of story they need pitched or written. Then, I provide them with whatever they need. My most successful runs have been during times when I held contract positions with an organization.

I served as a freelance writer, editor, and reporter for Businessweek for nearly a decade. Although I worked from home, I went into the office about twice a year, and I was on weekly conference calls. When our team won awards, I was included in the celebrations. It was a fulfilling job. I was free to work for other publications because I was not a full-time staffperson, nor did I receive full-time benefits.

In more recent years, I have worked for different publications for months or even years at a time. There is not much job security in these roles. But you do feel more like you’re part of the team and that can be motivating. In addition, it also serves as a boost to your network.

Develop a Thick Skin

You are going to face lots and lots of rejection and cutthroat revision of your work. If you can’t accept that kind of critique and disappointment, then this is not the field for you. So, make sure you are prepared and can take the heat. To be honest, I sometimes find it hard even after all these years.

Still, I look myself in the mirror, tell myself I’m good enough and not to take it personally, and then I make the necessary corrections or move on depending on the situation.

Also, I would not immediately rely on freelance writing to pay your bills. You should develop savings or keep freelance writing as a side gig at first. Ultimately, however, if you don’t try to put yourself and your work out there, you will never know if you can do it.

Feel free to ask any questions you have about freelance writing in the comments below.