A few weeks ago, I published a post called “Stuff I Wrote,” which was a round-up of some freelance work that I’ve been doing for Activewear USA.  A bunch of people asked me to share advice and tips on how to break into freelance writing, and while I was happy to oblige, I also struggled with what to say to everyone!  I have no advice that sounds like: “Do A, B, and C and you will become a freelance writer.”  My story is highly personal and specific.


I thought back to an oldie but goodie post called “How I Got Published!” At the time, I’d published one of my three books, and lots of readers had been asking me for publishing advice.  Again, I felt like my situation was so personal and specific that I wasn’t the best advice-giver, so I asked a few authors, as well as my agent, to talk about the process of getting a traditional book to print, writing an e-book, or self-publishing a book. I thought it’d be fun to do the same type of thing with this post – I know there are a lot of other freelance writers out there, so I hope you’ll share YOUR experiences with getting work so others can learn from everything you’ve done!


So – here’s my story.


I have actually been freelance writing for 12 years.  When I was 18 and a senior in high school, I was searching the Internet for advice on whether my best friend Lisette and I should room together when we went to college (we did, and it was awesome).  Anyway, I stumbled across a column on The Wall Street Classroom Edition website.  The site was the virtual version of a monthly paper that was mailed out to high school students across the country.  A lot of the magazine was written by professionals, but some columns were written by students. As I read a student-written article, I thought to myself, “Hey, I could totally do this, too!”  So I did something totally ballsy:  I emailed the editor and said that I could do a better job than any other student he had on staff, and that he should hire me immediately.


Seriously.  I said that.  I’m half-embarrassed and half-pleased with 18 year old me’s self-assurance.


Much to my surprise, the editor actually emailed me back.  I guess my ballsy email was actually well-written – after a phone call, he offered me the job!  That was back in 2002.


I wrote for the paper for free for a year, and then my editor started to pay me.  The WSJ CE has since shut down due to the recession, but I wrote for them for 5 years.  The first few years, I wrote about my personal experiences in college (very future blogger of me, huh?).  Then I started to interview and profile notable college students from across the country.  Most of my articles are no longer online, but here’s one from 2006 and here’s another from 2007 if you want to read my old work!  My editor at WSJ CE was the person who made me believe that I could make a living as a writer.  And, most importantly, his editing made me a much better writer – I’ll always be so thankful for him!


There was a brief period in 2007 that I didn’t do much freelance writing at all – at that time, I was working at an urban planning firm and most of my writing was tied up in technical documents.  I dabbled in a few paid projects that came my way because of WSJ CE connections.  I also wrote a few pieces for free for a Pittsburgh fashion website start-up.  But when I started my blog back in 2008, I dived back in.


Most of my jobs come from connections and referrals.  I’ve been doing this for a long time, and I’m lucky to work with awesome people who are willing to refer me for other jobs.  I currently work for a writing house that produces content for big companies.  I write about 4 – 5 articles a month about a ton of different topics.  Most of my work is published online, but a few pieces that I write get published in store magazines.


My favorite thing about freelance writing is that I get to learn about an incredible range of topics.  I have written about everything and anything, from articles on high-tech camping gear to techniques for keeping champagne fresh (spoiler: the best technique is to just drink it all – hah!).  My favorite thing is to interview experts, like a sommelier for the champagne article.


Could I live off my freelance earnings?  No.  I would have to pitch myself a lot more to make a significant amount of cash off it.  In my experience, online writing doesn’t pay as well as print, and print is hard to come by.  But I have fun writing, and the pieces I do each month pay off a few utility bills.


As I stated in the little graphic at the beginning of this post, I think it’s a wise business move to keep in contact with editors – preferably more than one person at each publication because people always come and go.   Don’t just send in your article and never e-mail your editor again; get to know each other!  Also – I place a lot of weight on making deadlines.  I’m not a perfect writer, but I have never missed a deadline in 12 years.  Editors value that.  And lastly, I believe it’s very important to pass on writing opportunities to other writers.  When I get a job that doesn’t work for me, I always try to refer someone else that I know.  I like to think of it as building writing karma.


Some other ideas:


Writer’s Market:  This book is packed with information regarding agents, editors, contests and awards, and pay rates.

Volunteer:  I wrote for free for an entire year to break into the business. New writers always need ‘clips’ – so offer to write content for a small business newsletter or a non-profit’s website.  I do think it’s important to value yourself so others will value you, but there’s nothing wrong with doing a little free work as you gain experience.  Just know when to say, “Enough! Time to pay me!”

Read this Blog:  I love The Renegade Writer’s blog.  There is a lot of great info there, especially the query letters tab.


Are you a writer?  How did you break into the business?



  • CM May 27, 2014, 9:30 pm

    I actually just made the switch to being a full=time freelance writer! I do content marketing – which means I write blog posts for lots of different companies. Most of them are ghostwritten, which might be an issue for some people, but I’m a fiction writer as well, so I actually prefer to keep my name out of it.

    For me, full-time is about 60+ blog posts a month and I spread them out between 7-8 different clients. It’s nice because it’s consistent. I know a minimum that I’ll be writing every month, which means i also know a minimum that I’ll be making every month. It’s definitely not the ideal type of writing that I would like to be doing, but I make (what I consider to be) good money and it’s given me more time to write creatively.

    One thing that I’ve learned is that most people are TERRIFIED of producing their own writing (especially with how easy the internet makes it for content to be widely distributed), which is problematic for business that want to keep up with marketing trends. There are tons of freelance options out there – not all of them are glamorous and it might take awhile to build up your client base, but it’s totally possible to do it full-time as your only job! I’ve actually found that my online writing pays way more and is much easier to come by than print writing.

  • Runner Girl Eats May 28, 2014, 5:54 am

    Great tips! I think that it is awesome that you were so ballsy with the WSJ! Getting published is on my bucket list so I will bookmark this for when I am ready to make that leap.

  • Angela @ Eat Spin Run Repeat May 28, 2014, 7:46 am

    Great post, Caitlin! I always love hearing how successful blogger got into freelancing and writing, and your tips are great (as is your ballsy-ness!) 🙂

  • Beks May 28, 2014, 8:44 am

    I’m still working on breaking into the business, itself, but I self-published my first novel back in 2012 (a move that I now realize was probably a bit premature), and am working on several other projects. I actually would like to start my own online publishing company.

  • Young Work at Home Moms May 28, 2014, 8:57 am

    Hmm. This is a very interesting article. However, I have to say I have been doing online writing since 2011 and it pays all of my bills each month. Some of months my income may be less than I like but I always make sure I have emergency savings available for months like that.

  • Lisa May 28, 2014, 10:40 am

    Very interesting post, thank you for sharing! I think that your passion for researching and writing about a variety of topics also shows in this blog 🙂

  • Rebecca May 28, 2014, 11:45 am

    I’m working on transcription, if that counts. Hah. I haven’t actually started transcribing anything yet, as I’m waiting for another test file with the website to be available (did a practice file and did okay, though!), and it wouldn’t a ton of money per month (basically a dollar per audio file I complete), but it would help a little, at least.
    Also looking into editing (writing or video) but not having a ton of luck just yet… But that’s probably because I’m too picky about where and what, and I’m not looking as often as I should. /sigh

  • Stephanie @ Whole Health Dork May 28, 2014, 1:28 pm

    Thanks so much for posting this! I had no idea that you’ve been writing for so long. I always find it so fascinating to learn about peoples’ backgrounds (that’s really general, but you know what I mean…).
    I’m not a writer, but I wouldn’t mind breaking in to writing a little, just for a little side money and for some experience, to see if I like it. I love writing on my blog and doing a little side piece, so I’d love to see where I can take it.
    Thanks again!

  • Katie @ Talk Less, Say More May 28, 2014, 2:01 pm

    Thanks for sharing your story! I’m definitely not looking to break into it and have it totally replace all my income, but I love the idea of doing something I love (writing!) to help pay off a few more of those pesky bills and maybe buy a few extra cups of coffee from my favorite place! 🙂

  • Katie @ Peace Love & Oats May 28, 2014, 2:03 pm

    This was great! I’ve been thinking about breaking into freelance writing for a while, but I just don’t really know where to start!

  • Kendall Covitz May 28, 2014, 3:18 pm

    Great tips! I love all of your work on ActivewearUSA!

  • Jasmine May 29, 2014, 11:36 am

    That was fascinating. I had no idea you did all that!

    Back in my blogging days, I wrote articles CONSTANTLY and for beans, so I totally understand that aspect of it.

    Great post!

  • Amy June 8, 2014, 8:52 am

    I just got a very small freelance gig, and I’m so excited! Thanks for the advice; it is so helpful!

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