How a One Month Pitching Challenge Revived My Freelance Writing Business

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Joe Dyton won July’s pitching contest – a one month pitching challenge just for those that are or have taken 30 Days or Less to Freelance Writing Success. I put $50 of my own money on the line to incentivize students to get over their fear of pitching and start submitting pitches regularly, in hopes that they land their first or next freelance writing client. Joe is here to share his results from the challenge and how it helped him re-prioritize his marketing strategy and get closer to achieving his goal of becoming a full-time freelance writer. 

For the last couple years, I have had my sights set on building up enough of a client base to one day become a full-time freelance writerUnfortunately, I spent a lot of those two years spinning my wheels.

I’d make a big push to get clients, then not hear back, get frustrated and stop my marketing for awhile. Or, I’d get busy writing for the clients I already had and would put marketing for new ones so far on the back burner I couldn’t even see it.

My freelance writing career was going nowhere fast.

It was frustrating, because I knew what I needed to do: market, market, market. And when I was tired of marketing, do it some more. I just needed a jolt to get me excited about the idea of pitching again.

Boy have I ever! Today, I’ll share with you how a one month pitching challenge revived my motivation and my freelance writing business.

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My Moment of Change

Luckily, I came across Gina Horkey’s 30 Days or Less to Freelance Writing Success course. At first, I was hesitant to sign up; it’s geared more towards freelance writers who are just getting started and I’ve been writing for more 15 years full-time.

And I have had a little success freelancing.

However, given the rut I was in, the low price of the course and seeing Gina’s  success in such a short time span (she was able to leave her job less than a year after getting started), I figured it was worth the investment.

I’m glad I took the plunge!

I got a lot of good reminders of things early on and some good tips for things I hadn’t thought of that could help my marketing efforts. This course alone had gotten me excited about getting my freelance writing business off of the ground, but then Gina upped the ante with…

A Friendly Competition

“A one-month pitching challenge given to everyone in the 30 Days or Less to Freelance Writing Success (extra accountability via Facebook) in July. And the winner would receive $50!”

(By the way, there’s one going on right now for the month of September and it’s not too late to get rolling!)

I didn’t hesitate for a second to enter.

I figured if I won I’d get $50, which would pay me back for the course tuition. And if I didn’t, I’d send a lot more pitches than I might have normally. It was a win-win in my book! 

The Outcome

Once the calendar turned over to July, I got busy. And I ended up winning the contest with 159 pitches!

Most importantly though, I got my name out there to a bunch of websites, publications, corporations and agencies.

Since the contest was about quantity and just putting myself out there as much as possible, I decided not to send out specific article ideas to magazines and blogs. All of my pitches were either job applications to places specifically looking for freelance writers or cold pitches to businesses, offering up my writing services for hire.

Where I Looked for Clients

1. Job Boards

I used a number of job boards to find leads:

I applied for straight-up freelance jobs that were open and also sent letters of interest/resumes to businesses that were looking for full-time employees and asked if they used freelance writers as well.

2. Google

Let’s face it, job boards have only so many openings. If I was going to compile enough pitches to win the contest, I had to find other ways to find places to pitch.

Once I exhausted job boards for the day, I’d go to Google and search, “marketing agencies in <xyz city>” or “real estate trade publications” (one of the subjects I have a good amount of experience in). These types of searches greatly expanded my avenues to pitch.

The Results

In part, they remain to be seen. I only say that because not every company, publication, website, etc., will respond right away.

For example, a company I pitched in April got back to me in July and offered me some work! As I’m writing this, I’ve heard back from about 10 of the 159 people I reached out to.

I got several, “Thanks for the note, we’ll keep your information on file if there’s ever a need.” However, I did land one steady gig, signed a contract with a writing service and had a PR firm ask me to come in for an interview (I applied for the job through Mediabistro, but said I was looking for freelance writing opportunities).

Hopefully, more of the businesses I reached out to will get back to me as people return from their vacations. (And we’ll make sure to do a follow up with Joe in a few months!)

Going Forward

I can’t say enough about how great Gina’s course was and how much of a factor it’s played in rebuilding my enthusiasm for growing my writing business. Now I make it my goal to send at least five pitches a day.

And the persistence has paid off. Since I took 30 Days or Less, I added another client to my list and was recently invited to audition (paid) for a marketing company. I’m still waiting to hear back on that one, but my fingers are crossed.

So my fellow aspiring freelancers, keep pitching! Remember, the worst thing that can happen is someone says no or doesn’t respond.

Then you just move on to the next person. If you need help developing a pitch or want to improve your current one, be sure to check out 30 Days or Less to Freelance Writing Success.

You’ll also be a pitching machine in no time!

Did you participate in July’s contest or are you currently competing in September’s? If so, how’s it going?

Ready to Kickstart YOUR
Freelance Writing Biz?
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Joe Dyton (@JoeDyton) is a freelance copywriter and journalist in Washington, DC and author of  The Aspiring Freelancer blog. He may be reached at Check out his site at

Photo Credit: Marta Pawlik via Unsplash

22 thoughts on “How a One Month Pitching Challenge Revived My Freelance Writing Business”

  1. Joe, I think you’re the official hero of the pitching challenge.

    Thanks for sharing. It seems you’re going strong in the September pitching challenge too.

    • Thank you, Mickey! I really want to build up my client base this year. I figure the best way to do it is reach out to as many people as I can. 🙂

  2. Joe, that is fantastic! I love your approach and the “just get out there” mindset. I know I need to do that. I talk about wanting to expand my exposure and get more clients and assignments in my niche, but I haven’t done a lot more than talk up to now! So far, every client I’ve had has come to word of mouth so this will be a new adventure for me.

    • Thanks, Malea! Yes, the way I look at it, the more I put myself out there, the better chance I have of getting work. Just take it a couple of pitches at a time; you’ll get more comfortable the more you do it.

  3. Awesome job, Joe! That’s impressive. Being consistent with my marketing efforts has been the toughest thing for me. That fear of rejection seems to take over. I think I’ll try a pitching challenge myself to get out there. Look forward to hearing how your efforts pay off.

    • Thank you, Mary! It can be scary at first, but believe me there’s nothing to be afraid of. I’ve been rejected plenty have lived to tell the tale. It may take a lot of “no’s” to get a “yes”, but when you get that “yes”, you realize all of that pitching was worth it!

  4. Great work Joe! A big part of getting good results is simply to make a consistent effort. 159 applications is a LOT. Congrats on the success so far, and hopefully you’ll hear back from a few more of those gigs you pitched!

    • Thank you, Daryl! I read a lot about how to find success as a freelance writer and no matter what I read, the one common theme seems to be the best way to find clients is to pitch, pitch, pitch! Ever since Gina’s contest, I’ve made it priority to get a few pitches in each day.

    • Thanks, Vicky! It certainly does! My biggest challenge over the years was to keep pitching even when I wasn’t hearing back from anyone. There was a time I’d get frustrated and stop pitching for awhile. Now, I just keep pushing ahead and tell myself that people WILL respond if I keep at it.

  5. Thanks for sharing, I enjoyed reading. Your article gave me some much needed encouragement to keep throwing out pitches for the September challenge.

  6. Wow! That’s just amazing and I’m inspired to give that a try myself. I imagine you’ll be reaping the rewards for quite some time to come. But I love that you’re being proactive and continuing to send out pitches daily. All the best!

    • Thank you, Charlotte! I encourage you to give it a try! Yes, the contest was a great launching pad for me; it built great pitching momentum that I wanted to carry into August and beyond.

  7. Joe, I am really impressed by your pitching work. After completing 15 years of freelancing business also, you still have the fire of the beginner. This is really incredible
    This shows your passion and love for your work. Thanks a lot for motivating all the writers. I will definitely keep these things in mind 🙂
    Thanks Gina for sharing Joe’s hard work with all of us.

    • Thanks, Yatin! I do in some ways consider myself a beginner; I’ve been writing for 15 years, but building a freelance writing business from the ground up is still a new concept to me. I’m absorbing as much content on freelance writing (and running a business) as possible. It’s been a great journey so far!

  8. Great article! Your passage about the Friendly competition had prompted me one idea – to organize a challenge for myself and take part in soothing like on-line writing competition, maybe even without any rewards, just to train my skills) where can find one? Thank you

    • I don’t know of any off hand, but you could always start an accountability challenge among friends (online or in person). Y’all don’t have to have the same goal, but could each be working towards your own goal and encourage one another?

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