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How a One Month Pitching Challenge Revived My Freelance Writing Business

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?
Grab two of our most popular workSheets and get started TODAY!

Joe Dyton (@JoeDyton) is a freelance copywriter and journalist in Washington, DC and author of  The Aspiring Freelancer blog. He may be reached at dytonwande@gmail.com. Check out his site at joedyton.com.

Photo Credit: Marta Pawlik via Unsplash

Gina Horkey

Gina Horkey


Gina Horkey is a married, millennial mama from Minnesota. Additionally, she’s the founder of Horkey HandBook and loves helping others find or become a kickass virtual assistant. Gina’s background includes making a living as a professional writer, an online business marketing consultant and a decade of experience in the financial services industry.

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