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5 Lessons I Learned from Winning a Freelance Pitching Challenge

I talk about pitching a lot.

Like a lot, a lot. And I’m sure some of y’all wish I’d just drop it already. BUT, I KNOW it’s the best way to get new clients and let companies know you’re available for hire.

That’s why I encourage the people who take my courses to also participate in my pitching challenges every few months. It’s a great way to get over the anxiety and fear that comes with putting yourself out there.

In fact, I believe in it so much, that I pony up my own money to reward the winner of the pitching challenge. You know, cuz some of us are motivated by money! 😉 And last December, Cruz Santana was our big winner. Today, she stops by to share the top five lessons she learned from taking (and winning) her first pitching challenge. 

The December Pitching Challenge changed everything about who I am as a writer, woman, and cancer fighter. Not only did I win Gina’s contest, but I took away from it a completely new way of thinking.

Having rocked my project for November 2015 (blogging my way through Gina’s course, 30 Days or Less to Freelance Writing Success for my website), I entered the month of December ready for action.

And boy, did I get exactly that!

The Five Hard-Learned Lessons That Forever Changed My Life

I have a notebook sitting beside me as I write this.

On those striped pages lives the complete list of tidbits and lessons I learned while participating in the December Pitching Challenge.

I’ll share with you my top 5, countdown style.

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5. Paid Job Boards Aren’t so Bad

I paid for my first job board membership ever on December 1st.

Even as I dragged my finger across the trackpad to move the on-screen cursor over to the magical button that would take my money, I had serious doubts about committing to spend $30 every month on Tom Ewer’s Paid to Blog Jobs Job Board.

I did more whining than pitching the first week I checked that job board account.

They showcased tons of work, but none of it was in my niche.

Disillusioned, I decided to make the best out of each of the 30 bucks I put into it by exploring gigs outside of my preferred fields.

4. Screenshots Are Your Friends

Among the crowded Internet sea of ads seeking talented, witty, sassy, and funny writers, you’ll come across every freelance writer’s mortal enemy… an online application form.

They don’t seem that bad while you’re hammering away at your keys, re-updating your cover letter for the 93rd time.

But, I assure you, they are they devil!

During the challenge, I filled out five of these pesky online forms without ever receiving a response.

When my very first response hit my inbox, I realized how lucky I was to have been overlooked all those times before. For the life of me, I couldn’t remember ever filling anything out for that particular publication. I tried asking a few probing questions to try and trigger some sort of chain reaction that would eventually change the perplexed look on my face into a smile of recognition. In case you’re wondering, I didn’t get that gig.

That happened to me once, maybe twice more before it occurred to me at last to snap a screenshot of the completed form before I sent it off.

I now store the screenshots in a folder on my desktop. Renaming them is easy enough, so I tend to stick with [COMPANY NAME – JOB TITLE – DATE].

Snapping screenies (what I call screenshots) has helped me in more than just this facet of my career. I love feeling prepared and ready for anything in those situations.

I still detest filling out forms, but at least I have a secret tool to give me a bit of an edge in the unlikely event someone does reply.

5 Lessons I Learned from Winning a Freelance Pitching Challenge and how cold pitching will boost your business

3. Pitching Costs You Money

There it is, I said it!

It does! There are only so many hours in the day, right? And until a prospect agrees to hire us (and then pays us), we’re out the time it took to put the pitch together.

The reason (I think) Gina talks so much about the best way, fastest way, this way, that way, and the right way to pitch is that it’s the part of the writing process you should spend the absolute least time on.

It’ll actually cost you money to take your time and create the perfect pitch.


Let’s assume that you’re the type of person who likes to check and recheck their work. Finally, an eternity-and-a-half later, you send out your Pulitzer Prize-worthy pitch to an editor (like I did)…

…and you never hear from anyone. Ever.

Time = Money.

Pitching spends up your time. Reading one hundred pitches takes up the editor’s time too.

Gina has, hands down, the most effective pitching templates I’ve ever seen. I use them religiously, taking out and adding in only what applies to me.

2. Someone Else Can Dream a Bigger Dream for You than You Can Dream for Yourself

My boss at Guyvorce inspired this lesson. The site grows everyday, and I can see my efforts in action all the time. It’s rewarding to put something out into the unknown, and have it be well received.

On top of all that he’s done for me, he’s even hired a few of my talented writer friends and colleagues.

1. Get Comfortable With Being Uncomfortable

It’s the most motivating lesson I’ve learned to date.

When we humans are reasonably happy in our overall existence and surroundings, we tend to remain stagnant. The old expression, “If it ain’t broke, don’t fix it,” reminds us not to go stirring up trouble if all is going well.

It’s not until things go wrong (and it threatens our comfort level), that we get creative about how we live.

Writing about divorce makes me really uncomfortable. In fact, I originally turned the job down fearing it would cut too close to home. My boss asked me to reconsider. And the rest, as they say, is history.

[Tweet “Here are 5 lessons I learned from the uncomfortable anxiety of #coldpitching. “]

The Uncomfortable Anxiety of Pitching

Up until the pitching challenge, I was selective of the ads I’d respond to, but the challenge took that away from me completely. I wouldn’t have won if I’d been selective of who I pitched to. I spent the month following the challenge inundated with work.

I’m grateful to be this exhausted from doing something I care so much about.

As it was going on, I needed line items to add to my spreadsheet to further my cause and win the challenge.

Four days in, I’d used up all the leads in my niche on the Paid to Blog Jobs Job Board. I read through other ads in different categories. One of those belonged to Dennis at Guyvorce. I pitched him and filled in the line on my spreadsheet with his information, never expecting it to go any further than that.

Now, look at me!

Not only have I learned more about the online universe (and how to manipulate it to my will) than I’ve ever learned before, but I just completed my final edits on my very first book. I am totally comfortable with being uncomfortable.

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In Conclusion

December’s Pitching Challenge shook me awake and caused me to redefine what my limits are. How far you will go will be restricted by how you define your personal boundaries.

I was hungry for the $50 prize and learned to get creative about how I looked for and found work. I joined a paid job board and whined quite a bit in the beginning because the site didn’t have very many openings I was willing to consider.

I was wrong. The membership more than pays for itself if you’re willing to use a dab of creativity when it comes to looking for well-paying gigs.

Avoid spending too much time crafting your pitches. Editors (like me) aren’t looking for perfect writers. We’re smart enough to know it’s an air you’re putting on. And you can’t write on air! Focus more on the direction and the flow of your pitch, its brevity, and closing it out on a positive note despite any discomforts you may be feeling.

What important lessons have your learned the hard way? How has the experience helped you to grow your online business?

5 Lessons I learned from cold pitching challengeCruz Santana is a cancer-fighting, millennial momma, professional writer, and editor with a background in science and medicine. She also offers web syndication services to fellow webpreneurs interested in watching their traffic counts explode out of control. Connect with her at her online home, The Freelance Dance.

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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