5 Lessons I Learned from Winning a Freelance Pitching Challenge

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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.

16 thoughts on “5 Lessons I Learned from Winning a Freelance Pitching Challenge”

  1. Great to see that you had some success with your pitch challenge Cruz!

    If you constantly keep pitching, especially high quality jobs, you’re sure to land some sooner or later.

    I can’t say that I feel “uncomfortable” pitching but I do tend to sometimes spend a bit too much time crafting pitches. I do have a “template” but I find that my best responses come when I am truly moved by a job listing to create a more original pitch, even if i do use elements from my template.

    The most important thing to do is to pitch, deliver quality work, and then wash, rinse, and repeat!

    • Thanks, Daryl! I had TONS of success! What Gina says is 100% true. When I got those 6 words through my head and embraced their meaning, I opened myself up for opportunities I couldn’t have imagined would ever happen to me.

      I pitched like a mad woman in December and haven’t had to send another one out since! Work is going great! I’m blessed to work as Gina’s newest VA and will soon (I’m optimistic!) pick up a third VA client!

      Pitching no longer makes me uncomfortable. Now that I’ve done it several hundred times, it’s become more like a game to me with cold pitches being my favorite to send out.

      The same is true for me. I write the best pitches when I feel moved by a prospect or spot a magazine or project I REALLY want to be a part of. It’s then that I write heart-wrenching ballads. LOL! Hey, they work. And ALL that pitching I did in December was FANTASIC practice for the big, bad world!

      Absolutely, Daryl! I agree! I’ll add one more step to that. This one comes straight from my co-worker, Mickey Gast. She’ll only work on projects she finds fun. If she doesn’t think she’ll enjoy the project, she’ll move on. I didn’t understand this until I applied it. You’ll see that your pitches get even BETTER!!

      Thanks for your comment, Darryl! Cheers to your success!!

    • By the way, in case you’re wondering what Gina’s magic 6 words were, it’s what she ALWAYS says, “Why not you, why not now?”

      I took it to heart and understood its meaning. If everyone else out on the net has 6-figure incomes, financial independence, health insurance, and retirement using the exact same formula I learned, I can have it, too!

      Keep pitching! Cheers again!

  2. Great post! I have stepped my pitching game up but still need to make a weekly quota to meet. It really does help. I have a template but I’m with Daryl in that if I like it I will go overboard a litle. I wrote a recent post on the value of pitching myself. It’s amazing how many people are freaked out by it. Congrats on your success!

    • Go, Nia!! Up that pitching game!

      I know what you mean. I’m someone who needs to have a target to aim for.

      I have to reign myself in sometimes from over prose-ing up my pitches (and sometimes my work, too!) when I’m excited about a prospect. But, as much as it might hurt to do or be challenging to figure out what should stay and what should go, try to remember that a busy, exhausted, (and probably a) momma of seven is receiving your pitch email on her end.

      To have the absolute best shot at getting it answered (and getting the gig), play by the rules and be brutal with your own pitches.

      Gina’s templates are great! Set yourself up with a target, like, “I’m going to pitch using Gina’s template and am only going to make 5 changes to it, including deletions.” You’ll see how creative you get, and you’ll be totally within limits (yours and the editor’s)!

      Thank you, dear! Cheers to yours!

  3. Hi Cruz! Hey Gina!

    This is so inspirational! Congrats Cruz!

    I just want to put out there, my pitching game sucks! I need seriously help with it so I won’t even pitch. What the heck is wrong with me? How am I going to make it as a VA offering content writing if I can’t get passed the pitch? Oy vey….

    Thanks for sharing this Cruz. It does give me hope that I’ll eventually get over myself and pitch away. But for now, I’m chicken. 🙂


    • Hi, Brenda!

      Thank you very much!

      You want to know a secret? Your pitching game will suck unless you win the #MarchPitchingChallenge, so go enter it now! Then don’t stop sending out crappy pitches until you win!

      LOL!! JK!

      But in a way, it’s true.

      Here’s all you need to know to make it as a VA:

      A.) Gina’s templates are free. They’re easy to use, user friendly, and get the job done. At first, try sticking to them exactly. Then as you start getting a few gigs, you’ll want to try different lines out in different places. Do it!

      Maybe no one has told you, but this WHOLE entire online world you’re trying so hard to break into and make money in, is one HUGE experiment in trial and error! Every entrepreneur out there who’s doing well started out trying, failing, trying, and failing, and trying…(you get the picture).

      If you need help, reach out for it. Email me at: cru3.santana.writes@gmail.com. If I can help you, I absolutely will!!

      B.) Working as a VA involves 10% knowing what you’re doing on day 1 & 90% Youtube-ing, Googling, and BS-ing your way through. You learn on the job.

      Content writing (like everything else) has rules to follow. It’s like learning another language at first. Start small. Pick three sure-fire guidelines from your Yahoo! Style Guide and follow them Every. Single. Time. Don’t have one? I got my hardcover on Amazon for $5.64 w/shipping! As you improve, add new things you learn to your list.

      Get curious about your field and learn, learn, learn!! If, “Why not you, why not now?” is my favorite of Gina’s mantra’s, yours should be, “Always Be Learning!”

      It’s like Noah from The Bible. When there was no ark built, there weren’t any animals around. When He built it, they came in droves!

      Build your VA business by asking for help when you need it. Clients WILL come! I guarantee it! But only if you build it.

      Chickens get eaten! LOL! I’m a weasel! My methods have become pretty sneaky! But, THAT, I’ll save for another post!

      Cheers, Bren!

      You’re among friends!

  4. This resonates with me so much Cruz, great post!

    I’m in the thick of pitching right now, attempting to land that first client. I’m using Contena Pro and I do feel overwhelmed with all of the jobs sometimes and not feeling like I’m qualified for a lot of them. This definitely helps put it into perspective. 🙂

    • Hi, Chad!

      Don’t be afraid to stretch your legs by pitching other niches. Good for you for wading through the hard stuff!! It will pay off in spades.

      I had originally included a sixth lesson but took it out because I was afraid it’d make the post too long.

      The word “no” hurts, but it doesn’t kill you. And if the old cliche is based on any fragment of truth, you’re stronger for it.

      Ergo, pitch anything you’re even a weeeee bit qualified for. If you get the gig, most editors will work with you on the deadline. Take sometime to reaquaint yourself with the subject matter by searching for it on YouTube.

      And, yeah, it can get overwhelming in an annoying way. The only thing I can tell you is that if you need a different strategy for sourcing leads, get creative. Or search for options in Gina’s old posts. I wrote one a while back on using Pinterest for it.

      Thanks for your comment! You’re doing great! Don’t quit.

      Chad, I’m right there wit cha. And so are a lot of us. 🙂 You got this!

      • Thank you for the extra info! I appreciate the thoughtful addition. 🙂 I’m thankful to have found such a great community and I know that the future is going to hold some great things. Cheers Cruz!

        • We’re all very tight-knit and love to help each other succeed. Truly, a win for one of us is a win for us all. Welcome aboard! We’re all very glad to have you.


          P.S.: I’m glad you got the link. Please let me know if I can help you with anything, dear!

  5. Hey Cruz

    The whole post highlights passion and love for your work. Apart from reading your post, I was going through your responses in the comment section. Real Gem. As I have told you earlier, you inspire me a lot with your ‘never-say-never’ attitude. Love you, buddy.

    To be honest, I’m very bad at the pitching game. These days, I am focusing on building my personal brand by connecting with influencers in my field. I’m aiming for big publications. The whole process is time-consuming, but I’m loving every bit of it. On the other hand, I’m about to launch my youtube channel. I don’t want to make any excuse for not pitching. I’ll definitely join some paid job boards in near future.

    I’m sure my hard work will pay off in the long term. I’m glad I came in contact with people like you and Gina. I love the positive vibe of the whole community.

    • Yatin, lovie, thank you for your kind words. I love what I do 100%! Not many folks out there can say that about their jobs.

      Everyday is different. It keeps me on my toes. And I work for people I admire, care deeply for, and want their businesses to succeed. By being a part of what they do, I get to share in their success too.

      I have this nutty dream. I’d give just about anything to get in the New Yorker. I’m writing as I write this cuz here I am dreaming of being featured in the Ferrari of publications when I can even manage to get in HuffPo! Ha!!!!! ?

      I know it’ll happen. I need to dedicate time in each day to working toward my own goals.

      I’m EXTREMELY proud of you! You can do anything! I get such joy from watching you move from project to project like a bunny leaping in a meadow.

      What publications are you aiming for?

      I’ve been pretty darn lazy in the pitching department. Maybe you’d be willing to be my comparability partner?

      I love you, too, My Yatin! Very much so!!

      • I’m aiming for the big shots: Entrepreneur, Inc, and Forbes 🙂

        I don’t think I’d be a great fit for your comparability partner. If you are lazy in the pitching work, I’m not even in the frame 😉

  6. A very amusing but helpful post Cruz! I take way to long to craft a pitch. You’ve motivated me to take some time to refine my pitch template.

    • I’m sorry it’s taken me so long to reply. I just saw this now. Oops! Sorry, love!!

      I’m glad you liked it! Thank you for reading it. I hope you’ll give it a quick share if you get a chance.

      I hope you’ll consider using some of the tips in the downloadable thingy to refine it. Be honest. Be you. That’s what editors care about. It’s the intro into Vicky the Writer! <3

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