How a Pitching Challenge Changed My Freelance Writing Career


I couldn’t believe it! Out of a very talented group of writers, I had actually won the pitching challenge that Elna started for her course students at the beginning of the year.

For a month, we tracked the number of pitches we sent, and the person with the highest number won. I ended up sending 50 pitches throughout the month and won the challenge.

It was hard work at times, and I didn’t pitch every day, but when I did, I made it count. I made a template that was easy to update or customize, and I sent 5 or more pitches on the days that I was pitching. I got into a groove and pretty soon the pitching process became second nature.

And it paid off.

I landed several new clients, some with recurring gigs, and onebig client, who hired me on for exclusive writing and editing.

I didn’t start out that way.

I Was a Struggling Freelance Writer

Let me rewind to a year ago, when I was a struggling freelance writer who hadn’t yet seen a penny for her work.

I was writing for free to build up my portfolio, and I hadn’t been paid for anything. I felt stalled and stagnant, and I was about to throw in the towel thinking I wasn’t cut out to be a freelance writer.

And then I discovered Elna (through LinkedIn, if you’re curious) and her course .

I already knew her course would be different than the other ones out there.

I had been reading her blog for a few months and I appreciated the honest, actionable advice that she provides for freelance writers.

And she isn’t afraid to show real-life examples or point out her own mistakes.

So I signed up for her course and then my freelance writing business changed. I landed my first ever paying gig a few days after I started the course and I knew it was because I had implemented some of the actionable and practical advice that Elna offers.

And as I went through each of the course modules, I realized I was missing some key factors in my freelance writing business, and that I had been making some BIG mistakes.

Here are five things that I learned from this pitching challenge and her course.

1. I Was Looking for Writing Jobs in All the Wrong Places

A year ago, I was scouring Craigslist and Guru for writing jobs. And I found a lot of them listed there, but what I didn’t know was that these ads were for low-paying writing gigs or content mills.

Sure, you can find good writing jobs listed there too, but they are few and far between.

In her course, Elna teaches us there are much better ways to search for higher-paid writing gigs.

And isn’t that what we all want as freelance writers?

Here are the types of places I looked for freelance writing clients:

  1. Problogger
  2. JournalismJobs
  3. Indeed
  4. Freelance Writing
  5. The Write Life Job board
  6. Contena (I bought a Pro Membership)

2. I Was Pitching all Wrong

In the past, I would answer an ad for a writing gig the same way I would answer a job ad.

Read: formal, boring and stuffy.

And that is exactly how NOT to pitch a writing gig!

I learned from Elna’s course that answering an ad for online writing doesn’t require a formal cover letter.

In fact, the opposite is true. The tone of a writing gig pitch should be conversational and easy to read.

But you still need to demonstrate you are a professional and skilled writer, and the course breaks down exactly what you need in your pitch email.

There are even templates for pitch letters included so it’s easy to get started.

Your pitch letter is definitely a showcase for your writing talent, so you need to craft it carefully to stand out from the crowd.

3. I Needed a Tribe

A year ago, I was a lone ranger. A solitary soul trying this writing thing all on her own. I felt lost and isolated, and just figured that loneliness was part of the deal of being a freelance writer.

I did have the company of my three cats, and, don’t get me wrong—I love my cats, but they’re hardly qualified to give advice or encouragement for my freelance writing career.

After signing up for Elna’s course, I realized things could be different. There is a whole community of writers out there who support each other and cheer each other on through the daily grind of running your own freelance writing business.

I belong to the private Facebook group for course participants and it’s made up of wonderful writers who are all there to help each other succeed in the best way possible.

No question goes unanswered and no post gets ignored. What a great tribe.

4. I Wasn’t Writing Proper Blog Posts

Sure, I knew you had to be creative and engaging when writing a post, but I didn’t know there was actually a proper way to structure the content.

Or that there are actual rules to follow when writing a blog post.

When I was writing pro bono, I was happily scribbling whatever came to mind and no one told me that blog posts needed a call to action, for example.

With Elna’s course I learned the correct way to structure a blog post and even how to format the post so it is easily uploaded into the client’s content management system.

5. I Didn’t Have a Website

Well, technically, I still don’t. But it’s in the works. That’s where I’m currently at in my freelance writing journey—at the website design stage, because, well, I need one!

I have managed to get by with my LinkedIn and Contently profiles, but there comes a time when you need a website to be a credible freelance writer.

It’s a place to list your services, showcase your portfolio, and even create your own blog. And you can be as creative as you want since you are in full control. I know I have a few special things planned for my own blog!

A writer website is a great marketing tool and it can help you attract clients and get writing gigs.

Wrapping It Up

I gained confidence in myself as a freelance writer, which gave me the courage to join the pitching challenge.

And I won, not just the challenge, but at freelance writing.

And you can too!

Over to you – have you had a chance to look at ?

The 20 Best Companies to Work for in Los Angeles, As Rated by the Women Who Work There (2019)

How to Start a Blog for Your Business in 3 Easy Steps