How I Found the Confidence to Step into Freelance Writing

Have you been thinking about starting a career as a freelance writer? Or maybe a freelancing “career” feels impossible, but …

Have you been thinking about starting a career as a freelance writer? Or maybe a freelancing “career” feels impossible, but you’re thinking about freelancing as a side job?

Maybe you’ve been checking out Contena and have seen a few listings that you could be a fit for, but something’s holding you back from applying.

Or perhaps you’re just getting started as a freelancer and you’re not quite sure you have what it takes.

Whatever stage of freelancing you’re in, chances are, you could benefit from building up confidence in yourself as a freelance writer.

Here’s the thing about confidence: it can be hard to have confidence in something that you haven’t really done before. People often think either you have confidence or you don’t, but that’s not really true. Confidence can actively be built when you know how to do it (we’ll get to that shortly).

First I want to share a story with you about my confidence as a writer.

I have been a writer for as long as I can remember. I wrote a book in third grade that was a career guide for kids; I interviewed local professionals to learn about their careers. I was in the journalism class in high school, and wrote for the school’s paper. In college, I started a draft of a chick-lit novel that I was convinced would one day be published (It hasn’t; it’s not even close to done!).

When I started my career as a Mental Skills Coach in 2006, I thought a great way to get my name out into the world would be to offer my writing services to publications. Most of my writing was for local programs in their newsletters or websites, but I was fortunate enough to get one (non-paid) opportunity with SportingKid Magazine (which is now only offered online, but was in print at the time).

I didn’t even care that I was writing for free; I was so excited to see my name in print. And, for the next ten years, I looked for opportunities to write. I didn’t realize I should be looking for paid opportunities. It literally took me a decade, and the launch of my blog, to realize that I was able to provide value to people through my writing. And that I should be charging money for my work.

When I stepped into calling myself a freelance writer, I had a Master’s Degree, a decade of professional experience in a specialized field, my name in at least 30 print publications, a blog, and two children.

You can look at this in a couple of ways. 1) I had no paid freelance writing experience, so my confidence could be low in this area. 2) I had a huge amount of valuable experience and knowledge to offer potential employers.

I chose to look at this in the second way.

Though you may not have much, if any, professional freelance writing experience, pull your confidence from what you do have:

  • Your education
  • Work or career experience
  • Life experience
  • Free writing you may have done (yes, the newsletters for the organization you volunteer for count in this way!)

When it comes to freelance writing; everyone begins somewhere. What you need to remember is that it’s not simply your professional writing experience that makes you a qualified candidate. If you are a person who has the knowledge and understanding of a topic (or the ability to research it), and the ability to write well and in the style the employer is looking for, then you are a strong candidate and need to remind yourself of that.

Focus on your strengths

This relates to the first point.

Rather than looking at why you’re not a good fit; focus on why it makes sense to hire you. This is important as you’re reviewing potential jobs, but also when you send pitches and apply. I once was hired by an online news site that is geared toward single Millennials without kids in the Bay Area.

Aside from being in the correct geographic location, I’m married, have two kids, and though technically my birth year makes me a Millennial, I don’t consider myself one. BUT- regardless of all of that, I told the editor all the reasons why I was a perfect fit. And guess what? I was hired! Not only that, the editor of that site later referred me to one of her colleagues who was looking for a writer who is a mom. So, it’s a good thing I told myself, and the editor, why I was a good fit for that site.

Remind yourself of your successes

Confidence in many aspects of life comes from being successful. Athletes who win games are likely to be more confident than those who lose. When you secure an account at your day job, you likely have more belief in yourself that you can be successful moving forward. The same is true with freelance writing: by focusing on the successes, we can build confidence.

However- the trick is to look at how you define success. Yes, getting hired for a freelance job you apply for is a major success. But, as you may have already learned, those don’t happen all the time. Use those big wins to build your confidence, but also look for the smaller successes you’re having. For example, pay attention to the times when:

  • You send a pitch you personally think is great: you now have a template for future work.
  • You receive a reply that technically is a “no” but they’ve said they’ll keep you on file for later.
  • The client who hired you for one article asks you to do another.
  • You get positive feedback from a reader on a post you’ve written (paid or unpaid).

Redefining success as a freelancer is important to both building and maintaining your confidence.

The truth about confidence

When it comes to writing, confidence can go up and down; it’s normal. You may feel great about something you write, and it only receives lukewarm reviews. The next day you’re feeling down about your ability to make money as a freelancer, and then you get a positive response to a pitch. Though freelancing can be unpredictable (especially as you get started), your confidence doesn’t need to go on the same roller coaster ride.

Instead, take the time to cultivate the habit of positive thinking by looking at why you’re a good fit for this career or job, focusing on the strengths you have, and redefining success as a freelancer.

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