Writing Contest: Share Your Biggest Freelance Fear to Win

Evan Jensen

Writing Contest: Share Your Biggest Freelance Fear. Makealivingwriting.comNOTE: Writing contest extended until Dec. 3, 2020. What’s your biggest freelance fear, and how did you overcome it? Enter our writing contest for a chance to win.

Fear has a way of holding you back as a freelance writer. It suffocates creativity. It gets in the way of taking risk.

Let it dominate your thoughts, and fear prevents you from putting yourself out there, marketing, sending query letters, connecting, pitching your dream clients. Sound familiar?

When fear plagues your freelance writing career, it’s like being in the middle of a Stranger Things episode. You’re expecting the Mind Flayer or the Demogorgon to rip you to shreds at any minute. Only it never really happens. It’s all in your head.

But if you don’t face your fears, fight back, and pursue your freelance writing goals, the results can be devastating. You roll around on the floor. You procrastinate. Days, weeks, months, maybe even years go by in this state of mind. Your freelance career goes nowhere. And that’s a terrifying thought.

In this writing contest, we want to hear about your gnarliest freelance writing fear, and what you did to overcome it.

Check out the rules for the writing contest and prizes for winners.

Punch fear in the face like this freelancer

Punch fear in the face, and do it anyway. That’s advice from pro freelancer Linda Formichelli. She’s kind of like Eleven (played by Millie Bobby Brown) from Stranger Things, for freelance writers.

During her long career as a freelance writer, she’s written for more than 150 trade and consumer magazines, a long list of copywriting clients, and several books.

Is she somehow impervious to the fears most freelance writers experience? Nope.

She just made a conscious decision to recognize fear and move forward, one pitch, one assignment, one day at a time.

Sounds like crazy mind control powers, right?

What are you afraid of as a freelance writer?

You’re not going to face the Mind Flayer or the Demogorgon. Your life isn’t at stake as a freelance writer.

But real fears that can hold you back as a freelance writer include things like:

  • Cold calling
  • Raising your rates
  • Dropping low-paying clients
  • Fear of failure
  • Learning SEO and blog writing
  • Working with a new client
  • Leaving content mills
  • Writing a book
  • Building a writer website
  • In-person networking
  • Using social media to connect with prospects
  • Landing a type of writing assignment you’ve never done before
  • Or simply getting started and fear of the unknown

Writing contest rules: Share your best fear-busting story

Question: What’s your biggest freelance writing fear, and how did you overcome it?

Answer the question for a chance to win. Here’s how:

  • Tell us about your biggest freelance fear, and what you did to overcome it in the comments below.
  • Only one entry per person.
  • Contest ends Sunday, Dec. 1, at 11:59 p.m.
  • We’ll review all the submissions and announce the winners here, and the Dec. 4 blog post.

Prizes for the best fear-busting freelance story include:

Grand prize: A one-year membership in the Freelance Writers Den + Pitching 101 (A $97 value, but currently on sale at 50% off).

Runner up 1: A one-month membership in the Freelance Writers Den.

Runner up 2: All my freelance writing e-books in a complete set.

If you’ve faced terrifying freelance fears and won the battle, enter the writing contest for a chance to win.

What’s your biggest freelance fear, and how did you overcome it? Comment below to enter the writing contest.

Evan Jensen is the blog editor for Make a Living Writing. When he’s not on a writing deadline or catching up on emails, he’s training to run another 100-mile ultra-marathon.

Your Shortcut to Success. Freelancewritersden.com


  1. Adejare

    I’ve always loved writing since I was little. Frequently , I get a “brain-rush” snd the only way to calm it is by writing down ideas or storylines that I’ll develop later.
    I started developing fears when I entered this competition last four years. I felt confident that I was going to do well, show what I’ve got and win a prize.
    But I didn’t.
    Not first prize, not second, not third. It was so depressing. The competition really got to me.
    Gradually, I began to have this fear of not doing well at all. So whenever I came up with an idea or tried developing one, I felt it wasn’t good enough. This totally limited my creativity.
    For years to come, writing and sharing it with others became a big problem for me. It hindered my work and soon I had ‘brain-rushes’ less frequently. I even stopped writing at a point.
    My breakthrough came when I was asked to read one of my old stories aloud in a class of over 50 students (It was the same story I submitted for that writing competition). Initially, I was scared. I thought I would bore them. But I didn’t. They were all held spellbound till I finished my story.
    I was commended and applauded for my good work (which I had considered a failure).
    So I learnt one lesson. It wasn’t that I wasn’t good enough. There were many other people better than me. Since then, I work harder at developing my skills in writing.

  2. Karen Dabney

    My biggest freelance writing fear was talking to people I didn’t know–interviewees and editors. It was agonizingly hard to make myself pick up the phone, type the email or walk up to the person and start talking. I feared rejection, negative reactions, and simply being ignored. But if I didn’t get the interviews and quotes I needed for the article, I’d miss my deadline or fail to produce the quality of article my client expected and deserved. So I also feared failure. I started freelancing for a local newspaper with a large, devoted readership. To my surprise, people were delighted to be interviewed for this newspaper, which specialized in upbeat, positive local news, people and events. But I was still afraid. Inspiration struck–I could be like an actor and act the role of a confident, cheerful writer and interviewer instead of my scared newbie self. Somehow it helped me work around my fear and begin the conversations. Over time, my interviewees’ and editors’ positive responses helped me gain confidence and develop good interviewing skills. I started having fun, and realized that most people were responding to me with the same respect and interest that I showed them. My fear of interviewing people is gone, and has faded to nervousness when pitching to editors.

  3. Natasha Ade

    I am from Kenya and my greatest fear is I can’t stack up to the global market demands.

    I want to do freelance writing and eventually build a money-making blog but this fear pulls me back. Not to mention, my family always mentions how unrealistic my dreams are.

    It makes me wonder, what if they’re right? What if I’ll remain in this low paying agency job until my writing career is over? What if I am in over my head?

    I genuinely don’t know what the future holds. But I’ll keep writing.

    And hopefully, if I get the guidance I need in these desperate moments, I’ll do more than I ever imagined.

  4. Mike Ogulnick

    There are several things I’m not afraid of, such as self-doubt, procrastination, and the ability to find an excuse for every suggestion or situation. I am the proud owner of many fears but the one that stands out is the inner voice that tells me I’m just not good enough.

    I do most of my best thinking as I’m trying to fall asleep. While my wife dreams, I come up with numerous ideas. I’ll write a children’s book about a little boy who won’t give up his blanket. I’ll write an article about what dealing with depression and doubt daily feels like. I’ll write a screenplay about a kid in high school who was so shy, he stood there while a friend asked a girl if she’d go to a dance with him. She said no, by the way. When I wake up and open my laptop, my mind goes blank. Suddenly, those ideas seem as far away as Saturn.

    That children’s book, article, and screenplay won’t be good enough. When my words are read by those in the know, I’ll find out that I’m just not as talented a writer as I’d like to think. As long as those words remain in my head, my potential is unlimited. Wrapping myself in that cocoon is quite comforting. It’s a place where nobody can judge my work except me, and of course I’m going to be supportive. After all, I’m my biggest fan. If only I didn’t become my harshest critic when I sit down to write.

    There is nothing I desire more than to break out of that cocoon and find out just how good a writer I am. This exercise is a wonderful first step. The stage is set, the house lights are down, and the audience is ready. Now, it’s up to me to create the show.

  5. Jake Myers

    Letting go…letting go of the past, letting go of things that I think bring me security, letting go of what is comfortable and familiar. That’s my biggest fear in freelance. I had to leave my job in order to make space for the time and energy it takes to really devote to freelancing and putting myself out there. When I have something that I think brings me a sense of security or comfort, I clutch it so tight. But by letting go, I could freefall into my true, congruent self and the universe is able to open up and catch me.

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