10 ways to overcome doubt, insecurity and fear as a freelance writer

kitten-lionBeing a freelance writer is like having to ask someone out every day for the rest of your life. Not only do you face rejection on a regular basis, but you face rejection of the most personal aspects of yourself — your words and ideas. It’s the emotional equivalent of standing naked in front of the world and saying, “So, what do you think?”

Clearly, a little doubt, insecurity and fear in this scenario is only natural. But letting those negative feelings control you and crush your goals and plans is not an option. So here are 10 strategies to overcome doubt, fear and insecurity and get into action as a freelance writer:

1. Ignore it

It seems simple enough, and it is. Sometimes we actually feed the inner doubt and negativity when we constantly pay attention to it. So you just had the thought “No one would want to read an ebook by me.” Who cares? It’s just a thought, and it’s not true. Recognize it as a useless, inaccurate assessment, and promptly ignore it and get to work.

2. Write it down

Let’s be real: Ignoring negative ideas doesn’t always work. So  next time you have a persistent negative thought about yourself, your abilities, your goals or your plans, write it down. Writing it down creates some distance between you and the idea and allows you to look at it and see it for what it is: a distraction that’s designed to make you less productive and less successful. Often times just by writing it down and seeing how silly it is, you can laugh at it and get on with your work. Don’t forget to cross out the irrational thought, delete it off your computer screen or crumple it up into a ball and toss it in the trash where it belongs. And if that doesn’t work, you can…

3. Replace it with a rational reality

So you’ve written down your negative thought. For example:

Foolish idea: I could never be published in Awesome Magazine.

Now, replace it with a rational reality.

Rational reality: If I study Awesome Magazine, come up with ideas that fit the magazine and consistently pitch those ideas to the right editor, there’s a good chance I will be published in Awesome Magazine.

And here’s another example:

Foolish idea: No one would want to read an ebook by me.

Rational reality: There are definitely people who would be interested in the information I have to provide. I need to identify my target market, write with that market in mind and promote my ebook to that market once it’s finished.

They key here is to get rid of the irrational thought and leave the rational reality in its place — then get to work!

4. Focus on the goal

Any time you find your attention wavering to the obstacles or to your own perceived inadequacies, direct your attention back to your goals and purposes. Remind yourself of exactly what you want to accomplish and why you want to accomplish it. This is why it’s helpful to have your goals and purposes written down in an easily accessible place.

I keep a notebook with my top three goals, topics I want to write about, outlets I currently have relationships with and those I want to write for, as well as weekly and daily plans. Some people prefer to keep notes on their phone or computer. Whichever format you use, make sure that your goals and plans are always nearby, so that if you feel yourself slipping into self-sabotage mode you can easily switch your focus back to your goals and get motivated again.

5. Just do it

This is a variation on the “Ignore it” suggestion. The best cure for doubt, insecurity and fear is action. Nothing shuts up the internal negativity and push-back like getting busy. Because frankly, it doesn’t matter what negative ideas your mind manufactures if you simply push through them and accomplish whatever it is you set out to do.

The difference between the giants and the nobodies is NOT talent — it’s hard work and the ability to get things done. As the saying goes, “Hard work beats talent when talent doesn’t work hard.” So whatever’s next on your to-do list, go and do it, regardless of any internal resistance.

6. Educate yourself

One of the best remedies for insecurity is knowledge. So if you’re having difficulty mustering up the courage or motivation to do a particular task, try educating yourself in that area. If you’re scared of pitching, read some books and articles on pitching, and practice writing some pitches. Share your pitch drafts with a trusted, successful writer friend or colleague and ask how you can improve them. Hire a writing coach. Take a class. And once you learn how to pitch, go ahead and send a pitch to a publication, even if a bit of fear remains.

It’s OK — and actually quite beneficial — to acknowledge that you need to gain more knowledge in a certain area. But it’s not OK to beat yourself up or dwell on your so-called flaws and failings. No one ever improved their situation by putting themselves down or making less of their abilities.

7. Make a list of your skills and accomplishments

It may sound corny, but it’s actually pretty effective. Make a list of all your skills, positive qualities and accomplishments. Be as specific and detailed as possible, and keep this list in your writer’s notebook with your goals, purposes and plans. Then next time you’re feeling like the world’s worst writer, look over the list and remind yourself of all the impressive things you’ve done, the many skills you have and the positive qualities you contribute to the world.

These positive attributes are the truth that dispel the lies that are your fears, doubts and insecurities. Realize that you have something valuable to offer, and get busy offering it.

8. Break your task down into more manageable parts

A task like “pitch Cosmopolitan magazine” can seem overwhelming. The way to reduce some of the fear factor is to break that big task into smaller, more manageable parts. For example, instead of writing “pitch Cosmo” as an item on your to-do list, you could break it down into these tasks:

  • Study Cosmo’s website and magazine
  • Come up with five article ideas
  • Pick one idea, do research and write a draft of a pitch
  • Get feedback on the pitch from a coach or trusted colleague
  • Revise the pitch
  • Find the correct contact information for the editor and send the pitch

Each of those action items is much easier to confront than the vague and slightly intimidating “pitch Cosmo magazine.” Complete a couple of these tasks each day, and by the end off the week, guess what? You’ve pitched Cosmo, and it wasn’t nearly as scary or difficult as you thought it would be.

9. Write down exactly what you’re afraid of 

Next time fear rears its ugly little head, write down what you’re afraid of — the exact terrible consequences that you’re sure will result from whatever action you’re scared to take. If you want to take it even further, write down all of the horrible things that could possibly result from you taking this action.

Will the editor print out your pitch and read it at the next editorial meeting while the staff howls with laughter before they collectively frame it and hang it on the wall under a sign that reads “Worst Pitch EVER”?

Will Amazon announce on their homepage that they’ve refused to sell your ebook because it’s so awful?

Will the social media police show up at your door and whisk you away to a secret bunker in the desert because you haven’t mastered Twitter?

Clearly, the answer is no. In most cases, the worst thing that will happen is nothing. The editor won’t respond to your pitch, your ebook won’t sell, and no one will follow you on Twitter. And then you can use that non-response as feedback to help you sharpen your skills and improve your game. As the old saying goes, “The only thing we have to fear is fear itself.”

10. Put it in perspective

Next time you’ve convinced yourself that the task you’re about to undertake is potentially the most horrible, excruciatingly difficult one in the world, put it in perspective. If we can send a man to the moon, I’m pretty sure you can learn a new skill, master the basics of social media or send a persuasive pitch to a publication. It may even be helpful to write down a list of more difficult tasks than the one you’re currently avoiding, such as climbing Mt. Everest, running a marathon or cleaning the bathroom.

The truth of the matter is that the task you want to accomplish is not that difficult, and the potential negative consequences are actually pretty mild. The real difficulty comes when your mind acts like a funhouse mirror and distorts everything. So get out of the funhouse, put the task in perspective and get to work. Remember, a task is only as difficult as you perceive it to be. In the words of Jay Z, “Difficult takes a day, impossible takes a week.”

Final thoughts

If the 40-hour-a-week wage slave cubicle life isn’t for you and you want to succeed as a freelance writer, you have to put yourself out there. You have to pitch your ideas. You have to pitch yourself. You have to take some risks. You have to act.

As important as goals, purposes and plans are, they only exist to guide your ACTIONS. You can spend hours upon hours refining your goals and purposes and coming up with brilliant plans, but sooner or later, you’re going to have to put those plans into action.

You’re going to have to scope out markets, come up with ideas, pitch those ideas, send letters of introduction and write killer pieces, over and over and over again. And you can’t do that if you’re constantly second-guessing or stopping yourself because of doubts, fears and misguided ideas about not being good enough.

Look at this way: One way or another, you’re going to be uncomfortable. Uncomfortable in the cubicle, or uncomfortable in the wild world of freelance writing. Pick one. If you choose the latter, then embrace the discomfort, feel the fear, and take action anyway. Get in the game and play. Don’t sit on the sidelines and endlessly plan out your game or make up reasons why you should stay on the bench just a little longer. Never, ever accept the idea that you can’t do something. In the words of Henry Ford, “Whether you think you can or you think you can’t — you’re right.”

If you have any tips for overcoming doubt, fear and insecurity as a freelance writer, feel free to share them in the comments.

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