Taming your fear of failure before it destroys your freelance career

Fear plays an important role in our survival. It stops us from wrestling that bear, from jumping into the Grand Canyon, and — at least this is my hope — from driving with the gas pedal held firmly to the floor. Fear has served our species well and has helped guide us through hundreds of thousands of years of existence.

In cases like these where our lives are at stake, fear is our ally, but it just as often becomes our enemy. Fear can take hold of us in situations not nearly as dire and can inhibit us from taking risks which could help us grow.

This becomes all too clear as a budding freelancer. I’m relatively new to the game, and, when I got started just a few short months ago, I had to battle against a nagging conga line of “what ifs” that made going out of my comfort zone difficult. Heck, I still fight this and I imagine I will continue to do so for years to come. The good news is that it does get easier.

It’s a natural reaction. Rejection hurts. We internalize it, make it personal. It becomes our failing rather than a failing of our process or our product. The failure is you or me.

Fear of failure can not only damage your freelance career — it can destroy it.

I failed, but I’m glad I did

A few years back, I decided to try my hand at freelance writing. I enjoy writing, and I’ve been told I’m decent at it. I rode that roller coaster all the way to the top: I had a pitch accepted by one of my dream publications. I worked hard to turn out my best work, but it wasn’t enough. They killed my story rather than publish it. I continued writing for a while after this, but my heart wasn’t in it. I couldn’t bring myself to get my work out there the way I had before. My career was over before it ever started due in no small part to the powerful grip fear had over me.

My skin is a bit thicker now, and I have more confidence in my front-end web development skills than I had in my writing. I’ve also learned to see rejection as a necessary step in the process. As a freelancer, I have to constantly be trying to sell my services. Most of these attempts are not going to work out for one reason or another, and that’s OK. I just have to make sure I’m making a few more attempts than I’m getting rejections.

As with any other source of pain, the impact of rejection is lessened with each experience. The first few sting a little, but they eventually become routine. Throughout most of our lives, we are trying to minimize our exposure to rejection. Freelancing, it’s far better to maximize your exposure so that you can start getting used to it. If you’re an introvert like me, this can seem especially hard. My best advice is not to think much about what you plan to do when inspiration hits. Your thoughts will inevitably turn to the possible rejection you’re about to receive. Try to jump in before your brain has a chance to catch up.

Practice failing to get rid of the fear

I’d also advise you to push yourself outside your comfort zone a little each day. Try a few of these exercises below. Some of them may in fact be inside your comfort zone as every personality is different. Find a few that seem like they might be a bit awkward or uncomfortable and start trying them whenever you can.

  • You’re at a meeting or some sort of event before it has started. There are a few people here already. Go right up to someone you don’t know and start a conversation.
  • There really are no dumb questions just like all those teachers said. If you want to understand something better, ask that question that’s in your head. Your peers have all been where you are at some point, so they’ll understand. If they don’t, they’re probably jerks anyway; you shouldn’t care about what they think!
  • Take an opportunity to speak in front of a crowd about something you’re good at or know about. This can be a great confidence boost if you present at small local events related to your field. Even if you’re new in your field, there’s likely some aspect of it, however small, that you know pretty well. If nothing else, you can bring the perspective of someone who is new in the field. You always have something to offer.
  • Post something you made online and ask for critique. Dribbble is a great place for designers. I’ve found Forrst to be pretty good for developers, and it also allows posts of design work. Your field likely has a number of different places where others will give you feedback on your work. One word of warning: You’ll sometimes have one or maybe two individuals who have no desire to help. Their goal is to demoralize you. As you’re reading your feedback, if you detect something that fits this description, just skip over it and go to the next. That post is about making them feel big rather than helping you get better. It’s best to move on. As a counterpoint to this, make sure you’re not discounting valuable criticism just because you don’t want to hear it. Be critical of your own response to the critiques of others.
  • Give yourself many chances to fail at whatever it is you’re doing. I’m quite fond of a quote from the late Randy Pausch:

    Experience is what you get when you didn’t get what you wanted.

    Every chance to fail is a chance to get better at dealing with it. It’s also a chance to succeed.

These exercises may or may not be related to whatever it is that you do. The point of doing them is to stretch yourself and to learn how to handle small failures. Regardless of your trade or craft, you’re going to need to sell something, and you won’t always succeed. Learning how to cope with this is instrumental to your future success.

At some point in your education or maybe while channel surfing past Animal Planet, you’ve likely come across the frill-necked lizard. It has a flap of skin circling its head which normally lies flat against its body. When it needs an extra boost to scare off predators, cartilage connected to the flap can cause it to open up making the lizard appear much larger and more menacing. Fear seems to have a similar ability to become bigger in our perceptions than the possible negative outcomes which can trigger it. The best way to counteract this is to get a few of those rejections under your belt. You’ll quickly learn that failing isn’t all that bad. Then, that lizard we call “fear” won’t be nearly so intimidating.

Now, it’s your turn…

What are your fears about freelancing, and how have you been dealing with them? Share your thoughts and experiences in the comments below.

Subscribe for more...

You'll receive "22 Simple Tasks That Will Better Your Freelance Career" and a sample of my guide, "Start Your Freelance Career" for FREE. You'll also get my bi-weekly newsletter on freelancing where I share transparent content, freelance tips, and stories from my journey freelancing.

  • Hi Devon,
    Thanks for your post, I can tell you are a talented writer! Gave some good insights into conquering the fear of failure, I am also an introvert.

    • Hey, Joe. It’s great to hear from you!

      It’s a bit of an uphill battle for us introverts to do these inherently extroverted activities that form the basis of running a freelance business. Sometimes it helps just to know that it does get easier. I may never be as good at promoting myself as a really outgoing person would be, but I can be better than I am now. That’s the only measuring stick that really matters.

      • Sure is, i’m just getting started but am loving every minute of it. Marketing myself to my ideal client and keeping on top of everything seem to be the most challenging things for me. As long as you are improving you are making progress and that will lead to success :)

  • Great article, Devon. Thanks for the inspiration.

    I’ve been freelancing as a developer for just over a year now, and still succumb to the fear from time to time. But I’ve set goals to overcome this, one being public speaking, which I’ve always been deathly afraid of.

    I recently took your advice and gave a presentation about WordPress to a local group of entry level users in the Burlington Writers Workshop: http://okaypl.us/blog/burlington-writers-workshop/

    It was a great experience for me, and it definitely helped to start with a small, local crowd, and a topic that I have a solid understanding of. After getting over the initial shakes, I realized that I really enjoy helping others learn, and I’m looking forward to my next speaking engagement.

    • So glad you’re starting to overcome this, Joey. For many of us, it’s just a matter of working up the courage to try in order to see that the cost of most failures is very low. It has to be low because they happen to everyone all the time!

      Keep pushing forward. The other thing I didn’t really mention in the post is that you will forget how easy and low-risk it is to put yourself out there. You’ll turtle up again and your fears will return if you don’t keep them at bay.

      Thanks for reading!

    • Just took a look at your presentation. It’s beautiful! How did you build it?

      • Ha – thanks Devon. I built it in Keynote. It’s actually one of the default themes, so I can’t take much credit, although I did edit the fonts some.

        From Keynote, I just exported to PDF and uploaded it to https://speakerdeck.com/ which I prefer over SlideShare.

    • Hey Joey, I want to chime in and say that I really dig what you’re doing! Your presentation (and entire site I might add) is really great. I’m glad to hear you took a step out of your comfort zone and that you enjoyed the experience from it. Keep up the awesome work, and thanks for taking the time to read and comment!

  • Pingback: Fear of Failling Response | theoneandonlytrm()

  • Pingback: Response to article for class | Blog: The Movie: The Game: The TV Show: The Website()


    I want to be a freelancer when I’m out of college and this has somewhat made me feel better about the topic. Keep rocking out that jam you call writing.

  • NicholasM

    Nice to see freelancers giving advice to others. Showing people that failure can help you grow is really inspiring and beneficial.


      Great comment, Nicholas! I’m sure he’d be happy to see what you have to say.

  • Tyler

    Great Post! I struggle with the fear of failure on a day to day basis. It’s nice top see i’m not the only one! Great tips though on how to overcome this, thanks for the advice!

  • Mr. G

    This is very good and helpful for my students at The Delaware Area Career Center. I am having them all read this and then apply this to their career.

    • Awesome! I hope your students can all take away something useful.

  • Michael Comer

    Thanks for the article Devon. I struggle with fear and failure in freelancing mostly because i don’t know what to work on, or what to do.

    • Thanks, Michael. Do you mean you have many tasks and you’re not sure where to focus your energy, or are you saying you’re a new freelancer and you don’t know how to get started?

  • Austin

    This is a really interesting stand on things and it really shows how people are always growing this was an interesting peek into this. I was fearful in not doing well at all in a competition and my fear drove me to work for hours on my project and I ended up winning first and moving on to states. I really grew during this time and the fear drove me further.

    • Really interesting perspective here. Your fear drove you to overcompensate. Congratulations on the win!

  • Madison

    It can be a struggle to share ideas and designs with others. The fear of failure or fear of a person’s disapproval often gets to me. It is a great reminder that sometimes we must fail in order to improve and become confident.

  • Travis Fitch

    I think freelancing is more of a good than a bad. Good should not put fear in people.

    • True, but we don’t always get to choose what makes the fear bubble up. If we’re conscious of it, though, we can have some control over it.

      Thanks for your comment.

  • Noah D

    I was a little nervous entering my video in a BPA competition with my team. I didn’t think I was gonna win. Later i found out my video won 1st place at the regional competition and we are headed rot states next month. Now I’m confident with my work!

    • Awesome! It’s great to have your fears assuaged with a great outcome, but I think even an outcome that’s not the desired one can still help with fear. Usually, the bad outcomes are not as bad as you would have imagined.

      Keep pushing, Noah!

  • Duc

    Hey Devon,

    thanks for that awesome post. It is very motivating to hear that I’m not the only one struggling. I have been turned down many times and the key is really to just keep trying. It can be very discouraging, but as you have said”I just have to make sure I’m making a few more attempts than I’m getting rejections.”

    • Thanks, Duc. I’ve actually come to appreciate rejection. It’s a pleasant departure from what may be the most common response you’ll get as a freelancer: nothing. With a rejection, I usually have some idea what I need to improve.

  • Elijah

    Great post insightful and encouraging

  • Natalie Berg

    This is a great article. I think many people can relate to this including me.

  • Lofton

    Great article! I found it very insightful, and it had me reflecting on all the times I was afraid to fail. Thanks for the article again.

  • Pingback: Taming your fear of failure before it destroys your freelance career | DACC Digital Design()

  • Pingback: 13 Blogs Every Freelancer Should Be Reading – Michael Ofei()

  • Pingback: The Ultimate Cheat Sheet for Mastering Newbie Freelancing Fears | Outsourced Freelancing Success()