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.

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