Overcoming Your Fears of Making a Big Career Change

I have just entered the world of full-time freelance work.

There are an incredible number of articles out there in the wide and wild inter-verse about taking big risks to create the kind of life you want and deserve. Quit your job and do what you love! the faceless internet proclaims, almost shaming you into believing that you’re not truly living your Best Life unless you’re making money doing the thing you love. To say I have bought into this idea over my years of working a 9-to-5 full-time job would be an understatement.

Did I take a leap of faith into pursuing my artistic dreams? Absolutely not. I have never been the type of person to make decisions lightly. In fact, I am terrible at making decisions, period, let alone taking risks of any kind. I weigh the pros and cons of every choice I make obsessively, paralyzed by indecision until something happens that forces my hand. In this particular case I worked steadily, doggedly even, towards building up alternative sources of income before being given a very special opportunity to perform that conflicted directly with my day job. Before this, I burned the candle at both ends, spending every second that I was not at work pursuing comedy and writing in my free time.

I cannot sit here and advise anyone to put their faith in the unknown. I am not a risk-taker, and I doubt that I ever will be. However, as a person who prefers a surefooted path, there were many personal obstacles that I put in place for myself to prevent me from doing the freelance things that I yearned to be doing full-time. Identifying these things has served to help me get out of my own way, and if you are struggling with making a big career decision of any kind, I hope they may provide some guidance for you too.

The following are some thoughts that I have had about becoming a comedian and writer.

Nobody is going to take you seriously

I stopped myself from believing that I could actually let go of my day job for quite awhile because the voice inside my head kept telling me that I was not worthy of calling myself a professional comedian and writer. I was too scared that other people would think I was ridiculous for giving myself such a lofty title, and because of this fear, I believed that nobody could ever take me seriously.

Though I am a comedian, I spent several years in an administrative position within the comedy community in Toronto. It was a wonderful job, but I really believed that nobody who knew me in this capacity could ever conceive of me as an artist. I imagined that no matter how hard I worked, I would never be considered a peer to some of the people that I admire. Most of the time, I convinced myself that the majority of people around me didn’t even know that I was a comedian and a writer. This only served to stop me from developing relationships with certain people whose work I have always appreciated from afar. By speaking to myself negatively, I wasn’t preventing others from taking me seriously, but rather prevented me from taking myself seriously.

I have always been very worried about being ridiculed for an over-confidence in my abilities, but this way of thinking is extremely problematic. There is nothing wrong with knowing that you are good at something and stating it as a fact, especially to yourself. People will take you seriously if you give them no other choice but to do so.

I’ve been working towards this for years but am I 100% qualified to take on this new challenge?

In a quote from Sheryl Sandberg’s Lean In, she makes the point that One reason women avoid stretch assignments and new challenges is that they worry too much about whether they currently have the skills they need for a new role¦ An internal report at Hewlet-Packard revealed that women only apply for open jobs if they think they meet 100 percent of the criteria listed. Men apply if they think they meet 60 percent of the requirements. This hit me right in the gut when I read it. I can’t even count the number of times in life I have prevented myself from trying something new because I believed I wasn’t absolutely qualified to do it. I have always worked so hard to prove (mostly to myself) that I am unequivocally capable in an attempt to quell the voice inside of me that whispers you are an impostor.

There is nothing wrong with learning as you go. Nothing. This is something that I repeat to myself often, especially now. I do not need to have every single element of my skill set mastered in order to tackle a new obstacle. In fact, I would argue that forcing yourself to learn as you go will not only help you take stock of just how qualified you already are, but give you some insight into where your focus for improvement should now be directed.

Why can’t you just be happy with what you’ve got!?

I told myself many times over the past four years that I should just be thankful for the things that I have, because by wishing for a different type of lifestyle I was being ungrateful.

Any kind of thinking that induces shame or guilt is unhelpful. My own brain is a huge culprit of this kind of negative self-talk, and I have to keep myself in check about it constantly. One way I do this is by reminding myself that I feel everything for a reason. I refuse to allow myself to dismiss my feelings by believing that they are irrational. I felt for a very long time that I wanted to leave my job, but I also felt during that time that I wanted to be financially secure, and I allowed myself to exist within that paradox. Was it comfortable? No. Was I being ungrateful for what I had? Absolutely not.

You are allowed to appreciate what you do have while envisioning a different (or better) set of circumstances. Life is beautifully complex in this way, don’t shame yourself out of your desires because of it.

Oh yikes, what if I fail, though? I can’t fail. That’s so embarrassing…

The fear of failure is the driving force behind all of the personal roadblocks I’ve set up for myself. Failure is terrifying. Failure is embarrassing. Failure is also completely subjective. The idea of trying out the thing I’ve been dreaming about and finding out that I am not actually able to do it was a major factor behind me spending way more time thinking about doing it than ever turning it into a reality. I took some distorted comfort in the ability to control the outcome of the situation by never really doing anything about it. If I did not try, I could not fail. If I could not fail, I could never be ashamed of myself.

I’m so exhausted by the idea that failure is something we should be embarrassed about. I have spent way too much time worrying about whether or not other people would make fun of me behind my back for trying something and failing. How sad.

The dictionary defines failure as a lack of success. I would argue that anyone who remains stagnant in the face of a challenge is already unsuccessful, so why not just try the thing you want to try?

I am no guru on what types of personal or career decisions are best for you. However, if all of the pieces of the puzzle are in place for you to do something that you’re really yearning to do, and the only thing holding you back is the fear of uncertainty and the voice inside your head telling you you’re not good enough to go for it, don’t be afraid to acknowledge that fact. Sometimes simply recognizing the patterns that are holding us back is enough to begin to change them.

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