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DREAM CAREER TOOLKIT: What if You Weren’t Afraid to Fail?

Shawn Tolleson gives essential keys to success in the entertainment industry starting with, don't be afraid to fail.

Shawn Tolleson is a career coach working with screenwriters and other entertainment industry professionals. She gives you the practical tools you need to accomplish your dream career. Check out blogs, videos, classes and more at! Follow Shawn on Twitter: @shawntolleson.

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Every year brings the possibility of great things. Every year I look to understand what my goals are for the year and what I can do better and differently to bring them about.

Many of you know 2014 was a year of great accomplishment for me. After nearly a decade of trying to get several different feature projects into production, I directed my first feature, Saturn Returns, which I also wrote. We are now nearing the end of post-production. I’m happy to report that even after all of these months in post-production and years in the making, I still love it and I’m really excited to share it with you all.

Another big accomplishment for me was how my coaching business grew last year even when I was in the midst of making a movie. It was an accomplishment to be able to continue helping people accomplish their own dreams even as I was accomplishing mine.

afraid to fail

And so, in examining what was different about last year, what finally pushed my big goals across the finish line in a way that hadn’t happened before, I’ve uncovered some new things to share.

Here goes…

Many of you have heard me talk about the 5 Keys to Success. In case you’re new to them, here they are:

  1. Crystal Clear Vision
  2. Strategic Plan
  3. Passionate, Committed Team
  4. Powerful, Consistent Execution
  5. Overcoming Obstacles

These 5 Keys are absolutely critical to you accomplishing anything of scope or magnitude, and accomplishing it fast.

I’ve taught these 5 Keys in various forms for years now. They are extremely powerful and effective. And so it’s funny, because in examining what was different for me last year, there’s one thing that I realize is being taken for granted in this list above:


You must have a true, deep, and even profound commitment to accomplishing your big dream. It’s a lot like the oxygen you breathe. Without commitment, your goal dies. It doesn’t matter how great your plan is or how well you’re executing it. The 5 Keys make very little difference without the foundation of deep commitment.

I have had a high level of commitment to directing my first feature film for many years. Those who know me well, know how hard I’ve worked toward it and how much I’ve sacrificed (I’m not unique in this way. Most feature film directors have worked very hard and sacrificed a lot to get their films made.)

So, what was different for me last year? Well, after years of being very committed, I got willing to dig down and confront my deepest fears. There’s a saying I know you’ve all heard: “What would you do if you weren’t afraid to fail?” This is a very cool quote, but what does it mean that you do – practically speaking? Our fears are everywhere. We confront them all the time, both consciously, and more important, subconsciously. How can we figure out what that fear is, in a given moment, and step over it powerfully, thereby changing the outcome?

I can tell you what I did: I asked myself every day “How committed are you, today, to directing your film in June?” Some days I even asked that question moment to moment. In a moment it looked something like this: “How committed are you, right now, to getting this thing done by X time so that you can direct your film in June?” Or, “What are you willing to do, right now, to turn this problem around so that you can direct your film in June?”

Now, let me be clear. I wasn’t willing to be a terrible person with no integrity. I wasn’t willing to sacrifice my marriage or abandon my children. I don’t condone any thing like that and that’s not what I mean by “what are you willing to do.”

I actually think behavior like I describe above is the easy way out of the tough choices and decisions. I’m talking about much harder stuff. I’m talking about how you face down your own secret fears and behave with grace and fortitude in the face of them. I’m talking about how you get out of your own comfort zone and challenge yourself to be the best version of yourself – to grow beyond your limitations, and by doing so accomplish bigger and better things.

These are just a few examples of practical ways to turn “What would you do if you weren’t afraid to fail?” into real-time, in-the-moment ways to confront your fear of failure and turn it around.

So my question for you, as we perch on the edge of a year filled with possibility, is what are you really committed to accomplishing this year? Not what you’ve been saying for a long time. Not what you keep trying to do, year in and year out, but what you’re really, truly, deeply committed to accomplishing.

Check in with yourself. Those things you’ve been saying for years now, are you willing to walk away from them? There’s no shame in letting go of something that isn’t what you’re really committed to. In fact, it takes a lot of courage. Imagine your life without the baggage of these big goals you haven’t yet accomplished. You might feel real freedom and possibility for the first time in a long time.

But, if you can’t walk away from them? If you know that in your heart of hearts you still really, deeply want to accomplish those things? Then, chances are that for it to happen, you need to take on a new level of commitment.

True. Deep. Profound. A commitment that changes what you’re doing and how you’re doing it.

Wow. I’m excited for you!

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