Do the Scary Thing First

Playing it safe out of the possibility of failure is perhaps the biggest disservice we do to ourselves and the world. We spend so much of our lives in our own heads pondering the worst possible outcomes, convincing ourselves that if we were to take a risk we would only fall flat on our faces and embarrass ourselves along the way. But deep down we all know that we are each much braver, bolder and brighter than we give ourselves permission to be.

Take a moment to imagine what your life would be like if every morning you woke up eager to complete the most daunting task of the day first. Imagine the fulfilment of going to bed each night knowing that while your knees and hands and legs shook, you did something scary that day. Imagine how much closer you would come to achieving your dreams if you decided right now to always work toward your goals, not without fear, but in spite of it.

Face Your Fears: Do the Scary Thing First

Do the Scary Thing First*

Your playing small does not serve the world. There is nothing enlightened about shrinking so that other people won’t feel insecure around you.

– Marianne Williamson

Here are some uncomfortable truths about how and why doing the scary thing first will ultimately improve your life.

Our joy only comes from courage

Think about it. Every time you have ever been truly happy has been because you did something that took courage to complete — it could have been a successful job interview, audition, or business meeting. And more often than not you succeeded in these circumstances only because you chose to let your quirkiest, most authentic, most vibrant self shine through you in that moment. How courageous a life would you lead if you chose to be this person not just in flashes but in one continual glow? What possibilities would it create? In the words of Honoré de Balzac, “All happiness depends on courage and work.”

If we never act in the face of fear we will die having only lived a half-life

Playing life safe has its perks: you will probably die having paid all your bills; you will probably have found financial security; you will most likely have had all of life’s bare necessities within your immediate reach. But you will never have lived a life of greatness.

You will never have known the triumph of taking a risk and watching it pay off bountifully after taking a hundred that didn’t. And you will for sure, as Theodore Roosevelt once put it, have left your mark amongst “those cold and timid souls who neither know victory nor defeat.” But if you live a life of risk and against all odds still fail, you will have failed “while daring greatly.”

Your self-worth will increase

When you start acting in spite of the fear of failure, you begin to know yourself on new levels. You stop accepting adequacy from your peers or half-hearted, lazy commitment. You start wanting the best for yourself and become unashamed about attaining it. You start to recognize that, as Marianne Williamson puts it, “Your playing small does not serve the world. There is nothing enlightened about shrinking so that other people won’t feel insecure around you.” You were brought onto this planet to be your best self and by doing so, you give others permission to do so too.

So allow this article to re-empower you with that permission.

Allow it to fill you with courage on the scariest days.


Allow it to help you realize that the more courageous you are on a daily basis, the less comfortable you become in the present moment. But have faith that what follows is comfort and joy beyond comprehension. What follows is your legacy.

And no one ever achieved their legacy by spending their life playing it safe.

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*The title of this piece refers to a quote by Lemony Snicket (aka Daniel Handler): “Do the scary thing first, and get scared later.”


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