The Art of Risk

A client recently said to me:

“Coaching with you is scarier than jumping out of a plane. Because it’s all unknown. I don’t know what we’ll find. How will it end? At least when you jump from a plane, you have a parachute.”

Coaching as an extreme sport? Hell yes. That's the #ArtofRisk Click To Tweet

I’ll admit, I’m the kind of gal to take that comment as a compliment. And to say my job isn’t to be the parachute. It’s to help you enjoy the ride and trust that you’ve had the parachute all along.

I’m also the kind of gal (and coach) who will look for the meaning in an aside, because there’s truth in what we utter.

I’d hazard there are three types of people who jump out of planes:

#1: The “Go-Getter”

TheGoGetter Photo

You love to take risks. You love the feeling of butterflies in your stomach and the uncertainty that comes with being 5,000 feet in the air. Extreme sports and events are your space to feel alive and you jump at every opportunity. This may translate to all areas of your life. You apply for the job, you say “I love you” first. Such a risk taker, you sometimes get hurt and it doesn’t always work out. But you are resilient, get back on your feet and search out the next opportunity to try again.

#2: The “Tag-a-long” 

TheTagaLong photo

A ‘go-getter’ talked you into it so you reluctantly say yes to skydiving. It’s not your first choice on a Saturday afternoon, but you’ll give it try even though heights make you sick. “Many people have jumped from a plane and only a small percentage of those people got hurt doing it,” you tell yourself, “These days jumping out of a plane is safer than driving a car…right?!” You have to push yourself out of your comfort zone or be pushed to take chances. You’re not risk-adverse but you’re not exactly seeking it out either.

#3: The “Do or Die”

The Do or Die photo


You are a person who only jumps from a plane if it’s on fire. The plane may be crashing and burning, yet you’d still hesitate jumping. You tell yourself, “The parachute is likely broken, I should just go down with the plane.” You would rather accept your certain fate than take the leap of faith. You like to control your own outcome. You’d rather die than take a chance. You’d also rather not act than be wrong, mess up, fail or make the wrong choice.

As we jump so we live.

This is what I tell my clients (and remind myself):  There is no guaranteed formula to taking chances in this life – because the outcome is always UNKNOWN. Even the most daring people experience doubt. Doubting your parachute will open or doubting yourself in decisions is part of the human experience, even for the boldest risk takers.

There is no guaranteed formula to taking chances in this life, the outcome is always #unknown Click To Tweet

Learning to tune out the doubt and jump out of the plane – that is where possibility lies.

I’ve seen it time and time again (and have felt the fear creep up in my own throat)—people who remain stagnant in their life and career because they fear the art of taking risks. They are afraid to ask for the promotion, apply for that job, go back to school to pursue their dream, ask that person out, leave the company to start the business of their dreams. The fear stops many people from taking the leap. Fear of Risk is a paralyzing way to live.

There’s just a nanosecond, though, between inaction and action. 

If you can overcome that, you’re on your way. Everyone feels a nervousness before making the jump in varying degrees. But, the second your weight shifts from the plane to mid-air, you’re free falling. There’s no turning back.

All of a sudden there isn’t much thinking happening—it’s all instinct. You’re not thinking about the parachute or the landing or the plane that just flew off. You are catching your breath while falling at 125 mph. Surrounded by breathtaking quiet and beauty, your point of view changes. Suddenly you see things you’ve never seen before. Experiencing feelings you’ve never experienced before. POSSIBILITY begins to reveal itself to you. You understand why so many people jump out of planes, regardless the danger it presents.

That shift from potential possibility to kinetic possibility: that’s when the CHANGE happens. The outcome doesn’t matter anymore because the journey itself is so incredible. You’re having such an amazing experience free falling that doubt and uncertainty fade away and you are exhilarated! All of your senses come alive and you are living it, no longer siting in the plane in fear. You’re doing it. You did it!

When confronted with a choice to take a risk with optimal reward or stay in place, consider:

Choosing exhilaration over ennui – Sure, the plane is comfortable and maybe your current dead end job is comfortable. Unhappiness and comfort can coexist. When presented with an opportunity to jump for the life you’ve dreamed of, choose to jump. Ennui keeps you small and contained. Jumping allows for expansion in a way you’ve never experienced. Even a small jump can ignite your passion and senses in a new way. Sometimes stepping into the uncomfortable space is the place where you will find your fire.

Choose magic over managing – As humans, we tend to gravitate towards control and predictability. We like to know what will happen next and to control the outcome. Yet with a little hard work and shift in perspective, there is an opportunity to master the MAGIC. Jumping from a plane gives the feeling of being one with the Universe. In the right place at the right time. Magical. Screw disappearing acts and rabbits being pulled from a hat—taking the leap, letting go of control and flying free of self-doubt are the magic you need to live your dreams.

Choose to leap (no matter what) over safety-  What if the parachute doesn’t open? What if I start my business and it fails? What if I lose everything? What if she leaves me? We remain in safe situations because of our disempowering relationship to risk. The possibility lies in turning it around: Flip those negatives in to positives and see only potential and possibility. “What if I win her heart?” “What if I end up on the Nasdaq?” “What if I win the Nobel Peace Prize?” “What if it makes me happy and fulfilled?” THIS is the mindset that will manifest the life you dream about. When you leap, spend less time looking at the ground and start looking toward the sky.

Grab on to your gut – Every commonsense fiber in your being (and likely everyone you know) will tell you not to jump. But your heart and soul led you to this moment. Trust yourself. When life gets challenging or scary, you will begin to doubt the reason you got on the plane in the first damn place. Notice the fear. Then grab your gut with one hand—and the parachute cord with the other–then take the step.

Enjoy the free fall – What a crazy, stunning, wild ride of a risk! There are ups and downs, failures and successes. In your free fall—your eyes are pressed open—you can see for miles. The wind takes your breath away. The silence is piercing. You’re alive. You’re on fire. Your arms are outstretched and you’re laughing out loud. You see that opportunity, like the horizon, is never ending. This beautiful, radical uncertainty.

You leapt to love your life.

Tomorrow is uncertain whether you keep your feet on the ground or free fall from a plane. Everything you deem impossible lies on the other side of the leap.

What kind of risk taker will you be? #ArtofRisk Click To Tweet


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