Risky Business

Navigating life as a risk-prone professional.

A few years back, as I was lamenting about my boredom to my therapist, she said, “You’re an experience junkie.” Probably not a specific diagnosis you could find in the DSM-5, but it definitely got my attention.

She definitely wasn’t wrong. I live for the adrenaline rush, the stimulation, the newness of throwing myself into an unknown situation.

  • Skydive (check)

  • Quit my job without another lined up (check)

  • Travel solo to a country where I don’t know anyone and don’t speak the language (check)

  • Sneak past security into the elevators of NYC high rises to drop my resume off in hopes of finding my dream job (check)

And while I’ve made some bold moves, all of this risk taking has required some serious support. I have the incredible privilege of supportive family, friends and colleagues along with a wonderful education and financial stability to balance it out. Great risks often require great comfort.

It’s not hard to connect the dots on how I came to the work that I do today. My role at Stoked is, at its core, to encourage organizations and individuals to take risks, be more innovative, get out of their comfort zone. I do this by being insanely curious about humans, emotions and values.

Over the course of several weeks, I put that curiosity into action and explored risk. I talked to friends, family and strangers about their relationship with taking chances and I took note of how risk showed up in my own life.

Here’s what I learned:

Our perception of risk isn’t always reality.

Megan, you can’t win if you don’t play,” quipped my neighbor. He buys a lottery ticket every single day at the prospect of hitting it big. While he’s never won a million dollars, the small wins keep him hopeful that one day he’ll hit the jackpot. While the overall odds of winning something on a $10 scratch off are 1:3.68, hitting the jackpot is highly unlikely.

Our perception of risk plays a role in our decision making, despite the odds. We heard from folks in NYC that skydiving is a risk they haven’t taken. However, the odds are that you are more likely to die in a car accident (one in 107) than you are from skydiving (one in 167,000). How is it that our perception of risk differs so greatly from reality? Societal and cultural norms play a critical part in determining how individuals and organizations take risks. While our perception can lead us to optimism and hope in making bold moves, it can also prevent us from taking risks that aren’t as dangerous as they seem.


Judgment — from yourself and others — can get in the way of risk.

“That’s not risky!”

On my first day of exploring risk, I had a hair appointment. As I sat down in Melissa’s salon chair, I told her about what I was up to.

Let’s do something different, let’s go shorter.

Do you have a picture?” she asked.

Nope, what do you think would look good.

On the first team call since my haircut, they noticed. I explained it was a part of my newsletter exploration on risk. “That’s not risky!” one person exclaimed in regards to my hair. AHA. There it is. The judgment of risk — it shows up both in our judgment of ourselves and from others. Risk is incredibly personal and relative. Ultimately, you get to decide — will you let judgment get in the way of making bold moves?


Risk taking is a muscle you can flex.

I am looking for a volunteer to join me on stage.

In a room filled with over 100 people, it felt as though the entire room was collectively having a moment filled with hesitation until the first hand went up. As Amanda joined me on stage, she whispered, “I am so nervous.” She wasn’t kidding — her nervous energy was palpable.

After we had the room roaring with laughter through a playful prototype we were testing, she later told me that being on stage terrifies her — but it’s something worth taking the risk for so she grabs on to any opportunity to push herself out of her comfort zone. How’s that for inspiring?


Risk requires support.

Do you want me to ask him for you?”, Baxter asked as I was obviously deflated from rejection on the streets of NYC. I was exhausted and honestly couldn’t muster the courage to ask one more person to talk to me about risk. Wall Street certainly isn’t known for being a friendly spot — and it was proving it. It felt like I had been rejected a hundred times and my tank was empty.

Take a risk. Or at least support one.

The great risks I heard and read about always involved support — most often another person, cheering you on , taking the risk alongside you or forcing you into something you didn’t know was coming. You have the choice every single day to not only lean into your support system — but also act as one for others. How can you show up as a cheerleader for someone in your life who is navigating risk? Who can support you in one you are ready to take?

At its core, risk is incredibly personal. While our capacity for it can differ significantly from others, and even from ourselves at different times in our lives, taking big risks is often something we are training for every single day. How are you stepping into risk today?

Check out Megan’s video as she and Baxter take to the streets of NYC to find out more about risk.

Megan McClendon

Lead of Innovation at Stoked

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