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Unleashing Your Inner Risk-Taker

by Jen Lawson Williams

A handful of steps toward increasing risk tolerance and failing forward​

What comes to mind when you hear the word “risky”?:

Dangerous? (check)

Business? (classic!)

No, thanks!? (ooh, same, friend, same).

When I hear that word, I always think the same thing: NOT ME.

I am not one for extreme sports, putting myself in physical or emotional danger or doing anything that generally keeps me out past 10 p.m. But, I do like to grow and learn new things. And I’d like to be more bold and brazen — especially in my career. It certainly seems exhilarating. And in theory, I understand how taking risks in business can pay off. Take these two super-famous risk-takers:

  1. Elon Musk invested his last $35 million in cash into Tesla in a down economy while unable to deliver the first car. The gutsy move paid off: Tesla is now worth $2.5 billion.
  2. John Mackey left his popular grocery chain in the 1970’s when demand for locally grown, organic, healthy food was virtually nonexistent. His bet could’ve been a major flop, but Whole Foods was purchased by Amazon for $13.7 billion last year…so flop, it was not.

I logically understand that there are benefits to risk-taking, and I understand pushing my limits could exponentially spur my personal growth — so why am I so bad at it? I sought out experts to better understand the answer, and I came across this definition by author Kayt Sukel who has been writing on the subject of risk for years and literally wrote the book on the subject, called The Art of Risk.

“RISK ISN’T GAMBLING…It isn’t extreme sports, junk bonds, illicit drugs or unprotected sex…Risk is simply a decision or behavior that has some probability of resulting in a negative outcome. That’s it.”

Kayt Sukel

And here’s the thing — every decision carries risk. Period.

It’s unavoidable. Your decision to get out of bed. To go to work. To read this blog. Risk…risk…risk!

Obviously, some risks are greater than others. But the fact is, any decision at any time could have some probability of a negative outcome. Smaller risks are less likely to end negatively by definition, and they are also less likely to lead to big revelations or Tesla-like business results. But I realized that if I’ve already been taking risks, small ones, even without knowing it, maybe it wouldn’t be too difficult to nudge myself into “riskier” territory, and therefore be rewarded by bigger growth.


To grow my risk tolerance in 2019, I knew I had to accept that risk is part and parcel of every single decision I make, every single day — big or small, life-altering or seemingly inconsequential. I had to acknowledge, then overcome, the fears that hold me back. I needed a framework, and practice, to retrain my brain to be more open to risk. Luckily I found another expert. Educator and entrepreneur consultant Dr. Sharon Porter has developed a 5-step system for opening up your mind to risk in a way that keeps fears at bay:

Step 1: FIRE BULLETS, THEN CANNONBALLS
  • Start with small risks before moving on to larger risks with greater consequences. Follow your instincts. Learning to live with failed risks on a smaller scale will prepare you for failing forward on a greater scale.

Step 2: PREPARE, ACT, ASSESS, ADJUST

  • Before you act, prepare as well as you can. What do you need that would make potential failure easier to take or the win more likely? Then, after you move forward with a risk, you must evaluate your risk’s effectiveness and make changes accordingly, optimizing toward the win.
Step 3: BE OPEN TO EVERYTHING; ATTACHED TO NOTHING
  • Often, preconceived ideas hinder our risk-taking ability. For instance, “Idea love”, bias, past history, or a desire to stick to the plan…notions we bring with us to the decision-making table can quickly become chains that hold us back if we cling to them too rigidly. Be tethered to nothing other than the value notion that “the best idea wins” — even and especially if it’s the risky idea.
Step 4: BE AUTHENTIC
  • When you show up as who you are, vulnerability is present. When vulnerability is present, trust is present. When trust is present, you are not afraid to fail because you’re owning the outcome — win or lose. Trust your gut, don’t pretend, and be honest with those around you about what you’re doing and what the costs might be.
Step 5: GO AHEAD, FAIL
  • Failure is an opportunity for growth. We know this rationally, and yet fear of failure is the #1 risk-killer. Failure should be an option. As long as you are learning from your mistakes, you are experiencing growth. Failure is simply a stepping stone to your success. Again, the caveat is you must learn from the failed event. When you are unafraid to fail, you are more apt to take risks.

Instead of “Win or Lose” think of it as “Win or Learn.” Develop a “failure script” to help you move past fear. Here’s an example:

“If I’m successful, I’ll gain….

“And if I fail, I might lose…

“And by failing, I’ll learn…

“And if I do nothing, I’ll lose…

Quantifying the possible outcomes seems so simple, but it’s not a step we typically take. And rarely do we evaluate the value of the potential learning opportunity. Nor do we think about the risk of inaction. That’s a choice, too. And as we’ve learned, all choices carry risk.


So all this to say, I’m looking forward to the failures I will have, because that will be a sure sign that I’m taking more risks. And by keeping these five steps front and center, I’m hopeful I can change my response to the word “risky” from “not me” to “I’m in!” I’ll get back to you about the extreme sports, though.


Originally published at https://ideas.redpepper.land/unleashing-your-inner-risk-taker-84a904f40df0 on March 18th, 2019

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