The Risk-Taking Equation

When people ask me about the risks I’ve taken in my career, they often presume that I am fearless. Nothing could be further from the truth. I'm as worried as the next person that something I try will fail. Fear of failure is a natural element of any risk-taking process.

In fact, I’m faced with not one but two fears whenever I weigh a new choice. One is the more classic fear of failure (what I call FOF), but the other is my fear of missing out on a new  opportunity (commonly known as FOMO). Generally speaking, when I take action it’s because the size of my FOMO is greater than the size of my FOF, and when I fail to act is because the reverse is true.  

Classic wisdom suggests that if we deeply visualize what success looks like for ourselves, we can make our way there. I use this technique when I’m already in motion on a hard journey, but it doesn’t help people move from inaction to action if their FOF is raging as high or higher than their FOMO. What if the key to action is not just visualizing the positive and driving our FOMO, but also visualizing the “failure state” and its implications in order to reduce our FOF?

Being trained in sales and business development, I’ve learned the value of looking straight in the face of the “failure case” in order to succeed. In sales, embracing the high likely  “fail” rate of calls going in,  is the key to actually building a big pipeline. When you expect that 8 out of 10 sales calls are a no, you KNOW you need to make 10 calls to get to one yes and become less offended or surprised when brushed aside. You actively anticipate the failure state before you start, and imagine what you will do after once you encounter it (make the next call, ask why someone said no, etc).

In the case of business development, any big deal has the opportunity for upside (that’s why we do them!) , but often has the potential to fail as well. When negotiating contracts before a deal even starts, the job of a business development leader is not to plan for the “upside” case, but most often to protect against the downside case. Here too, visualizing failure is key to getting the confidence to ultimately proceed and it comes from understanding the implications for a miss and what you’d do to rectify it.

So, for all the talk of “avoiding” thinking negatively about potential outcomes, I believe actively managing our FOF is one of the most productive things we can do with our mental energy. When we face the specifics of our FOF, we actually understand the agency we have if something doesn’t turn out the way we want. At that point, we can evaluate what moves we would make if a miss occurs and actually have the potential to reduce it enough to act.

I’ll leave you with a quote I love from the Harvard Business Review article, "Visualize Failure.” As the author contends, the irony is: “when you visualize failure, you're actually visualizing success. You're watching yourself navigate, survive, and move through failure. And that's an art that doesn't just help you succeed; it helps you live.”