Risk loves company

As I continued reading Finish by Jon Acuff, I had a lightbulb moment where I connected his points about perfectionism with some insights on risk-taking I learned about in Thinking Fast and Slow by Daniel Kahneman. 

Kahneman explains that CEOs and other business leaders encourage risk-taking because they know that risk is necessary for higher returns and they're OK spreading it among their teams. The individual business leaders under them, on the other hand, are risk averse because failing as an individual feels like complete failure. So, their interests are opposed -- the CEO wants risk and is OK if a few of the leaders fail while taking risks, but the leaders avoid risk because they don't want to be the dummy who messed up. 

The CEO's mindset might not make sense to you. Here's why it should: I give you $10,000 to open an ice cream stand and you take some risks. Even if you completely fail, I only lose $10,000. But, if you take risks and create a new style of ice cream that's wildly successful, I might make $100,000 or even $100 million. So, if I have 5 people opening ice cream stands, it makes more sense for me to encourage all 5 to take risks -- the downside is limited, but the upside is unlimited. But, you probably don't love the idea of being the ice cream failure (who wants to ruin ice cream?). 

As I read Finish, it clicked for me that we often have the leader's mindset, not the CEO's, when it comes to our personal goals. Perfectionism forces us to look at our goals in isolation when in reality we should look at them more like an investment portfolio. 

For example, I had a goal of creating a consistent, successful interview-style podcast about creativity. I ran into all sorts of unexpected stuff and eventually I gave up on it. In isolation, that effort was a failure. But, at the same time I was taking that risk, I was taking a lot of other related ones at work (using the research I had done on podcasting to try other things, too). Some of those risks have been much more successful than I ever imagined the podcast would be. 

So does the one failure make me a failure? Not the way I look at it -- I see it as a good indication that I'm taking enough risk and fighting back against perfectionism. I'd be worried if I looked around and didn't see any areas where I was failing.