Is It Too Late To Learn How To Risk?

As a child, I hated getting in trouble. I did everything I could to avoid it like the plague. I always tried my best to play by the rules and do what was asked of me at home, at school, and at church.  I did not like stepping outside of the parameters given to me because I didn’t like getting punishments. Now that I think of it, I was like a well trained Pavlovian dog!

I know this definitely carried until my adulthood and translated me into being very risk averse.  I’m not one of those people who would take an action if I did not think it would give me the results I anticipated. I’ve never like playing games that I didn’t think I stood a good chance to win. Any chance I can minimize my risk, I usually take it.

In many ways, this mindset has served me well. I’ve always been a relatively responsible adult, (minus some credit card indiscretions in my 20s). I’m sure being risk averse has spared me many accidents or tragic outcomes simply because I have played things rather safely. But when I start to reflect on what I have accomplished and what I still desire to, I have to admit that I have only amassed a series of very small wins in life.

I have lived enough to know that without taking big risks, it’s hard to have big rewards. Most of the people in business or life that I tend to admire usually have one trait in common: they are risk-takers. None of the great companies or leaders celebrated in the likes of Forbes, Inc., or Entrepreneur achieve their great successes without taking huge risks.

So as the half-century mark in my life looms ahead of me in less than a decade, I’m starting to have second thoughts about my low-risk way of living and thinking. I’m looking towards my future and how many more viable and juicy years I have left to accomplish the things I want to accomplish. When I consider the time frame, I feel the weight of mortality. And now it causes me to rethink risk-taking.

The things I want to accomplish before I close my eyes for the last time are big. No, they’re huge. At least for me. On the one hand, it is exciting. I think your vision for your life should definitely be bigger than yourself. But as I think about how much time I theoretically have left, I’m realizing that I am going to need to take quantum leaps forward. And quantum leaps are most certainly risky.

So now I’m asking myself after spending my whole life being very calculated, “Is it too late for me to learn how to risk?” More importantly, how do I learn how to take risks? Big risks. The kind of risks that pay off handsomely. Frankly, the question (and the implications) scares the bejesus outta me. I have a kid. I have responsibilities. I can’t just quit my job and run off with the proverbial circus to follow my dreams of being a tightrope walker, can I?! But then again, maybe I can, right? Tightrope Walkers do it without a safety net, right?

But that is that “crazy” kind of risking that I’ve never liked. I mean just the thought of it makes me break out in hives! So I wonder if there’s another way I can look at risk and ease my way into it quickly. I wonder if there’s a course I can take to learn how to quiet the voices in my head and still my inhibitions long enough to make bold but wise decisions?

I doubt that the entrepreneurs and business leaders I love to read about are taking risks with wild abandon. They very likely researched their options and have decided to go with what would potentially bring them the most return. Now I know that not every big risk pays off handsomely. Sometimes they fail abysmally. As much as I want the big rewards, I have to also be prepared to accept defeat in the process.

So it makes me think that maybe my question isn’t about learning how to take bigger risks.  Maybe I should be asking how can I learn to make smart calculated decisions that have bigger payoffs than I’m used to, in spite of my fears. And maybe I also need to know how to increase my resiliency to get back up and dust myself off again and try again if I attempted to jump the Grand Canyon of my goals and missed by a mile (or 500).  Recently, I shared with you that in the past, I haven’t always bounced back well from setbacks.

Maybe this isn’t even a real question at all. In reality, I wake up and take risks of all sizes every single day. They are just risks that I’ve become used to. Maybe that is the real key: I probably need to get more comfortable with taking bigger leaps of faith than the ones I’m used to.

I don’t know.  I don’t have a nice, neat answer on this one.  I’m simply letting you in on a running conversation I’ve been having in my head (that in itself is risky :)!).  I would truly love to know what you think so leave me a comment below and let’s grow together!

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