Failure to Fail: What I’ve Learned from Playing it Safe

“The greatest danger for most of us is not that our aim is too high and we miss it, but that it is too low and we reach it.” – Michelangelo

In poker, I hate going bust. The few times I do push all in, I make sure it’s with a hand that can’t lose. Then the new guy hits an inside straight on the river and Snap! I’m watching from the sidelines for the next 2 hours. My preferred approach is to die a slow death. Little bets and bluffs until my chips vanish like the picture of Marty’s brother in Back to the Future.

But here’s what I’ve learned from playing it safe: when we aim too low we never unlock our potential.

I don’t know if I’m a good poker player because I never risk enough to learn from my mistakes. Underneath it all, isn’t that the real goal? To level up. To bump into your limits and raise them higher?

So many times in life it’s not the thing we want. It’s what we think the thing will give us. The promotion, the bigger house, the nicer car that will make us feel successful, validated or cool. But the title is never fulfilling enough, the house never big enough, the car fast enough.

Instead, what if your desire was to maximize your potential?

But that would mean being willing to fail. Note: I am not saying you will fail; rather I’m saying you need to be willing to fail in pursuit of your natural best.

Here’s a story. You’re waiting in line to pick up your daughter from ice skating practice. She hops in the backseat and you ask “how’d it go today?” “Great! I didn’t fall even once!” she smiles. “That’s awesome!” you celebrate, as you condition your daughter to link success with playing it safe.

I’m guilty of this myself. I became the best tennis player in my high school sophomore year. Once I became #1, I started playing it safe. I practiced my best shots more, my weaker ones less. Played matches against kids I knew I could beat. Shied away from big tournaments. I didn’t want to risk the “thing” I worked hard to earn. By my senior year, I was still the best player in my small school but those kids around the city I used to beat had passed me by.

When we have nothing to lose, failure brushes right off. But when we’ve built our stack of chips, something changes.

Darwin tells us it’s evolutionary. We don’t want to risk looking weak in our tribe because that means getting kicked out of the band, voted off the island or left to starve alone. Freud tells us it’s psychological. We fear not being enough. Failure cracks the cozy cocoon our ego has built for us.

Personally I worry about time. If I fail at this, then I am going to have to restart. And if I have to restart, then I’m falling behind and losing time. It’s better to stay steady, hold my position, and not risk what I’ve earned (as my poker chips slowly vanish).

Have you ever had a breakthrough idea at work and then thought…

“Hey I’m already a VP, Director, Manager, (insert your job title here). Why take the risk of proposing this new thing that could fail and hurt my image? Let’s just keep this running as is.”

If you have, then we’re both guilty.

Interviewing for the promotion. Proposing the business strategy. Trying out for the team. Kissing the girl. These are all things that expose us to the possibility of failure. But, paradoxically, the risks I’ve taken have created the biggest leaps in growth and happiness in my career and life.

Can’t you say the same when you look at your life?

Given the perspective of time, even the risks that didn’t work out don’t feel like failure. They feel essential.

Warren Buffet said “I don’t look to jump over 7-foot bars. I look around for 1-foot bars that I can step over.” And that’s the right strategy. Just as long as your 1-foot bar builds on itself. If it doesn’t, you become the poker player or the high school tennis version of me, not Warren Buffet. His 1-foot bar is much higher today than when he made his first investment in 1941.

By continuously reaching to maximize our potential, we set progressively higher goals that can build to something amazing.

I’m not necessarily suggesting you quit your job to be an artist, invest your life savings to start your own business, or jump out of an airplane to unlock your potential.

What I am suggesting is that you ask yourself, “in what area of my life am I playing things too safely?”

Published by brianhquinn

I believe we are all capable of incredible things. If you're going to doubt anything, don't your limitations. So that’s what this blog is all about. How do we shed those limitations to chart career paths based on our interests and talents rather than lines on a resume? Join me and find out.