When I was a kid and my dad wanted me to try a new sport, I resisted. I had a million reasons, but my dad believed only one. You don’t want to try anything you don’t think you’re going to be good at.

As much as I protested, deep down I knew he was right. The possibility of failure scared me. I didn’t want to look silly, unprepared, untalented, or *gasp* wrong. Putting myself out there in some unproven way was risky. Honestly, it still is.

Risk frightens me. I tend to nose around the edges, vetting every situation before I have to take a stand. I hold back in meetings until I can assess whether anyone will support me. I consume information like crazy in an attempt to assure myself of the outcome of situations that haven’t yet happened.

My dad was right (shh…don’t tell him): I don’t want to do things when I’m not sure whether I’ll succeed. If I don’t think I can win, I won’t play.

While some amount of risk aversion is healthy, lately I’ve begun to think that running scared causes me to forgo much of life’s richness. What have I missed because I was reluctant to try?

I consider my brother, who is so much like me and yet so very different. He just accepted a position at a startup company fueled by big dreams and venture capital. The job he’s leaving is incredibly secure, pays well, and has a pretty clear path for upward mobility. He chose to accept the risk and go after something bigger.

And then there’s the friend who asked me for a favor. There are a million practical reasons not to do it; the risks are high. But are they really? The worst case scenario, the one that comes with total failure, is far less severe than other things I’ve faced, and it only gets better from there.

As is my custom, I sought advice from people I trust. Two of them categorically told me to say no. After that, I almost didn’t call the third. I’m so glad I did.

She shared the same concerns as the first two, but she also listened to me tell her why I hadn’t been able to just walk away. She gave me thoughtful commentary and reminded me of something really important.

When we’re making decisions, we usually act from the downside. We consider the worst case scenario and react accordingly. What we often forget is that there’s also an upside. What happens when things go right? Is the opportunity for good worth forgoing? What about the people who take a chance and actually succeed? Life is short. We all want to leave something to be proud of, so sometimes we have to take chances.

I’m paraphrasing, of course, but she’s right. It’s a balancing act. Instead of giving the good any weight at all, I make choices based on the worst case. I know the opposite approach is equally imprudent, but the truth is, I rarely consider the upside at all.

That conversation flipped some kind of switch in my head. I’ll always be risk averse, but I realize I need to take a few more chances.

So I entered a writing contest. I’ll look to learn something rather than win something.

I’ll start running again (assuming my knees cooperate) even though my pace is minutes slower than my best. I’ll embrace the things about it I loved rather than try to match my PR.

I’m considering my friend’s request with new eyes. I’ll put more emphasis on how I can help rather than how I can be hurt.

I’ll try to say yes more often to things that scare me.


There is freedom waiting for you,

On the breezes of the sky,

And you ask, “What if I fall?”

Oh but my darling,

What if you fly?

–Erin Hanson


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