How to End Your Love Affair With Playing it Safe (Even if You’re Terrified)

brokenheargraffitiHow often have you talked yourself out of a dream in the name of playing it safe?

Playing it safe has its merits. There’s a time and a place for it. For instance, if the ways in which you’re considering throwing caution to the wind have a high likelihood of killing you, landing you in jail, or hurting others, you should definitely play it safe. But since most of us aren’t masochists or sociopaths (I’m just going to assume that you’re not creepy), it’s unlikely that your deepest desires are going to take you down a road of irreversible damage.

If you live in a constant state of fear of the unknown, and this fear leads to paralysis about trying new things, you’re cheating yourself. Is there a chance that you’ll flop? Yes. Of course. And so what?

Your love affair with playing it safe is not one of reciprocity. It’s a relationship in which you give, and playing it safe takes. It takes away from adventure and exploration. It takes away from learning. It takes away your opportunities. It greedily fills the spaces where growth and change could otherwise occur. It’s a horrible partner. It squeezes, and stifles, and suffocates, and it convinces you that it’s for your own good.

Perform a simple risk/benefit analysis

“People who don’t take risks generally make about two big mistakes a year. People who do take risks generally make about two big mistakes a year.” – Peter F. Drucker

Being rash and impulsive isn’t the same thing as taking healthy risks. If you’re not sure how to differentiate between the two, grab a pen and a paper. Seriously, go! I’ll wait right here. Got it? Okay, it’s brainstorming time. Spend five minutes writing down every single thing you can think of that you haven’t pursued because you’re playing it safe. Nothing is too big, small, or silly.

When you’ve got your list, read each thing out loud to yourself. Ask yourself, “If I do this, what are all of the potentially negative outcomes? What is the absolute worst thing that could possibly happen? How likely is it that these things will happen?”

Really. It might sound overly simplistic, but you don’t need to make this complicated. If you determine that there is a 78% chance of death or disfigurement, maybe it’s best to let that dream remain in the realm of fantasy. If there’s a 78% chance that you’re going to suck at it and someone might laugh at you, take a deep breath and go for it.

The monster under the bed is probably a crumpled up pair of pants

Taking risks can be scary. Believe me, I’m not trying to downplay your feelings. I have an intimate relationship with that fear. The more emotionally invested I am in something I’ve written, the more terrifying it is to let other people see it.

A lot of artists feel like they’re giving part of themselves away when they publicize their work. Having your art rejected or criticized can feel an awful lot like you are being rejected or criticized. Whether you’re an entrepreneur, a writer, or a painter, you’re putting yourself out there in a very vulnerable way.

The cold, hard truth is that not everyone is going to like your work. For that matter, not everyone is going to like you. The bad news is that this can be painful. The good news is that it won’t kill you.

Out of everything I’ve ever written, one of the pieces I was the most afraid to publish was a poem called The Most Dangerous Neighborhood in Phoenix. I paused over the publish button for a very extended minute before I convinced myself to do it. A couple of hours later, I had to talk myself out of deleting it. Why? Because it was real. It was personal. It was about my life and my deeply held convictions.

I knew that it was good. I also felt fairly certain that it was going to piss some people off. I wasn’t wrong about either of those things. I got nasty messages. I saw one woman shred me in a public forum. About six or seven of those folks demanded my attention. It didn’t feel great.

You know what else happened? It was shared so widely that I got thank you notes from all over the place, from people I didn’t know. Even better, I met some incredible people in my own neighborhood because of that poem. It was the first piece I was ever invited to perform at a cultural event, which led to me meeting and working with some of the most talented and inspiring female performance artists in Phoenix. After that, I got to read it to a class of college freshman, and discuss it with them.

I had been so afraid of the criticism I knew that it would receive, but when the criticism came, it wasn’t the scary monster I had imagined it to be. It was about as harmful to me as a crumpled up pair of pants lurking in the shadows under the bed. Had I stayed in bed with my eyes scrunched shut, too terrified to lean over the edge, I never would have discovered the truth. The good so far outweighed the bad that it totally crushed it out.

What fears do you need to overcome in order to end your love affair with playing it safe? What would you do if you believed that you could thrive and succeed, even if some of your risks didn’t lead to the results you were hoping for? What would support and encourage you to take a step in that direction?

If you feel like sharing insights from your brainstorming session, tell me all about it in the comments. I’d love to hear what you’re dreaming about.


  1. love this. i stopped playing it safe on a cold night in december when i answered an not so simple text from my son with one word. yes. and that yes began the change and the dust off of a long held quiet dream that i have been holding on to since i was a young girl. and whoa gamechanger. i feel like me, fully. finally. and even though it will be a long road of mistakes and there are lots of times i look foolish, feel foolish and know this will continue on for the years it will take me to fulfill this dream, i also feel strong and amazing and am so glad i said yes, to myself. i am dreaming about becoming an ironman. and i do my first sprint triathlon this summer but really 3 months into training and i already know that i so got this. and i love it. all of it.

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