When is it Time to Stop Playing it Safe?

My neighbor and her pooch had gone out in the snow on a scouting mission. “There’s another one spun out next to the car blocking the street.” The prominent Road Closed sign had been ignored by those who were sure they could make it. In the Pacific Northwest, we may not get a lot of snowy/icy weather but when we do, it’s a mess. The terrain is hilly, there’s a paucity of equipment, and a distinct lack of driver judgment and experience.

I was that naïve soul sliding sideways down Seattle’s Madison Street many decades ago. It should’ve occurred to me there was a reason no one was out there. Then there was the incident of being high-centered on a snow-covered traffic barrier where a police officer asked what the heck I thought I was doing, a legitimate question. I was smarter years later when car exhaust condensation turned to ice at stop lights leaving no traction for forward momentum. I pulled over and walked the half mile home in my dress shoes—a vast improvement over my poor judgment when a left turn on ice placed my car in a neighbor’s yard for days. The walk in dress shoes led to bringing hiking boots if the weather looked like it might turn. I’ll avoid snow and ice in the city if I can but what if I want to get out in the mountains for winter recreation?

Of course, this piece isn’t just about driving. As Will Rogers said, “Good judgment comes from experience, and experience comes from bad judgment.” To learn, most of us have try things out ourselves. We may seek advice but it’s experiential learning that sticks. On the other hand, we receive plenty of unsolicited guidance. If you’d adhered to all of it, your life would probably be unnecessarily safe and smaller. Think of all the stories you wouldn’t have.

Babies put things in their mouths to explore the world around them. Adults don’t usually place non-food stuff into their mouths but random thoughts do pour out. We interfere where we shouldn’t, champion ill-considered ideas, shove against boundaries when we’re told something can’t be done. In our quest to experiment, we scoot past literal and figurative signs to slow down or stop. When taking a risk results in success, we’re hailed as innovators. And the other times? That’s the learning that informs future behavior. We can’t—and shouldn’t—always play it safe.

If you’re in an environment that values stability at the expense of innovation and growth, consider the tradeoffs. Caution doesn’t typically incubate new ideas. The alternative doesn’t have to be to run with scissors; there’s a reason you have discernment (and a memory!). But don’t be so afraid of sliding downhill that you never attempt the scary or edgy. If you’re ready to step out, here are some ideas:

• Put a toe in the water. Float your idea and see if anyone else is interested. Having company can be a confidence boost.

• Interview people who have done what you want to do. For example, you don’t have to quit your job to investigate what it would be like to start your own business. Ask experienced business owners what they love about having their own company and what they wish they’d known. You get to decide if their experience has any relevance to you.

• Don’t come to a screeching halt just because an uncomfortable emotion shows up. If it’s fear that’s got you in its grip (and you aren’t literally sliding down an icy hill sideways), ask the emotion what it’s protecting you from. If the answer is a puny excuse like embarrassment or potential failure, stare it down. You’ve survived both before.

• Microdose really difficult emotions. Baby-step your way to a larger, scarier goal. Become familiar emotional discomfort rather than darting away from it. If you stop being completely derailed by worry, you can inch your way toward that which in the past might have induced panic. Behaviorists call this systematic desensitization. Increase your exposure to something feared in small and controlled ways until it’s no big deal. Afraid to learn to swim? Get yourself to the pool and wade into the shallow end. If that’s too much, just get to the pool, smell the chlorine then leave. Next time try dangling your feet in the water from the side. Keep getting closer to being comfortable in the pool until you’re ready to sign up for that class.

• Challenge your negative self-talk. For example, “I couldn’t possibly” can be countered with, “Oh, there it is again. What if I could do this?” Or keep it simple with something like, “Well, that’s an interesting reaction,” and let the drama subside. Not every thought deserves your complete attention.

John A. Shedd said, “A ship is safe in harbor, but that’s not what a ship is built for.” You’re designed for experimenting, having experiences, learning, and living your life to its fullest. Get out there and collect your own stories.