“What is the craziest thing you’ve ever done?” is the question he poses to us at the lunch table. An inquiry like this never fails to incite mild panic inside me; “crazy” is largely absent from the vocabulary of my life. I’m with a group of colleagues at a conference in Charleston, SC and feeling some pressure to come up with a respectable, yet sufficiently zany, yarn to tell. We’re sitting at a little nautical- themed restaurant on the water, finally the relaxed feel of vacation in the air, out to experience the city before most of us head to the airport.
I’m reminded of my spur of the moment trip to Ft. Lauderdale several years ago. Alone. Over Christmas. Most definitely out of character. More than the decision itself to take a last minute junket, the risks I take to get from here to there are most unlike me. It is snowing. On my way to the airport I receive a text message that my flight is cancelled. Not just delayed, cancelled. Alarmed, I wail over my cell phone to a friend, a seasoned traveler, who advises me to continue to the airport and get on any flight I can. Upon arrival I am somehow able to get a new ticket, at no additional cost, and check my bag. People all around me are advised to wait a day to leave the city; the airport will be closing. At the gate adjacent to mine, there’s an open door, an empty seat and a promise from the airline employee that this flight is absolutely certain to leave Chicago. I’m torn, having never willingly hopped on a plane knowing my luggage is not joining me. Do I start my vacation now or risk no vacation at all? Buckling my seatbelt, my heart swells with satisfaction. This is living, I tell myself and the guy from Alabama next to me.
Sitting in the middle seat I can hardly believe myself. I am going to a place I’ve never been, on my own, with the possibility that I’ll have nothing more than the clothes on my back for some time. Good thing I like my dress. Am I crazy? Not according to my favorite HBR contributor Peter Bregman, just allowing myself to enjoy the feeling of taking a risk even though it may be an epic fail.
Bregman writes in "The Unexpected Antidote to Procrastination" that when we practice taking risks we can condition ourselves to accept the negative feelings that accompany failure or a bad outcome. He makes this observation as he watches surfers, noting that all have one thing in common: No matter what, they always end up falling into the water. Knowing that a fall is the inevitable outcome of a decision to ride each and every wave they choose, trains surfers to get back on the board and do it again, even if the fall might hurt. This logic begs the question: If we knew that a fall is a non-negotiable part of the deal, wouldn’t we learn to throw caution to the wind and take risks all the time?
So this week I encourage my friends at the lunch table to join me in my "crazy" and extend their stays in Charleston another day. My decision already made, having conditioned myself over the years to do this vacation thing alone when chance puts me in a city I’d like to explore, I have nothing to lose if my attempts to entice a few partners in crime fail. I am here either way. The wonderful world of mobile airline apps doesn’t allow them to spend too much time weighing the pros and cons; making it possible to book new flights before we even make it back to the hotel. Decisions made, my friends spend next to no time in the hell that is imagining negative consequences, meaning we jump immediately into the fun. No surprise the unplanned excursion ends up being the best night of the entire trip.
According to Bregman we actually prolong negative feelings when we protract the decision making around taking risks, spending far more time in the angst of procrastination than we ever would in the anguish of a bad outcome. I think he’s right.
I find that the simple exercise of pretending those around me have no opinion of the decision I’m about to make frees me to move out of my comfort zone and take a risk. Who cares if I stand in the middle of King Street to capture a breathtaking row house with my camera? Is anyone really noticing that I’m at a table for one dining alfresco at Amen Street Fish & Raw Bar? Are people talking about the woman sitting alone at the pool enjoying her coffee? I doubt it. But wow, not only would I have missed out on stunning photography, sumptuous She Crab soup and fish tacos, a glorious morning in the sun if I had been concerned, I would have been kicking myself all day for my self-inflicted paralysis.
My risks may not seem risky to you at all. But the common denominator is that we all get stuck at times. To keep moving forward we need to add a little crazy to our lives, whatever that means. Timely that I should happen upon this quote today from Marcus Aurelius: “The art of living is more like wrestling than dancing.” I think it’s apt to say that the time we spend wrestling with ourselves sometimes gets in the way of a life that could be spent dancing.
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