Playing it Safe

September 21, 2012 Leave a comment

The following is a letter by Akaya Windwood, President of the Rockwood Leadership Institute and member of the IISC Board of Directors.

About a week ago I was in my car on my way home, and traveling toward me on the busy sidewalk was a young man (20-ish) on a skateboard. It took a moment for me to register that he had a toddler-aged girl on his shoulders. Neither of them had helmets or shin pads or any protection whatsoever.

My first thought was “Stop! Get that child off his shoulders — they could both be killed if he hits a rock! This is child endangerment!!!” All my alarms started clanging, and I was on HIGH alert.

And then I noticed their faces. He wasn’t going fast, but was moving smoothly and with expertise. He was also grinning from ear to ear, and the look on that baby’s face was sheer and unadulterated joy. It’s been a long time since I’ve witnessed such unselfconscious bliss. Their expressions took my breath away.

I pulled over for a moment, caught between abject fear and utter delight. My heart was pounding in outrage and the child in me was whooping in happiness. What a dilemma.

Reflecting on it later, I realized that leadership can often feel like that, especially when I’m taking a risk, or trying a new skill. On one hand — “If I take this risk and fail, what could happen to me, to Rockwood, to our community, the world!?!?” On the other — “How terrifically amazing might it be if…”

How often do we lead from a place of managing fear of possible disaster rather than going all-out on something that thrills our hearts? What are the consequences of this?

Please hear me — I’m not espousing child endangerment or recklessness. But I am questioning what we lose when we listen overmuch to our own fears and the fears of those around us. There are many risks to take, but the greater risk is the choice we didn’t attempt because of those fears. We risk missing out on the exhilaration and joy that is possible when we take a chance and leap into the unknown now and again.

These are unprecedented and changing times. We need new tools and ways of leading. We will need to take new risks, and undoubtedly we’ll fall down and stumble — perhaps even break a bone or two. While it’s important that we’re not reckless, it’s equally important that we’re not so cautious that we become moribund.

So I’m going to push myself to be a little less “safe” and see what happens over the next several months. I invite you to join me in whatever way makes sense to you.

From my heart to yours.

September 2012

No Comments

  • Cynthia Silva Parker says:

    Too funny Akaya! I had a very similar experience with some teen skateboarders yesterday while I was in Baltimore. They were moving through rows of stopped cars at the height of rush hour. I heard one motorist yelling at them, sounding more angry than worried for them. When they got onto the sidewalk near me, the mother in me wanted to say something like “be careful out there” at the very least but I caught myself. They were enjoying the thrill of being in motion together and I didn’t want to interrupt that. And, in fact, they knew how to manage the risks, getting onto the sidewalk when the cars really started moving.

    So let me add to your thought the joy of taking a calculated risk TOGETHER, and the power of knowing how to manage that risk without losing the thrill.

  • Sara Oaklander says:

    Such a powerful message, Akaya, in the story you tell about the young man and little girl on the skateboard is a compelling metaphor. There’s real wisdom in your challenge to self and others. Very much aligned with Gibran’s earlier blog on fearlessness and The Case Foundation’s fearlessness principles:
    Thank you for putting this out to all!

  • Curtis says:

    Thanks, Akaya. Beautifully expressed. I think of this as the ongoing challenge in leadership between the “vertical” (development oriented and risk-taking) and the “horizontal” (doing things right, managing risk). That balance is always in flux, and the great leaders seem to know how to adjust to circumstance.

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