On the way to a dinner the other night I heard Frank Sinatra sing the line “You’re all dressed to go dreaming.” It turned out to be the first line of “Moonlight Becomes You,” which I later found out was written by James Van Heusen and Johnny Burke in 1942 and recorded by Sinatra in 1966.

It was a misty night, perfect for allowing myself to fantasize about what one would actually wear to “go dreaming.” A ball gown like Cinderella’s? A lace trimmed nightgown? Virginal or sexy? Jeans and a flannel shirt for curling up to dream by the fireplace? Or perhaps the song is implying that moonlight is sufficient attire for dreaming?

We dream at night. Sometimes, in the light of day, our dreams are tantalizingly close, but just out of reach. And sometimes we recall them but are bewildered by their meaning. If they are daydreams, we may be called into account for not paying attention to more important matters. How often I have been  told to “stop daydreaming!”

Many inspirational leaders have spoken to us about dreaming. The Reverend Martin Luther King Jr.’s “I Have a Dream” speech still resonates decades later. Gloria Steinem said “Without leaps of imagination, or dreaming, we lose the excitement of possibilities. Dreaming, after all, is a form of planning.”

Thinking of all the predictable and uninspiring planning processes I have been part of, I wish we could organize “strategic dreaming.”  Wouldn’t it be wonderful to capture the freedom and spontaneity of dreaming in more of our every day lives? To say to our staff, scurrying to come up with agenda items for the weekly meeting, “we’re going dreaming?” Vision statements are intended to be based on our collective dreams for the future, but too often we become bogged down in all the reasons we can’t achieve these dreams. Leadership means creating an environment for dreaming and saying yes to the dreams.

Barbara ViniarComment