Tony Woodlief | Author


My work with non-profits over the years has given me the opportunity to sit down with a number of philanthropists. I’m just now flying home from visiting Tucson, Arizona, where I met with several people who have led very different lives, but who share a characteristic that I wish were more true of me. Quite simply, they have an expansive view of the possible.

I’m an analytical hypochondriacal pessimist, flavored with a dash of unreasonable hopefulness. Give me any situation, and I can tell you ten ways it’s bound to go south, and at least five of those ways involve me personally getting cancer in the process. The whole world is going to hell in a handbasket, and my corner of that handbasket is the bleeding hell-bound edge, and the only thing keeping us from striking flaming brimstone sooner is that the cerebral thrombosis working itself into creation inside my skull needs a little more time to quicken.

I’m sure of this, yet I daydream of sweet blessed peace in a cottage on a quiet hillside where I write in the morning and garden in the afternoon and my sons and their children visit me to talk about literature and God and to regale me with their stories of happiness and success. It could happen, I tell myself. I might get a lot better at saving money. Somehow my next book could maybe become a bestseller with a movie series spinoff.

Existential dread and insecurity, tinged with irrational dreams, is a recipe for failure. My only saving grace is that I’m driven by a relentless combination of fear, guilt, and regret.

Don’t knock it until you’ve tried it. I hit more deadlines than I miss, and I get the bills paid. Still, it’s a poor recipe for life.

That’s why I’m often enthralled by the big personalities I encounter in my work. In the past few days I spent time with a woman who forged a music and acting career in New York many years ago, who endured with grace and self-sacrifice a great personal tragedy, and who has since given generously to medical and educational causes. She is now in the midst of composing a host of piano pieces. She has lived, and is living, a very big life.

I broke bread with a man who, when he was younger, was so disgusted with the corrupt incumbent in his state senate district that he refinanced his car and used the extra cash to challenge and unseat the rat. He still serves in office, has forged a successful set of business ventures, and at the same time is building a non-profit that brings veterans into classrooms to speak to schoolchildren about American values and public service.

I had iced tea with a lady who likewise challenged a politician she saw to be unprincipled, who is more technologically savvy than many adults half her age, and who invests her time and money in a variety of charitable causes. And I spent time just today with a man who dropped out of Dartmouth to fight in the second world war, came home to forge a career, and has since built a set of very successful businesses. He’s also become quite an expert on western American art, and he’s active and witty and sharp as a tack.

They’re different ages, from different walks of life, but what these people share in common is that they believe they can accomplish what many of us shrink from attempting. They’ve achieved far more than most people, and in the process failed far more than most. They recognize what I often forget, which is that you can’t have one without bearing the other.

This has set me to wondering how I, as a parent, can cultivate in my sons the same belief in possibility, the same courage, the same willingness to get knocked down repeatedly and still strive.

I’m ashamed to admit how often I’ve discouraged my dreamer, ten year-old Caleb, from trying something I know won’t work. He’s the kid who wants to go into commerce. “Dad,” he says, “I could draw pictures, and then set up a booth at the end of our driveway, and sell them to people who drive by.”

Instead of helping him build the booth, I explain to him the economics of the street-corner art world. One dream deflated.

“Dad,” he says, “I want to design a train in the sky so that people can get from place to place really fast.” Instead of getting him some maps and markers to begin planning it out, I tell him that migration patterns make fixed-rail transportation systems highly cost-inefficient. One more dream killed in the crib.

I’m thinking I need to dive in wholeheartedly and help my children fail. It’s not my job, after all, to tell them how their ideas won’t work. It’s my job to inculcate in them bravery, and creativity, and hope.

And then, when the art sales booth or the transportation system redesign hits the wall of reality, it’s my job to help them shake off the disappointment and dream the next dream.

It takes so much energy, doesn’t it? Helping them try, failing alongside them. But it’s our job, isn’t it? So here is my vision for my boys: that they will discover what is possible by dreaming big dreams, and acting without fear, and picking themselves off the ground with thankfulness when they fail.

That’s my big dream. That’s the great thing I want to accomplish.

On Key

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