Do You Know Where the Shadows Are?

Do you know where the shadows are?

I thought I did.

I’d been running the same stretch of road for more than fifteen years and had never fallen. Then one bright, sunny morning I found two old men far more interesting than the sidewalk beneath my feet.

They were walking through the park across the street from where I was running. One of them was dark-skinned and dressed entirely in white. His hair and beard matched his clothes. Against the green grass and the early morning light, the contrast was striking. The only word that came to mind was majestic. The two men walked slowly, deep in conversation, completely unaware that a stranger jogging down the sidewalk had become fascinated by a conversation he couldn’t hear.

If you plant a tree next to a sidewalk, there’s one thing you can count on: eventually the roots will lift the concrete.

That morning I never saw the raised section hidden under the shadow of a Chanticleer Pear tree. It wasn’t invisible. The sun was bright enough that I would have seen it if I had been paying attention. My attention, however, was somewhere else.

When I tripped, I stumbled forward nearly ten feet before my left foot caught my right leg. I executed what could be described as a graceless tuck-and-roll and ended up flat on my back in the grass.

Approaching fifty, every fall begins with the same question.

Is anything broken?

Finding myself uninjured (except my pride), I turned toward the park. The two men had stopped walking and were now looking across the street at me. I stood up, brushed myself off, and continued running, pretending my dignity hadn’t just taken the hardest hit of the morning.

I’ve traversed that stretch of sidewalk hundreds of times. I know where the uneven terrain is, sometimes hidden in darkness and sometimes obscured by shadows.

Or… at least I thought I did.

Thinking back, I realized something unsettling. I knew that I was aware of the spot, but because I was distracted, I didn’t recognize the danger I already knew was there.

How much of life works exactly the same way?

We spend years accumulating experience. We learn where the shadows are. The first failed investment teaches us something about risk. The first major disagreement in a marriage teaches us something about listening. The first sleepless season with young children teaches us that fatigue changes how we think. The first business that struggles teaches us that optimism isn’t a substitute for cash flow.

Experience gives us a map, but it can’t guarantee we’ll look at it.

Over the last year, I’ve made several expensive trips through familiar shadows.

When I started my company, I knew businesses run out of cash. I’d spent decades consulting with companies whose successes and failures usually came down to ordinary things like margins, inventory, pricing, and cash flow. But I convinced myself that if I built a remarkable team and worked hard enough, investors would arrive before the runway disappeared.

I wasn’t ignorant. I was looking somewhere else.

More recently, I gained nearly forty pounds over the course of two years. I knew exactly how people lose weight. Eat a little less. Move a little more. Sleep enough. Instead, I added running to an already overloaded schedule without changing much of anything else. I lost no weight and gained sore knees.

Again, I wasn’t lacking information. I was standing in a familiar shadow, looking in the wrong direction.

The same pattern shows up in smaller ways.

I know that reaching for my phone first thing in the morning almost always guarantees a distracted day. I know that five hours of sleep eventually sends me into an emotional ditch.

I know that my wife deserves more than the exhausted leftovers of whatever energy remains after I’ve tried to solve everyone else’s problems.

None of those truths are new. They’re simply harder to see when life gets busy. Experience doesn’t give us immunity, just a better awareness of where we ought to be paying attention.

Children don’t know where the shadows are because they haven’t lived long enough. Newlyweds don’t know where they are because they’ve never walked that road before. Young entrepreneurs don’t know where they are because success hasn’t yet taught them where optimism ends and reality begins.

The strange thing is that experience creates its own danger. Once we’ve walked the same road enough times, we stop looking down.

A friend of mine recently died of a heart attack.

If you had been asked to predict which of your friends would suffer a major cardiac event, he would not have been on the list. At all. He was an accomplished outdoorsman, an expert rock climber, and appeared to be in excellent health. He died on the way to the hospital.

There are shadows no amount of experience prepares us for.

• A sudden diagnosis.

• A phone call in the middle of the night.

• The loss of a job.

• The death of someone you love.

• A child making decisions you desperately wish they wouldn’t make.

Those are the kinds of shadows that arrive no matter how diligent our attention is. As I get older, maybe that’s why humility becomes more important than confidence.

Some shadows are the consequences of distraction while others are simply part of being alive. Either way, they diminish our ability to see clearly.

I’ve spent a considerable amount of time in my life trying to find the light. In recent months, I’ve started wondering if wisdom is more about recognizing when I’m entering a plance where my vision is naturally reduced than chasing sunlight.

A shadow is different from darkness. You can still see but it diminishes clarity.

That raised sidewalk wasn’t a hidden danger. I knew it was there. It became dangerous because I stopped looking.

Something tells me that’s true of far more than sidewalks.