"Hitching" - Lessons for Discerning Leaders

How do you make a wise decision when there are no easy answers?  What do you do when you’re not sure what to do?

Careful discernment is the easy response, but what does that look like in actual practice?

I learned about this early in my life.  

Let me tell you the story.

For most of my teens and early 20s, I didn’t have a car.  So I hitchhiked.

You’ve heard the warnings about whether and when to ever pick up a hitchhiker.

But what about the question from the hitchhiker’s side of things?

Maybe you think all hitchhikers are desperate drifters or loafers who will take anything that comes along. Why else would they be out there on the side of the road?  But hitchhikers  have to make choices.

Believe me, not every ride is one you want to accept.

I’ve had some close calls.

For instance, this one time, a sixty-something man picked me up outside Flatbush, on the way to Amboy, New Jersey. I asked about his life. It turned out he fought in the Battle of the Bulge. He talked about his ex-wife and his girlfriend. About his son who sold woodstoves.

I was lulled by his patter, and by the warmth of the car, when, out of the blue, he said, “What do you think of heroin?” I got the sense that, for him, this was more than a leisurely topic.

I was scared as hell because I thought he might be on heroin at the time – or that he wanted to force it on me.

So I kept shifting the subject away from heroin, and asking him about the war. 

I was glad to jump out in Amboy and wave him goodbye.

When you’re on the side of the highway, it's tempting to say “yes” to whoever comes along.

It’s cold out there.  You’re standing around, shivering, trying not to look like a serial murderer, waiting for someone to take a chance on you.  

As cars and trucks whip by, the pressure to be desperate comes easily. But you have to stay alert.

Because the kind of people who stop for hitchhikers are rarely Boy Scouts.  Your sober leading citizens don’t pull off in the breakdown lane and wave to you to hop in.

Usually, it’s a man with a flair for life, who doesn’t worry too much that you might be carrying an axe or a pistol.  Most stoppers are not unacquainted with the wild side. These are not your deep thinkers.

What I’m saying is, this driver could be anyone. Could have pulled over for any reason. You just don’t know. You need a ride, but you’re not obliged to hop in. So, what can you do?

If you’re smart, you don’t assume the best, and you don’t assume the worst. 

What’s different about hitchhiking is that whatever you’re going to do, you’ve got about 14 seconds to decide.  Here’s what happens:

A car pulls over about a hundred yards in front of you. You grab your pack and run to the passenger side of the car, motioning to the driver to open the window. That’s when the 14 seconds begin to tick.

“Where are you headed?” you can ask. “Is it ok if I ride all the way?”

In this moment, the information you’re gathering isn’t only what they tell you. It’s also how.

Do they slur their words? Are they cagey?  Hostile?  A bit too eager to help? 

People tell you so much beyond the words that they use.

During the window exchange, you’re checking things out, like a bee deciding on a flower to pollinate.  It all happens quickly.

First, you look right at the driver’s eyes.  Are they glazed or clear?  Then you quickly but nonchalantly case the inside of the vehicle. What’s on the seats?  Is there a dog that could be salivating all over you on the ride?  Anything weird you’re noticing?  (Once I noticed a picture of a naked man on the dashboard.  “I’m headed in a different direction,” I told the driver.)

After the brief detective work, you take a partially-informed leap of faith.

Looking back, despite the risks, I received a big benefit from the whole experience: honing my intuitive discernment skills.

Hitchhiking taught me how to pick up clues quickly that turned out to serve me later on in social interactions. To be able to tell that someone is nervous, or hiding something.  To see that this isn’t the right time to ask the penetrating question.

Sure, when sizing people up, I don’t always get it right.  But I’ve become pretty good at sifting out trustworthiness.

Most people don’t last long as hitchhikers.  They might say it’s because it’s too cold out there, too lonely, too uncertain.  Maybe they decided not to tempt fate by risking danger or breaking the law.  But more often than not, the people who quit aren’t very good at sizing up situations quickly and accurately. 

Lessons for Leaders

If you want to get somewhere in life, put yourself out there.

You make better decisions when you have something to lose.  Skin in the game brings focus.

Resist the automatic urge to say yes or no.  Do some thinking.

You rarely have to be desperate.  Until you’re clear, shift into neutral and gather information.  Pay attention to what isn’t spoken.

Unlike hitchhiking, you usually have more time than you think.  Slow down, take a walk and get yourself calm.

Shoot for reasonable clarity, not certainty. 

There are no guarantees when taking a leap of faith.  Look for an upside that outweighs the downside.

One synonym for discernment is wisdom.  Sharpen it slowly, over time, in situations where there are no easy answers. 

And on the way, enjoy the ride.