Introducing Drew Jennings

On Saturday, I introduced Drew Jennings to the newest chapter of the Cum Laude society at Montclair Kimberley Academy.  By definition, the Cum Laude society is small.  I’m including my remarks below so that students and families who were not present can see them.  Many people in our community knew Drew . . . and his life is a wonderful example of how to live bravely and wisely.


I met Drew Jennings on the first day of the first English class I ever taught at MKA.  He walked in with as raucous and loud and large – and hairy – a group of boys as I have ever seen in a high school.  Though clearly friendly with the bunch, Drew sat apart from them, and they gave him a hard time about that.  He had an easy way of swatting off their teasing and breaking their code.

It was clear to me from the start that Drew’s friends were very excited that they had a new teacher to break in.  And they made it known that they were going to have a lot of fun – at my expense.  I did what any reasonable new teacher, looking to win the respect and admiration of his new students, would do . . . I told them that I would kick them out of class, each and every class, if they didn’t shape up.

That afternoon, the entire group, Drew’s gang, dropped the class immediately.  But Drew stayed.  He actually came up to me soon after and said, I can’t wait to read the books on the syllabus.  I’ve been waiting for a class like this.

Honestly, I was confused.  I was confused that he hadn’t gone off with his friends.  And I was confused that he liked the books on the syllabus.  The books were way off the beaten path, off what was revered as “The Canon” back then.  The fact that Drew had heard of some of them, chose them, chose not to follow along with his friends, was counterintuitive for a young man.

This observation meant, of course, that I was starting to get to know the real Drew Jennings.

Even then, he had a willingness, perhaps even a driving impulse, to break from the pack, regardless of the size and strength of the pack.

And he had an openness to experience.  Having studied some of the psychology of learning both as an educator and a parent, I now know that openness to experience is a key feature of the creative life.   Back then, in Drew, it scanned as wanting to work with an untested, possibly erratic new teacher, and wanting to read books that went beyond literature, into philosophy and what might be called wisdom.

These themes – breaking with the pack, openness to experience – ripple through Drew’s still-ripening biography like some kind of “high lonesome” sound from the music that Drew, and his father, love so much.

Listen for that sound:

At MKA, during high school, Drew took many of our toughest classes: AP Bio, Honors Econ, AP French, AP English.  He had an A- average in those courses, but his teachers – many of whom are here today – celebrated him most for his willingness to take risks or to pick difficult topics for his research papers and projects.

He was an outstanding athlete, but played a sport each season regardless of whether or not he could be the star.  So, on the soccer field, he walked among the stars.  You have never seen a throw-in like Drew’s – he turned the ball into a javelin.  On the basketball court, he also turned the ball into a javelin, which is decidedly not the point of the sport.  But he played anyway.  He competed.  He dove for loose balls.  He threw the necessary elbows.  Whatever coach, and the team, needed.

VP of the student body he was also the MKA ping-pong champion – that used to be a big thing.

A peer leader, he also played the harmonica.

A popular, sought after student – among his peers and his teachers – he often disappeared into the woods as an amateur bird watcher.

You can hear that breaking from the pack, that openness to experience, running parallel to all the trappings of his conventional success.  Each time he got an A in school, it seems, he tuned into a frequency that was beyond grades, beyond the kinds of success that would be defined for him, conventionally or institutionally.

Which is not to say that conventional or institutional success eluded him.  After graduating from MKA in 2004, he studied History at Dartmouth, where he also interned at the History Chanel.  Next, he joined Citibank, then Oliver Wyman Consulting in the Hedge Fund Advisory Group.  The story, from here, would be pretty obvious if it weren’t for that high lonesome sound chirping in the background.

In 2013, Drew dramatically cut off the corporate path to through-hike the Appalachian Trail.  That’s 130 days up the Eastern Seaboard, alone except for the fleeting connections he might make with other mustachioed and nickname addled hikers on the trail.  It’s worth reading his reflections from around that time.  I found them on a blog he kept back then:

I left for the trail on a whim. My life immediately prior to leaving for the trail had become unfulfilling and had me hurtling down a path of . . . general unhappiness, which scared me given I was only in my mid-20s.

On the first night I knew [the aloneness] was something I needed to embrace – something that would help change me. I could feel something warm developing inside me, snaking its way through my body, probing the depths. It felt good and old – primitive and unfamiliar; it left my smiling for no reason during the day and it sharpened my senses at night. My connection to woods through which I wandered got stronger, and embracing this feeling, I carried it with me throughout my journey.

Drew’s story doesn’t end there, of course.  He lives in Denver now, with his wife, Casey, and he works for Google.

But the lesson here isn’t one about a young man who went into the wild and then rushed back to stability.  He went into the wild – continues to do so, in fact – so that he would never become too comfortable with stability or success.  So that his balanced life would, in itself, become an act of continuous balancing, which means a life of continuous challenge, continuous tightropes, continuous homage to the rocky trail and its distant frequency.

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