From Broken Boys to Whole Men: #3 – Mentoring and Mentors

The other day, I was talking with someone after worship at my church, and he was expressing his disappointment at a recently-terminated mentoring relationship with a young man.

He felt he had failed the young man, but also that he was out of ideas for how to help him—that the youth wasn’t trying, that there was little investment from his end in using the mentoring relationship to improve his life.

I’m not a scholar of mentors and mentoring, so I cannot outline the qualities successful mentors have in common. I don’t even have any idea how to mentor intentionally.

I suspect that saying, “I’m a good mentor,” is a bit like saying, “I’m humble.” Once one states it aloud, others start to disbelieve you.

I believe mentoring is as mentoring does.

Mentoring programs can broker relationships that have a good chance, on paper, of succeeding, but there’s no guarantee.

In my experience, we fall in with a good mentor or protégé almost by accident. Circumstances enable us to find each other, or cultivate the right conditions for a life-changing relationship to occur.

Take Dick Baker, chaplain and health teacher at Western Reserve Academy, where I went to high school. Boarding school often forms mentoring relationships because you spend lots of time with your teachers, administrators, and coaches—in class, dorms, extracurriculars, on the field.

But it was also his empathy, willingness to listen to me at my most vulnerable—and his ability to respond authentically and humbly—that caused me to call him my first mentor. He showed me what it meant to be a man who was kind, receptive, compassionate, as well as funny, informal, and disarming in his manner.

He doesn’t know it, but our relationship is one reason I’m a pastor.

Bill Appling taught me more about music, aesthetics, quality, work ethic, and what it is to have a life’s calling than almost anybody else in my high school career. Here was a famous composer, director, pianist, editor of a Scott Joplin collection who had played Town Hall in NYC, who devoted his life to working with young people through music and mentoring thousands of them into lives of meaning and purpose.

Bill would sometimes stop us in the middle of a glee club rehearsal and go off on a tangent about quality, or life, or the soul of a song we were singing—and far from being a diversion, it’s what I most remember about him and what he taught me. He had a way of gazing at you very seriously, over the top of his glasses, that told you what he was about to say was all-important.

And it was.

Joe Drever was a Chicago South Sider from Bridgeport, the son of a physician, and my first AA sponsor. Paradoxically, it was the way he helped me look beyond sobriety, to see my life and work and relationships with a balanced perspective, that ushered my life into its next chapter.

All three of them are dead, but their legacy with me lives on. Any mentoring ability I have is more “caught” than taught.


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