Negativity Cleanse, Day 11: Q&A with Win Bassett

Greg Behr
6 min readFeb 12, 2016

In this project, I know I need to delicately cull the negative and positive individuals I find around me. This involves retaining friendships with the negative but not allowing them to affect me the way they have in the past. As James Rebanks wrote: “We will be affected by the wider world…But we hold on to who we are.”

More importantly, I want to follow the lead of the people I see striving to lead positive, thoughtful lives.

Of those people, the person I though of first is Win Bassett. Win and I are old college friends and he was at the table when our mutual friend made the toast I described in an earlier post.

Win is one of the most well rounded, positive and intelligent people I know and I hope you’ll soon know, too.

First off, give us a little background on you:

  • I grew up in a small, rural town in southwestern Virginia. Because I received a good scholarship offer from N.C. State, where my father and grandfather went to school, I headed to Raleigh for engineering. I enjoyed the education, but I knew I’d be a miserable engineer. I went to law school at UNC (my mother has been a paralegal for most of her adult life) and became a patent litigator at a 900-attorney international law firm. The big law life didn’t suit me, and I’m fortunate to have met the Honorable Colon Willoughby, the elected District Attorney at this time in Raleigh, during my internship in his office in law school. I called him and lamented that patent litigation in a giant firm would never capture my heart, and I was trying cases two weeks later as an assistant district attorney under him.
  • After some time, I found myself dealing with a lot of teenagers charged mostly with nonviolent crimes. I kept seeing the same kids each month, and it broke my heart. I experienced a lot of more distress because I couldn’t find help for them — I saw no rehabilitation and only punitive measures. I could have spun my wheels inside the system, or I could have helped outside. I chose outside and decided to make a switch to secondary education, and more specifically, character formation.

We’ve known each other for more than 10 years now and I’ve known you as a graphic designer, a lawyer, a beer enthusiast, association head, marathon runner, divinity school student, poet, voracious reader and now teacher. What drives you to constantly seek new challenges?

  • Guilt and anxiety that I’m never enough. And curiosity. And that we don’t last long before we return to nothing. Here’s part of a poem for you: “As for mortals, their days are like grass; they flourish like a flower of the field; / for the wind passes over it, and it is gone, and its place knows it no more.” Some guy named David wrote it, and an editor later titled it “Psalm 103.”

What specifically led you to your most recent callings to attend divinity school and teach?

  • My narrative arch has been tied together by education. I had plans eventually to teach law — start out teaching at night at a small, local school and transition over time into full-time academia. I came to the realization that I could better serve young adults who were still impressionable, still vulnerable. I also knew I had to serve in independent schools. I’m a product of relatively poor public schooling, and I was fortunate that I had a wonderful home life. Public school don’t have the resources for character formation — the part that happens outside the classroom. I knew if I went into public schools, I’d been just as frustrated as I was inside the justice system.
  • Now I’m thinking, “How do I go from being a criminal prosecutor to teaching, mentoring in a secondary school?” I stumbled upon the book With Love and Prayers by Father Tony Jarvis, the retired headmaster of The Roxbury Latin School in Boston and an Episcopal priest. The book is a collection of his addresses to his boys over his thirty years of serving the school. His words changed my life, and I knew I had to study under him. Fortunately, Yale Divinity School had recruited him to start an Educational Leadership and Ministry certificate program for their students interested in serving in schools as teachers, chaplains, coaches, administrators.
  • I went to Yale Divinity School and earned a Master’s degree in religion and literature, taking about half my classes in the divinity school and half of them in Yale’s English Department. I was awarded a Yale Teaching Fellowship, and I had the opportunity to teach a section of the undergrad class “Poetry Since 1950” under the mentorship of English Department Chair Langdon Hammer during my entire last semester. I had never felt more at home teaching those students despite my being in exile in New England!
  • During my search for school position, I knew I wanted to go back to the South. Serving under a good headmaster was more important to me than being in a good school, but the two usually go hand-in-hand. My now-fiancee (a Yale Divinity alum who was serving the vulnerable of Philadelphia during my time in New Haven) grew up in Nashville, and the Music City was at the top of our list. Fortunately, the headmaster of Montgomery Bell Academy, a 149-year-old boys’ school, was a longtime friend of Father Jarvis’. We met about five times over the course of a year, and the rest is history. I now teach English, coach cross-country and track, and mentor boys. My sincere gratitude will remain with Father Jarvis and Brad Gioia for this opportunity until, as poet William Cullen Bryant writes, I rest in the bosom of the globe.

You’re one of the most positive people I know on social media (which is where we are all prone to be our most negative), what’s your philosophy for sharing information and opinions?

  • Life is too short to be negative. And no one cares about negative opinions. People care about the good, though. It’s as if Modernism and its rejection of optimism exists but doesn’t move. Hope, the good, moves souls.

We all change over time, but I would say you are a very different person from when we knew each other in college whereas I would say I’ve remained somewhat the same. What led to the maturation that I think has earned you the admiration of everyone you know?

  • The only direction from my starting point was to go outward — this led to my maturation. I grew up in a small, rural, southern town. I knew nothing different from conservative politics, prejudice instigated by xenophobia (Catholics were idol-worshippers), and conservative strains of mainline Protestantism. Along these same lines, I could not see why anyone would want to go to a school that did not have a giant football program. I didn’t attend my first Mass until I was in law school. I had never heard of the school “Davidson” until I was 21 (despite its being three hours away from my childhood home). N.C. State brought me out only slightly from my sheltered past, but it was my time in Chapel Hill that changed me into who I am today. This white boy studied justice for the first time (and for three years) and began to think differently.
  • What else did it? Teachers who mentored and cared, classmates who challenged me, and for the first time, I started reading and writing.
  • If I’ve earned the admiration of everyone who knows me (which I don’t believe I have), I’m not taking enough risks!

What recommendations do you have from your personal experience that could help people like me struggling with our own negativity?

  • Read Job and poets — Dante, the Russians, Christian Wiman. They paint pain and suffering like no others.

What media should we consume if we want to steer away from what is an increasingly negative and judgmental cultural scene?

  • Paper only and no periodicals except for literary journals. Thomas Merton said he didn’t read any periodicals. If it was important enough, he though, it would end up in a book. Buy books from independent booksellers, and subscribe to hard copies of poetry journals. Write to figure out what you think.

In addition to all of the above, Win also write essays, interviews, reviews, and poetry (The Atlantic, Oxford American, Paris Review Daily, The Washington Post, Poetry Foundation etc.). I encourage you to Google him and read his work!

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Greg Behr

Communications pro. Event manager. Minimalism blogger.