Episode 31: With Ben Sherman (On Growing Up in Arlington, Dealing With Loss at a Young Age, Surviving High School, Coin-Flip College Decisions, Philosophy, Non-Profit Work and Polyamory)

“All About the Ben”

Welcome back to Jonah Asks.

Ben Sherman is a friend who goes back to high school. We also worked and lived together for a couple years in 2002–03. It was great to reconnect with him after a decade or so. Ben has taught philosophy and now works in the non-profit world helping people in workforce development. Ben is thoughtful, compassionate and at times, quite funny. Please enjoy Ben responsibly.

Thanks for listening!



Theater at Arlington High

“The theater crowd at Arlington High School was just…deeply strange. They had their own pagan icon: the sacred oar. Every year, after the final performance, there would be a sacrifice to the sacred oar. My freshman year, they had bought a full-size dead squid from a butcher shop…and it got weirder after that.”

In 2003, there was a terrorism scare, due to guerilla marketing for the Aqua Teen Hunger Force Adult Swim DVDs. Glowing objects that were unidentified and hard to reach near major infrastructure. The authorities were, I suppose understandably, concerned, it being the post-9/11 world. These two guys that I knew were arrested and became minor celebrities briefly.”

The Coin-Flip: Oberlin vs Brandeis

Ben went to Brandeis. It’s a secular school but based in Jewish traditions. Ironically, none of my Arlington friends that went there were Jewish. Arlington had few Jews.

Ben had to decide between going to Oberlin and Brandeis and couldn’t make a decision. His dad had left it up to him entirely. At the last minute, he was about to flip a coin. His dad sat down with him and they made a list of pros and cons. It was still a tie. So he flipped a coin. And ended up at Brandeis, in Waltham, MA.

Experiencing Different Sides of Arlington -

Surviving High School: bullying and Social Life, Finding Real Friends, Embracing Weirdness and the Rocker Aesthetic

In the mid-90s, Arlington was right on the edge of gentrification. You said there were different Arlingtons. People who ran the school board would talk about an out-an-out clash between old Arlington and new Arlington and we were right in the middle of it. We were not a ritzy town, we were not a working class town, we were both things at once. That caused some weird splits and polarization.”

Ben: “In my experience, the portion of the school community that prioritized toughness and toxic masculinity…in a lot of cases, representing the young side of a working class that was being elbowed out of where their families had lived for years, was this hostile force. For me, it was having people randomly gay-bash you. Having people threaten violence.”


Identity: Weirdness and Agency


Employment — Ben Works in Workforce Development

The fight for progress. Employment numbers, opportunities and low wages.


Family and Grieving

Ben’s mom died of cancer when he was 8. He was the oldest of two boys. His dad remarried a few years later. Reflecting back on that time, Ben remembers when he was an early teen, thinking about how few memories he had from the year or two after his mom died.

“It was a memory hole even at a time when it was surprising for it to be a memory hole.”

Meeting His Step-Mom

“It was as smooth and warm a step-mother introduction to the family as I’m aware of.”

Observing the pain of grief:

Ben recalls seeing his Dad cry for the first time and being genuinely confused.


Mortality, Trust and Psychology

How we cope with childhood and how memory works.


Polyamory: Ethical Non-monogamy

Ben explains his definition of polyamory and his experience in relationships.


Younger People and the Problem of Endless Options


The Idea of Fatherhood as Seen From Afar


Generations, Trust, Intimacy and Too Many Options


Waltham, MA, Communal Living in 2002

Ben and Jared Make a Vague Plan

“Let’s find collective housing so we’re paying a lot less per room right out of college.”

Internet cables split ten ways.

“You had people who were individually not really competent to run their own lives, but you put them together, and you had a pretty good overlapping skill-set.”


Bugaboo Creek Steak House

“It never could decide if it wanted to be Chuck E. Cheese or a dive-bar. The attempt to be both at once was pretty weird. (While serving steak).” Low-Budget Applebee’s in the Yukon.


Student Debt, College and Connections


Existential Questions

The future of higher education, the future of the planet and jobs.


The Cost of Living, Internet Availability



Weezer “In the Garage”

Soundgarden “Black Hole Sun”

Jonah Hall makes Jonah Asks, a podcast about being human. Conversation-interviews with friends and friends of friends about how to live on Earth in 2020.