Upham's Corner Online

The City School - A Philosophy of Counterculture

Posted: June 20, 2011     Nancy J Conrad

The City School - Philosophy of CountercultureA simple question, inquisitive minds, a willingness to explore into uncharted areas of social concern - these were the ingredients that gave life to The City School, a nonprofit organization that is making a significant difference in the lives of students in the greater Boston area. 

Todd Fry, a Milton Academy English teacher, was willing to start an independent study course to explore answers to the questions posed by one of his students.
  • Why are we living so near Boston yet we don't know anything about homeless people?

  • Why aren't we learning about homeless people?  This is obviously something important and going on in our community but it's not being addressed.
The independent study course was followed by City School's first program in 1987, a youth outreach weekend.  Soon Milton Academy students began learning about homelessness and poverty - who the homeless were - mostly children and families, learning to see past the stereotypes and moving from theory to the practicum by serving at homeless shelters.

One of the most import products of this effort was an understanding of the importance of peer-to-peer conversations and peer-to-peer learning.  Young people were learning together, learning from each other's differences and from their relationship to their community. 

While the adults, the knowledge-givers were essential in the learning process, insightful understanding and motivation for getting involved with social justice came from peer-to-peer interactions.

In 1995 City School matured into a second phase of outreach with their first summer program - 34 students in the program across difference.  It was no longer wealthy, privileged Milton Academy students learning about homelessness.  It was young people from 27 different high schools - young people of color, varying economic status and geography, coming together to talk about homelessness and social justice. 

Fast forward to today - the agenda has expanded beyond homelessness to include many other aspects of social justice including prisons and HIV AIDS.

The City School - Philosophy of Counterculture
Ruby Reyes serves as one of The City School's two co-directors. She loves talking about the school, its philosophy and how they carry out their mission in the community, and she uses the term "counterculture" often. 

Ms. Reyes: Our special sauce is that we at City School really do live a counterculture life.  What do we mean by this?  
  • First, we recognize that people live very insular lives.  This leads to not supporting people we don't know - our neighbors. 

  • Second, we want to make sure that NEVER happens here within the programs and places under the sponsorship of City School. 

    • This is a place of love. 
    • This is a place where we respect each other. 
    • The young people who come here experience this as a place of support. 

We've had young people from rival gangs who come here and know that when they're here, they treat each other well.  For us it is a very neutral space.  We target a culture of genuine love and support - whether that means giving feedback, whether that means asking people to respect a speaker who is not as vocal as other young people.  It is very much a youth centered space, so young people are learning from one another. 
  • They're talking
  • They're sharing. 
  • They are learning to support one another respectfully.
UC News:  Tell me more about counterculture.  Does that mean counter the standard culture?  Counter the normal culture?  Counter the accepted culture?  All cultures exist.  If you are counterculture, does that mean you are pro-chaos?

Ms. Reyes:  No, let me explain.  It's not very often that you are part of a community where you are genuinely cared for.  That's what we mean by counterculture.  For a lot of our young people, our society is not loving or caring.  We here at City School have to set the norm, set the stage from the beginning of the young person's year with us.  We want to guarantee that the young people we care for will continue to experience a loving and caring environment throughout their time with us. The City School - Philosophy of Counterculture

When students learn that the City School space is safe, they begin to share how they feel and express themselves with their peers.  Often by the end of the school year, the shy and awkward student leaves having become greatest friends with "total strangers." The norm has become a  willingness to converse about topics you would never expect to talk about in your life.  That's the type of environment we create here.

UC News:  So let me see if I understand.  You've looked at society as a whole and have decided to "counter" the deleterious characteristics by creating an environment that is loving, caring and accepting,

Ms. Reyes:  Yes, but another huge piece is crossing difference. We genuinely bring young people together across difference.  Whether that is a young man who comes here from Wellesley who is super wealthy and whose family is well off to somebody who lives up the street, whose family does not make a lot of money and who's never left their neighborhood.  It is our mission and our work to bring young people together across difference. We try so hard to be intentional about that, really reach into recruitment in areas where our numbers are not strong. 

An example:  We reach out to suburban families for our summer program, both colored and white but with an emphasis on people of color because they can be so isolated in the predominately white suburbs. 

Samantha Casseus, a three-year veteran of the program, highly recommends City School to her friends.  "It's had a greater influence on my choice of career than my regular schooling has.  City School broadened my horizons.  I feel that after this year when I graduate I will be able to use the knowledge that I've learned to go further and help in the world."

The City School - Values & Guiding Principles

Youth as leaders and agents of change
We believe that having governance roles within the organization is one way we can show youth the power of their voices and that this helps to build strong and active leaders.
Activism and taking a stand
We believe the action takes many forms, including service, direct action and advocacy, and that the way TCS models the process of organizational advocacy develops its students' leadership potential.
Liberation and social change
We are committed to addressing injustices in ways that lead to the liberation and self-determination of all people.
Social justice education
We are committed to teaching young people about social justice issues and believe that this knowledge moves them to transform and act.
Participatory and experiential education
We are committed to creating a learning environment that honors everyone's experiences, that respects and prioritizes the voices of young people and that is interactive, hands-on and caring.
TCS as a learning community
We believe in a strong learning community where everyone is both a teacher and a learner.
Critical thinking
We believe that we must keep self-awareness as we think critically about societal issues that this is essential to strengthening leadership skills.
Diversity and anti-oppression work
We believe that the move toward justice means understanding, respecting and including the ideas and experiences of individuals from all backgrounds as a way to build allies and combat oppression in all its forms.


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