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The Upperclassmen’s Collective: Group Therapy for High School Juniors and Seniors in Chicago

The transition from high school to college is one of the most formative and challenging periods in a young man’s life. Academic pressures, shifting friendships, identity exploration, independence, and uncertainty about the future can create stress, confusion, and self-doubt. Many young men struggle to talk openly about these experiences, or feel they should “figure it out on their own.”

Wellington Counseling Group is proud to offer The Upperclassmen’s Collective: Boys to Men, an 8-week group therapy experience designed to support high school juniors and seniors during this pivotal time. Led by Martin McGovernCatherine Baker, and Taylor Rike, this group provides a safe, supportive environment where young men can learn, reflect, build skills, connect with peers, and prepare for the next phase of life with confidence and clarity.

Sessions will be held in person at our River North office on Thursday evenings from January 15 – March 5, 2026 (excluding holidays).

What Does This Group Look Like?

The Upperclassmen’s Collective offers a structured yet conversational space where participants can:

  • Explore their identity, values, and sense of self
  • Learn about emotional awareness, communication, and stress management
  • Discuss changing relationships with parents, peers, and partners
  • Navigate expectations around masculinity, achievement, and independence
  • Build practical skills for college: time management, boundaries, decision-making
  • Process fears, hopes, and questions about the future
  • Receive guidance in a supportive, nonjudgmental setting

Each session incorporates reflection, psychoeducation, skill-building exercises, and group discussion. Our facilitators use accessible frameworks including parts work (IFS), mindfulness, and relational processing to help participants better understand themselves and interact more effectively with others.

Thank you for your interest in the group! Please fill out the brief form below, and we will be in touch with you about the next steps! 
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Student's Name (First Last) *
Student's Grade Level *
Parents / Guardians Names
Phone Number *
Email *
Why are you interested in joining this group? No need to be overly formal in your answer! 
Do you have any questions about the program?
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