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Gap Program Instructor


Job Title: Gap Program Instructor

Season: Fall: August 26th, 2024 to November 20, 2024

Reports to: Gap Program Director

General Responsibilities

Gap at Glen Brook’s Program Instructor works closely with the Gap Director to deliver a semester of programming to gap year students.  The Program Instructor brings their own authenticity and skill-set to the work of supervising and facilitating this dynamic gap program. We are currently looking for an instructor with a passion for youth mentoring and facilitation, wilderness leadership experience, basic culinary skills, and/or homesteading or farming skills.


Specific Responsibilities

Student Welfare

  • Serve as the primary staff presence around meals and during evenings and weekends.
  • Serve as the first line of communication for the gap cohort in the house, fielding questions as diverse as “What is the water-to-rice ratio again?” to “I’m feeling anxious, can we talk?”
  • Maintain a high level of safety awareness, risk assessment, and group dynamics.
  • Ensure students understand and abide by rules and guidelines.
  • Respond promptly to medical or mental health concerns.
  • Assist gap students in cultivating wholesome meals and a wholesome meal culture (family dining, home-made and home-grown, etc.)
  • Schedule time to do weekly well-being check-ins with each Gapper.


Student Learning and Role Modeling

  • Teach, guide, and inspire through formal and informal mentorship and teaching.
  • Co-lead wilderness trips and mentor participants in planning and packing for hiking, canoeing and camping trips.
  • Based on skills and experience: plan and lead workshops on various topics that center around sustainable living skills (i.e. wilderness skills, herbalism, community building, crafts, ecology, carpentry, etc.)


Necessary Experience

  • Enthusiasm for the benefits and complications of community living.
  • Experience leading groups on multi-day excursions in outdoor environments.
  • Experience in conflict resolution, group facilitation, and/or teaching.
  • Strong ability to connect well with people, and to develop meaningful mentor relationships with emerging adults.

Requisite skills:

  • Strong communication skills.
  • Outdoor/backcountry medical experience—at least WFA; WFR preferable.
  • Clear driving record.
  • Lifeguard certification.
  • We can help you complete a WFA and Lifeguard certification if needed.

Preferred skills:

  • Experience with farming, gardening, or farm education.
  • Confidence with basic home cooking.

Dates and Compensation

  • Employment Dates: Mon, Aug 26 to Wed, Nov 20 2024
    • Program Dates: Sep 3 to Nov 17.
  • Total time: 13 weeks
  • Rate of pay: $577/wk plus room & board; Total Pay: $7,500
  • You will be scheduled 2 days off per week. 

Additional Responsibilities

All Glen Brook employees commit to getting our work done as a whole, whatever the work may be.  This means that, occasionally, we work outside our specific department and assist on other projects—for example, every Friday all staff and gappers participate in a “ Work Party” together.  In this vein, some days or weeks may be longer than others. 

To Apply, please submit a cover letter, resume, and 2 references to:

Tori Heller, Gap Program Director,

Interested in This Position?

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