Creative Writing Instructor Jobs in Chicago, IL (NOW HIRING)

Location: On-site at partner schools or community locations (varies by assignment)
Schedule: Typically 1–4 instructional hours per week, primarily after school
Program Length: Approximately 8–10 weeks per assignment
Start Date: Rolling opportunities based on school partner schedules
Compensation: Starting at $50+ per instructional hour, with rates varying based on the assignment, instructor qualifications, experience, location, scheduling needs, and other program-related factors.

ABOUT THE OPPORTUNITY

Concorde Education is seeking experienced and engaging Dungeons & Dragons instructors who are interested in providing instructional services for after-school enrichment programs at partner schools.

These programs use collaborative tabletop role-playing games to help students build communication, creativity, problem-solving, teamwork, improvisation, and positive group participation skills in a structured, age-appropriate setting.

This posting is intended to identify qualified professionals who may be considered for future independent contractor instructional assignments as opportunities become available.

ASSIGNMENT SCOPE

Assignment details vary by school and may differ in grade level, schedule, duration, student enrollment, and program focus.

Depending on the specific assignment, instructors may facilitate activities such as:

• Character creation and role development
• Guided storytelling and collaborative adventure building
• Basic game mechanics and decision-making
• Problem-solving, strategy, and creative thinking
• Teamwork, communication, and inclusive group participation
• Improvisation and narrative development
• Age-appropriate encounters, quests, puzzles, and campaign progression

Instructors are expected to deliver engaging, organized instruction while maintaining a safe, inclusive, and appropriately supervised learning environment that aligns with school expectations and Concorde Education program standards.

RESPONSIBILITIES

Depending on the assignment, responsibilities may include:

• Lead structured, engaging Dungeons & Dragons or tabletop role-playing sessions.
• Prepare age-appropriate adventures, encounters, materials, and session plans as needed.
• Facilitate collaborative storytelling while encouraging participation from all students.
• Adapt gameplay to student age, experience level, group dynamics, and school expectations.
• Maintain a positive, inclusive, and well-managed instructional environment.
• Ensure all content remains school-appropriate, respectful, and inclusive.
• Communicate professionally with designated school personnel and Concorde Education representatives regarding attendance, scheduling, and program needs.
• Follow all applicable school policies, site procedures, safety expectations, and emergency protocols.
• Arrive prepared and on time for scheduled instructional sessions.

QUALIFICATIONS

Qualified applicants typically possess:

• At least 60 completed college credits or equivalent relevant instructional, creative, tabletop gaming, or youth development experience
• Experience running Dungeons & Dragons, tabletop role-playing games, storytelling games, or similar collaborative games
• Experience working with children or adolescents in schools, camps, community organizations, after-school programs, or similar settings
• Strong facilitation, communication, leadership, and group management skills
• Reliable, professional, and organized work habits
• Ability to maintain age-appropriate, inclusive, and school-appropriate content

Preferred backgrounds include:

• Teachers and aspiring educators
• Experienced Dungeon Masters or tabletop game facilitators
• Writers, creatives, theater/improv instructors, and storytelling professionals
• Camp counselors and youth program leaders
• College or graduate students studying education, English, theater, creative writing, game design, or related fields

MATERIALS AND RESOURCES

Curriculum, lesson objectives, game materials, and instructional expectations vary by assignment. Some programs may include established lesson plans or campaign materials, while others may allow instructors to use age-appropriate original adventures, tabletop resources, or instructor-developed activities that align with assignment objectives and school expectations.

COMPENSATION

Compensation is determined individually for each assignment and may vary based on factors including assignment complexity, instructor qualifications, relevant experience, geographic location, scheduling considerations, specialized expertise, and school partner requirements.

Compensation details are communicated prior to assignment acceptance.

APPLICATION AND ONBOARDING

This posting is intended to identify qualified professionals for potential future independent contractor instructional opportunities.

Submitting an application does not create an employment relationship or guarantee placement, assignment offers, minimum hours, future work, or continued engagement.

Applicants selected to move forward may be invited to complete additional screening, provide documentation, complete onboarding requirements, and establish an independent contractor profile. Completion of these steps does not guarantee assignment selection.

Assignment offers remain contingent upon factors including program availability, instructor qualifications, school partner approval, scheduling compatibility, successful completion of any legally required background review or clearance process, and final written assignment confirmation.

Applicants should not provide criminal history information unless specifically requested as part of an applicable, legally compliant screening process.

EQUAL OPPORTUNITY

Concorde Education is committed to providing equal opportunity in the selection of independent contractors and does not discriminate on the basis of any characteristic protected by applicable federal, state, or local law. Where applicable, qualified applicants with criminal histories will be considered in accordance with governing law, including applicable Fair Chance and Ban-the-Box requirements.