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Job description
Vision : A world where all young adults are empowered to find, define, and follow their passion into the workforce or entrepreneurship, while influencing adults, validating the dreams of the next generation, and transforming communities and families from around the world.
Mission : To transform communities by inspiring young adults to leverage their passion through mentorships, collaborative events, and innovative workshops.
For more information, please visit our website at
Position Overview
YourPassion1st is seeking a dynamic, fluent Spanish-speaking Mentor to guide our youth cohort through an immersive cultural and leadership experience in Cuba. This is not a standard "chaperone" role; you are a cultural bridge, a coach, and a mentor.
We are looking for an individual who embodies the spirit of the community. Cuban heritage or deep familiarity with Cuban culture is strongly preferred, as we value an authentic connection to the history, rhythms, and resilience of the island. You will help our young adults (ages 11-24) navigate the complexities of international travel, cultural exchange, and personal growth.
⭐ Key Responsibilities
1️⃣ Pre-Trip Experience (10–12 Weeks Prior – July & August)
Virtual Workshop Facilitation: Lead and support youth-facing virtual workshops every Saturday in July and August. Prepare the cohort for cultural nuances (social norms, history, and language immersion).
Onboarding & Engagement: Design the youth onboarding experience (welcome communications, "What to Expect" guides, packing content) to ensure youth feel excited, informed, and confident.
Fundraising Support: Work collaboratively with the youth to design and execute a fundraising campaign prior to the trip. Provide guidance on budgeting, goal setting, and community engagement.
Anxiety Reduction: Proactively address fears around travel, culture shock, and group dynamics through digital engagement (texts, prompts, challenges).
2️⃣ Responsibilities During the 14-Day Cuba Experience (Sept 29 – Oct 14)
Own the Daily Rhythm: Manage the day-to-day flow of the trip—morning energy setting, transitions between activities, downtime, and evening reflections. Ensure youth always know what's happening, why it matters, and what's expected .
On-the-Ground Translation & Mediation: Serve as the primary Spanish translator/mediator during excursions, cultural exchanges, and interactions with locals.
Youth Engagement & Energy Management: Monitor engagement levels and adjust pacing to combat fatigue, culture shock, or overstimulation. Ensure youth are actively participating, having fun, and emotionally supported.
Experience Quality Control: Partner with local guides to enhance storytelling and context. Ensure all cultural experiences feel intentional, respectful, and youth-appropriate.
Reflection & Memory-Making: Oversee daily reflection elements (journaling, group discussions, creative expression) to ensure youth are capturing the experience for long-term identity development.
3️⃣ Post-Trip Experience & Continuity (90+ Days)
Debrief & Re-Entry Support: Lead structured debrief sessions after return to help youth process reverse culture shock, emotional highs/lows, and the overall meaning of the trip.
Mentorship Continuation: Maintain the mentorship relationship with the young adults. Support them in translating the experience into confidence, purpose, and future opportunities.
Legacy Building: Ensure youth remain connected to the YourPassion1st community through follow-up sessions, storytelling opportunities, and ambassador pathways.
Required Qualifications
Experience: Minimum of 3+ years of proven mentoring or youth development experience with young adults in the 11-24 age range .
Language: Must speak fluent Spanish (reading, writing, and conversational).
Cultural Proficiency: Deep understanding of Cuban culture, history, and socioeconomic context. (Cuban heritage is highly preferred).
Documentation: Must possess a valid passport valid for at least 6 months past the return date.
Travel Readiness: Willing and able to travel internationally to Cuba (and potentially other countries) without restriction.
Background Check: Must be willing to undergo and pass a comprehensive background check (required for youth safety).
Emotional Intelligence: High emotional intelligence and cultural humility. Ability to manage logistics, people, energy, and emotions simultaneously.
🧭 Time Commitment
July – August: Bi-weekly pre-trip planning meetings + Saturday virtual workshops.
September 29 – October 14: Full participation in the 16-day Cuba experience.
Post-Trip: 90+ days of mentorship continuity and debrief support.
Compensation
All expenses paid for the 14-day trip (flights, lodging, meals, excursions, and incidentals).
Volunteer Leadership Role with a small honorarium/stipend provided for pre-trip and post-trip work (to be discussed).
Why Join YourPassion1st?
Impact: Shape the worldview of the next generation while reconnecting with the heart of Cuban culture.
Community: Join a family of passionate mentors dedicated to transformational travel.
Ownership: This is not a passive role—you will design how the experience feels and lives on in these young adults' lives.
How to Apply
Interested candidates should submit a brief statement of interest and your resume explaining your connection to Cuba and your mentoring philosophy to:
Chris Thomas
Please include the subject line: Cuba Mentor Application – (Your Name)
Worksite address
chicago, IL, 60290, US
Who can apply
Review the original listing for work authorization, qualifications and employer requirements.