Dr. Chris Jackson on Leading from the Ground Up

The Ruckus Report

Quick take: From pushing a broom to leading the boardroom — Dr. Chris Jackson’s journey from custodian to principal at his own alma mater proves that grit, humility, and authentic community connection matter more than pedigree when transforming schools.

Meet Your Fellow Ruckus Maker

Chris Jackson rose from custodian to administrator in his hometown of San Bernardino, fueled by hard work, family, and perseverance. A husband, father, and lifelong learner, he overcame personal loss and humble beginnings to inspire others. Raised by his grandmother after being born to teen parents, Chris worked his way through every level of education — from custodian to teacher, coach, instructional coach, athletic director, and eventually principal of Cajon High School, where he met his wife as a 15-year-old student. Author of “From Broom to Boardroom,” Chris’s journey proves that with grit, purpose, and love, anyone can rise, no matter where they start.

In this episode, Dr. Chris Jackson challenges traditional education paradigms:

Key Insight #1: Every Job on Campus Matters Equally

• What’s broken: Creating hierarchies that separate administrators from the real work of schools, losing connection with staff and community
• The shift: Leading with servant leadership — picking up trash during lunch, building relationships with custodians, and blurring the lines between “management” and service
• Impact: Instant credibility with all stakeholder groups and authentic empathy that comes from walking in everyone’s shoes

Key Insight #2: Bloom Where You’re Planted First

• What’s broken: Always looking for the next promotion instead of excelling in your current role and building relationships where you are
• The shift: Do your best work in whatever sphere of influence you have, ask questions, and let opportunities find you through positive relationships
• Impact: Chris went from custodian on Wednesday to teaching his own class on Monday — but only because he had built trust and demonstrated excellence where he was

Key Insight #3: Community Connection Beats Credentials Every Time

• What’s broken: Leading schools as an outsider who doesn’t understand the community’s needs, values, and challenges
• The shift: Live in, understand, and serve your community in their image — being able to say “I’m your neighbor” during difficult conversations
• Impact: When parents challenge decisions, Chris can respond: “I live two blocks from you, I went to school here, my parents went here” — eliminating the “you don’t understand” barrier

Your Do School Different Challenge

Ready to implement these ideas? Start here:

1. Tomorrow: Put on a metaphorical “straw hat” — spend time doing work typically done by support staff to build authentic relationships and understanding
2. This Month: Identify one person in your orbit whose expertise you can learn from, regardless of their title or position — ask them questions about their work and challenges
3. This Semester: Audit your community connections — are you living, shopping, and engaging where you serve? Find three ways to deepen your roots in your school community

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