Learn More About Don’s Journey

Don Carpenter’s passion for social enterprise and organizational development is deeply rooted in the leadership philosophy of two of his greatest mentors—his father and his Uncle Jack. In the late 1970s, Don’s father pioneered a collaborative model in Pittsburgh that brought together leaders from faith, business, civic, and community sectors to address marginalized communities—eventually growing into a national movement with international reach. This larger vision for collective impact taught Don how values-driven leadership, unified in vision and voice, can transform entire cities. His Uncle Jack, on the other hand, focused on strengthening small-town communities, emphasizing depth over breadth and the power of “sticktuativeness.” Witnessing both approaches instilled in Don a core belief that true impact arises when people are prioritized over programs, and that genuine collaboration only works if no one cares who gets the credit. These lessons continue to shape Don’s own leadership journey—balancing big-picture thinking with a commitment to meaningful, long-term relationships.

This conviction underpins the core values that motivate Don today. He believes in partnering with people over going it alone, prioritizing the leader over the organization, and championing open, honest dialogue rather than top-down leadership. Anchored by these principles, he has spent more than 35 years co-creating and guiding eight social sector initiatives in collaboration with dedicated community stakeholders. From Crosstrainers (Pittsburgh, 1990) and Urban Youth Advocates (Pittsburgh, 1993) to out-of-school-time programs in St. George, Maine (including Trekkers, Inc., an award-winning, evidence-based six-year mentoring model), Don’s work has consistently centered on people and relationships first. Later ventures like Florida Dreamcatchers, The Landing Place, The Aspirations Incubator, and the Rural Youth Institute exemplify his commitment to fostering collaborative, innovative solutions that address both local and statewide needs.

Over his career, Don has also learned to avoid “Founder’s syndrome” by embracing humility and shared ownership, recognizing that an organization thrives best when the community truly takes the reins. “Less Don is more” became a guiding mantra, ensuring each initiative he helped create could flourish beyond his direct involvement.

Today, Don’s work focuses on cultivating relationship-centered leadership, resilience, and capacity building—underpinned by robust systems that drive mission impact. Rather than aligning himself with any single organization, he now elevates transformative ideas that empower leaders to collaborate and innovate. His unique edge as a strategic partner lies in his ability to be both intuitive and practical—seeing around corners, offering gentle yet honest feedback, and helping people get “unstuck” without causing defensiveness. Clients praise his calm presence, deep listening, and readiness to meet teams exactly where they are, guiding them through transitions, strategic realignments, and cultural shifts.

The personal mission statement that truly captures Don’s leadership philosophy is this: “You can only lead others as far as you lead yourself.” By continuously investing in his own growth, Don remains steadfast in his commitment to helping leaders and organizations foster transformative change—rooted in relationships and driven by impact.

Beyond his professional world, Don splits his time between Naples, Florida, and Tenants Harbor, Maine, savoring the outdoors and spending time with his wife and children. Cycling, swimming, and golfing in the sunshine are among his favorite pastimes.