Drew Sullivan: From What to Why

Episode Summary In this special episode of Gratitude Through Hard Times, host Chris Schembra welcomes Drew Sullivan, a purpose-driven dealmaker, speaker advocate, and Senior Vice President at APB Speakers, for a raw and hope-filled conversation about the courage it takes to stop hiding and start living authentically. Drew’s story is both ordinary and extraordinary. Growing up as a middle child with ADHD in a sports-obsessed town, he was labeled as “wrong” more often than he was encouraged to be curious. Teachers told him to be quiet, behavioral charts measured his worth, and well-intentioned parents and doctors tried their best but often focused on what he did rather than why he felt what he felt. Those early messages led to decades of self-doubt, addiction, and feeling “othered.” But Drew’s life didn’t end there. Sobriety became his turning point, not just quitting substances but rebuilding identity from the inside out. He realized the same curiosity and big-heartedness he was punished for as a child had become his superpowers as an adult: the ability to connect deeply, ask better questions, and champion others’ voices. Chris and Drew unpack big ideas that apply to everyone, whether you’re a parent trying to raise emotionally healthy kids, a leader navigating change with your team, or someone working on your own healing. Together, they talk about how to move beyond trauma without ignoring it, how to strengthen relationships through curiosity and vulnerability, and how connection isn’t just nice to have, it’s essential for growth. They dive into practical tools and powerful frameworks: The Military-Style Debrief — After any event or risk, ask three questions: What went well? What could have gone better? What will we do differently next time? From What to Why — Lasting growth comes not from obsessing over what happened but from exploring why it happened and using that insight to break harmful cycles. Ubuntu Philosophy — “I am because we are.” Success is never a solo act. Long-term fulfillment comes from shared humanity and supporting each other’s growth. Inside-Out Living — Stop chasing outside validation (titles, applause, perfection) and build a life anchored in authenticity and personal truth. This episode also wrestles with one of today’s cultural tensions: the “cult of trauma.” We live in a time where looking backward has become a primary mode of healing, therapy, revisiting wounds, and retelling past pain. That work is necessary but incomplete. Chris and Drew challenge listeners to balance reflection with forward momentum, to ask not just what went wrong, but how do we build what’s next? Their conversation is deeply practical yet profoundly human. Drew shares intimate stories — from being excluded at eighth-grade basketball tryouts to the loneliness of early sobriety — and turns them into wisdom for anyone trying to live and lead differently. Chris opens up about his own childhood with ADHD and how empathy and gratitude saved his life and career. Together, they model what it looks like to have brave, healing, and hope-filled dialogue. At its heart, this episode is a call to action: to show up for yourself and others with dignity, curiosity, and presence; to give gratitude in a way that lands; to stop letting shame and isolation write your story; and to embrace connection as the bridge between pain and growth. Whether you’re a parent, an educator, a leader building culture, or someone just trying to live a more wholehearted life, you’ll leave with practical tools and renewed belief that storms don’t last forever, and that you’re not alone in the work of becoming. 10 Great Quotes “Not all gratitude given is gratitude received. We have to give in the language others like to receive.” — Drew Sullivan “Solutions are not found in the what; they’re found in the why.” — Drew Sullivan “Every storm has to end at some point — the clouds have to clear.” — Drew Sullivan “Don’t play hide and seek with yourself. Stop letting your thoughts hide.” — Drew Sullivan “If you want to go fast, go alone. If you want to go far, go together.” — Chris Schembra quoting Ubuntu “Without connection, there is no growth. It’s the water and fertilizer for real progress.” — Drew Sullivan “We spend so much emotional energy reliving what went wrong that we forget to dream about what can go right.” — Chris Schembra “Vulnerability 101: be honest about the truth of your life, not just where you are now but where you came from.” — Drew Sullivan “The greatest present you can give is your presence.” — Chris Schembra “When you know better, you do better — but only if you act on what you’ve learned.” — Drew Sullivan 10 Key Takeaways Empathy must lead to action — Listening and understanding are powerful, but transformation only happens when you do something with what you’ve learned. Reframe challenges into opportunities — Shift from “what went wrong” to “what can we do differently next time.” Ask “why,” not just “what” — Understanding the why behind behaviors, decisions, and pain creates the foundation for healing and growth. Connection is non-negotiable — Personal and professional growth withers without deep human relationships. Redefine vulnerability — Sharing your real story — even messy parts — builds trust and invites connection. Inside-out living beats outside-in validation — Chase alignment with values and purpose, not just achievements or appearances. Parents and leaders shape futures — Taking one extra step to understand and affirm can change someone’s entire trajectory. Reinvention is always possible — Like the Real Housewives metaphor, we all deserve new eras and second chances. Don’t let your past pilot your future — Carry your “stone,” but build the strength to make it a co-pilot, not the driver. Gratitude is a bridge — When expressed thoughtfully in someone’s love language, it deepens relationships and accelerates healing.