Ryan Leak, How to Work With Complicated People and Live Generously, Episode 283
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From receiving life-altering generosity in his youth to helping global audiences navigate complicated people and personal growth—Ryan Leak’s journey is one of resilience, faith, and intentional leadership. In this episode, Ryan shares the early experiences that shaped his calling, how generosity became a family legacy, and why working well with others starts with owning your own complexities.
A sought-after speaker, content creator, and the author of Leveling Up and Chasing Failure, Ryan’s newest book How to Work With Complicated People offers a deeply practical roadmap for thriving in diverse workplaces. Drawing from personal stories, biblical principles, and years of executive coaching, Ryan helps us rethink how we view conflict, collaboration, and character.
Whether you're leading a team, navigating difficult relationships, or trying to grow in self-awareness, Ryan’s wisdom will shift your mindset and challenge your assumptions about leadership, giving, and grace.
“If everybody else doesn’t change, it doesn’t mean I can’t.” – Ryan Leak
“Nobody believes they’re the toxic one. But the truth is, we’re all complicated.” – Ryan Leak
“If you make your life about giving more than getting, you’ll always have the life you actually want.” – Ryan Leak
This Week on The Wow Factor:
How a stranger’s generosity kept Ryan in private school—and changed his trajectory
The values of giving without keeping score
Why “working with complicated people” starts with personal reflection
How to lead with grace and expect humanity, not perfection
The inspiration behind Ryan’s book and how it’s designed to help workplaces thrive
What Cornelius in the Bible taught Ryan about inclusive leadership
The discipline of creating content that adds value—whether in 60 minutes or 60 seconds
Why Ryan’s favorite act of generosity is paying off someone’s debt with one phrase: “Not anymore”
Ryan Leak’s Word of Wisdom:
If you make your life about giving more than getting, you’ll always have the life you actually want.
Whether it's your time, resources, encouragement, or presence—when you walk into every room looking to give rather than receive, you shift not only the environment but your own fulfillment. Giving isn’t about keeping score. It’s about creating impact that outlives you.
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