The Design Of Leadership Beyond Yourself: Meet Jon Houghton
Season 11, Episode 79

Read Time
1 minute
What if leadership isn't about producing results, but helping people become who they're capable of becoming?
Jon Houghton has spent much of his life helping people grow.
For more than twenty years, he served in leadership roles with Young Life, developing leaders, building teams, and helping others discover their gifts and purpose. Then, after a successful career doing work he deeply loved, Jon made a surprising decision. He left.
Not because something was broken.
Not because he was unhappy.
But because he felt called to explore a new challenge and discover what another chapter might hold.
Today, Jon serves as CEO of Holy Post Media, a company creating thoughtful conversations around faith, culture, leadership, and life in an increasingly polarized world. Through Holy Post, Chicago Fellowship, and countless conversations with leaders, Jon continues to ask questions that matter.
Questions about identity.
Questions about purpose.
Questions about what it means to grow.
In this episode of Design Of, Jon shares the lessons he's learned about leadership, feedback, community, faith, and personal transformation. Along the way, he reflects on mentors who shaped him, the risks of staying too long, the challenges of starting over, and why some of the most important work leaders do has nothing to do with performance metrics.
One moment in particular stayed with me.
Jon shared a question that has quietly followed him throughout much of his life:
"Am I lovable if I'm not impressive?"
It's a deeply human question.
And it opens the door to a conversation about ambition, achievement, identity, and the freedom that comes when we stop trying to prove ourselves and start helping others flourish.
This conversation isn't really about leadership.
It's about becoming.
And helping others do the same.

In This Episode, We Explore
Why Jon chose to leave a successful twenty-year career and start a new chapter
The transition from nonprofit leadership to leading a growing media company
How healthy leadership begins with self-awareness
The difference between helping people perform and helping people grow
Why feedback feels threatening and how to receive it differently
The role faith plays in leadership, relationships, and community
Building meaningful connections in a culture that often lacks depth
How mentors help us see things in ourselves we cannot yet see
Key Takeaways
Great leadership starts with personal health and self-awareness.
You cannot help others grow if you are unwilling to grow yourself.
Feedback becomes less threatening when your identity is rooted in something deeper than performance.
Meaningful community requires intentional effort and vulnerability.
Growth often begins when we leave something comfortable and familiar.
The best leaders help people become more fully who they were created to be.
About Jon
Jon Houghton is the CEO of Holy Post Media, a media company focused on thoughtful conversations about faith, culture, leadership, and public life. He also leads Chicago Fellowship, a community that brings together nonprofit and marketplace leaders seeking to grow personally, professionally, and spiritually. Prior to Holy Post, Jon spent more than two decades with Young Life, helping develop leaders and organizations across the country. His work today centers on creating meaningful conversations, building healthy communities, and helping people become who they're capable of becoming.
Listen now.

