WHEN CHRISTIANS MESS UP — Chris Messina on Grace, Authentic Leadership, and Taking the Right Next Step. (S5E41)
The Shepherd at Work
Saturday, October 10, 2026 - 26 minutes
🎶 “I am a C… I am a C-H… I am a C-H-R-I-S-T-I-A-N…”
Yes.
That's actually how this episode starts.
And it might be your first clue that this isn't going to be your typical conversation about leadership—or politics.
In this episode, Krystal sits down with Chris Messina, a technology entrepreneur, business leader, husband, father, and community servant for a refreshingly authentic conversation about what it means to lead as a Christian when you don't always get it right.
Because Christians are human.
We mess up.
We say the wrong thing.
We make the wrong decision.
We disappoint people.
So perhaps the question isn't if we'll mess up.
It's:
What do we do next?
Chris and Krystal talk candidly about the difference between pretending Christian leaders have everything together and having the humility to acknowledge when we don't.
Own it.
Learn from it.
Ask forgiveness when necessary.
And then take the right next step.
That is authentic leadership.
But there's another part of Chris's story that raises a pretty interesting question:
What on earth is a business guy doing running for mayor?
Chris has spent more than 30 years in business, including founding and leading medical-technology companies. He has served on boards spanning business, healthcare, education, and nonprofits. He holds an MBA from Harvard Business School as well as degrees in economics and city and regional planning.
And now he's running for Mayor of Orange County, Florida.
So we explore what happens when leadership moves beyond the walls of your company and into your community.
What makes someone leave the relative predictability of business and willingly enter public service?
How does faith shape the way you lead when people disagree with you?
And can the lessons learned building organizations actually translate into serving an entire county?
Chris's campaign describes his vision as emphasizing economic diversification, government efficiency and accountability, public safety, families, and responsible stewardship of taxpayer resources.
But this conversation isn't simply about a campaign.
It's about leadership.
Because whether you're leading a company, a family, a ministry, a team—or stepping into public service—you are eventually going to get something wrong.
The question is what happens afterward.
Don't hide it.
Don't fake it.
Don't let it define you.
Own it, seek God, and take the right next step.
👉 Learn more about Chris Messina and his campaign: https://www.chrismessina.com/about-chris/
🎧 Listen. Own it. Give grace. Take the right next step.
