Resilience and Adversity
What Adversity Actually Teaches You About Leadership
My mother died by suicide when I was 20 months old. I built a roofing company to $35 million. I ran for Congress and lost. I lost a business partnership that cost me everything I’d built. None of that is a motivational poster. All of it made me a better leader.
Why I Talk About Adversity
Most leadership content treats adversity as a chapter in someone’s success story. The hard thing happened, the lesson was learned, the protagonist emerged stronger. Neat. Clean. Wrong.
Real adversity doesn’t resolve into bullet points. It sits with you. It changes the way you make decisions, the way you handle conflict, the way you show up for people who are counting on you. And if you’re honest about it, rather than performing it, it makes you a fundamentally different kind of leader.
I’ve spent 20+ years leading teams, building businesses, and speaking to audiences about what happens when life doesn’t go according to plan. Not because I enjoy talking about pain. Because the people in those audiences, the managers with struggling teams, the founders staring at bad numbers, the leaders carrying things they haven’t told anyone, they need to hear from someone who’s actually been there.
This page collects everything I’ve written and learned about resilience, adversity, and the messy, non-linear process of turning hard experiences into better leadership.
Losing a Parent Before You Can Remember
My mother Joyce died by suicide with a gun when I was 20 months old. I don’t have memories of her. What I have is the shape her absence left in my life: the questions I learned not to ask, the conversations I learned to redirect, the emotional walls I built without realizing I was building them.
For 36 years I didn’t talk about it. Not to friends, not to business partners, not to my own children. I thought silence was strength. I thought keeping it together was the same thing as being together. I was wrong, and that mistake shaped my leadership in ways I couldn’t see until I started being honest about it.
When you grow up absorbing a trauma you can’t articulate, you develop a specific set of skills. You get very good at reading rooms. You learn to manage other people’s emotions because you’ve never been taught to manage your own. You become hyper-competent as a survival mechanism. Those skills translate directly to leadership, which is why nobody noticed anything was missing. Including me.
The turning point came when I finally spoke publicly about my mother’s death. I expected pity. What I got was connection. People came up after talks and told me their own stories. Team members opened up about their struggles. The relationships around me deepened. I became a better leader not by acquiring a new skill, but by dropping the mask that had been in place since childhood.
Building and Losing a $35 Million Business
I co-founded a commercial roofing company and grew it to $35 million in revenue with 180 employees. Then I lost it. Not because the business failed. Because the partnership did.
The details matter less than the lesson: you can do everything right operationally and still lose everything because of a relationship breakdown. That’s a kind of adversity that business schools don’t prepare you for. There’s no case study for the moment you realize the thing you poured a decade of your life into is gone, and it wasn’t because of the market or the economy or a strategic mistake.
What I took from that experience: resilience isn’t about bouncing back quickly. It’s about what you do in the months and years after a loss when nobody’s watching and there’s no audience to perform for. It’s the quiet work of rebuilding your identity when the thing that defined you is gone.
I rebuilt. Not the same company, not the same way. But I carried every lesson about trust, about partnership agreements, about protecting what you build, into the next chapter. That’s what resilience actually looks like. Not a motivational speech. A better set of decisions.
Running for Congress and Losing Publicly
In 2016, I ran for Congress in Wisconsin’s 5th Congressional District. I lost in the primary. Not close. Decisively.
There’s a specific kind of adversity that comes with losing publicly. Your name is on a ballot. The results are published. Your neighbors know. Your kids’ teachers know. People you were asking for support now look at you differently, not with malice, but with that uncomfortable sympathy that somehow feels worse.
What that experience taught me about resilience: you don’t get to control the narrative. You can prepare, strategize, work harder than anyone else, and still lose. And then you have to figure out who you are when the thing you were working toward doesn’t happen.
The campaign didn’t give me the office I wanted. But it gave me a crash course in fundraising, coalition building, public communication, and making decisions under constant scrutiny. Every one of those skills followed me into business leadership. The loss was real. So was the education.
What I’ve Learned About Resilience
1. Resilience Is Not a Personality Trait
It’s a practice. Some people look resilient because they’re good at hiding damage. Real resilience means processing what happened, learning from it, and making different decisions going forward. That takes time and usually professional help.
2. The Best Leaders Have Been Broken
Not damaged beyond repair. Broken in the way that teaches you empathy, humility, and the limits of your own competence. The leaders I trust most are the ones who can tell you about a time they failed and what it actually cost them. Not as a humble brag. As a scar they’ve integrated into how they work.
3. Vulnerability Is Not Weakness
It took me 36 years to learn this. Being honest about your struggles doesn’t undermine your authority. It establishes a different kind of authority, one based on trust rather than performance. Your team already knows you’re human. The question is whether you’re going to be honest about it.
4. Recovery Is Not Linear
After losing my business, there were days I woke up with a plan and days I woke up and stared at the ceiling. Both are part of the process. The pressure to “bounce back” quickly is real, especially for leaders who feel like they need to have it together for everyone else. But rushing recovery is just another way of avoiding the work.
5. Your Story Is Your Competitive Advantage
Every difficult thing that’s happened to you, if you’re willing to be honest about it, becomes a tool for connection. Not manipulation. Connection. When I tell an audience about losing my mother, I’m not trying to make them cry. I’m trying to give them permission to be honest about whatever they’re carrying.
Speaking on Resilience and Adversity
I speak regularly to corporate audiences, associations, and leadership groups about resilience, vulnerability, and the real experience of leading through adversity. These are not motivational talks in the traditional sense. I don’t sell a five-step framework or a morning routine. I share what actually happened, what it cost, and what I learned. Audiences respond because they’re tired of polished speakers with manufactured stories.
My most requested topics in this area include: Leading Through Personal Crisis, Vulnerability as a Leadership Tool, Rebuilding After Professional Loss, and The Business Case for Emotional Honesty.
Writing on Resilience and Adversity
I write about the intersection of personal adversity and professional leadership. Not theory. Experience. Here is the full collection:
What 36 Years of Silence Taught Me About Vulnerability in Leadership
How 36 years of silence about my mother's suicide shaped my leadership and what happened when I finally spoke.
How Grief Changes the Way You Lead
How unprocessed grief shapes leadership decisions, team dynamics, and organizational culture. Khary Penebaker shares what losing his mother taught him about leading with honesty.
What Construction Taught Me About Resilience
How building a commercial roofing company taught lessons about resilience that apply to every industry. Real stories from the job site to the boardroom.
How to Talk About Trauma Without Turning It Into Performance
The line between vulnerability and performance in leadership. How to share your story authentically without making it about the reaction. From Khary Penebaker.
What Audiences Ask After I Share My Story
The most common questions audiences ask after hearing Khary Penebaker speak about resilience, grief, and leadership. Honest answers to the questions people are afraid to ask.
Frequently Asked Questions
How do you define resilience in a leadership context?
Resilience isn’t about toughness or never being affected by adversity. It’s the ability to process difficult experiences honestly, learn from them, and make better decisions going forward. In leadership, that means being able to hold space for your own struggles while still showing up effectively for your team.
What makes your approach to speaking about adversity different?
I don’t package adversity into an inspirational arc. I talk about what actually happened, including the parts that don’t make for good LinkedIn posts. I’ve lost a parent to gun violence, built and lost a multi-million dollar business, and run for public office. Those experiences aren’t a brand. They’re my life, and I share them because audiences deserve honesty, not performance.
Can resilience be taught or is it something you develop through experience?
Both. You can learn frameworks for processing adversity, building emotional regulation, and making decisions under stress. But the real teacher is experience. What I’ve found is that people who’ve been through difficult things and done the work of integrating those experiences become the most effective leaders. The key is doing the work, not just collecting the experiences.
Is vulnerability appropriate in all leadership settings?
No. Vulnerability needs to be strategic and contextual. Sharing your story in a keynote speech is different from sharing it in a quarterly review meeting. The goal is authenticity, not therapy in front of your team. I teach leaders how to calibrate their openness: enough to build trust, not so much that it creates discomfort or shifts the emotional burden to others.
How does your gun violence prevention work connect to your leadership message?
My mother died by gun suicide. That’s not separate from my leadership story, it’s the foundation of it. My advocacy work with Everytown for Gun Safety and my time as Board President of Planned Parenthood Wisconsin C4 grew directly from the same experience that shaped how I lead. When I talk about resilience, gun violence prevention is part of that conversation because it’s part of my life.
Bring This Message to Your Organization
If your team is navigating adversity, change, or uncertainty, I can help. Not with platitudes. With real experience and practical insight from 20+ years of leading through the hard parts.