The question I get asked most after a keynote is not about business or leadership. It is: why do you talk about your mother’s death in front of strangers? They ask it carefully, like they are worried the question itself might hurt me.
Why I started
I did not plan to become a speaker who talks about trauma. I planned to be a business speaker who talked about leadership and sales and scaling companies. But every time I stood on a stage and told the sanitized version of my story, something felt off. Like I was leaving out the part that made everything else make sense.
My mother Joyce died when I was 22 months old. Gun violence. That loss shaped every decision I made for the next four decades, whether I acknowledged it or not. The drive to succeed, the fear of failure, the need to prove I was enough. All of it traced back to a thing I never talked about on stage.
The first time I told the full story publicly was during my 2016 congressional run in Wisconsin’s 5th district. I was terrified. What happened afterward was not what I expected. People came up and shared their own losses, losses they had carried privately for years. That exchange changed how I understood the purpose of telling this story.
What it costs
It is not free. Every time I tell that story, I feel it. Not the raw, consuming grief of my twenties, but a low hum of sadness that stays with me for the rest of the day. I have a therapist. I prepare before every talk. I know which lines are the hardest to deliver and I’ve rehearsed through them enough that I can hold steady.
But I’d be lying if I said it does not take something from me. It does. The question is whether what it gives back is worth what it takes. For me, the answer is yes. Not every day, but on the days that matter.
What it gives
Permission. That is the word I keep coming back to. When I stand in front of a room and say the hardest true thing about my life, it gives other people permission to do the same. Not on stage. Just in their own lives. With their families. With their friends. With themselves.
People who carry losses they have never named will sometimes find those words after a talk. That is why I do it. Not because it is easy. Because silence costs more.
About Khary Penebaker
Khary Penebaker is Division President at MetalMaster-RoofMaster, the Upper Midwest division of Wolkow Braker Roofing Corp. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees (2014-2025) and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership in commercial roofing, architectural sheet metal, and civic engagement.
Common questions
How do you speak about trauma without retraumatizing yourself?
Preparation and boundaries. I have told my story hundreds of times. The pain is there but it is not raw anymore. I know which parts hit me hardest and I have rehearsed through those. I also know when to stop.
Do audiences respond well to personal vulnerability?
Overwhelmingly yes. After every talk, someone comes up and shares their own story. Vulnerability gives permission. That is the point.
Should speakers share personal trauma on stage?
Only if it serves the audience. If sharing your story gives them language for their own experience or motivates them to act, share it. If it is just catharsis for you, work that out with a therapist, not an audience.
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Last updated: June 28, 2026