Loss has a way of humbling even the strongest among us. I’ve faced many challenges throughout my career as an entrepreneur and business coach, but nothing prepared me for the raw vulnerability of losing my mother.
The last time I saw her, she recognized me and kissed me goodbye. As I was leaving, my wife Julie asked, “Are you going to be okay?” She knew what I didn’t want to admit – this would be the last time I’d see my mom alive.
I brushed it off with confidence. “No problem. I’ll be fine.” After all, I had already experienced my father’s passing and handled it with composure. I thought I understood grief. I was wrong.
When Strength Fails
Just a day later, I was in the shower when Julie came in to tell me my mother had passed away. As she went downstairs, something unexpected happened – my heart broke. Not metaphorically, but in a way that physically manifested. I dropped to the floor. My legs couldn’t support me. Tears streamed down my face, mixing with the shower water as I sat there, completely undone.
My 14-year-old son found me there, broken and vulnerable. He held me, this child comforting his father, telling me “It’s okay, Dad.” But I couldn’t function. I had never felt my heart break before in my life.
I had never felt my heartbreak before in my life.
The Humbling Power of Grief
This experience taught me something profound about humility. Throughout my career at Leigh Steinberg Sports & Entertainment and in my various entrepreneurial ventures, I’ve often shared what has become my favorite quote: “You’re either humble or you’re about to be.”
That shower floor moment was my humbling. Despite all my success, all my preparation, all my experience with loss – I was brought to my knees by grief. No amount of business acumen or emotional intelligence could have prepared me for that moment.
Grief has a way of stripping away our pretenses. It reveals our humanity in its rawest form. For someone accustomed to being in control, to coaching others through difficult situations, finding myself unable to stand was a profound lesson in humility.
What Loss Teaches Us About Leadership
As leaders, we often feel pressure to project strength at all times. We believe vulnerability is weakness. My experience has taught me the opposite is true. Real strength comes from acknowledging our humanity, including our capacity for heartbreak.
This experience changed how I approach coaching others through difficult times. I now understand that:
- True resilience isn’t about avoiding pain but moving through it honestly
- Vulnerability creates deeper connections with those around us
- Our children often have wisdom beyond their years
- No amount of success insulates us from the fundamental human experience of loss
The image of my son holding me as I cried remains one of the most powerful moments in my life. It inverted our roles completely – he became the comforter, the strong one. In that moment, he taught me more about emotional intelligence than I had learned in decades of business.
Finding Strength in Vulnerability
I share this deeply personal story not for sympathy, but because I believe in the power of authentic experiences. Too often, especially in business circles, we present sanitized versions of ourselves. We talk about successes and strategic failures, but rarely about the moments that truly break us open.
My mother’s passing revealed to me that our greatest strength often emerges from our moments of greatest vulnerability. When we acknowledge our heartbreak, we open ourselves to deeper connections and more authentic leadership.
That shower floor moment changed me fundamentally. It humbled me in ways no business setback ever could. And in that humbling, I found a deeper capacity for empathy, for connection, and for authentic leadership.
So when I say “You’re either humble or you’re about to be,” I speak from experience. Life has a way of bringing even the most successful among us to our knees. The question isn’t whether we’ll face such moments, but how we’ll allow them to transform us when they come.
Frequently Asked Questions
Q: How did losing your mother change your approach to business coaching?
After experiencing such profound grief, I began incorporating more emotional intelligence into my coaching practice. I now emphasize that acknowledging vulnerability isn’t weakness but actually creates stronger leadership. This personal experience gave me a deeper understanding of how life events impact professional performance, allowing me to connect more authentically with those I coach.
Q: What advice would you give someone going through grief while trying to maintain their professional responsibilities?
Give yourself permission to feel the full weight of your loss. Don’t rush the grieving process or put on a brave face prematurely. Communicate openly with colleagues about what you’re experiencing. Most importantly, remember that processing grief honestly will ultimately make you a more empathetic and effective professional, even if it temporarily disrupts your work.
Q: How did your son’s response in that moment affect your relationship with him?
That moment created a profound shift in our relationship. Seeing my 14-year-old son step into a caretaking role showed me his emotional maturity and compassion. It deepened our bond and established a new level of mutual respect. I gained a new appreciation for his wisdom and strength, which continues to influence how we relate to each other today.
Q: What does your quote “You’re either humble or you’re about to be” mean in the context of personal loss?
This quote takes on deeper meaning through personal loss. No matter how prepared or strong we think we are, life has ways of humbling us that we cannot anticipate. Loss strips away our illusions of control and invulnerability. The quote reminds us that humility isn’t just a virtue to cultivate—sometimes it’s a state that life thrusts upon us through experiences that break us open.
Q: How can leaders balance vulnerability with the need to project confidence?
Authentic leadership doesn’t require choosing between vulnerability and confidence—the strongest leaders embody both. Share your experiences thoughtfully, being honest about challenges while demonstrating how you’ve grown through them. This balanced approach creates trust and inspires others more effectively than projecting invulnerability. Remember that people connect with your humanity, not your perfection.
