Leadership and Loss: Lessons from an Unexpected Journey

Navigating Grief as a CEO

Losing a loved one is never easy. Losing them unexpectedly is even more jarring. I recently experienced the sudden loss of my stepfather, and in the wake of that loss, I found myself in a unique emotional and professional crossroads. As a CEO, my mind doesn’t just shut down at the end of the day. It’s always running, clicking through the needs of the company, the team, and the future. But this time, my personal loss hit me hard.

Even through the shock and grief, my desire to not let my team down remained dominant. It wasn’t just a responsibility—I truly wanted to be there. I wanted to lead, to show up, to deliver what I had been preparing for weeks. But I also had to sit with a difficult truth: Why did I feel the need to push through, even when it was clear that I was in the midst of something deeply personal and painful?

The answer, like most things in leadership, was layered.

The Conflict Between Leadership and Self-Care

We were just about to have our company-wide meeting. I had carefully crafted my opening remarks, practicing them in both Spanish and English. It wasn’t just another meeting for me—it was a moment of connection with our team, something I take seriously. Yet, as the reality of my stepfather’s passing set in, I found myself warring internally:

• Should I show up despite my grief?
• Would my absence send the wrong message?
• Would my presence be helpful, or would it be driven by my own ego?

It took some honest reflection to realize that ego was a big part of my internal struggle. As leaders, we sometimes feel irreplaceable. We believe that without us, things might fall apart—or at least not go as smoothly. That’s a dangerous mindset, and one that I had to confront head-on.

In the end, I chose to step back. I chose my family. And in doing so, I also chose to trust the leadership, our foundation, that we’ve built at Acklen.

The Power of Trusting Your Team

Fast-forward a few days. It’s midnight, and I’m watching the recording of our company-wide meeting. I see my senior leadership team (SLT) step up. As the first team member greeted everyone, I smiled. Then another leader delivered the opening speech I had worked so hard on. It was flawless.

Matter of fact, the entire meeting was excellent.

That moment was a powerful reminder that leadership isn’t about being present at every moment—it’s about building a system that functions even in your absence. As CEOs and executives, we often feel like we are the linchpin holding everything together. But the truth is, our real job is to create a structure that can withstand challenges, even when personal crises take us away.

The fact that I was able to step back for three weeks without the company missing a beat is a testament to the leadership team we have built. That’s what true leadership looks like—not dependency, but sustainability.

Lessons in Leadership from Loss

This experience reinforced several leadership lessons that I’ve always believed in, but now feel even more deeply:

Walk the Walk, Talk the Talk

As leaders, what we preach to our teams must also be what we practice ourselves. At Acklen, we prioritize family. That’s not just a nice sentiment—it’s a core value. Yet, when I was faced with my own moment to live by that value, I struggled. Leadership isn’t about setting the culture—it’s about embodying it.

Ego is the Enemy

Ego whispers that we are irreplaceable. It tells us that without us, things will fall apart. But real leadership is about empowering others, not making ourselves indispensable. When we let go of ego, we allow our teams to rise, to take ownership, and to show just how capable they truly are.

 Strong Foundations Make Resilient Organizations

If your company can’t function without you for a few weeks, something is broken. Sustainable leadership means investing in people, developing talent, and trusting the team you’ve built. It means having systems in place so that personal losses, illnesses, or unexpected events don’t derail progress.

Leadership Can Be Lonely, But It Shouldn’t Be

C-Level roles can feel isolating. It’s easy to fall into the mindset that everything rests on your shoulders. But when you’ve cultivated the right team, that weight is shared. Watching my leadership team step up and lead with excellence during my absence reinforced the idea that leadership isn’t lonely when you build a team you can trust.

Gratitude for a Strong Team

I took three full weeks off. Three weeks! And I was able to do so because of the incredible leaders at Acklen. I want to give special thanks to Fernanda Mezquita, Dan McCarthy, Lionel Johnson, Jen Fields, Brooke Jaynes, Colin Callahan and Chelsey Gonzalez for stepping in and leading during that time.

You all represent the very best of our company, and I am profoundly grateful.

Final Thoughts: Leadership and Loss

Loss has a way of shaking us to our core. It reminds us of what truly matters and forces us to confront our own values. For me, this experience was a powerful reminder that leadership is about building something bigger than yourself. It’s about developing a team that can carry the mission forward, even when you need to step away.

To anyone navigating personal loss while leading a company—give yourself permission to grieve. Lean on your team. Trust the culture you’ve built. And above all, remember that leadership isn’t about being present at every moment—it’s about ensuring that the organization can thrive, with or without you.

To my team: Thank you. To my family: I’m here. To my stepfather: I miss you.