One of the questions I’ve been asking myself lately is…What does success actually feel like?
For most of my life, I measured success the way many of us do. I focused on goals, accomplishments, and milestones. As a baseball player, it was making the team, winning games and championships, and eventually getting drafted.
Later, as a speaker, it became writing books, getting hired by great clients, growing my business, and reaching professional goals that once felt almost impossible.
I’m incredibly grateful for these experiences. They’ve challenged me, stretched me, and opened doors I never imagined.
But if I’m honest, none of those accomplishments created the lasting feeling I thought they would.
There was always another goal to chase, another opportunity to pursue, another mountain to climb. And while ambition has served me well in many ways, I’ve learned that if we’re not careful, we can spend so much time pursuing success that we never stop to define what it actually means to us.
When I look back on the moments when I’ve felt most successful, they usually aren’t the ones other people would point to.
I think about sitting around the dinner table with Michelle, Samantha, and Rosie, talking and laughing about nothing in particular. I think about a conversation after one of my keynote presentations when someone shares something personal with me or how the conversation touched them. I think about long walks, meaningful conversations with friends, quiet mornings, weekend retreats, and moments when I feel completely present instead of wondering what’s next.
These things don’t usually end up on a résumé. They don’t generate headlines or applause. But they’ve become the experiences I treasure most.
One of the challenges we face is that we’re constantly surrounded by other people’s definitions of success. Social media, our workplaces, and even our own upbringing can subtly convince us that success is about achieving more, earning more, or becoming more. There’s nothing inherently wrong with those pursuits. But they become problematic when we never pause to ask whether they’re actually leading us toward what we truly want.
I’ve worked with leaders who have achieved extraordinary things professionally, yet quietly admit they’re disconnected from the people they love most. I’ve also met people who haven’t reached every goal they once set for themselves, but who have built rich, meaningful lives full of purpose, gratitude, and deep relationships.
This reminds me that success isn’t only about what we accomplish. It’s also about how we experience our lives while we’re moving through the world.
When do you feel most alive? Who are you with? What are you doing?
And if someone looked at your calendar, would they see these things reflected in how you’re spending your time?
The goals matter. Growth matters. Achievement matters.
But I don’t think they’re the destination.
For me, success feels like being connected to the people I love, doing work that has meaning, continuing to learn and grow, and ending the day knowing I was present for the moments that mattered.
That’s the kind of success I’m interested in pursuing.
We’re all in this together.
