The Lonely Leader: Why You Don’t Have to Carry It Alone

Every leader knows the feeling: the higher you rise, the lonelier it gets. Leadership can feel like standing on a stage with no one in the wings, carrying weight with no one spotting you.

When I had my first real paying job out of college, I worked for a leader I deeply respected. She was courageous, fighting for underserved communities, and even in who she hired, you could see her convictions lived out. But one day, a local media outlet ran a negative story about her and plastered her face on the cover of their paper.

I was crushed. She felt isolated. I saw up close how lonely leadership can be and how quickly the spotlight can turn cold. That experience planted two seeds in me. First, it showed me the impact that media could have. Second, it shaped my resolve: I would never let myself be isolated like she was.

So I made a list of 20 to 25 people. Some I knew well, others I only admired from a distance. They weren’t all alike. Different ages, races, genders, and perspectives, but they had one thing in common: I respected the way they led. I reached out to every single one. Almost all of the people on my original list responded. Many said yes to a meeting.

This is what made the difference: I didn’t just send a blind message. I researched each person. When I finally sat down with them, I wanted my questions to show I had done my homework. I wanted them to know I valued their time, their story, their leadership. I always offered to pay for lunch.

Years ago, someone from Milwaukee asked to meet. I knew some of the work he was doing and was curious, so I said yes. But within minutes, he began asking me for all my contacts. I paused and asked, “Do you know what I do?” He admitted he didn’t. His assistant just told him I was someone he should know. I ended the meeting kindly, but I gave him some advice I still believe today: when you meet with someone, know who they are. Even more importantly, know what you can offer them, not just what you want to take. Relationships are not transactions. Real leadership is built on mutual respect, not shortcuts.

That one decision, to reach out to people I admired with humility and authenticity, changed the trajectory of my leadership. Looking back, I can’t begin to count the blessings that came from those conversations. My next job, working for a congresswoman, came because one of those 20 to 25 people recommended me. Many of them became mentors and friends. I wasn’t alone anymore.

Finding my circle didn’t just change my leadership. It changed me. It made me realize something deeper: when leaders carry the weight alone, the whole team feels it.

Lonely leaders don’t just suffer personally. Their teams suffer too. Isolation narrows perspective, slows innovation, and drains resilience.

Over the years, I kept seeing that same loneliness in leaders across the state. Brilliant, accomplished people who were siloed. Isolated. When I’d ask if they knew their counterparts in other cities or sectors, the answer was almost always no.

That’s one of the reasons we created the 365 Leadership Summit. Yes, it’s a space for professional growth and leadership development. But more than that, it’s a place where leaders can exhale. A place to be reminded that you’re not the only one carrying the weight. A place where people can leave knowing, I am not alone.

It’s also why I began leadership development coaching. Too often, leaders feel vulnerable and alone but have no safe space to process it. I wanted to walk with them in those moments and remind them that even in the hardest seasons, they don’t have to carry it by themselves.

The real danger isn’t the weight. It’s carrying it alone. If you’re leading alone, you’re carrying too much. Build your circle. Do your homework. Show up with respect. Create space to breathe.

If you’re not sure where to start, here’s how I did it:

• Do your homework. Learn about the people you admire before you reach out.
  Diversify your circle. Seek leaders of different ages, races, and perspectives.

• Reach out intentionally. Don’t wait for the right time. Create it.

• Offer value, not just requests. Even as a young professional, I offered to pay for lunch.

The lonely leader is not a stronger leader. The connected leader is. You don’t have to carry it alone.