The Loneliness of Leadership

We don't talk enough about the loneliness of leadership. Before a leader can do any leading externally, they need to be a leader to themselves.

The Loneliness of Leadership

I often feel lonely as the CEO of Uncharted, and I don’t talk about that loneliness enough.

It shouldn’t be a surprise, but it’s always comforting to meet other folks who say “me too” when it comes to the psychological rollercoaster of leading a growing organization. In one day (and sometimes in one hour) I can feel both confident and validated in my work, and then, in the next moment, feel like an imposter.

So much conversation is around the technical dimensions of growing impact-driven organizations and what it takes to scale (things like marketing, operations, impact measurement, hiring, systems, etc.), but the interior psychological landscape of leadership is often neither explored nor mapped.

Before a leader can do any leading externally, they need to be a leader to themselves. Sometimes this means whispering: “I forgive you... and keep going” in those moments after a big mistake, and sometimes it means “I’m proud of you” after a big win.