Reflections on 2019

Advice to Myself In 2019

I’m finding that the advice I offer is often the advice I most need to hear myself, so I’ve been paying attention to what I say out-loud this year, and these themes came up repeatedly: Healthy people lead healthy companies. Courageous people do courageous things. Transformational cultures create transformation out in communities. Underneath strategy, there is always psychology.

These ideas were present for me this year because I witnessed just how powerful healthy human relationships can be in doing an organization’s work, and conversely just how derailing unhealthy human dynamics are. I noticed in myself unhealthy dynamics of anxiety and fear and how those influenced people around me, and I observed how much stronger I was as a leader when I showed up from a place of rest and confidence.

There are no shortcuts through advice columns or business books that lead to changing the psychology underneath the strategy. That requires creating those rare cultural spaces where humans can lean into each other and hold space for the truth to emerge.

2019 Lessons of Leadership

2019 taught me that I am at my best when I can hold three things together in my mind:

• Being kind to myself: I tend to be hard on myself, but I’m giving Uncharted the best I have, so being kind means letting myself be proud of how I show up and giving myself the permission to ease back and chill out even when I feel the pressure to keep pressing forward.
• Thinking big: Everyone says “think big” as if it’s this naturally easy thing to do. I’ve found it to be quite hard to consistently think big and outside the familiar paradigms we operate in, so I’m working to create the psychological conditions to think abundantly.
• Being skeptical of the stories we tell ourselves: I tell myself stories all the time about how well I am doing, how poorly I am doing, how self-aware I am, how delusional I am, how smart I am, how much of an imposter I am, and stories about Uncharted: how we’re going to change the world of philanthropy, how we’ll be found out for being naively idealistic, how we’re really onto something, how we’re completely adrift. Sometimes I find I’m telling myself opposite stories within the same hour. And I’m learning the wisdom of just being skeptical of the stories I’m telling myself. Things aren’t as good or as bad as I think they are. Premature conclusions are presumptuous, and perhaps rooted in my own ego or desire to categorize things that are hard to understand. Be patient, the story is still unfolding.