Uncharted Insider - March 2022

On 10 years in

Uncharted Insider - March 2022

Hi everyone,

Welcome to the March edition of the Uncharted Insider. Do you know someone who would enjoy the Uncharted Insider? Forward this email to them and they can subscribe here.


This upcoming Monday is the 10-year anniversary of my first day at Uncharted (then called Unreasonable Institute). On April 4th, 2012, I walked into the office for my first day without any idea of what to expect. I didn’t know then what I know now: that the next 10 years would be some of the best of my life. So, if you’ll indulge me, I’ll take a different approach in this March 2022 Insider to share a few reflections.

On Belonging

I can’t remember the exact moment when I felt like I belonged to this organization and to its people, but it was a feeling that preceded me doing my best work. We often tell ourselves a story that someone needs to prove themselves in order to be trusted, but we have the order backwards. Normally, we think it is great work that produces belonging and trust. But it is belonging and trust that produces great work. The sooner we can create a sense of belonging in an organization, the sooner we can bring out the best in our people.

On The Moments

The mistake of the responsible leader is to obsess with fixing problems instead of creating memorable moments marked by magic and unexpected delight. I often evaluate myself based on my ability to solve problems and fight fires and move things forward, but I’ve learned that what makes Uncharted a truly extraordinary culture is the way our team co-creates elevated, unforgettable moments. An organizational culture is the average of every shared moment together, which is why designing our moments is how we design our cultures.

On Being Misunderstood

A mentor once told me that being a CEO is the worst job for a sensitive, responsible person who wants to be liked. In my case, I love this role, but there have been many decisions that have caused heart-wrenching pain. Being forced to let people go in the middle of the pandemic. Saying no when all I wanted to do was say yes. Bringing the unvarnished truth to a team who didn’t want to hear it. As a people-pleasing decision-maker, the hardest decisions I’ve had to make have been the ones where I knew, by virtue of information asymmetries or confidentiality or something else, that I would be misunderstood. I’m learning that our endurance and effectiveness as leaders is more a function of our ability to accept being misunderstood than our ability to ensure everything is understood.

On The Inner Landscape

The underpinnings of any good long-term strategy are simply the patience and confidence to see it through. Underneath strategy, there is psychology. The workplace is a stage upon which we act out the stories we tell ourselves about ourselves, which is why I find the words of Parker Palmer so true when he says: "Go far enough on the inner journey, they all tell us—go past ego toward true self—and you end up not lost in narcissism but returning to the world, bearing more gracefully the responsibilities that come with being human." Organizations and institutions are made up of humans. The biggest ones in the world are still dramatically driven by individual personalities. History marches forward based on our ability or inability to explore the vast interior landscape within us.

On Being Saved

There were times over the last few years when Uncharted (and I) got pushed around by partners, funders, and corporations. I sometimes just let it happen, waiting for them to come to their senses or someone to come to our rescue…until I realized that we had to rescue ourselves. We need to stand our ground, carve out our truth, hold fast to our boundaries, and define our reality. I’m learning that no one is going to come and save you.

On The Small Things

The way we care for our people is imprinted into our products, our services, our brand. The way we do the small things is the way we do the big things. The way we show up in our private moments is the way we will show up in the big, public moments. Everything is practice. Impact starts at home.

On Power

Maybe it is the invisible water of white supremacy and patriarchy that we are all swimming in, but it seems like so many of us are more interested in fighting for how to redraw the lines of power than we are in fighting for our collective liberation. Upstream of all equity-based strategies are epistemological and spiritual beliefs about leadership, power, and trauma. Is power zero-sum or positive-sum? Is leadership about taking up space, holding space, or shaping space? How thin is the separation between oppressor and victim?

On The Long View

I’ve marveled over the years at just how powerful the heuristic is of “taking the long view.” We are in rare company when we elevate our thinking to strategic, long-term horizons. It’s so unnatural and hard to do; we seem to be a species obsessed with and bound by our nearsightedness. Almost any situation is reframed and clarified when we imagine how we’ll think about it next week, next summer, next year.

On Giving Ourselves Credit

I punished myself the most when I gave myself too much blame for the outcomes and too little credit for the effort. There were long seasons when I struggled to fundraise. There were moments when I fell short. There were deliverables that just weren't good enough. But in each of those moments, I neglected to recognize an atomic truth: I did my best. When we give ourselves more credit for the effort and less credit for the outcomes, we are getting closer to the truth of exactly how much and how little we can control.

On Patience

When we dig into the chronology of change, it becomes clear that change doesn’t just occur overnight, but instead germinates slowly for years before bursting onto the scene. I’ve struggled to communicate this to funders; Uncharted’s impact is best viewed on a 10-year scale, not a 10-week scale. The angel investor Charlie Songhurst once said we shouldn’t study what makes people successful, but rather study what makes people fail and then simply try to avoid those mistakes. He said that it is survival that begets greatness, not greatness that begets survival. Our work with our ventures has taught us that when we believe in people early and trust them for long enough, they will do stunning things.

On Powerlessness

We live in a world that is all about our power, how to build it, when to seize it, if we should share it, but it is the moments when we are struck by our utter powerlessness amidst it all that we are, perhaps, most alive. When our swelling ambition and endless striving is punctured with a prick of powerlessness, we remind ourselves of the certainty of our mortality, the limitations of our reach, the ephemera of it all.

Something Personal

In his 10th decade of life, right before he passed away, my grandfather wrote his autobiography on a desktop computer his family had set up for him. He had never used a computer before. He had never learned to type. But he wrote 80 pages, saving each one as an individual word document because we neglected to tell him that you could just tab down and keep typing. Whether it’s just the next decade or our very last decade, it’s never too late to try something new, to start a new chapter, to begin again.


As always I welcome your feedback and ideas.