Uncharted Insider - December 2021

The lessons in leadership of 2021 and how we are training our minds

Uncharted Insider - December 2021

Hi everyone,

Welcome to the December edition of the Uncharted Insider. As I mentioned last month, this is the first edition of the Insider I’m publishing directly from this Ghost platform.

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Similar to past December editions, I am taking a different approach with this final Insider of 2021 by sharing a few of the most important leadership lessons from this year.

On Withholding Hard Truths

The quickest way to reduce your sense of self-importance (and increase your self-care) is to entrust the people around you with the difficult information you believe that only you can handle. We tell ourselves these stories that if the people around us knew.... (insert hard truth), then they would be stressed and burdened and de-stabilized. There is merit to waiting for the right time to bring people in, but there is also power and liberation in believing in people to be 1) capable of handling the truth, 2) capable of taking action on that truth, and then 3) capable of caring for themselves with that truth. The sooner we understand the true story about the people around us, the sooner we understand the false story we tell ourselves about ourselves.

On Being Misunderstood

Show me a people-pleaser in a leadership role, and either I will show you an ineffective leader who busies themselves with the shuffle-work of trying to please everyone or I will show you a leader deeply tormented by the necessity to make hard, long-term decisions and endure their ensuing discontents. I’m learning that the endurance of a leader is directly tied to that person’s acceptance that sometimes they will be misunderstood by the people they so desperately want to understand them. If you can't tolerate being misunderstood, then you can't be trusted to make long-term decisions.

On Accountability in an Age of Victimization

One of the prickliest leadership challenges this year was (and still is) balancing the external norms and beliefs in the broader zeitgeist with the internal cultural values of Uncharted. In conversations this year with other leaders from other organizations, the question came up again and again: how do you hold people accountable to specific outcomes when so many are inclined to claim a special type of victimhood that abdicates all personal responsibility? How do you be a leader who is conscious of and sensitive to systems of oppression, histories of trauma, and undeniable but invisible power dynamics while also not kowtowing to a culture that escapes accountability through victimhood (a cultural cousin to “cancel culture”)? I don’t know…I really don’t, but it seems that the leadership that is needed in such an age is one of charging teams to co-create cultural norms that fuse inclusion with ownership. Victimization culture externalizes responsibility. Ownership culture internalizes responsibility.

On Shaping Space

The leadership that we need is less a function of filling existing spaces (zoom meetings, slack channels, internal team meetings) with brilliance and vision and more a function of shaping new spaces where the most important, nuanced conversations are navigated. I continue to return to what Tressie Cottom said this year: “We are having the thickest conversations in the thinnest spaces.” This is a problem at our societal level, so leaders need to transcend this default inclination toward conversational thinness with cultural practices that create thick, participatory spaces that are capable of offending and reconciling and then moving forward. Ego-driven leadership takes up space. Fragile leadership holds space. Brave leadership shapes space.

On the Heartbeat of Organizations

I am learning there are impact organizations that have lost the artistic, human heart that beats at the center of everything they do. Being purpose-driven is no stand-in for an organization’s soul. You can probably think of organizations that have impressive results but that are missing some je ne sais quoi. The last two years have presented an assault on the artistic heart beating inside our organizations and institutions. We’re remote, we’re burnt out, we’re faced with short-term stressors and long-term existential threats. Which is why leaders can’t neglect nurturing their organization’s soul. I think this is why I love poetry so much: underneath all the strategies and tactics, we must dare to believe there is poetry to our work, and as we wrap up another year at Uncharted, I am reminded of the ways our team continues to apprentice ourselves in the art of nurturing our organization’s soul.

Curiosities for 2022

In originally drafting this Insider, I imagined a section of leadership reflections for 2021 (which you’ve just read) followed by a section of curiosities for 2022, but I’m going to wait until next year to expound upon future curiosities. It’s so tempting to leap forward, but maybe our work in these last days of 2021 is to rest and let this last year finish its metabolizing within us, to let next year greet us only when it’s ready.

As I wrap up my 12th Insider of the year, I’ll finish with a selection of poems that have stirred me.


Final reflection

I recently read a devastating and beguiling book called Bewilderment by Richard Powers. The protagonist is a young boy who is undergoing neurofeedback therapy via an “empathy machine” where he is able to tap into the mind of his late mother. He attends sessions where he trains on her mind, increasingly adopting her best traits and tempering his spiky, impetuous personality. It seemed strange at first: the notion of training our minds… Why would we intentionally let our minds be shaped in ways that distance us from ourselves? But the truth is far more uncomfortable: we are letting our minds be trained all the time. For many of us, they’re being trained by social media, by the 24-hour news cycle, by the unrelenting quest to win games of status and comparison. Sam Harris, the neuroscientist and philosopher, says “the quality of our minds dictates the quality of our lives.”

We spend so much time thinking about training our bodies over our lifetime through regular exercise, but we are largely blind to the ways we are unknowingly training our minds through our relationship to content, our relationship to technology, our relationship to the pace of our lives. Whether we know it or not, we are letting our minds be trained. There is perhaps nothing more stirring than the realization that we have a choice of what we allow to train us: the people, spaces, ideas, and technologies. When we admit to ourselves that we are always training, it opens up the potential for us to make conscious, different choices. It might just invite us out into the old-growth forests, or back into the studio with our dusty set of watercolors, or onto the blank page of our own journal, or into the poetry that seeks us out, even the parts of us that we’ve hidden all year long.


Time spent in peace is the last true luxury. Wishing you time in peace in the last few days 2021. See you in 2022.



One quick thing to note: This is not the official Uncharted newsletter; this is just a monthly letter from me.

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