The Insider - 9 Reflections on 2022

Looking back on 2022 with nine reflections

The Insider - 9 Reflections on 2022
Photo by Madara Parma / Unsplash

Hi everyone,

Welcome to the December edition of the Insider. Thanks for following along this year.

One request: Can you think of three people who might appreciate the Insider? I’d greatly appreciate if you'd forward this email to them and suggest that they subscribe here.

Similar to past December editions of the Insider, I’m sharing learnings and reflections from the year in this month’s edition.

On Humility

I was in awe of the way our merger with Common Future was pushed forward by what seemed like invisible tailwinds at our back. Something so monumental and complicated as the merger of two completely separate entities into one combined organization seemed to be propelled by a profound meant-to-be-ness. I know how hard I’ve worked over the years to achieve far less—or nothing at all in the case of fundraising and sales and hiring. So it was humbling to have our merger culminate in a way that seemed like it was moving forward under its own power. It reminds me of writer and professor Tressie Cottom's distinction that our intelligence is not something intrinsic within us (as is often believed), but rather a correspondence between us and the norms, technologies, and timing of a particular moment. Similarly, our successes and our failures, whether they are organizational or individual, are the results of the many factors, circumstances, and timing that mix with our own efforts and visions. When we let go of success or failure being the domain of a person or a team and consider success to be something between us and the wider world, then we’re able to see ourselves with the humility we need and the world with the wonder it deserves.

On the Questions Between Chapters

After ten years at Uncharted, the question I’ve returned to in 2022 has been: How do we show up when we’re in between major chapters in our lives? One practice that was recommended to me was to pose three questions: 1) What from the last chapter should be left behind? 2) What do I want to bring with me into the next chapter? And 3) What things new and different do I want to introduce? I love this question sequence. It’s a framework that’s allowed me to move forward in a way that has been both reflective and forward-looking.

On Artificial Intelligence

In the future, I believe we will look back on 2022 as the breakout year for artificial intelligence, with this year as a metaphorical Rubicon in four ways:

  1. Artificial intelligence will challenge our belief in the primacy and singularity of human intelligence. The intelligence of machines will expand our understanding of different types of intelligence: from the intelligence of trees to octopuses to machines. If AI helps us to question our anthropocentrism, we might be closer to conferring moral rights and obligations onto beings that have alternative forms of intelligence.
  2. Artificial intelligence will lead us to partner with machines in different ways. In short order (2-3 years), we’ll observe a major reshuffling of what parts of our roles we outsource to machines and what parts we continue to do ourselves. The job loss due to AI is overestimated, but the way that AI will change almost every job is underestimated.
  3. Artificial intelligence will force us to become truth-tellers. Generative AI will dramatically reduce the marginal cost of producing new content, but these systems cannot distinguish between true and untrue (making them vectors for misinformation). This means that there will be unique value in humans who can 1) discern what is true from what is not, 2) apply relevant knowledge to specific contexts, and 3) act ethically.
  4. Artificial intelligence will invite us to reimagine our understanding of originality (and intellectual property). Our ideas, our art, and our beliefs are the products of millions of formative experiences and inputs; rarely are they the ingenious epiphany of a singular individual. If a human partners with a computer that draws upon thousands of copyrighted images and paintings to produce a unique piece of AI-generated art, is it original?

On Addictive Technology

I sometimes ask myself, “What will our grandchildren think was totally insane that we currently accept as totally normal?” I imagine they will be shocked that we knowingly gave our kids the handheld devices that have become weapons of mass destruction to our attention, our sleep, our brain development, our democracy, and our ability to form healthy relationships with other humans. We’ve gone from connecting online to performing online, from social networking to social media, which has rendered us less mentally healthy and more mentally fragile. Thoughtful regulation and policy are needed to protect users, but we also need to “prepare the child for the road, not the road for the child,” as the adage goes. Improving the road conditions are necessary, but we have control over how to become better drivers. Long before addictive technology came about—since the beginning of civilization—we have been training our minds through how we spend our time, whom we spend it with, and where we direct our attention. When we increase the consciousness of our attention, we increase our power to direct it.

On Time and Trade-offs

By far the best book I read this year was Four Thousand Weeks by Oliver Burkeman. It’s a meditation on our belief that we can do it all, even when we’re bound by the constraints of a finite amount of time in a life. For too long, I’ve been convinced that the way to resolve the tension between the finitude of our days and the boundless ambition of my mind is to find hacks and optimizations: to get faster and more effective so I can bust through the trade-offs and attempt to achieve it all. But Burkeman grounds us in the four thousand weeks of an average lifetime, and gently nudges us to accept the inevitability that we will never be able to do it all. Whether we’re aware of it or not, every choice is a trade-off. We cannot have both. Accepting this allows us to step out of the constant games of optimizations and into the peculiar timelessness of moving with full attention from one moment to the next.

On Work Time

Our relationship to time is a theme for me, which is why I’m fascinated by everything from Burkeman’s spiritual meditations on time all the way down to the daily management practices of wisely structuring time during a workweek (preferably a 4-day workweek!). I’ve been a poor manager of my time for years, believing that working long hours was the only path to success, stuck in the debtors’ prison of being perpetually overscheduled with back-to-back meetings. Every time we reinforce the belief that working hard is a badge of honor in our work culture, we reinforce our inability to ever break free from working hard. But by doing the difficult work of clarifying priorities and setting boundaries, we can break this cycle: the less we’re available to everyone, the more we can be focused, and the more we’re focused, the better work we will do, and the better work we do, the less we have to work, and the less we have to work, the more available we can be.

On My Relationship to Work

If we give everything we have to work, then we need to be prepared to let work take everything we have. For a long time, I took pride in giving everything I had to Uncharted. I convinced myself that great sacrifices were required to achieve great things, and those sacrifices were often more self-created than externally-imposed. Work had become too close to me somehow: the distance between who I was and what I was doing was shorter than I wanted. If we convince ourselves that greatness is a product of sacrifice, then we come to believe that the costly, personal sacrifices we make are not warning signs or ineffective approaches, but rather markers of our progress towards our future vindication and triumph. I’m learning that a healthy relationship to work is a daily negotiation between the different parts of ourselves: the endless ambition of our minds, the finite capacity of our bodies, and the mysterious emotions wrapped up in our identities.

On Rest

The poet David Whyte says that "Rest is the conversation between what we love to do and how we love to be." I believe we often get this wrong, thinking the moments of true rest are mental and physical departures from the unrelenting demands and logistics of our lives. But Whyte rephrases rest as moments of conscious reconciling with doing and being, and I found this to be true for my sabbatical. My seven months of unemployment were less an escape from any work and more of a reconciling with who I was, what I loved, who I had become through my work, and what becoming was still ahead. It was an opportunity to listen patiently and—to paraphrase Mary Oliver—slowly beckon the soft animal of my body out into the open, to give it the room to love what it loves.

Something Personal

I proposed to my girlfriend Lisa a few weeks ago. I knew Lisa wanted something private—away from people and surprises—so I proposed in the living room of our home on a quiet Saturday afternoon, with Lisa’s dog Emma by our side (I also proposed to Emma with beef-flavored cookies). I’m an emotional person, and I knew that I wouldn’t be able to keep it together and would likely forget everything I wanted to say, so I wrote a long letter that slowly built to the proposal. True to form, I was a sniffly mess as I struggled through the letter, but Lisa said yes, and we are engaged :) We’ve celebrated with our families over the last few weeks, and we’re excited for a life of new horizons ahead.


Up in the mountains,


P.S. A final note: I want to acknowledge an invisible but important human behind the Insider: Jonathan Yagel. He has been the editor of the Insider this year, and his edits have made these monthly letters more readable and insightful. You have him to thank for each one not being twice as long as they are already. He’s an extraordinary writer, editor, and marketer—check out his newsletter at the opposite end of the brevity spectrum.