The Insider - May 2022

On social enterprise funding models, social media, burnout, and letting go and moving on from Uncharted.

The Insider - May 2022
Photo by Marita Kavelashvili / Unsplash

Hi everyone,

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

Earlier this month Uncharted announced that we are merging with Common Future. You can read the full announcement here and my personal reflections here. While we announced this merger a few weeks ago, both teams have been working for months to combine the respective teams and expertise into a unified, more powerful organization committed to building an economy that works for everyone.

In my last Insider, I shared that I will not be taking a role at Common Future. I am taking a sabbatical this summer as I consider my next steps, but I’ll continue to write this monthly Insider where I’ll explore similar topics and ideas at the intersection of social change, entrepreneurship, technology, leadership, and culture. Let’s dive in!

On Manipulation

One of the sad ironies of the social sector is that many nonprofit social enterprises are often fighting for long-term change with a short-term business model. I felt this time-horizon mismatch often at Uncharted, and I noticed how it led to decisions governed by short-term motivations. We had multi-year ambitions, but we were trying to cobble together one-off grants and ephemeral funding priorities from foundations to keep the lights on for the next six months. In many ways, our greatest organizational vulnerability was the tyranny of the short-term, and I struggled to align long-term strategy with long-term funding. I came across a quote recently (that I can no longer find) that said something to the effect of, “the more short-term our thinking, the easier we are to manipulate.” That seems to perfectly capture the relationship between organizations and funders in the social sector. One of the best heuristics when doing anything strategic is to ask: will this model and this approach allow me to play long-term games with long-term people? As Naval Ravikant says: “All the benefits in life come from compound interests. Whether it’s in relationships, or making money, or in learning.”

On Accountability

Political scientist David Polansky said recently that our society is “simultaneously characterized by wildly disproportionate accountability for trivial transgressions and zero accountability for profound institutional failure.” How can such extremes of accountability coexist in the same moment? My sense is that the factors contributing to this inconsistency are numerous, but that social media is the stage upon which we’re witnessing both the death of nuance and the control of attention. How we show up and perform on social media is shaped by how we anticipate other people will respond, either with adulation or condemnation. Our own behavior is as much a way to police the spaces we occupy as it is a way to avoid being canceled ourselves (social psychologist Jonathan Haidt calls policing on social media “distributed totalitarianism”). But in the process of tearing down individuals for trivial transgressions, social media shifts the spotlight of our attention away from institutional failure. Algorithms are designed to addict and entertain, and it is far more entertaining to watch the canceling of a person for their unsavory beliefs than it is to uncover the provenance and nuanced emergence of institutional decay. If social media is democracy’s “new public square,” then both its leaders and users have a responsibility to interrogate the ways it directs our attention and our accountability.

On Burnout

It’s no secret that the American workforce is burned out, but I believe we are misattributing the drivers of burnout to simply long hours or external factors like “the pandemic” that we consider outside of our control. When we credit burnout to busy seasons or to remote work or the pandemic, we’re letting ourselves off the hook. Developing an anti-burnout strategy can create a competitive advantage for companies looking to retain talent (​​burned-out employees are 63% more likely to take a sick day and 2.6 times as likely to be actively seeking a different job). This is one area where the most thoughtful and human-centered companies are in the top 1%. They’re taking responsibility for burnout and making different choices:

  • Prioritization: At the root of our inability to prioritize is a fundamental misunderstanding of how trade-offs work. When we believe we can do it all and have it all, we prioritize it all. When we believe there is an opportunity cost to every action, we make better choices for our team.
  • Clarity: Burnout is exacerbated when roles aren't clear, managers aren’t clear in their feedback to direct reports, deliverables aren't clear, and the distinction between important and unimportant work isn't clear.
  • Technology: Collaboration tools like Slack and email prevent people from engaging in deep, focused work, instead requiring and rewarding constant attentiveness to interruptions. We spend two hours each day recovering from distractions, and it takes an average of 23 minutes to refocus after getting distracted.
  • Flexibility: The greater the workplace flexibility, the less the workplace burnout. 76% of workers would be more willing to stay with their current employer if they could work flexible hours. 84% of working parents said work flexibility is the number one most important factor in a job.

Can you help?

  • I’m starting a new, separate newsletter for business leaders on the future of work. From the 4-Day Workweek to building a world-class culture to staying on the cutting edge of the latest trends in the workplace, the Smart Workweek Newsletter will cover it all. Sign up here.
  • What are the best articles you’ve read on the drought in the American west?

What I’m reading

  • Having on average 10 more trees in a city block improved health by a level comparable to an increase in annual income of $10,000. The ecological determinants of human health. Here.
  • How food delivery, ghost kitchens, and the obsession with convenience is reimagining our relationship to food. Is this the future we want? Here.
  • The internet is financializing everything. How Web3 is creating an ownership layer of the internet and what that means for society. Here.
  • The 300,000 smugglers who smuggle goods back and forth over the mountains between Iran and Iraq. The world’s most dangerous and mountainous trade-route. Here.
  • Tackling climate change requires more patient forms of investment. The competition for the attention of investors between NFTs and clean energy infrastructure. Here.
  • How social media is making us unfit for democracy. How these platforms bring out our most moralistic and least reflective selves. Here.
  • Poetry: A book of poems by Wendell Berry called Leavings on transitions, love, and the soil. Here.

Something Personal

Common Future is keeping the Uncharted office in Denver, and they used it as the location for an in-person retreat a few weeks ago. It was the first time that the two teams were together as one, and despite no longer being officially on the team, I was invited to stop by for a lunch break. It was a warm reunion to see former Uncharted colleagues and meet Common Future people I had only known as faces in a Zoom square for the many months that we orchestrated our merger. When lunch ended, everyone jumped into an afternoon team-building session. They were continuing forward, and I quickly realized it was my time to leave. I slipped out of the room, down the empty hall, and walked out the door of our office for the last time.

In reflecting on the last 10 years at Uncharted, it’s clear that my identity has been wrapped up in the work, in being productive, in building a team and nurturing a culture, in feeling the responsibility of it all, and there were so many times when I walked out of that office invigorated with a mind that was spinning about our next move. But on this day, as I left with everyone else still inside, as I wandered out into the sunshine of a Tuesday afternoon with no plans and no professional responsibilities…it was the physical embodiment of what I had known conceptually: that I was walking away and letting go.

The absence of any responsibility for the organization felt like a strange lightness for me, almost like that feeling of leaving the house and sensing you’re forgetting something, but not knowing exactly what that might be.

Maybe this is the phantom feeling of a mind trained over the years to be responsible and thorough and productive. Maybe the work now is to apprentice into this strange lightness. Maybe that undertaking shouldn’t be considered work at all, but rather should be perceived more as a receiving than a doing. I don’t know. It seems both as hard and as easy as what Mary Oliver says in one of her poems: “You only have to let the soft animal of your body love what it loves.”