The Insider - May 2023

On defining reality, the pendulum swings of nuance, rising insurance premiums due to climate change, and a marriage ceremony

The Insider - May 2023
Photo by Lauren Pippin

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.

On defining reality

At the heart of every company, there is a story about what’s important and what’s true. It extends beyond a company’s mission and vision and into the cultural practices within the team, the folklore and rituals, and the way a team responds when things go well or things get hard. If you had told me when I was the CEO of Uncharted that one of my most important jobs was to shape a story that defined reality for our team, I would have stared at you blankly. But with time and space, I’m learning that one of the misunderstood and undervalued dimensions of leadership is shaping reality. Leaders need to be aware enough to see reality for what it is and brave enough to define it for what it could become.

Here are three reflection questions to start this conversation:

  1. What narratives about what’s important and what’s true are dominant in our team?
  2. Are those the right ones for us?
  3. How can our words and deeds tell better stories?

The pendulum swing of nuance

I’ve been trying to figure out why I’ve been bothered by this profile of Elizabeth Holmes in The New York Times. I think it’s because it’s an example of a pattern I’ve seen elsewhere in contemporary media (from mainstream press to social media).

  • Step 1: Someone says or does something that is broadly perceived as wrong or offensive, and we pile on our reproach and cancel them or their ideas. Example: The recent protests and canceling of a speaker at Stanford Law School.
  • Step 2: There is a growing recognition amongst some that maybe we’ve gone too far by reducing people to two-dimensional villains or reducing ideas to dubious conspiracy theories. Perhaps the truth might be more complicated, and needs to be revisited. Example: The revisiting of the COVID lab-leak theory, after it was roundly considered conspiratorial.
  • Step 3: There’s an overcorrection in the effort to reintroduce the nuance that was originally missing. The absence of nuance is followed by the oversaturation of nuance. Everything becomes relative. Example: This podcast about JK Rowling attempts to redeem the author’s image by introducing new storylines and nuance. But this added complexity only creates a convenient relativism that shortchanges the truth.
  • Step 4: The truth is lost in this sea of content, and we lose collective anchor points about a shared reality. Example: This profile of Holmes is a project in character rehabilitation to the point where we’ve partially lost sight of why she’s going to jail for 11 years. She’s not Elizabeth anymore, she’s actually Liz (with a higher voice).

Our media environment is suffering a crisis of nuance: either we are missing it entirely or we are steeped in it to the point where we’ve lost the plot.

Dispatch from climate tech

The effects of climate change are causing an economic crisis for insurance companies. As waters rise, storms strengthen, and floods spread, insurance companies are going out of business, leaving state-backed insurance plans as the insurers of last resort. A warming planet translates into greater risk to insurance companies; and greater insurance risk translates into higher premiums for everyone else, according to an op-ed in The New York Times. Here in Colorado, the Marshall fire destroyed 1,000 homes in 2021, causing over $2 billion worth of damage and a 17% year-over-year increase in insurance premiums, state-wide. For all the climate change appeals centered on ethics and caring for future generations, sometimes it’s the cold, hard economic truths that wake people up.


What I am reading

  • 57% of our time at work is spent communicating in meetings, email, and chat. That’s the finding from research by Microsoft on the modern-day workday. Axios.
  • The rise of the water broker in the American West. How the ways we transact our water is changing—and not always for the better. Grist.
  • “I’ll be honest, I have no idea what a gigawatt-hour is, but I do know what a $279 million investment will do for our county, and I know what impact 575 jobs will have on our community.” The climate infrastructure goldrush in small towns thanks to the Inflation Reduction Act. Wall Street Journal.
  • Wage arbitrage and remote work are creating waves of digital nomads who descend on places like Mexico City and Lisbon, raising prices and pushing locals out. Rest of the World.

Something personal

A few days ago, Lisa and I got married in a private ceremony with our family in the courtyard of our home in Denver. On the morning of the wedding, I reflected on the winding road of past relationships, the seasons when I was laser-focused on my career, the moments of piercing heartbreak. It all flooded back through tears. If I could have told my younger self that I would be this happy and this at peace, I wonder if he would have believed it.

As a way to honor that winding road for both of us, Lisa and I chose to have the following stanzas from a poem by David Whyte read at our ceremony:

There is a faith in loving fiercely
the one who is rightfully yours,
especially if you have
waited years and especially
if part of you never believed
you could deserve this
loved and beckoning hand
held out to you this way.


From Italy,