The Insider - December 2024

Hi everyone,

Happy new year! Here's the last Insider of 2024.

I'd love to hear from you in 2025. Just reply to this email to say hello.

The shape of ambition

I have loved this question from David Brooks this year: If the next five years is a chapter in your life, what is the chapter about? I don’t know what chapter is next, but I’ve come to think that one of the central themes of this current chapter has been a reshaping of ambition. Growing up, I always thought that I wanted to be a classic entrepreneur: build a big company, contribute to an incredible culture, make a dent in the world. But in the past year, I’ve started to give myself the permission to acknowledge something that had been true for a while: that I didn’t love being a CEO, that I felt burdened by managing a team, that I am actually less interested in building a traditional company. An ambition that was once a vector pointed at the corner office is now less pointy and more rounded. It is an ambition for a craftsman’s approach to high-quality but unscalable work. It is an ambition that knows there is nourishment in a few things done well. It seeks enough time to notice the deep delights in small moments. It yearns for spaciousness and a flourishing life outside of work. Its shape is less industrial factory and more woodworking shop.

Developing finesse

It’s tempting to think that we’re growing as leaders when we read the newest leadership book or article, but often these academic exercises are distractions from the real work. They are predicated on the belief that more knowledge translates into better leadership. But the journey to become a leader who is worth following doesn’t follow such neat rules. Great leadership doesn’t exist outside of its context. There are no immutable playbooks. No timeless gospels. It is more instinct than knowledge, more self-reflection than best-practice, more situational awareness than leadership-by-framework. In German, the word Fingerspitzengefühl translates as "fingertips feeling," or the intuitive flair or instinct to deftly navigate an uncertain situation. The best leaders I’ve seen practice the art of Fingerspitzengefühl: knowing when to lean in and when to lean out, when to speak up and when to stay silent, when to dream big and when to return to what’s always been true.

The urge to be righteous

A recent article in The Atlantic claimed that the era of wokeism is now dead. It explores “how liberal America came to its senses” and shed its illiberal, intolerant tendencies of the last decade. I am not sure it’s entirely dead, but I do think something quite peculiar happened in progressive circles over the last 10 years. I look back on the wild years of 2020 and 2021 with bewilderment at how progressive organizations lost the plot and kowtowed to fear (myself included). The stakes felt high: you could be cast as a racist, get cancelled, lose your job. The social psychologist Jonathan Haidt described the dynamic as one of “decentralized totalitarianism,” no single dictator, but a collective self-policing. What stands out now was how fundamentally unkind the whole thing was: there was little room for assuming positive intent, or giving people the benefit of the doubt, or trying to understand the deeper context. All that mattered was if someone was offended. Perhaps this period of illiberal wokeism is just the latest instantiation of a flaw that’s been programmed into us for centuries: to let our fear manifest as righteousness and to convince ourselves that it is better to be a finger-pointing saint than it is to make actual progress in the company of well-intentioned sinners.

Blaming climate change

Natural disasters now routinely cross the billion-dollar threshold, and climate change appears to be the obvious culprit. At least that’s what we’ve been led to believe. But the math tells a different story. The biggest driver of billion-dollar disasters—like hurricanes, wildfires, and severe storms—is not a changing climate but a country that is expanding into areas prone to disasters. More people and more assets in harm’s way means bigger price tags. One insurance company estimates that 80% of the losses from severe storms can be attributed to the increase in asset exposure. People are flocking to Florida, where population growth was the highest in the country in 2023. Texas is similar; its population has grown by 40% in the last 20 years. What was once a Texas prairie is now a Dallas suburb, and when a hailstorm passes overhead, there’s simply more in the way. There’s more in the way in the Wildland-Urban Interface (WUI) too: the WUI covers 9% of land in the U.S., but is now home to 39% of all houses in the country. Climate change plays a role in expensive disasters, but so do the factors that have led to our sprawl, like expensive housing prices in cities, poor urban planning, and the cultural obsession with home ownership. I wonder if we'll ever question our reflex to rebuild after the next disaster.

Should we work together?

Newsletters are like trees. The best time to build one was a decade ago. The next best time is now. 

Is your team spread too thin to consistently produce a high-quality newsletter? If so, you might be leaving opportunities and revenue on the table. I’m building a newsletter agency that offers high-quality, consistent newsletters as-a-service. If you want to cut through the noise in 2025 and build trust with your audience, just reply to this email.

What I am reading

Here are some of my favorite long-form articles from 2024.

• What the childhoods of exceptional people have in common. The correlation between extraordinary outcomes and non-traditional formative years. Escaping Finland. 
• He used to make $300,000 per week fixing other people’s screenplays. But in that cushy life, he was ignoring the call to produce his own, original work. The New Yorker.
• “I have a theory that chasing things that scale makes you need therapy, and the therapy is pursuing things that can’t scale.” Anu’s Substack on pursuits that can’t scale.
• How to invent the perfect college applicant for $120,000 per year. A college counselor for the children of billionaires says a lot about American society and its myths of meritocracy. New York Magazine.
• The global economy is powered by fiber optic cables snaking their way along the bottom of the ocean. An article in The Verge featured the invisible seafaring industry and infrastructure that keeps the internet afloat.
• Illegal eel smuggling is a $4 billion a year industry. It is the world’s most profitable wildlife crime, and its epicenter is Maine. The New Yorker.
• The best version of today’s internet is a group chat. Gone is the promise of mass scale and mass reach. In its place is a much smaller internet. Posting Nexus.
• In the Parkland shooting, was it the cowardice of the police officer that held him back? His lack of training? Are we asking too much of police officers? I changed my mind three times reading this article in The Atlantic.

Something personal

A few years ago I asked my therapist if there was a common pattern she saw across all the clients in her practice. She knew immediately: people would rather choose a familiar dysfunction than a healthy, thriving life that’s unfamiliar. It’s like that quip, “I know I live in hell, but I know the names of all the streets.” The status quo is a powerful glue.

How common it is to throw obstacles in our own path that prevent us from stepping into something unfamiliar but extraordinary. Lisa and I have discussed this often in 2024: How can we be stretched in ways that help us to see ourselves differently and escape the small stories we get comfortable in? This was the driving intent behind our decision to live in New York City for a month and Mexico City for another. We love our life in Denver, but we wanted to develop the practice of tasting whatever was on the other side of the unfamiliar.

My biggest takeaway from our travels wasn’t some insight about experiencing a new city, it was about experiencing myself in that new city—observing how a different setting cultivated a shifted mindset and drew forth a new side of me. 

New York makes you want to be excellent at one thing. It’s a city that showcases those who are the best in the world at their chosen speciality. And you want to find that one thing for yourself. Lisa and I would be taking the subway home late at night after a Broadway musical, gushing about how stunningly talented each performer was. It made us want to be excellent the next day in our work.

In contrast, Mexico City makes you want to taste everything. It’s a city of unexpected discoveries: small restaurants with the most exquisite food, romantic outdoor cafes under a canopy of grees, neighborhood tortillerias where you can get 12 steaming hot tortillas for 50 cents. The city invites you to become a bon vivant, a poet, a foodie, a lover of art, a speaker of Latin languages, a reader of Gabriel García Márquez. Where New York pushes you to specialize, Mexico City invites you to immerse in all five senses. New York City speeds you up, Mexico City slows you down.

Who we are is inseparable from where we choose to place ourselves—whether that’s a city, a job, a community. It makes me wonder if it’s a mistake to try to change everything inside of us before changing everything that surrounds us. Maybe we give ourselves too much credit by believing that transformation happens from the inside out. Perhaps we just need to open ourselves up and let the outside in.

~~~~

From Colorado,

Banks