The Insider - November 2023

On the bias for inaction, the need for context, the attack on our attention spans, and the power of Think Weeks

The Insider - November 2023
Photo by The Cleveland Museum of Art / Unsplash

Hi everyone,

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

On a bias for inaction

Recently I’ve been studying how to invest for retirement, and I’ve been struck by how different the principles of long-term investing are from the “best practices” of entrepreneurship. 

In investing, inaction is better than action. The goal is to set it and forget it, tending to your asset allocation the way you tend to the batteries in your smoke alarms—maybe twice per year. In entrepreneurship, we’re told the best entrepreneurs have a daily bias for action, an unrelenting pace that starts early in the morning, a hunger to step in and solve problem after problem. 

In investing, the best investors advocate for a general distrust in oneself: you can’t beat the market because no one can. Don’t meddle because you’ll probably mess things up. Create automated systems that leave no room for impetuousness and ego. In entrepreneurship, we’re told that the genesis of all success is a belief in yourself and a willingness to do whatever it takes. We design our organizations to leave plenty of room for brute force and human heroics. 

For the hard-driving entrepreneur, choosing inaction seems like an abdication of responsibility. For the long-term investor, it is a sign of maturity. For the entrepreneur, action is the understandable response to time being short. For the investor, inaction is the understandable response to time being long.

I’ve noticed in myself as an entrepreneur how my bias for action has often been a form of what Brene Brown calls “over-functioning”: an overactive response to make myself busy during times of stress. I’ve seen this in other entrepreneurs, too: their bias for action is not necessarily a proportional response to what their business actually needs as much as it is a form of productive paranoia, a reflexive need to do something when facing the pressure to do everything.

Of course, entrepreneurship is a vastly different game than investing for retirement. But I think that for many entrepreneurs like me, we convince ourselves that our hyperactive productivity is necessary when it is, in fact, a stress response, or worse, some way for us to tell ourselves a story of our own importance. What becomes possible when we challenge ourselves to advance our organizations and make progress, but only through doing less?

On the need for context

The spirit of the Insider has never been about reaching a massive online audience. I am not trying to aggressively grow its readership or make it go viral. Instead, I’ve found the accountability of writing to an audience nurtures a discipline to think deeply and wrestle with the ideas that arrive half-formed throughout the month. I don’t write what I’ve already learned—I write to discover what I am learning. For me, writing is wrestling. Sometimes it flows. Sometimes I find myself bent and contorted in the labor of smoothing out a jagged idea that isn’t quite ready.

I’ve begun to realize something that maybe should have been obvious long ago: I am a better writer and more courageous idea-wrestler when I know the reader has context about me. When I try to write to a faceless, monolithic audience, my writing is generic and predictable. But when I know that the reader on the other side of the screen has context, I feel braver. I hold myself to higher standards. I aspire to be honest because that shared context is a form of accountability.

The writer Jenny Odell says something so simple it’s profound: write for people who have context. Context is a thickening agent that makes our writing textured and beautifully prickly. Without it, our writing can come out wispy and bland, which is the direction I see a lot of online writing going. The architecture of platforms like X/Twitter leaves little room for context, and AI-generated writing is designed to be generic and predictable because it is the average of all the writing that’s ever been done online. 

As the academic Tressie Cottom so thoughtfully frames it, we are having the thickest conversations in the thinnest spaces. In such spaces, our writing becomes disembodied from human context. We begin to write in generic platitudes and pithy maxims because that’s what feels safest to write to an audience that doesn’t have context. We begin to shape our writing—and by extension our thinking—around calculations like: what will have the greatest impact for people who don’t have much context? What will get the most shares by people I don’t know?

When you write without any ambition for scale and distribution, when you anchor your writing in the mud and muck of human context, you will write with more honesty and pluck, and your writing will become an invitation that is sometimes accepted by the people on the other side of the screen to respond and participate in that co-wrestling with you.

On attention spans

As social media has become more deeply integrated into our lives, it’s changing the way we write. At first, social networks were treated as a distribution mechanism for long-form articles and other content—anything published would be broken down into more digestible tweets and social posts. Now, the situation has almost reversed: many publishers write first for social media, testing to identify what pithy insights resonate, and then expand into long-form content around those one-liners. As an example, consider this manifesto by Marc Andreesen. In form, it’s a 5,000-word essay. In function, it’s just a loose collection of tweets and hot takes.

Ezra Klein has said that we become like any medium we use most often. If we spend our days on Twitter, we start to think in tweets. If we spend our days reading long-form journalism or fiction, we will nurture an attention span that is longer and more patient for a narrative to slowly take shape. The question we ought to ask ourselves is what medium do we want to become most like?


What I am reading

  • Technology doesn’t make our lives easier, it makes them faster. A critique of the promise of technology to make our lives more convenient. Brett Scott Substack.
  • Emissions from California’s wildfires have essentially erased the state’s success in reducing greenhouse gas emissions since 2008. Voyager Ventures released a memo on the state of fires in 2023 and the newest fire-tech solutions.
  • The University of California University system is abandoning carbon offsets as part of its decarbonization strategy. MIT Technology Review.
  • An argument to quit your job to carve out the space for exploration. The case for sabbaticals and active unemployment. Palladium.
  • The politics of Chick-Fil-A have drawn criticism from the left for years. Now they’re drawing criticism from the right. The history of the brand and the principles that anchor it. Fast Company.
  • This year-old article on the infighting inside of progressive organizations resurfaced many memories for me. How meltdowns brought nonprofits and advocacy groups to a standstill. The Intercept.

Something personal

Think Weeks were popularized by Bill Gates as a chance to escape the constant distractions of everyday life to spend an entire week in learning mode: reading books, exploring ideas, wandering in thought. I’ve done them solo for a few years, and they’ve consistently been some of the most creative periods of my life. Last year, I tried my first think week with Michael Thomas, a friend whose intellectual rigor, original thought, and polymathic range I’ve come to admire. We flew to Mexico, rented an Airbnb, and spent a few days reading, exploring ideas, testing theories, and eating vegan tacos. Michael and I just returned from another learning retreat where we carved out a few days for intellectual and entrepreneurial exploration. Such spaciousness is a privilege, but learning retreats are more possible than we might think. Protecting the smallest spaces to let our curiosity roam—even just two hours—can be enough to revisit the curiosity of our childhood, a curiosity that might have faded into the background of a life defined by adult responsibilities and full schedules.