Hi everyone,

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

On letting the work find you

I am finding that life’s best opportunities are often disguised as unremarkable blips on our radar, or even possible distractions. In 2012, when I needed a full-time job, I stumbled across a Twitter post for an unpaid summer internship. I took it and then spent a decade building Unreasonable and Uncharted. A few years ago, someone reached out to say their newsletter writer had taken an unexpected leave of absence and asked if I could step in for a few weeks. I’ve been writing their newsletter every week since (over 175 editions). That side gig made me wonder: could I do this for other companies, too? Today, we're a business with 14 clients, a full-time General Manager, and a small group of talented writers and editors.

The modern mythology of entrepreneurship is all about the doing. Nothing stands in the way—at least we are told—of the high-agency entrepreneurs we elevate as heroes. And yet, I have found that some of the most rewarding opportunities emerge as much from the doing as from the receiving. I have come to respect this beautiful reciprocity between action and inaction, between willing something into existence and letting something land in my lap. Our work has a way of finding us—through the side doors, the free gigs, the one-off conversations, the chance encounters. At a time when I am tempted to set big goals and choreograph the year ahead, it is a reminder that our master plans are their own forms of resistance to the winding plans life has for us. We would do well to remain open to the things that look like nothing. If we’re willing to give them a chance, sometimes they have a way of becoming everything.

On the hard edges

I was shocked to read an article in The Atlantic about the explosion of undergraduates who are claiming disability. At Harvard and Brown University, one in five undergraduates is registered as having a disability. At Stanford, it’s two in five. At UC Berkeley, the number of students who claim disability has quintupled in the last 15 years.​

It’s an example of concept creep: having a disability used to mean one thing, and now it means nearly everything. But it’s also an example of how easy it is to make bad decisions rooted in good values. It is considered a foregone conclusion that values-driven leadership is enlightened leadership. We are told that today’s best leaders make values-driven decisions. They hire values-aligned candidates. They build teams and cultures around shared values.​

But I’ve seen firsthand—and have been complicit in—a values-centric approach to leadership that leads to an ever-expanding justification of what aligns with a value.​

If we value inclusivity and accessibility, can we justify decisions that exclude certain people? If we value learning from our mistakes, can we justify accountability for failure?​

Comforted by the warmth of our positive intentions, it is easy to forget that our values are most powerful when they have hard edges, real consequences, and clear lines between what’s in and what’s out. The strength of our ideals is more a function of discipline than vision, more an act of cutting away than adding to.

On the specific ingredients of our flourishing

It might be one of life’s great mysteries that we can go for decades and not know the specific ingredients that lead to our own flourishing. There is plenty of general advice about living the good life, but I’ve found it strangely difficult to identify and implement the set of principles and practices that I know, empirically, bring forth my best self.​

Perhaps the difficulty lies in the fact that we are too close to our own life to see it clearly; a farsightedness of selfhood. Or maybe the truth would have a chastening effect, pushing us to tiptoe into the liminal space that stands between our familiar unflourishing and the unfamiliar flourishing on the other side. And then there is the whip and whirl of life—the sheer velocity of it all—that blurs and blinds. What if we’re just moving too fast to pay attention to what brings out the best in us?

​It is easy to speculate on the reasons, but that might allow us to delay the actual work: taking the time to map out the moments of our past flourishing and then engineering more of them into our future. There are a million ways to live someone else’s life, but very few ways to live our own.

Should we work together?

These days, I’m building a small business obsessed with the craft of writing and producing exceptional newsletters. With our team of thoughtful writers, experienced magazine editors, and data-driven email marketers, we tell ambitious stories for the inbox.​

Our newsletters have brought in 5-figure clients, 6-figure LP commitments, and 7-figure opportunities.

  • For a timber company, we conducted in-depth research into the history of teak wood and its ethically complex supply chain. For an organization building the future of responsible tech, we reported on the recent trend of AI companions fueling delusions.
  • We write the newsletter for Obvious Ventures, a VC fund exploring the frontier of generative science, and we run The Epicenter, an inbox-centric media publication focused on climate resilience and adaptation amidst increasing natural disasters.
  • We’re helping brands launch their own Substack platforms, and we ghostwrite for executives, too: helping them refine and publish their ideas to their audience.

Amidst so much mass-produced AI content, we’re finding the market is hungry for its opposite: the craftsmanship that comes from the slow, human artistry of researching, writing, and publishing stories that matter. (See this recent Wall Street Journal article Companies Are Desperately Seeking ‘Storytellers’ for more on this trend.)​

If you’re looking to tell such stories and resonate with your audience in 2026, let's chat.

What I am reading

The end of December is for reading (and rereading) the best articles of the year. I’m sharing a few of my recent selections that tie into five topics (and one tribute) that have me thinking:​

The rise of AI agents

I am intrigued by AI agents and how they’ll change how we work. I loved this blog post by Anthropic about the small shop in their office lunchroom, run by an AI shopkeeper. It offers a window into how AI agents are increasingly taking on more responsibility, with varying success. Pair with this (satirical) podcast about AI employees.​

Maximalist beauty in a minimalist world

I love hearing stories of people who reject the conventional wisdom, especially when that wisdom advocates for personality-less commodification. This New Yorker article profiles New York’s most famous house-stager and how he stages and sells the city’s unsellable apartments.​

Moving offline

Designing offline, analog experiences will be a new form of luxury in 2026. This article on X reflects on the perils of being “extremely online.” I’m curious how you’re thinking about cultivating a vibrant offline life in the year ahead.​ Reply to this email and share your thoughts.

Financial nihilism

Does the old playbook of building wealth still apply? I’m interested in how different generations think about personal finance, wealth building, and the American dream. This article in The Wall Street Journal framed the idea of financial nihilism; this article on X explored the prison of financial mediocrity; and this article in Bloomberg considered whether the distinction between investing and gambling is shrinking.​

Ambitious storytelling

It can feel lavish to read fiction or immerse yourself in a story that has nothing to do with getting ahead, applying the five key takeaways to better [x], or staying on top of the news. There were a few stories in 2025 that felt like stories for the sake of stories, and this article in The New York Times was one of them; this article from The New Yorker was another.​

A tribute

Finally, I found myself struck by this heartwrenching essay by Tatiana Schlossberg, who died yesterday. As a new parent, I found it devastating and sobering.​

Something personal

In the quiet, in-between moments of being a parent—in the middle of night when I’m trying to soothe Emilio back to sleep or after dinner as I’m picking up the house—my thoughts will drift to my own parents, and I’ll think about all the moments I never knew about: the moments after I went to bed and before I woke up. The moments they were planning for my future and coordinating my logistics. The moments that enabled so many other moments. The moments that led to this moment, right now.​

So much of what goes into making our lives beautiful and vivid is invisible to us. It is the behind the scenes work of those who care for us: the back-and-forth between our friends to plan a surprise party for us; our aunt driving across town to the post office to mail us a birthday card; a teacher staying up late to prepare the next day’s lesson plan; the extra hours our parents worked to pay for the hobbies we eventually abandoned.​

Sometimes, if we’re lucky, we might catch glimpses of the moments we never knew about. We might hear echoes of the countless hours and profound love that became the substrate of the life we now live. We might find ourselves doing exactly what our parents must have done for us, decades ago.​

To see it all is to see too much. It would be a burden. But it is enough to be vaguely aware that there are entire worlds that are out of sight; that our becoming was the triumph of many; that it might even be presumptuous of us to think of ourselves as the protagonist in that bigger story.​

I have found it to be a rare delight to peer through this looking glass—to see myself, my son, and my parents as separated by time and distinct in soul, but still implicated in a story none of us will be able to fully grasp. It is enough to know that the story exists, and to thank my parents for all the moments that will remain unseen and unknown in my own life, as that cycle continues in the lives of the next generation.

~~~~

To everyone who "will keep trying to remember,"

Banks

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