Season One of Hoo Boy was the Season of the Hedgehog. Season Two—I’m excited to announce—will be the Season of the Fox.
“A fox knows many things, but a hedgehog knows one big thing,” quothe ancient Greek poet Archilochus, apparently. Unfortunately, he didn’t read The Artist’s Way1 by Julia Cameron, so we don’t have piles of morning pages explaining the quote. But, in 1953, we got an essay on the idea from the philosopher Isaiah Berlin. In “The Fox and the Hedgehog,”2 Berlin divided writers into two groups: the foxes, who study and write on a variety of themes and subjects, and the hedgehogs hammer on one idea over and over again.
Over the last five years, I’ve noticed an explosion of hedgehogs writing online, and it’s easy to see why. It seems like there’s a new “The X Guy” every day (“The Writing Guy,” “The Public Speaking Guy,” and so on). The hedgehog’s toolkit—picking a narrow audience and delivering for them—is a good one. It’s easier for people to rally around your banner when you’re the guys making a podcast about M&A than it is to start a general business podcast.
We used this niching formula at Mattermark. We wrote every day for four years on venture capital and startups in The Mattermark Daily.3 We featured up to five articles—each with a brief editorialized summary—by startup investors and another five by “operators” (people working at startups). At peak, over 100,000 people subscribed, and more than half of them opened our newsletter every day. Still, we ended up selling Mattermark in what TechCrunch called a “disappointing outcome,”4 and I’ve had a chip on my shoulder ever since.
Having written “The Daily,” as we called it, for part of the newsletter’s life, I felt like I should have been able to replicate its success. I found myself repeatedly turning to ye olde niching formula to no avail.
After Mattermark, I started Holloway, where we published books on business and technology. We settled on writing a newsletter, Good Work,5 “A hand-curated newsletter devoted to exploring how we choose to spend the 90,000 hours that will make up our careers.” I replicated The Daily’s format, featuring links to relevant content, but mixed it up by adding an introductory essay, which I’d try to limit to four paragraphs.
It turns out brevity, like most things people prefer, is not easy. Or as mathematician, physicist, and philosopher Blaise Pascal put it:
“I have only made this letter longer because I have not had the time to make it shorter.”6
Good Work’s audience grew to five or so thousand subscribers, but despite how much I loved writing the newsletter, I couldn’t justify how long it took.
After Holloway, I began coaching other founders and took two more swings at The Way of the Hedgehog with newsletters about coaching or issues that repeatedly came up with founders I worked with. I briefly collaborated on a newsletter with a much more experienced executive coach, Jerry Colonna, and eventually launched Season One of Hoo Boy.7
At first, Hoo Boy was easy. Anyone who has ever coached startup founders will be familiar with the deja vu of hilariously similar-but-different, situations popping up again and again. Not only did these situations provide me with endless material, they fed my curiosity as I’d learn more about each subject as I wrote.
But the subjects founders brought up, and the ones I got curious about, while adjacent to or relevant to, leadership and best practices for building a business, began to deviate enough that I didn’t know how to coherently integrate them into Hoo Boy.
In early August, I read In Over Our Heads by Bob Kegan and came across a passage that made things click for me:
“These expectations [for adulthood] are chronicled, and even shaped, in the growing collection of cultural documents academics call (with no irony) ‘literatures’: ‘the marriage literature,’ ‘the management literature,’ ‘the adult education literature,’ and the like… for the most part, these literatures do not talk to each other, take no account of each other, have nothing to do with each other. The people who create the leadership literature do not read the parenting literature… there is no place to look to consider what is being asked of the adult as a whole.”8
I remember where I was when I read this because I laughed at how much it fit my experience of the last three years (and didn’t). At least half, if not closer to three-quarters, of the founders I coach will eventually show up to a session asking if they can use the hour to talk about “something ‘not exactly work-related.’” Spoiler: it’s about the person they’re dating or married to. I emphasize that I’m not a couples therapist, but I’m happy to listen if they think it will help.
It doesn’t take a rocket scientist to connect the dots that the wisdom that can unblock us with relationships between co-workers might be applicable at home (and vice versa). But I now have a pile of books on couples therapy I’ve worked my way through, equally out of my curiosity and to be better prepared for the next “not-exactly-work-related” topic in a coaching session.
This fascination with marriage and intimacy and “literature” is a perfect example of a subject adjacent to or relevant to leadership but distinct enough that I struggled with how I could write about it publicly. I’m not a couples therapist, and a part of me is afraid that those Big Bad Couples Therapists with their Big Bad Degrees will come after me for being the academic version of a street rat.9
The fear of being declared a charlatan by psychologists I don’t know, have never met, and whose names I don’t even know, combined with the chip on my shoulder from Mattermark and the patience to sit with both to understand them, led me to stop writing Hoo Boy in February. I couldn’t focus on business tactics and mental models in my writing when my curiosity was pulling me elsewhere.
Since then, I’ve been wrestling with how to coherently give readers an idea of what to expect from my writing without zipping up a poorly sewn hedgehog costume. I thought, “Who else does what I want to do?” and “Whose writing do I really admire?”One writer came to mind above all others: Maria Popova at The Marginalian (formerly BrainPickings). Maria’s about page reads:
“a one-woman labor of love, exploring what it means to live a tender, thoughtful life of purpose and gladness, wonder-smitten by reality, governed by the understanding that creativity is a combinatorial force: ideas, insights, knowledge, and inspiration acquired in the course of being alive and awake to the world, composited into things of beauty and substance we call our own.”10
Maria has succeeded as a fox in a hedgehog’s world, writing about basically whatever she finds interesting, and it turns out lots of other people find that stuff interesting—since she started writing online in 2006, her efforts have been completely run by donations. I want to do something way more like Maria has done than become yet another “The X Guy.” And while Maria is no hedgehog, the subjects she explores make sense together:
“science, art, philosophy, and the various other tendrils of human thought and feeling, a private inquiry shimmering with the ultimate question, the great quickening of wonderment that binds us all: what is all this?”
Like Maria’s writing, I expect mine going forward will, in a fuzzy sense, “make sense” together. But I can’t connect the dots looking forward. I can’t tell you exactly what to expect, like the hedgehog can. What I can do is share a few of the questions—other than, “How can I use everything I learn to be a better coach to my clients”—I’m interested in exploring and finding ways to talk about in plain language:
Where Season One felt like a carefully prepared lecture to an audience with meticulous attention to detail and design, I’m hoping Season Two will feel more like popping into a friend’s garage with a beer or two and saying, “Hey!” I hope you’ll enjoy it, and if you do, I hope to hear from you.
Hoo Boy, indeed,
Andy.
Many of the newsletters I love have a section where the author drops a small collection of links to whatever cool stuff they’re into. The “On My Mind Lately” section will be that for the foreseeable future.
Thanks to Rachel Jepsen and Nathan Baschez for reading and editing drafts of this post.
Footnotes