Hanging Out in Essay-Land

You are what you make

If you spend most of your time painting, you will turn into a painter and you will live in Painting Land.

(You won’t necessarily be a good painter, but you’ll be a painter.)

Even when you aren’t painting, in Painting-Land, you will think about how what you’re seeing as you walk down the street might manifest as composition, color, and brush strokes.

I haven’t painted in decades. But for almost two months I’ve been publishing to this Substack regularly. Writing regularly means spending time sitting down to write blog posts — that’s not a surprise. What is surprising is how much my resolution to publish regularly¹ has affected my thinking when I’m not sitting down to write. I’ve recently found myself — in conversation, when reading, in the shower — asking myself "how would I turn this thought into a Substack essay?"

Mentally, I am in Essay-Land.

Essay-Land

Writing pieces (like this one) on Substack is an exercise in a certain kind of communication. If I do it well, I’m coming up with a thesis that is both non-trivial and possible to explain in 1000 words or so, and I’m spelling it out in writing with perhaps a personal story, a picture, or a few data points.

If I hold myself to writing, say, two pieces like this each week, it means that I often try to morph random shower-time thoughts into the form of a 1000-word essay. That happens because I am mentally in Essay-Land.

Suffice it to say that there are other mental places one can inhabit: 1000-word essays are not the only form for thoughts and communications!

In the early days of Facebook and Twitter, I found myself mentally trying to craft pithy, clever, sometimes argumentative notes about a hot topic or something I experienced — 140-Land.

When I’m fundraising for a startup, I will find myself in Pitch-Land, thinking in terms of stories, both verbal and visual, that explains how my company will grow and win. What’s the problem that exists, what’s the unique insight I as a founder have, and how will my team apply that insight to build a great business? When I would speak with another founder or even looked at a business in a totally different sector, it felt only natural to use that Pitch-Land mindset and apply the same mentality.

Early in my career, I spent the bulk of my time building machine learning models — to detect or predict fraud, to predict the winner of a sporting event, or to assess the probability that someone would click on an email. In Predict-Land, almost everything is a prediction model.

I’ve seen other Lands inhabited by those around me, even if I’ve never lived in them. PowerPoint-Land exists in many large companies, where people think in twenty-five slide decks that detail the next corporate initiative. Memo-Land is common in politics, where strategists lay out their preferred approach in a couple of pages. DesignDoc-Land allows an engineering team to lay out what they’re building and articulate key architectural considerations. There’s an easy to mock LinkedInPost-Land in which the writer is constantly thinking about things like “what I learned about business from [going to a concert last night / throwing a birthday party for a two year old / etc].” I’ve taken a few steps toward writing a book, and greatly appreciate the Chapter-Land mentality one must inhabit to structure and then compose a full book.

There are pros and cons to each of these forms of thinking, and not all Lands are created equal. I don’t really ever want to live in PowerPoint-Land or AngryCommentsSection-Land. And I don’t have the talent or the personality to live in Songwriter-Land or FootballCoach-Land or any of a hundred other places that you might find yourself.

You can perhaps be a dual citizen and inhabit two or three of these lands, but you probably can’t live in ten of them.

Choosing a Land

I have long been intrigued by Jeff Bezos’ edict that Amazon employees write memos and not use PowerPoint decks.

That approach doesn’t just dictate how Amazon conducts meetings — it pushes Amazon employees to think about problems in a specific way. You will come to see the world differently if you think in six page memos rather than in slide decks.

None of the companies I’ve worked at (early PayPal and LinkedIn) or founded (Team Rankings, Circle of Moms, Bonafide, Change Research) has had such a strong edict. One can argue that there’s a benefit to flexibility: it allows team members to bring their different strengths and communications skills to the table and apply them as they see fit. But in future lives, I expect to take a few steps in Jeff Bezos’ direction, and be more prescriptive about approaches that encourage deeper thinking.

Being in Essay-Land is, in part, a means of saying that I want to think about problems and ideas and systems the way in an Essay-Land style. If I keep writing essays like this, I’ll get even deeper into Essay-Land. Hopefully get better at writing these sorts of essays, and perhaps apply those skills to the companies and organizations I’m involved with.

Which Land do you want to inhabit?

1. I was aiming for 5-6 posts a week. I haven’t managed to maintain that, and I’m still in the process of figuring out my cadence.