A break from your (ir)regularly scheduled Thoughts + Things programming. Instead of recommendations, an essay I wrote on writing that I hope you’ll enjoy:
There's a line I loved from The Cultural Tutor in this interview with David Perrell:
"The part I enjoy about writing is the part when you're least constrained... I can think of few things more enjoyable than that; when you're not worrying about why or what or who or when or how. Something strikes you and you go."
Isn't that what we're all chasing when we write or try to do anything creative? And there are certainly many ways to get there. But lately, I've been thinking a lot about audiences and formats and how they might induce this ease of writing. That led me to a simple question: why is it so much easier to write a letter than an essay?
Could digging into that question help my writing feel less constrained? In fact, could adding a constraint free me up to create? In short, I think it all comes down to who we're writing for, or to.
Writing is hard, but Writing for an Ambiguous Audience is Max Difficulty
I've attempted to write longer-form content in various capacities in recent years, and found a few things to be true:
The most successful form of writing for me (if publishing is our success benchmark: a low bar) has been this newsletter (Thoughts + Things). I think there are two reasons for this: I've got a fairly clear formula for them and the set of constraints makes sense: pick 3 to 5 things I've read/watched/listened to lately and write. It's easy to get started, and they can't be too long. And they're almost for me more than anyone else. Not quite a journal, but closer to that than lots of other types of writing.
Speaking of journals: this is by far the easiest form of writing for me. Why? I suspect that journaling has the clearest and easiest audience to write to: myself. Sometimes I journal for my current self and other times I more intentionally write to my future self, but there is no doubt about who is going to read it.
I have the hardest time writing about expansive topics I'm excited about. Put simply: writing essays. My experience usually goes one of two ways: I start with a small idea or central argument that quickly starts to expand into a bunch of disjointed ideas. I struggle to connect them or find a coherent plot line for the piece and lose steam. Alternatively, I start building up a word count and soon find that there are endless components to explain, points to preemptively counter-argue, examples to define and research more, and so forth. The essay sits at 80-90% "finished" indefinitely, is put aside for months at a time, and eventually becomes too big in my head to ever have a chance of being published. The culprit? I don't know who I'm writing for, and thus I'm trying to write for everyone.
I recently shared my frustration with my friend Dan Hunt after a failed writing session. He suggested the same final point was the culprit: that my struggles seemed to be rooted in the fact that I did not know who I was writing for. My urge to continually add more and more complexity--kaleidoscoping outward as I go-comes from a foolish strategy to write something that could at once appeal to an unknowingly wide audience and have enough depth for those already familiar with the subject.
To be clear: the best writing can seem to have this quality. The clearest thinkers and communicators can explain wildly complex ideas more effectively than most of us can explain the basics. And in art, much of the most powerful work becomes universal by way of radical specificity. But part of creating anything good is creating something bad first, and this failure to hold an audience in mind can be a hurdle in creating anything at all. It certainly is for me.
Letters: an Audience of You
I spent some time reflecting on Dan's advice, which led me to the most drastic example: the question about letters and essays above. Like journaling, letters are relatively "easy" to write. Sharing words with a friend, loved one, or even a stranger (say, an author you admire) is much easier to start and usually easier to finish than writing to a wide audience. It's a beautiful constraint that scopes your audience down to the most extreme: one person, you. My journals are sometimes styled like this when I'm writing explicitly to a future version of me.
In letters, you can appeal to their sensibilities and humor, you probably know their range of understanding and interest in certain topics, and you might even make references that only they would understand. You likely don't need to spend much time wondering about whether they'll care about what you have to say; a letter is a great way to increase the likelihood of your writing being ready, after all! The stakes are much lower: for many would-be letter recipients, they're just happy to hear from you in a personal and intentional way.
This got me thinking: letters can be a useful constraint for clarity and creativity. While the recipient may not be representative of any larger audience, let alone the one best fit for what you have to say, letters force us to accept that there will indeed be a reader. Not everyone, not no one, but someone. And when we write with that in mind, we're unlocked to write with style and personality and intimacy and most often, the constraints fade away and we can write.
A favorite example of this style’s effectiveness is some of Graham Duncan's writing. All of his essays are excellent, but two of my favorites are in fact letters that he has repurposed for a broader audience (Letter to a friend who may start a new investment platform; Letter to a friend who just made a lot of money). These offer generalized wisdom in a highly personal and intimate form, even if we readers weren't the original intended recipient. Similarly, Paul Graham's sensational recent essay 'How to Do Great Work' is not a letter but uses "you" over 600 times. In fact, his essays are overwhelmingly written directly to "you."
The Classic 'Audience of One'
There's a lot of wisdom about narrowing down your audience in any creative endeavor, especially to the proverbial "audience of one," yourself. Tim Urban (known for his excellent and stick-figure-filled blog Wait but Why) puts it this way in an interview with Tim Ferriss:
"I assume that my audience is a stadium full of me. I’m writing the exact post that I would be thrilled to get. That’s my focus group right there, right in my head."
I was fortunate to speak with Zach Braff about the same idea earlier this year. Zach remixed advice he took from Quentin Tarantino:
"You have to speak your authentic self onto the page. The idea of spending all this blood, sweat, tears, and energy on something that doesn't at least strive to be the most authentic story that is your voice...
Don't think about an audience; don't think about anything else but: 'What's a movie I want to see? What's my taste?"
There's a reason you see advice like this so often. It turns out that there are many people out there with your sensibilities and interests. Even so, it can be hard to accurately model how much context your audience should have, the frames that might be interesting to them, and the right way to construct your thoughts to make them most compelling even to someone who is default-interested.
The letter's ability to connect you with someone real, versus a theoretical version of yourself or others is extremely powerful. I often return to a quote from Charlie Kaufman's BAFTA speech. While not explicitly meant to do this, I think it captures the beauty of this forcing function that letters create: to share something of yourself with the world, and specifically in contrast with writing for yourself, to share something with another:
“Do you. It isn’t easy but it’s essential. It’s not easy because there’s a lot in the way. In many cases a major obstacle is your deeply seated belief that you are not interesting. And since convincing yourself that you are interesting is probably not going to happen, take it off the table. Think, ‘Perhaps I’m not interesting but I am the only thing I have to offer, and I want to offer something. And by offering myself in a true way I am doing a great service to the world, because it is rare and it will help.’”
Lower the stakes if you have to: sharing something with someone can be enough.
Second-Person Fiction: Another Audience of You
This got me thinking: what are other ways to "hack" attempts at writing and overcome this challenging notion of an ambiguous audience?
Two of my favorite pieces of emotionally resonant fiction use the second person remarkably well: Mohsin Hamid's novel, How to Get Filthy Rich in Rising Asia, and a single chapter late in Gabrielle Zevin's Tomorrow, and Tomorrow, and Tomorrow.
While not as explicit as in a letter, the use of "you" unlocks the fiction writer and the reader to overcome friction related to the perceived audience. There's something implicit about the second person that causes you to write as though you've narrowed your audience down. It's a bit like writing about yourself: with intimacy and specificity. But it expects a level of context and detail needed for your reader to embody the character that you might otherwise omit if you were writing in the first person.
It says: I am writing to this reader specifically, to you; the one who is willing to put themselves in the shoes of my character; the person who is willing to allow me to narrate their life. It says to the reader: this author is speaking directly to me; I am the subject of this story, even if I have to pretend.
Teaching and Other Mediums
Another example that can resemble the letter is teaching. While it doesn't typically apply to in-person group learning, tutoring is a good example to use as a model. And unsurprisingly, much of the best internet educational content is structured exactly like it: a teacher speaking directly to you, the student. Educational content on YouTube uses this style effectively (this is as good an excuse as ever to shout out CGP Grey).
One of my favorite podcasts, David Senra's Founders, applies this same style to a medium that's dominated mostly by conversations that the listeners get to eavesdrop on. Instead of talking to guests, David tells "you" the listener about the biographies he reads, and uses language like "back when you and I studied Steve Jobs earlier..." It's effective and engaging, but I also suspect it helps David's words to flow. He can riff (with his seemingly boundless energy) on these people that inspire him with same the lightness, authenticity, and enthusiasm he might while talking to a friend.
Back to Essays, and Maybe Making Anything Else
It's not lost on me that I've just written an open-audience essay about why it's so much easier to write or create for someone in particular. But I hope that this frame might be useful for me to feel less constrained in the future. I think that regardless of the medium (and even in business), making something for somebody specific can be a great way to start. It clears the path in front of you and allows you to move forward.
I suspect that even for essays, working outwards from writing to one person or a small group of friends, generalizing as you edit could be an interesting frame to start with. This essay was largely inspired by conversations with a few friends and a letter to one about this very subject.
I'd also enjoy reading more writing that embraces the reader as "you.” I don't think it's a coincidence that some of my favorite internet essays, fiction, YouTube content, and podcasts all have an audience of you. And I hope to explore more writing in this style myself. I'm sure you must be thinking that I've missed the perfect meta-opportunity to start. Oh, well. There's a bit of it in here. I'm just happy to be writing to you.