Learning to Write (on the Internet)

I've had the same New Years Resolution for the last three years. Write More. And every year, for the past three years, December would roll around and I would have inevitably...well...not written. There were a series of impediments that always seemed to stand in the way. Not enough time. Not knowing what to write about. Fear of writing uninspiring or boring essays.

This post marks the 12th essay I've written & published in 2020. One post a month (though I started late and crammed in December). I have finally fulfilled my writing resolution of 2017 🙌

I've found writing to be an incredibly fulfilling way to spend my quarantine, and I want to share the practical lessons I've learned from (most failing) to develop a writing habit. There's plenty of good resources on how to write (recommend here, here, here, here), so this isn't meant to be a comprehensive how-to guide for starting a blog.

But if you're thinking about starting a writing habit in 2021 or stuck in a rut on your writing, here's how I overcame it.

Multiplayer Writing > Single Player

There was one takeaway that rose above the rest: writing is better when you write with others. Your essays will get better with crit and revisions, yes, but the experience of creating the essay is more fun when you write with friends.

The trope of the recluse writer returning from the cabin with a masterpiece in hand is eclipsed many-fold by the press rooms, the writers workshops, the smokey Parisian writing clubs. For many years I thought I needed a cabin and some quiet, when in reality I needed a crowded and busy writers’ room.

We started a writing community in our work slack channel for people trying to write more (#yolo-writers). It became a place where you can share a rough draft and get honest feedback on it. It created accountability (and FOMO) when everyone is sharing their drafts and publishing. It's a messy exchange of ideas on all kinds of topics that people are thinking about, but there is no shortage of new connections and ways of thinking about the idea.

Having a personal "editorial board" is helpful for a few reasons. The first is that it builds confidence, because you share your post with someone who is not you and they will typically have (at least some) nice things to say. The second is that they help you unpack the important pieces of the post.

Our #yolo-writers channel turned writing from single-player game into a multi-player game.

Build Your Writing Funnel

One of the ways a "funnel", or series of steps you need to go through to get your ideas out into the world:

  1. Idea - first you need to pick something to write about, which can be a challenge if there are no constraints.

  2. Draft - this is where you take your idea and bang out a first draft. It requires hands on the keyboard, good space to think, and a touch of inspiration

  3. Edit - You need to take what is unlikely a good first draft and turn it into something that you think is valuable (either to the reader, or yourself)

  4. Publish & Share - You need to hit the Publish button, and see the post live on the internet, and share it with folks

By thinking about your essays as a funnel, you can figure out where you are jammed. Do you not have enough ideas? Are you not converting those ideas into drafts? Does it take too long to edit them?

Here's a snapshot of my writing funnel stats. You can see that I have a backlog of ideas for blog posts, a bunch of active drafts, a few in the Editing, and 11 published.

This is a pretty different approach to writing than what I've come across in school or work. In those contexts, there is a clear assignment and corresponding topic. There's a due date. With personal writing and essays, all of these constraints are relaxed so you can pick ideas up write, and edit as you please.

Ideas 💡

I have many more Ideas than I have Drafts. That's because (a) many of my Ideas are not actually interesting enough to warrant an essay and (b) it's a lot easier to add an idea to my list than to write an essay.

I like to have a place to put ideas as they come up. I have a Notion writing board and I'll create a new post with the headline as the idea, and link to whatever made me think of the idea. Sometimes I'll add some initial thoughts, but at this point I really just want to capture the idea and return to it later when I'm ready to write.

There's a great segment on This American Life, where Ira Glass goes into the writers room at The Onion. The writers go through a brutal process every week of creating over 600 headlines for the satirical paper, only to whittle the list down to 16 articles that actually get written. The problem is that many of the headlines are funny on the surface, but there's no depth to the joke.

I've found the same with essay ideas. By the numbers, only about 1 in 5 of my ideas have actually materialized into an essay. This isn't from a lack of trying, many of them just don't go anywhere. Which means that ~80% of the ideas I think are good at the time, turn out to not be viable ideas at all!

Ideas will come throughout the day — on a run, in a meeting — so it's good to have an easy way to capture and figure out if it's a good idea later.

What topics should you write about? "Write whatever you want!" is not super helpful, but is the reality when starting out. This turned out to be the biggest impediments for me when getting this project off the ground. I didn't think I had a unique perspective on a particular topic. But I was pleasantly surprised to see how that vague concern came crumbling down.

It turns out that nobody sees and thinks about the world the way you do. Every thought and problem you've solved is unique to your experience. By sharing your experience, you can hear from others who have faced similar challenges and came to different conclusions, or can use your experience to guide their own.

There is a specific type of idea that I've found really fulfilling, and easy to write. "Project" posts document a specific project that you've attempted. It can be big, or small, functional, creative, engineering, art, analytics, home improvement. It doesn't matter. Abstract Capital and Squatbot are two examples this where the bulk of the work is in working on the project. Just make sure you document as you go!

Draft ✍️

Once I had an ideas board going, I'd pick an idea and write a first draft.

Your first draft is going to suck. You will probably despise the idea by the time you are finished with your first draft. You will regret your decision to write at all. It's pretty painful.

As I write these words, I am filled with self-doubt. Is this point I'm making here so obvious? What do I know about blogging? It's natural in the draft stage to feel impostor Syndrome. Push through.

The best advice I can share is to think of this draft as 30% "done"-ness of what you will eventually publish. This can help alleviate some of the self-inflicted doubts and writer's block that comes with aiming for perfection. Your goal is to sketch out the idea, not to write a Pulitzer-winning piece.

I've found weekend mornings — after the first cup of coffee begins to kick in — to be the best time to pull up my ideas board and start drafting.

Edit ✂️

Next comes the editing process. I like to let my Drafts air out on the shelf for a day or two after writing. I'll re-read and edit for clarity, before sharing with my "editorial board" (aka #yolo-writers)

At work, we created a slack channel called #yolo-writers with a few folks who were interested in writing more. Whenever anyone is ready for feedback, they share in the channel and a few people respond with feedback. We loosely follow the "ABCD" framework for giving feedback:

Here's an example of the type of feedback you can get in #yolo-writers (from Osama):

Publish & Share 🖨️

Hit the button! I am admittedly not great at marketing what I write. I write because it's personally fulfilling and helps clarify my thinking, so I'll point you to some strategies that Lenny Rachitsky recommends on building his newsletter community. But it's a really great feeling when someone references or engages with something that you wrote. Remember that feeling next time you're procrastinating or feeling embarrassed about a draft.


Keep Your Stack Simple. KYSS. I repeat: Keep Your Stack Simple.

There was a point during the year where I was running Google Lighthouse tests to figure out how to optimize my page load performance for a Next.js app running on Vercel powered by a Notion backend. I wanted some analytics so I got Segment implemented and built a dashboard in Amplitude.

Worrying about my writing tech stack turned out to be a very good way to distract myself from actually writing. This is a common trap I've seen others fall into. My only advice is to recognize that this is a means of procrastinating, take a break instead of falling down an optimization rabbit hole, and come back when you're ready to write.

In the end, I simplified:

There's a bit of copy-pasting between Notion —> Substack to get a post live, but I like being able to keep the Writing Funnel on a board in Notion and prefer the editor.

Write for Your Why

There are a lot of reasons to write more. It can help clarify your thinking, sharpen your ideas, build your community, release the pent up ideas in your brain. Reflecting on the reason why you're picking up a writing habit can help quell the internal excuses that are preventing you from doing it. At the end of the day, the why is personal.

If you are just getting started...don't write for others, write for yourself! The biggest mental blocker I had was in trying to fulfill some vague expectation of (future, imaginary) readers...when in reality, the value came from the messy exchange of ideas (internal and external) that is writing on the internet.

I hope my essays help others in some small way. That they can apply an idea to a problem in their life. But if they don't, I am 100% content to have written it down and shared.

And for those who are planning on writing more in 2021, I wish you the best of luck. I am happy to brainstorm, edit, or commiserate anytime.