Writing My First Essay, Project Serialization, and Expectations meeting Reality

The Writing Process & Project Serialization

Earlier this year, I found immense joy in discovering people online and digging through the archives of their mind via their writings. In doing so, I picked up interesting mental models, discovered valuable content, and even made a few friends.

Inspired by this, I decided to start participating in this magic of the internet by creating my own little space online where I can share ideas (and clarify my thinking in the process), spark conversations with interesting people, and support others who are playing their own game.

But where to start? Did I need a website? A Medium? What to write about first? What do I have to say that hasn't already been said? Unsure of the answers, I decided to just start. After all, starting is always the hardest part.

Naturally, I started in hard mode with an unlisted blog and a self commitment to publish something every day. Well, I made it about a week before I started skipping days, and then ultimately stopped working on it altogether. Fail.

A few weeks later I decided to try a different approach and started my newsletter Inputs, Outputs. When I sent out the first email, I didn't have a real game plan for it. I just thought that it'd be a low friction place to start and allow me to turn my content consumption into creation. A few weeks later, I had the process down to get it out every week. Hell yeah. Step by step.

Feeling good about getting the newsletter out consistently, I decided to circle back and try my hand at an extended essay. What would it be about? Despite my giant backlog of half-baked ideas, I decided to slay my dragon and write the Unique Shared Experiences post — something several friends have encouraged me to write for about 18 months.

18 months in the pipeline is a long time. Every time I thought about it, I'd put it off. Why? Not sure. Maybe fear? Lack of clarity? Whatever block I was avoiding, I knew that I'd be cheating myself if I wrote anything else first.

So off I went.

Honestly, I dicked around for the first two weeks. I'd open a doc, start typing, and then let my mind wander on whatever interesting observation I had that day. This led to lots of words, but no substance. It wasn't until I listened to a great podcast on Project Serialization arguing that you're better off starting, grinding, then shipping one thing at a time. This way you get the gains of focused attention, accomplishment on delivery, and are less fragile to outside factors that may interfere with your project plans.

Since what I was doing clearly wasn't working, I decided to try serialization. Then after 50+ hours (yikes) of writing, editing, wrestling with my ego & expectations, re-editing, soliciting feedback, and staring at my screen, I finally shipped it. Finally.

It was fucking brutal though. I had all of these expectations for how it would be perceived leading to an obnoxious number of edits and rewrites.

Then last Sunday, when I published it on Twitter, I had a tinge of anxiety about how it would be perceived. The end result? A few dozen readers, some engagement on Twitter, but that's it.

Yup, that's it. Not even a "good job bud" from my Dad.

I felt so silly. What the fuck was I worried about? The internet is an abyss of content and at the end of the day, no one cares (broadly speaking). Not in a negative way. It's just that there's simply so much going on that people don't really pay attention.

No one cares that it took 50 hours vs 5. No one cares that the article was a challenge to write. All that people care about is the output...and even then, not so much (especially for writing projects). Seriously, it's simply not a big deal to anyone but me.

This realization is fantastic and I don't think you can get it without actually going through this process of meeting your expectations with reality. By getting this out (with all my expectations), I've lifted a huge burden off my shoulders. Publishing served as a forcing function to get me to realize that no one cares. Now I can continue to write and be so much more relaxed about it.

So that's what I'll be doing — writing consistently without the ego. In fact, I've split my writing projects in two — first I have Inputs, Outputs which is where I'll continue to share content I've found interesting each week while including essays like this. Then, I'll be chunking away at an extended article series I'm writing on my post-Superhuman journey of clarifying goals, values, and mission.

Outside of this burden being removed, I've found that getting started with this sort of thing comes down to setting up good systems for yourself and reducing the friction. Writing every day to an unpublished blog had good intentions, but the lack of accountability, habits, and systems (with feedback loops) led to failure. Writing a newsletter that takes me an hour to compile based on content I've already read that people will expect every week? Simple (but not easy).

Then stacking writing projects and sharing them to that newsletter? Good next step.

Now it's just a matter of continuing to ship consistently.

Onwards.