How a daily writing habit sparked my creativity

5. Million. People.

I couldn’t believe my eyes. 5 million people had seen a piece that I wrote. It was spontaneous. I just wrote that post because the topic was interesting to me, and I promised myself I would write something that day. 

I started blogging when I was 15 years old. I remember nights where I wrote blog post after blog post, riffing on my favorite topic at the time (technology and cool gadgets). It was great fun. So I figured when I’d pick up the habit again over a decade later, it would come naturally.

It didn’t. In March 2020, I tried writing a post every day at Medium, and I failed miserably. It just didn’t work. But this time in 2022, it did. Here’s what I did differently:

Passion met profession, and things got weird

While I’m lucky enough to make a career out of writing, intertwining passion and profession comes with its own challenges. For example, I work with software companies as an editorial director, which is similar enough to writing but very different. In “Big Ideas, Small Papers,” I wrote about writing faster—sometimes in 15 minute chunks—and publishing quickly, without as much editing as I’d like:

As an editorial director, publishing this type of writing feels improper. It’s so far from my professional definition of acceptable, that it feels embarrassing to publish. It’s certainly not my best work—not well-considered, could use more fact-checking, and with really rough sections. It’s more a confession than a curation, a burst of ideas collaged together in a post. 

As an author, I also know that this type of writing is essential to the creative process. I intend for this blog to be considered the same way someone might tweet; ephemeral, impermanent, and delete-able. It’s like a stream of consciousness (like Susan Orlean drunk tweeting).

Looking back now, I realize a lot of what went wrong: I was trying to do too much with each post (e.g., coin a new term, try to make money at Medium, etc.). More importantly though, I was trying to finish a new thought process every day, which is naturally impossible. 

Writing to start, not to finish

As I got better at my job, my standards for good and complete writing improved. Naturally, I also grew to treat every single thing I wrote like a finished piece. But more recently, thanks to Venkatesh Rao and Sonal Chokshi, I think about each blog post I’m writing as a starting point, or at most a development point. Each post is a very blurry snapshot of the creative process

 #The100DayProject started again on February 13, 2022. The day after that, I decided I started blogging each day again, and made sure to keep it short and sweet.

Picasso has said, “If it were possible… there would never be a ‘finished’ canvas but just different states of a single painting.” And Walter Isaacson writes in his biography of da Vinci, “Relinquishing a work, declaring it finished, froze its evolution. Leonardo did not like to do that. There was always something more to be learned, another stroke to be gleaned from nature that would make a picture closer to perfect.” 

Every blog post is just a version of an idea, a potential new starting point. Just like Marginal Revolution or Seth Godin’s blog, or Fred Wilson’s blog, most of my blog posts will not be complete points. As a result: no conclusions forced, no new ideas necessarily, just here’s something I’ve been thinking about. (I like swyx’s three strikes rule as well.)

The practice has created a lot of energy for my writing and ideas. It’s something of a self-fulfilling dynamic: the more I write, the more I can write about.

Uniting the judge and the madman

The nature of creativity is dualistic. You need to start and finish, adapt to chaos and constraint, use spontaneity and structure, amongst many other balances. One of my favorite illustrations of this comes from professor Betty Flowers, courtesy of Rachel Jepsen’s “Chaotic Good”:

What happens when you get stuck is that two competing energies are locked horn to horn, pushing against each other. One is the energy of what I’ll call your ‘madman.’ He is full of ideas, writes crazily and perhaps rather sloppily, gets carried away by enthusiasm or anger, and if really let loose, could turn out ten pages an hour. 

The second is a kind of critical energy—what I’ll call the ‘judge.’ He’s been educated and knows a sentence fragment when he sees one. He peers over your shoulder and says, ‘That’s trash!’ with such authority that the madman loses his crazy confidence and shrivels up. You know the judge is right—after all, he speaks with the voice of your most imperious English teacher. But for all his sharpness of eye, he can’t create anything.

Jepsen adds: 

For Flowers, chaos isn’t only necessary to create anything, harnessing chaos is possible and our ultimate creative state. Self-editing is part of the creative process, but the initial idea, the first spark of truth that ignites a new piece of writing and fuels the remainder of the process, is born out of chaos (just like the universe!).

At my blog, the only criteria is for me to have fun, and it’s acceptable if some of the posts are only the beginning of a thought. A well-considered thought process requires tons of revisiting, revising, and editing. It’s not something any person can start and finish in one day. What is doable is taking a snapshot of a longer process, starting a new thought process, or adding to a layer of a previous thought process. 

For my finished work, I’ll share that in my business, in my books, and at Fast Company.

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