Aug 31, 20213 min read

Starting over

My struggle with perfectionism, i.e. how to publish a blog post once every 3 years.


I don’t know how relatable this is, but I have two deeply-ingrained habits when it comes to communicating online:

  1. I relentlessly edit all forms of written communication, such as Slack messages, Github PR comments, and email. Immediately after I send something, I go back and apply little irrelevant edits, even though the original message communicated my point just fine.
  2. I’m a hyper-lurker in all my online communities. Even in the rare cases I have something unique to contribute, I generally start typing a response, get halfway through, then close my browser window.

I suspect that these habits stem from an insecurity around publicly looking stupid, so I censor myself as a defense mechanism. After all, if I never express my opinions, I can’t be wrong! Flawless logic.

These habits had a toxic influence on this blog’s sad 6-year history. When I started writing, my hope was to become a superb teacher. I carefully considered my “target audience” of programming newcomers, only posting things I felt they would find helpful. This mindset produced three bad outcomes:

  1. I didn’t write unless I had something truly insightful to say. Note that my standards for “insight” were nothing more than a stab in the dark since I had no readership.
  2. I seldom wrote, so I never hit a stride, nor did I improve in proficiency or comfort with the process.
  3. What little writing I did was almost entirely devoid of my personality and inner life.

A few years ago, I read James Clear’s book Atomic Habits, and his story about the proven relationship between practice and art struck a chord with me. A photography professor at University of Florida divided his students into two groups, a “quantity” group and a “quality” group. The quantity group was graded solely on the amount of photos they produced and submitted. The quality group only needed to submit one photo as close to perfection as possible.

In the end, most of the best photos that the class produced came from the quantity group. So it seems great art is about consistent producing and iterating rather than obsessing about perfection.

I struggle to relate this story to writing, since writers have a limitless capacity to edit their work. Indeed, this used to be my writing process:

  1. I brainstormed ideas, rejecting 99% of them as too unoriginal or trite
  2. I produced a rough draft for my 1% idea in a day or two
  3. I edited it for several days, sometimes even weeks, after that, trying to get as much feedback as possible from friends and family
  4. I got in my head about whether anyone would find anything I say valuable
  5. I scrapped the post

There’s not enough motivation in the world to keep me going through a more than a cycle or two of this process.

The questions I want to answer going forward are: when am I done with my posts? How do I best improve as a writer and teacher? I’ve seen enough to believe the answer involves caring less that I’m being insightful, unoriginal, or uninteresting.


I’m making the priority for my blog the practice of sharing my thoughts. Someday I’ll need to find a better balance between editing myself to produce premium-quality work vs. getting used to sharing my thoughts publicly. For now, I’m going to optimize for the latter.

Who is this blog for then? Who’s my “target audience”? There’s value in the answer primarily being “me”. I love the idea of capturing my beliefs about life and work, being able to look back later at the way I’ve grown in my thinking and skills. Someday if I ever develop a readership, which no longer matters to me much, I hope it’ll give my readers a connection to who I am.

Before I redesigned my blog, I toyed with the idea of removing publication dates. I was embarrassed by the infrequency of my writing. I see now that was simply another way of censoring myself. I’m choosing to leave them up as a means of honesty, and I’m betting on a more consistent and fruitful future of writing.