Debugging Writer's Block

Published: 2021-10-08
Tagged: essay writing

The hardest part of writing for me is dealing with writer's block. It appears almost every time I sit down to write–I'll have everything ready: the time, the space, and the super exciting idea I want to share. But right then, the words won't come! And when they eventually do, they come out in awkward strings that beg to be deleted, but I keep at it.

Soon, though, the excitement surrenders to frustration accompanied by a steely determination to get to the finish line. Predictably, this produces writing that feels dry and forced, leaving me disappointed and exhausted. Mistaking the symptoms for causes, I tried style guides: "Style: Lessons in Clarity and Grace" by J. William, "The Art of Plain Talk" by R. Flesch, and, of course, Strunk & White's "The Elements of Style."

While my writing became somewhat better, the process remained frustrating and slow, yielding an essay once every 6 to 8 weeks. But I kept going at it, hoping that sooner or later I'll discover some advice or feedback that will remedy my problem. And then, one day, it happened–I stumbled on an interview with Jerry Seinfeld and because I love his comedy, I gave it a listen. Unexpectedly, at one point he shared this advice about writing:

  1. Set a hard time limit on your writing sessions.
  2. Reward yourself after each session.
  3. When you finish a piece, don't show it to anyone for at least a day.

It seemed simple, and having little to lose, I decided to give it a try. Long story short, it worked pretty well–I wrote about 1.5x to 2x faster. What's more, the process became fun, which made the output less dry and forced. It was great! But after enjoying this state for some time, I got to thinking: how does this advice work? And can it be applied to other problems?

Admittedly, my understanding of how the mind works is pretty shallow. It's mostly informed by sources like The Elephant in the Brain, Kaj Sotala's posts about IFS, and van der Kolk's book about Trauma. There's also quite a bit of bias that comes from writing software, eg. "everything is a system!" But anyway, here's my working theory about why this advice worked for me:

  1. Writing is hard[1]! It takes a lot of time and effort to get better. And even if you do produce outstanding work, there's the uncertainty that, at the end, nobody will read any of it.
  2. System 1 takes notice of this and decides it doesn't like the upfront investment and unlikely payoff. It would prefer something immediate and sure, like cleaning or exercising
  3. System 1 communicates this through emotional resistance, which in my case took the form of guilt–guilt about not being good enough and wasting all these beautiful mornings and evenings.
  4. The guilt feeds into the feeling of frustration, making it more difficult to write, which produces more frustration–effectively creating a death spiral that should get me to do other stuff.

Now, here's where Seinfeld's advice kicks in:

  1. Setting hard time limits generates feelings of accomplishment after each session. Previously, when my writing time was unbounded, I always felt I could have done more–no matter how much I've already done. But with limits in place, I choose how much to do (hm, preference curves?) and then move on to other tasks, guilt-free.
  2. Rewarding myself after each session physically reinforces the feeling of accomplishment. Though it felt like cheating at first, it made me reflect and realize that this truly is a marathon.
  3. Keeping a piece of writing to myself for a day allows me to meditate on it: savor the feeling of finishing something, and consider the process and what it produced. Afterwards, it's much easier to digest external feedback.

In other words, Seinfeld's advice makes the payoff from writing feel certain and predictable. All you need to do is sit down, exert a reasonable amount of effort, and then enjoy a job well done. Then, when you're ready, repeat the process. As a result, System 1 doesn't worry about wasting time and energy, so it stops emitting guilt signals.

I believe this can be generalized to: figure out what is creating internal resistance, then dissolve it by experimenting with different ways of seeing a problem. For instance, let's say you're nervous about attending in-person meetups. Let's also assume that there are no physical reasons for this–it's in a nice part of town, nobody there is contagious, and everyone there is a decent human being.

Now, listen closely to what System 1 is trying to say. Is it afraid you won't make a good first impression, perhaps because of your looks? Or is it worried that others will find you uninteresting? Or... well, you get the idea. Next, try different ways of looking at the situation. Do you have to make a great impression on every single person you meet? Does everyone have to find you interesting? How would it look and feel like if just one other person visibly enjoyed your presence?

If any of the above sounds familiar, that's because these are fairly well known ideas from LessWrong. The first bit, the one about listening to System 1, is pretty much a combination of Noticing and Focusing. The second bit is close murphyjitsu. And yet, even though I had practiced these techniques beforehand, it still took a random podcast interview to get me on the right track. Shouldn't have I debugged my problem sooner?


At the meta-rational level, I think I failed to apply enough Dakka. So while I applied murphyjitsu to the problem of dry and forced style, I completely missed the larger problem of emotional resistance. And even though it still took me weeks to finish one essay, I mentally marked my problem as solved. Had I used more Dakka, I probably would have spent considerably more time looking for the right problem to solve.

What I took away from this adventure is that, first, it's helpful to think about applying more Dakka–and then double it. It might force you to redefine the whole problem. And second, don't underestimate how influential System 1 can be. Here, it may help to take the outside of whatever is giving you trouble–it could simply be yourself.


1. We're all taught to read and write in school, so it seems that writing should be easy, right? That's what I thought, but then I realized how different school-level writing is from the stuff you can find in books or magazines. This is because at school we are taught to write by formula–the report, they five-paragraph essay, etc. Simplifying it like this allows us to teach young humans a baseline level of communication skills. And remember that, in school, teachers are paid to read whatever students' produce.

But in the real world, where time and attention are scarce, ignoring inputs is the default. Here, all the dull, lifeless, and boring writing withers away as if it never even existed. Here, to survive, an essay or story needs to be interesting and put together well. That's why the quality gap between school-level and real-world writing is so great, and why it takes so much effort to cross it.


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