On Frustration

I wrote two separate pieces that I thought would become this week’s letter, but I scrapped them before I was finished. Each of these pieces devolved into a rant about what was going wrong with a painful decision point I had at the beginning of the week. This frustration became my creative rut. It’s a series of second guesses given by a very harsh, inner voice.

I started writing the first paragraph of the first draft, and really hated it. I deleted the paragraph and started over, but the writing sounded worse. The thing I’ve come to compromise about longer format writing in the past few months is that deleting a whole paragraph, paragraphs, or almost the entire piece is okay. In fact, I encourage it because it allows you to go back, read the piece with the deleted text and recognize what’s missing from it. Also, since you’re not looking at that bad paragraph, you’re not going to use that as a reference. As the saying goes, out of sight, out of mind.

I learned from this first draft that I shouldn’t try and shape writing around a quote. I included a stanza from a song and tried to tie it together. But I re-read the quote and I re-read the subsequent paragraph; they were not saying the same things. That made me feel like the core idea was jumbled and I really don’t know what I’m supposed to say.

The placeholder title didn’t help either. In school, they teach you how to write a generic thesis before your write your essay. However, in practice, my thesis usually emerges after writing for a bit and trying to recognize what my piece is about. For example, in this piece, the thesis is trying to dissect what is so difficult about writing. In my first draft, it started as how to tear down barriers, and slowly turned into a piece about how to come to grips that one day, you’re going to die, so you should use that to stop fearing things you have no control over. Eventually, the piece started ranting about the issues in my personal life, and I know how no one wants to hear someone bitch in a longford essay. That’s when I decided to scrap it and start over.

I know I’ve written about this before, but I love revisiting this concept of shitty first drafts. Anne Lamott introduced it in her book, “Bird by Bird”, an excellent guide to writing that I’ve read at least twice. The problem that I encountered with this first draft was sheer frustration that I wanted to write something meaningful and beautiful, but turds kept coming out no matter how I tried to edit the piece. The second draft was getting better. Initially, it sounded great. I trudged along, knowing my writing was a work in progress and would need severe editing, but it didn’t matter because I was churning paragraph after paragraph. When I would finish the piece, I would go back and edit those sections. And then, nearly finished with the piece, I start ranting about the discomfort of this week’s events again. It was supposed to be about networking, which quickly turned into how to build meaningful relationships, which quickly turned into why a personal relationship of mine went south.

In hindsight, prep work may have helped with these pieces. However, I recognize if I put too much time in prepping a piece, like making outlines or brainstorming ideas, the less I would actually want to write about that topic. I start drafts because I know they would at least give me a prototype of what the piece could be. In Robin Sloan’s last newsletter, “Primes”, in late March, he showed a screenshot of all the drafts that he had for that piece. His Gmail inbox, shown below, has at least 20 ideas for the drafts or things he wanted to share, but didn’t make the cut. When I saw that, I was amazed that I’m not the only one who has a troubled time sticking to one topic. The drafts aren’t all bad news or failed starts. They also have some idea that I cannot yet figure out, and when I do, it will be addressed in a later letter.

Robin Sloan on Primes newsletter drafts

I write all of my letters in Evernote which has this feature to look at past revisions of a note. If I ever wanted to, I can re-read a draft and see all of my deleted sentences and paragraphs. All of this data is saved upon future investigation on the topic.

Looking at my the sidebar where all the notes live in my “Drafts” folder, and there are at least half of the notes that will never see the light of day. They’re a constant reminder to tell me writing drafts and crafting ideas don’t get much easier. In a way, I want it to be like that because if it was easy, I wouldn’t really enjoy the activity. It calms my mind knowing frustration is part of the process because I know there’s always something I need to improve.