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I am attempting to begin writing a Substack newsletter, but I have hit a serious problem: I am a chronic, crippled perfectionist. I can't get through a sentence of any given post without freezing up and becoming unable to continue. It is the same situation with my programming; I can't work on any of my projects because I can't stop criticizing my own code. I tried taking a few weeks off of working on both writing and programming, but it hasn't helped in the slightest.

What do I do? I can't get anything done and it is really taking a toll on me. I have so many things I want to do but I can't get out of my own head and just do it. I have tried following online courses and guides, but none of them have helped.

Does anyone here have any suggestions?

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It is the same situation with my programming; I can't work on any of my projects because I can't stop criticizing my own code

Pseudo-code

The method for roughly scripting functions without bothering with working (much less 'perfect') code, is to write pseudo-code.

Sometimes partial-code, sometimes a brief description, or just placeholders –– whatever creates the bones of the project.

The goal is to create a template of the larger project while excluding the need to judge it on syntax or perfectionism – details that should evolve after the main structure is established.

By metaphor, outlining is the method writers use to create a template without getting hung up on undeveloped narrative voice, rhythm, and tone.

Outlining

You say your problem is 'crippling perfectionism' – not procrastination, and not a lack knowing what to write. I believe you. This is not a 'creative juices' problem.

You might be struggling with the wrong tool-set at this step of writing. Another metaphor: you're holding the thin-hair detail paintbrushes, but what you need first is some broad strokes to define the overall picture.

When I outline, I write in 'pseudo-code'. Some is partial prose, some of it is explanations of what's suppose to happen, and some is just placeholder text to jog my memory later. In other words, there is no format.

If I get lost into the details I could write the same scene for hours and it never go anywhere just wallow in 'tone', so I have learned to step back and place my story beats first, then connect from beat-to-beat.

It's still creative writing of course, but I know what it needs to say.

Snowflake Method

Snowflake Method is similar to outlining in that you know the broad message, but you don't know which key 'beats' need to flesh out.

It works by starting with a very simplified (reductive) single sentence of the topic:

"Sam Altman testified at the US Senate yesterday."

As you add necessary information to this too simple sentence, it will inform you what information needs to expand to create the larger article.

"Sam Altman, the CEO of Open AI, testified before a divided US Senate, advocating a government license for AI developers."

–– Add a paragraph about Open AI, another paragraph about the various viewpoints in Congress, another paragraph about what he said (this is a very simplified explanation). Keep going until the too-simple sentence (and the article) has the relevant information.

Be Utilitarian

Newsletters are not 'creative writing'. You need a practical, utilitarian system that puts structure on the page without activating your perfectionism.

I think it might be especially useful to put unadorned facts on the page, in a logical order, where it's almost impossible to be clever or decorative. It won't prevent you being a perfectionist, but it will prevent perfectionism from blocking the first steps.

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  • That snowflake method makes a lot of sense and I will give it a try. When try to write, I have been outlining before I write but I even stress over the structure of my article, so it doesn't work.
    – Duel
    Commented May 17, 2023 at 23:01
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Whenever I'm writing I have trouble getting into the flow because I'm constantly going back and rewording/editing what I just wrote, so to stop myself from noticing the problems in what I just wrote I change the font to something I have trouble reading (particularly messy handwriting in a small font size). hope this helps.

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Writing is revision

Every published novel and short story started with a first draft that had little resemblance to final version. And, only the authors and the editors and the agents ever see those drafts. This fact creates the illusion that stories from The Great Gatsby to Goodnight Moon sprang forth from the authors' minds fully formed. They did not. The authors wrote their first drafts and then revised them, often over and over. Alright, I can't comment on how many drafts it took to produce "Goodnight, Moon." But, "The Great Gatsby" to another four months of intensive revision before F. Scott Fitzgerald considered it satisfactory. Published, awarded winning authors I've spoken with talk about going through five to eight drafts of their novels, over six to sixteen months before they considered them ready for sharing with a wider audience.

The principles to keep in mind when writing is that criticism is kills creativity. Creativity is the life blood of good writing. So when I sitting down to write, I turn off my inner critic. You can practice silencing your inner critic by setting a timer to five, ten, or fifteen minutes, and then writing. Refuse to fix spelling errors. Refuse to fix mistakes. Just write. Then, do something else for fifteen minutes, and repeat the exercise. Afterwards, you can edit your writing and fix it. It may not be perfect. That is fine. It may not be good. That is fine, too. It may be trash. That is okay.

Because within this no good, less then fine, meh writing, lurks ideas and associations that your conscious mind could never access. And, those elements are what make for great writing.

Practice silencing your inner-critic to let your subconscious express itself. Once its done, you can through it away or you can edit it make make it better. But the only thing you can write perfectly the first time is a shopping list or an insincere apology or an answer on Writing@SE.

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First of all, as a psychotherapist working with procrastinators all the time, I suggest psychotherapy. You need to tackle the self-deprecating basic assumptions that drive the perfectionism, and no Q&A here is gonna solve that.

When it comes to writing, I advise you get a copy of How to Write a Lot by psychologist Paul J. Silvia. A brief summary of the basics:

  • prolific (i.e. non-procrastinating) writers have made writing a habit
  • approach writing like a job (nothing must keep you from writing, unless it is life-threatening)
  • if the blank page scares you, write anything: your thoughts, what you see, what you did yesterday, what you saw on tv, it doesn't matter as long as you make writing a habit
  • in the beginning, do not write against a deadline or any other expectations – just write, the quality does not matter
  • write at the same time, at the same place, and every day
  • begin with a minimum of 30 minutes per day during the first week; measure how long you actually wrote, divide the weekly sum through the number of days, and plan to write that long every day during the second week; in that way, slowly increase the writing time up to the maximum that feels comfortable for you (procrastinators want to avoid work, so don't set yourself up for failure by expecting to write eight hours a day)
  • if you work on a project (and writing has become a habit), do not attempt to write for more than 4 or 5 hours a day; stop when you notice you become unfocused or you no longer know what to write or the quality deteriorates below your usual level: your "writing battery" is empty (research shows the maximum effective work duration per day is between 4 and 6 hours, and Silvia found most writers stay below this maximum)
  • research, planning, outlining etc. are all part of writing and should happen within your writing hours (just like meetings, billing, and answering the telephone are part of your job and you don't do it in your free time)

My personal addition:

  • do not set yourself performance goals (like daily wordcount) that you can fail and that make you afraid, but time goals (i.e. work hours); think of a worker with a punch clock: as long as you are at your job, you are fine
  • experiment with outlining versus discovery writing; if you want, partake in NaNoWriMo (even outside of November)
  • remove any distractions (phone, internet): writer I believe it was Neil Gaiman who said he wrote in a shed in his garden where he was free to do nothing (that is, no pressure to write) but boredom usually made him begin writing eventually, because there was nothing in the shed except his writing tools (no internet, especially) – psychologist Roy F. Baumeister summarizes his years of research on willpower with: the best method for self-control is to avoid situations where you have to exert self-control
  • do not endlessly polish one work to reach perfection; writing requires learning, and the first of everything is rarely good (no apprentice carpenter will create a master cabinet in his first year, no beginning jogger will win the New York marathon); instead, put your first novel away and write the next book, i.e. train like any other artist or craftsperson
  • get a bread job that you enjoy and don't plan to live by writing; on average, writers write 3.24 books before their debut publication; average age at first publication is around 40 years old; on average writers in the US earn $6,080 per year by writing
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As someone who writes both code and fiction, I can reassure you that a lot of us feel this way from time to time. Ultimately though, there is no such thing as perfection in writing - it's an intensively subjective discipline.

Code has more rigour, and measurable ouputs like performance stats and cyclomatic complexity, but there's still many valid solutions to the same problem.

You need to practice a mindset of improving quality through iteration in both cases. When you have a blank screen, allow yourself to "rough out" a first draft. Turn off your inner critic and say to yourself "this is just scaffolding I need to build in order to progress to the next stage. I will rip it down later, and nobody else ever needs to see it".

Artists start with sketches, writers start with drafts.

So, if I'm on fiction, I have "writer mode". Writer mode is a genius, with no inner critic. You simply write whatevers in your mind straight onto the screen, no revising, no re-reading at this stage. Even if you just write bullet points or comments to yourself, that's fine.

Later, you put on your "editor hat". Now you can go back and hack through whatever you've written, improve it and rewrite it. Continuing doing this stages, applying more polish and perfectionism with every edit. Eventually, you'll reach a point where you're happy enough with it.

For code, write a solution that works, even if it's a single-method mess of comments, nested foreach loops and unholy variable meltdown if necessary. Write a few unit tests that confirm the code produces the right results. Go back and begin seperating out code segments into their own methods. Ensure the tests still pass. Continue revising until your code is clean, concise and clear in intent.

For both disciplines, accept that you are on a learning curve with no fixed endpoint. You cannot 'complete' either, just like you cannot 'complete' life (well, except maybe dying?). Over time, you'll find it easier to create rough drafts which are closer to the final iteration, but even this varies from day to day.

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  • Your advice for coding is actually really good, thanks. I actually got something done using your advice, albeit it was a very small task.
    – Duel
    Commented May 17, 2023 at 23:02

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