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What I Learned From a Year of Writing

This is my 80th piece. The 25th of November marked 1 year of consistent writing. Eighty doesn’t feel like much at all. Especially because 50% of it is 💩. I know that from the perspective of year 2, that’ll seem generous. The percentage of crap is probably higher. I re-read old pieces in my spare time and sometimes I cringe really hard. Other times I’m like, woah, did I write that? That’s pretty good!

Regardless, committing to writing every week for a year is no small feat. I wanted to quit at least 5 times because my writing felt lame and uninspired. A chore that caused anxiety. But I couldn’t, well, wouldn’t quit because I committed to writing for a year. I had done Landmark earlier in 2022 and one of their main tenets was I am my word. As I do, I took it way too seriously and kept my word. As it’s trendy to say before giving the most ridiculous advice, this is not writing advice [proceeds with advice].

Usual advice vs my process

Most writing advice is:

Do a brain dump → edit, edit, edit.

My process is:

Write a sentence → edit → another sentence → re-read the first and edit the second sentence → write another sentence → re-read the first two and edit the third sentence etc.

I edit as I write because it gives me clarity. Then I edit again once the piece is finished. Then edit some more a day later.

I write my newsletters 2 weeks in advance and I keep coming back to re-read in the meantime. By the time this comes to your inbox, I’ve read and edited it at least 7x. Writing is mostly editing. Editing is mostly deleting.


Experts (?) say that designing a beautiful article requires short sentences and lots of white space for the user to feel good. It supposedly makes your words feel more powerful. It makes sense at face value given that collectively our attention span has shortened to that of a goldfish. And a well-designed product is more pleasing than a crowded one 👇

Compared to 👇

However, as a reader, I hate short, one-sentence paragraphs. It makes me feel like I need to refocus after every sentence. Like I’m getting punched in the face with unfinished ideas and before I can regroup, there’s another one-sentence punch coming. I’m sticking to the white space advice for now but my hunch is that it’s bad advice. It’s for writers like me who don’t have the skill to express themselves well. I read content with long paragraphs all the time provided it’s good writing. That’s a mastery level long-paragraph writers have that I don’t yet. What I aim for though is for my writing to sound conversational. I think that makes it readable.

Writing for better thinking

“If you’re thinking without writing, you only think you’re thinking.” — Leslie Lamport

This could not be more true! I think I have an opinion or an interesting perspective until I have to write it down. It’s difficult to express yourself in a coherent, clear fashion and not get humbled. An abstract stream of thought I called an opinion in my head seems like a half-drunk ramble on paper. I’ve grown the most this year because I was consistently writing. Ideas I held as true were scrutinised under the microscope of ‘You have to explain it in a way that makes sense to the reader.’ Why do I believe what I believe? I don’t know. I was too lazy to inspect it before I started putting pen to paper. Writing is a process of fine-tuning thinking. It allowed me to change my mind on quite a few topics. As Paul Graham put it:

“Ideas [in your head] can feel complete. It's only when you try to put them into words that you discover they're not. So if you never subject your ideas to that test, you'll not only never have fully formed ideas, but also never realize it.”

How I measure progress

I learned early on that measuring myself by the subscriber count is going to be painful. Extrinsic motivation didn’t work because I made writing a long-term commitment.

  • I’d rather have a small but engaged audience. So every 3 months I delete anyone who hasn’t read my newsletter in a while.
  • It’s best to set intrinsic value measures. Like what I shared earlier about personal growth. I grow because I write. That’s motivating for me.
  • Another measure is how many ideas expressed earlier I’ve improved on or now disagree with. That’s where re-reading my earlier material comes in.
  • The last metric is am I enjoying this? Most writing advice is — ‘target the pain point of your audience and provide the solution’. I’ve tried that at the beginning and it’s not for me.

As Morgan Housel says: “Write the kind of stuff you like to read. Writing for yourself is fun, and it shows. Writing for others is work, and it shows.”

Is writing worth it?

For me, it’s right up there with exercise and eat well advice.

Many people assume they’re bad at writing because it’s hard. This is like assuming you are bad at weightlifting because the weight is heavy.
Writing is useful because it’s hard. It’s the effort that goes into writing a clear sentence that leads to better thinking. - James Clear

Instead of pushing myself to be a good writer, I’m now pushing myself to be a better writer. If I keep going, I will at least get better by 1% every year. Thanks to writing, I’m a better thinker now than I was a year ago. I hope you take up writing too.