What I've Learned From Writing 100 Newsletters

This week marks a big milestone for me: 100 newsletter issues! 🙌🎉 (Go sign up if you haven't already! Or go check out the archives of the last 100 issues!)

Am I an expert at writing now? 𝔸𝔹𝕊𝕆𝕃𝕌𝕋𝔼𝕃𝕐 ℕ𝕆𝕋. But I have learned a few helpful things along the way:

Writing happens all the time, all around you

When I started trying to write more, I was under the impression that writing was Serious Business™ and happened mostly while looking suitably thoughtful in front of a keyboard. I felt I needed something like Thoreau's cabin and King's routine to produce real work.

However, I've come to realize that a lot of my writing DOESN'T happen at a desk — it's in the ideas that bounce around in my head all week and the gentle, intentional pursuit of them. It can be an idea that occurs during a walk, a stray thought in conversation with a friend, or a series of events that sparks something. If I observe where my thoughts go and press into them, THEN when I sit down at a keyboard, I have something to work with.

There are still times I sit to write and there's absolutely nothing there, but the more I intentionally observe my thoughts and patterns, the more my subconscious helps push ideas to the front.

Writing helps me think

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

— Leslie Lamport

When I try to capture an idea with words, I begin to see the 'shape' of it. Is it full of holes? Is there a special seed, but a lot of cruft? Is it a strange and weird thing that should never see the light of day? (I have a whole drawer full of those...) Writing it out creates a more concrete concept than simply letting it float around—it forces me to be more structured about my thinking.

Consistency really is key

"Write consistently" is probably the #1 recommendation of writing advice, and well ... they're not wrong! The more I write, the easier it becomes. Publishing short thoughts every week creates an accountability contract with myself that forces me to write, even on the weeks it would be much easier not to.

Yet it can still be a struggle to keep coming back, and I've had to give myself some grace on busy weeks. I've written before about struggling in the gap, but I like this advice from Jeet Mehta about the WHY:

"If you’re in it purely for the promised land of love, praise, followers, and fame from millions of people - it’s impossible to sustain. In every field, it takes years of practice, repetition, and “failed performances” before the first hit."

— Jeet Mehta

The WHY and FOR WHO of what you're doing is very important. Approval and admiration of others, while very natural and tempting to fall into, is a horrible metric for... pretty much anything.

Rather, I've found that when I write for myself, or perhaps that one person who has the same very specific problem, it's liberating and much easier to keep pressing through the struggle!

The bar is lower than you think

I was also concerned when I started writing that I wouldn't have anything unique or worthwhile to say. I was encouraged by this post by Jeremy Keith, who implores us all to remember that the combination of our perspective and experience IS unique to us.

"In other words, while it seems like there’s never a good time to write about something, the truth is that there’s never a bad time to write about something"

— Jeremy Keith

And we need more voices, more perspectives, more experiences, because THAT'S what makes the web weird and wonderful!

And also why I'll keep on writing! And why you should too!