Here’s how to solve the problem of founder writer’s block

This is what works for me.

Don’t undervalue what you already know

Whatever you do know how to do, somewhere online there is someone who doesn’t know that yet. No matter how simple and obvious it seems to you, the internet will find you someone who hasn’t learned that yet.

Any time I give the same advice to three founders, it’s something I should blog about (I blog on Medium behind the paywall because I coach startup founders professionally and this is my best IP). I tick the repeats off as they happen and around 6–9 times later I’ll review the original blog post because my thinking may have evolved and the way I teach the lesson may be more refined.

You don’t mentor startup founders? That’s OK. You could adapt this rule: anytime you repeat a process in your startup three times, and it’s a process you suspect other founders probably don’t use, write a blog post about that.

You will find a lot of founders have never heard of that process and will be grateful to learn from you.

Look for the underlying cause of your block

I used to write professionally in print, so the idea of a blog post not being 100% perfect is the primary source of my writers’ block because print can’t be edited once it’s printed.

For years I had several hundred half-written blog posts in draft!

I have beaten this by forcing myself to hit Publish on any draft blog post I start to write, no matter whether I think it’s ready for an audience or not. Usually my bar is much higher than my audience’s.

Most of the the audience for your blog posts is in the ‘long tail’, over a period of months or years.

So when I hit publish on a short, clumsy, semi-complete blog post, it doesn’t matter if a few people read it – the vast majority of readers will see version 2, version 3, or whatever.

Polish something you already have

It’s so much easier to read an old blog post and make one small edit to make it even better than it was. So I spend some of my time writing new drafts, but more of my time reading old posts and making them a little better. I’ll also write a blog post about a workshop I just gave (or took) and have written many blog posts after a good conversation with a founder.

I don’t have a publishing schedule but when I know it’s been a while, if I don’t have something to write about, I’ll just throw it open to one of the founder groups on Facebook I’m part of, or ask people on Twitter and LinkedIn to request a blog post on a topic.

I’ll usually only write one post from people’s suggestions, but I’ll usually get another 4–5 great ideas that I would have never thought of myself, and knowing that my audience requested a post on that topic helps me start writing.

Draw it, badly if necessary

Sometimes I get blocked because I can express a concept or a process in a whiteboard diagram than I can in writing. In that case, I don’t let myself worry about how bad I am at drawing: I get my iPad Pro and Apple Pencil an start drawing. Sometimes my diagram is the whole blog post, sometimes it’s the illustration that draws in the reader or really locks-in the learning.

Say it out loud

Sometimes, if there’s something I need to write about but I don’t know where to start, or what the final structure of the story will be, I find it helps to just talk about it with a microphone turned on. I’ll open Pages on my Mac, not because I love Pages as a word processor, but because it supports speech-to-text, and by speaking on the topic to Pages, and then reading the resulting text, I can often find the elements of the story I need, such as the place to start, how to finish, and a few nuggets of wisdom.

Answer a question

If you don’t have time to write a blog post now, write an answer to someone else’s question on Quora, ProductHunt, LinkedIn or Facebook. ‪This blog post originally began as an answer I wrote to @anthilemoon’s discussion on ProductHunt “How do you build a writing habit? ✍️”‬

‪Share your thoughts: @anthilemoon https://www.producthunt.com/makers/1-makers/discussion/1439-how-do-you-build-a-w‬riting-habit

Tweet about it

Sometimes my blog posts start as just one tweet. I can’t get the whole blog post into a single tweet, but the character count constraint forces me to write concisely, and to make a solid point in what is essentially a paragraph of text.

Then I’ll start expanding on my first tweet with a series of tweets in a thread, and in each tweet, I’ll try to progress the story further, but also make each tweet stand alone.

It’s a great way to write a strong linear piece with a solid beginning and end. It can also become a great way to promote a blog post, once you’ve copied each tweet into a new draft blog post and tweeted a link to the blog post in your final tweet.

Here’s an example:

Q: The investors have asked for a business plan, what should I do?
A: Everybody has a different idea of "business plan" ranging all the way from a sketch on the back of a napkin to a printed and bound manuscript so big and heavy that would hurt if you dropped it on your foot…

— alan jones (the good one) (@bigyahu) August 4, 2021

Know when to hit Publish

That time is probably now. You can always come back and improve it later.