Couch to 1k – Daily Writing Challenge


Hey friends,

I’m trying out a new experiment. For the next 30 days (at least), I’m going to write 1,000 words every day. I’m calling this “Couch to 1K” just for fun.


I’ve been inspired by the likes of Nathan Barry and Sean McCabe, online creators who’ve built engaged audiences and multiple revenue streams through writing online. Nathan (now the founder of ConvertKit, a $20m/year software business) has lots of blog posts talking about how writing 1,000 words a day changed his life.

Sean goes a step further. He writes 2,740 words a day, which adds up to a million words per year. This writing habit yields tweets, blog posts, videos, podcasts and even several books a year.

But writing isn’t just about feeding the content machine. It’s also be the best way to refine our thinking, flesh out our ideas and expand on insights we stumble upon.

Over the past few weeks I’ve found myself spinning my gears without making much progress. I’ll listen to a podcast, take a few notes, write a tweet or two, maybe plan a video, but generally when I’m in front of a computer, I tend to waste time because I don’t have a default activity to do.

I’m hoping that by committing to 1,000 words a day, my default activity will be to write. Like right now, I’m on a weekend on-call shift at work. It’s been pretty busy all day, but it’s now 5pm and I’ve got some time to take a breather. Instead of sitting on my phone scrolling through Twitter, I’m writing this piece in Notion. That’s a win in my book 🙂

What will I write about?

Anything really. I might look through the list of video ideas and riff on one of those. I might look through my Resonance Calendar to find a book or podcast that’s recently resonated with me, and write about that. I might even ‘just’ write in my personal journal. It doesn’t matter. What matters is hitting that target of 1,000 words a day.

The System

I won’t lie – yesterday when I had this idea, I spent over an hour trying to figure out which app to use for it. Roam vs Notion vs Evernote vs Ulysses vs Drafts vs Bear. Then I realised it doesn’t matter. Whichever app I use, I can track my word count either within the app itself, or by just copying/pasting the day’s writing into a word document if I’m feeling particularly ghetto.

It would be nice to build a perfect system before starting the journey, but much like making a detailed revision timetable, it’s an exercise in procrastination. It’s far more important to just start writing and figure out a system that works along the way.

Join me

There are a tonne of blog posts from people who say that a regular writing habit changed their life. I’m hoping it’ll do the same for me, and I’m hoping it’s something I’ll be able to continue beyond just 30 days.

If you’d like to join me in taking this challenge, hit the <reply> button and let me know. Over the next few weeks it’d be nice to hear what our collective struggles are, and we can share tips to make building the writing habit easier.

Have a great week!


PS: This email is 597 words. Just a few more to go today 🙂

This Week on Not Overthinking

Not Overthinking is the

weekly podcast

hosted by me and my brother. If you enjoy these emails, you’ll hopefully like that too. You can listen on Apple PodcastsSpotifyGoogle PodcastsStitcherCastro (my favourite podcast app) or any other podcast app – just search for ‘Not Overthinking’.

68 Bits of Unsolicited Advice | Not Overthinking

This week, we dig into Kevin Kelly’s recent blog post “68 bits of unsolicited advice”. We go through the list and talk about a bunch of the advices (?) that resonate with us.

My Favourite Things This Week

1 – Article –

What counts as ‘enough’? It’s a widely debated and subjective issue but it’s broken down brilliantly by David Heinemeier Hansson, founder of Basecamp, in his article, appropriately entitled, ‘Enough‘.

2 – Article –

As I was writing the script for my latest video, I was reminded of Kevin Kelly‘s seminal essay ‘1000 True Fans‘. It’s a great discussion of the power of gaining a small but loyal audience – I’m glad I took the time to revisit it.

3 –


– This is a great read about why Speed Matters. I constantly find that whenever I move fast with stuff, everything is just better. And whenever I’m slow, everything is worse.

4 –


– I listened to the entirety of Alain de Botton’s fantastic book How to Think More About Sexon Audible over two car journeys. It should be required reading for everyone.

Quote of the Week

Never forget why you’re really doing what you’re doing. Are you helping people? Are they happy? Are you happy? Are you profitable? Isn’t that enough?

From Anything You Want: 40 Lessons for a New Kind of Entrepreneur by Derek Sivers. Resurfaced with Readwise.

Tweet of the Week

This Week’s Video

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4 months ago

I have recently heard this idea again on the podcast of yours. Quick google search and here am I.