Death for the dreams of a writer

Good morning!

Inside this Sunday:

  • I’m reading about working general to specific.
  • I’m working on conversations about wine and puzzles, and turning the YouTube channel lights back on!
  • I’m thinking about the crazy ones.

I started writing again!

Nothing to publish yet, but this week I sat down on consecutive mornings and worked on a new essay, from outline to drafting. It was my old routine from mid-2020 coming back again and I couldn’t be happier. I truly missed it, and look forward to publishing some new work in the coming weeks to share with you.

By the way, the time-blocking I wrote about last edition is going really well. I have chunks of time in my day for creativity for a change, and I’m putting it to good use.

I’ve been thinking quite a bit about authenticity in the context of writing, and specifically, writing copy for websites.

When you view the website of something you want to buy, you get a feeling.

Either that feeling is one of your heart singing, “this is for me, I know, like and trust this person/brand”.

Or you are turned off.

For me, it’s pretty binary.

I’ve had to learn to trust that feeling. Too many times I’ve rationalized it away, purchased the thing, and ended up disappointed.

It’s very hard to pinpoint exactly what it is that’s giving you the feeling.

This makes it incredibly hard when you’re the person writing the copy.

To help with this conundrum, I think of it like this: if you write from your heart, if you write authentically, then people will feel that. It won’t be for everyone (and often, it’s the act of trying to please a broad spectrum that defeats authenticity), but for those that it is for, they’ll be your biggest fans. And as we all know in the creator economy, all you need are 100 true fans.

The challenge, therefore, for writers: how do you pour your soul out in words, such that a reader is confronted with the stark choice, do I like this or do I not?

Because anything in between is death for the dreams of the writer.

See you in two weeks,



The most popular link was my new business venture (and it’s very draft website) with Robbie and Marie – the Course Creators Collective, or C3 for short.


Working General to Specific

A friend, Eric Jorgenson, recently proposed a new mental model which he calls Working General to Specific. He uses the example of how sketch artists start with very general shapes and progress to detail work.

This has a number of benefits:

– it ensures efficient use of time (detailed work that is more subject to change happens later)

– you get roughly right first, so you are never precisely wrong

– you get to invest in the right areas of detail, at the right time

This reminds me of course creation, specifically finding product-market fit (which of course, applies to more than course creation, damn, I went specific to general there).

It pays to be sufficiently broad in your proposed solution so you can attract enough people to learn from. By listening to the pain points of these early adopters you get much closer to what your customer really wants (as opposed to what you think they want).

The article has a few more examples of this, and it’s clearly an Idea-In-Progress, so feel free to reach out to Eric on Twitter to contribute.

Full 4-min read


How Did You Learn That?

In ep 34 I imbibed with legendary South African wine master Harry Melck. Harry is an eighth-generation descendant of a well-known Cape wine family and has received the highest qualification from the Institute of Cape Wine Masters. His passion and knowledge of the wine industry know no bounds. This was a fun vineyard stroll through the history, science, and storytelling power of wine.

More on episode 34

In ep 35 I puzzled on what makes a great puzzle and why solving a really complex one can sound like the universe is singing. My guests were Mark Goodliffe, who holds the Guinness World Record for most wins of the Times Crossword Challenge, and Simon Anthony, a Sudoku master who has represented the UK at world competitions. This was one of my best podcasts yet, in that it felt like we were all just riffing on the beauty of the subject.

More on episode 35

YouTube Channel

I’m firing it back up!

This week we worked on an edited version (complete with B-roll) of my conversation with Nat Eliason – learn how to learn with Nat.

Watch the 8-min video


“To believe your own thought, to believe that what is true in your private heart is true for all men, that is for genius.” – Emerson

I’m returning to this quote again. It is so incredibly deep. On the one hand, we all have such diverse experiences, it would take a crazy person to think that what they believe is true for everyone else. But when that thing is a world-altering idea, it’s justified. Steve Jobs believed we needed personal computers and music in our pockets. And he was right.

Here’s to the crazy ones.

This email newsletter was originally shared with subscribers on July 11th, 2021. To receive the latest newsletters twice a month, sign up below!

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