Hey :)
This was the first coaching session of the year.
This was the first coaching session of the year.
We’d barely warmed up and my client asked me a question I always enjoy being asked:
“You’re probably the most avid reader I know.
From the books you’ve read recently, what would you recommend?”
I love this question — not because I have a clever list ready to go, but because I think in exactly the same way.
What he wasn’t asking for was “the best books in his industry”.
He already knows those. He’s already read many of them.
He already knows those. He’s already read many of them.
What he was really asking was:
What should I read that will stretch me?
What will challenge how I think — not just give me more of the same?
That’s always the filter I use myself.
Reading outside your own lane
As a coach and consultant, it’s very easy to stay inside your own theme.
Leadership books.
Business books.
Coaching books.
Strategy books.
Business books.
Coaching books.
Strategy books.
There’s a point where that stops helping.
You just end up rehearing familiar ideas, wrapped in slightly different language.
So when I think about what to read — and what to recommend — I’m usually looking for ideas that come from different fields altogether.
Psychology.
History.
Philosophy.
Performance.
Power.
Decision-making.
Books that don’t tell you what to do, but quietly change how you see things.
Another small habit I’ve picked up:
I often use the appendix or references of a good book to find the next book.
Pull on the thread. Follow the trail.
That’s how some of the best, lesser-known books show up.
What I was optimising for
There were a few bits of context that mattered in this conversation:
- I know what they have already read
- I know what tends to resonate with him
- I know what wouldn’t be useful right now
So I wasn’t trying to give him “the best books ever written”.
I was thinking:
- What might challenge long-held assumptions?
- What could disrupt a familiar narrative?
- What might open up new ways of thinking about life and business?
- What could give him new mental models, not just new information?
That’s the lens.
The books I suggested
These are the books I recommended — and an important note here:
I only ever recommend books I’ve actually read.
If I haven’t read it, I don’t suggest it. Simple as that.
If I haven’t read it, I don’t suggest it. Simple as that.
Here’s the list.
- The Art of Learning by Josh Waitzkin
A very different perspective on learning, performance, and pressure. Great on audio — and Josh reads it himself. - The Crux by Richard Rumelt
Helped reshape how I think about strategy. Strategy as problems, not plans. A bit dry in places — still worth it. - The Motive by Patrick Lencioni
A short fable about leadership and motive. Not complex, but quietly uncomfortable in the right way. - The Outsiders by William N. Thorndike
A book about CEOs you’ve probably never heard of — and why that matters. - The 80/20 Principle by Richard Koch
And honestly, anything he’s written. Repetitive in a useful way. - The Almanack of Naval Ravikant by Eric Jorgenson
Mental models, leverage, wealth, happiness. A modern thinking manual. - The Great Mental Models by Shane Parrish
Better as a physical book, but still strong on audio. Trains how you think. - Poor Charlie’s Almanack by Charlie Munger
A masterclass in mental models and second-order thinking. - Same as Ever by Morgan Housel
First principles and patterns. Focused on what doesn’t change. - Mastery by George Leonard
Different from Robert Greene’s Mastery. About practice, patience, and the long game. - Range by David Epstein
A useful counterweight to narrow specialisation. - The Prince by Niccolò Machiavelli
Not a comfortable read — but an illuminating one. - Leonardo da Vinci by Walter Isaacson
Polymath thinking. Curiosity. Contradiction. A reassuring read if you create for a living.
The real point of the list
This isn’t about having an impressive reading list.
It’s about exposing yourself to ideas that don’t automatically agree with you.
Ideas that:
- unsettle you a little
- challenge familiar stories
- give you better lenses to see the world
If you’re reading this and thinking,
“Some of those have been sitting on my shelf for years…”
That’s probably the signal.
Pick one.
Start there.
And if you’ve got a book that did this for you — especially one that isn’t commonly recommended in your space — I’d be genuinely interested to hear it.
🗣️ 👀
Chris.
Chris.