Human luck doesn’t even out.
Regression to the mean explains that in statistics, outlying events tend to be overcome by average ones. But in society, the opposite is often true. A small headstart becomes a bigger one, or a small stumble can turn into something that is hard to overcome.
Individuals can work to amplify their good luck.
And society is obligated to create the conditions for bad luck to fade into the background.
We don’t do either one as much as we could or should.
The index is the search bar, the random access to the facts we can look up.
The table of contents, though, that’s a point of view. It’s a taxonomy of how to understand a complicated idea. It’s the skeleton of the narrative and the pedagogy for learning.
We’re at risk of becoming all index.
The world could probably benefit from your table of contents.
I’ve spent months creating something I’m excited to share: The Mentor Deck. Here’s an invite for 2,000 people to purchase and test the very first edition.
Reading a book changes how you think. But turning those ideas into action? That’s where most of us get stuck. You need more than insights—you need a coach who can take your specific situation and turn it into your next steps.
The Mentor Deck is 52 cards, each one a gateway to an AI conversation. Powered by Claude, each interaction gives you access to a virtual mentor trained on the complete works of transformational thinkers.
Here’s how it works: Pick a card that matches where you’re stuck—decision making, marketing, sales, finance. Scan the QR code. Start a conversation that acts as a firestarter for you and your team.
When you engage with these coaches, something shifts. You find space to expand, to slow down, and to tell the truth about your roadblocks. It’s the missing piece between reading and doing.
[You can try a sample conversation here. Spend just ten minutes and you will see the impact.]
I created virtual coaches that the AI trained on some of the most important ideas and authors of all time. And once you’re in the artifact, you can guide the conversation where you need it to go.
The information was there all along, but the cards help you find it and give you a useful way to have a generative conversation.
What you get:
I’d love your feedback on which ideas should be included in future decks and how to make the experience more compelling and useful. This beta is all we have available… the full production of decks will be shipping at retail, at a lower price, in November.
You can purchase the deck bundle here. We ship this limited first edition on August 11th. Only 2,000 are being sold in this beta edition. Thank you for helping me make a ruckus.
Sneakers are better for running a marathon, but shoes are better for a wedding reception.
This is the better of utility. Finding something that does the job it sets out to do.
And then there is the better of taste. Yellow mustard might be better than Dijon mustard. Not for me, perhaps, but for you.
When we sacrifice utility for taste, it pays to acknowledge that we’ve done so. Just because you like the shape of the bridge you just designed doesn’t mean it’s going to support trucks that drive over it.
No important movie has ever been a solo project.
While we can see a director’s point of view from movie to movie, the collaborative nature of the work is evident. Actors, cinematographers and musicians all change what we see. And because of the huge amount of time and money involved, compromise (and the resistance to compromise) are a dominant force as well.
A book might be a solo act, but it’s often influenced by a great editor. Few of these professionals get the credit they deserve (and sometimes they’re called agents or spouses.)
And with rare exceptions, paintings are done by just one person.
Great directors are also great project managers. And broken-hearted screenwriters often began with a misunderstanding of what they were getting into.
When we set out to create, it helps to understand who our collaborators are and to choose them wisely. A well-trained AI, an insightful editor, an A&R person running interference–these are choices.
Understand the medium and your resources before you begin.
When a system becomes complex and our knowledge peters out, we’re tempted to assert, in the words of Gilbert Ryle, that there’s a ‘ghost in the machine.’
“How does the stoplight work?” “Well, it knows that there’s a break in the traffic so it switches from green to red.”
Actually, it doesn’t ‘know’ anything.
Professionals can answer questions about how. All the way down.
[This is one reason why the LLM AI tech stack is so confounding. Because there are no experts who can tell you exactly what’s going to happen next. It turns out that there might be a ghost, or at least that’s the easiest way to explain it.]
Of course, we make strategic errors all the time.
Not enough time. Incomplete information. A fast-changing system.
Sooner or later, a significant strategic error occurs. Don’t beat yourself up.
Now what?
The real problems occur after the error is made.
Don’t follow a strategic error with an investment error, or an effort error or a time error. Don’t follow it with an emotional one either.
Sticking with our original error, devoting our savings, well-being and future to proving ourselves right–that’s the real error. Don’t invest in the cover up.
After you make a strategic error, announce it. Own it. And then move on.
Anything that works in practice can work in theory.
When a theory tells us something that is working is impossible, we’ve either measured wrong or the theory needs updating.
Theories exist to explain, predict and understand. They are supposed to help us see and improve the world around us, and they’re never finished, just ever better explanations seeking to catch up with reality.
If a theory is effective, use it.
When it’s not, don’t blame reality.
(HT to Lee Anne Fennell)
It’s tempting to go to an extreme. Unreasonable design standards, quality or hospitality are an effective way to gain share, delight customers and spread the word. To be unreasonable in service of your customers is a practice and a commitment.
Along the way, though, reality sets in. The boss has multiple priorities. The uncompromising edges of unreasonable are truly expensive. They take time and effort and money… and they’re unreasonable.
And so, we pull back a bit. We go much of the way, but not quite to ridiculous.
The thing is, rational, compromised unreason has a name: it’s called normal.
If you want the benefits that come from being unreasonable on behalf of your customers, you’re going to have to pay the price as well.
Unreasonable works precisely because most people aren’t driven to go all the way there.
A while ago, I ate in a restaurant that had no menu. The waiter simply walked over to the table and said, “what do you want?” As bold a statement as this is, it made many diners uncomfortable and often led to people ordering without much imagination.
Around the same time, I found myself in an out-of-the-way diner that had a 29 page menu. It took our group a long time to figure out what to order (and then we discovered they were out of just about everything.)
A menu (not just in a restaurant) serves many functions. It’s not simply a list of what you have, it’s also a prompt for what you believe in, want to do or contribute. The menu gives the customer an opportunity to respond, not simply to initiate.
When a prospect asks, “what do you have?” and the answer is “what do you need?” we haven’t made much progress.
Adobe Photoshop is hitting a real menu problem when it comes to AI. Every week, it seems, they announce powerful new features. But they’ve lost whatever coherent menu structure they used to have, and worse, the typical user can’t imagine what to do next.
A disciplined menu structure doesn’t limit user choice, it increases it.
