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“And” fatigue

Digital abundance creates a new problem.

Most of our lives are filled with “or” decisions. You can have this or that. You can save money for the big party or you can go out for lunch. You can have exactly one thing for dessert–cake or fruit.

But the war for our attention has given us more than a million things to watch on YouTube, another million songs to listen to on Qobuz, and unlimited bingeing (which didn’t even use to be a word) on dozens of streaming channels.

No or. Simply and.

This means that choices have fewer consequences. It means that time counts for less, it simply fades away. And it turns the sharp relief of choice into the borderless fatigue of ‘whatever’.

Even when it’s possible to avoid a choice, it may make sense to make one.

The seduction of grad school

For a certain cohort of high-performing students at famous colleges, graduate school feels irresistible.

If you’re good at school, the challenge and offer of law school, med school or a famous business school means you get to do more of what you’re good at. You’re offered a high-status badge, a path to a well-paid job and several years of more school instead of the scary freedom of choice of what happens next.

And so, literate and passionate young people talk about their dreams of helping people, running for office, fighting injustice or exploring their passions as entrepreneurs. And grad school is supposed to be the path.

The problem is that these graduate schools aren’t optimized for any of those things.

Leaving medical school with a pile of debt and your twenties mostly gone pushes you to sign up for the doctor track, which is increasingly about systems and forms, not actually engaging with patients. Law students who came in with dreams of social justice often postpone these dreams for decades as they work for big money at big firms for long hours… You get the idea.

If you want to sit with someone and help them, a career as an occupational or physical therapist is certainly more hands on and direct. If you want to make a difference by writing or arguing, three years of law school and a bar exam aren’t the most leveraged ways to do that. And entrepreneurs need to know a lot, but not what they teach in a typical MBA program.

The stratified work of big name investment banks, consultants, law firms and fancy doctoring is increasingly veering away from the actual contributions of people who have an impact that they can measure and be proud of.

If that sort of work is for you, go for it. But do it with intent.

If not, then perhaps it makes sense to start on the work right this minute. Not with a full certification or permit, but simply creating the sort of change you seek to make, in small steps, right now.

Portfolio theory

One show can make Netflix’s year. One stock can make the numbers for an investor. One player can drive a team to victory.

The key is, “I’m not sure which one it’s going to be, but it’s going to be one of these.”

The challenge with falling in love with the potential of just one egg is that we often end up making the entire basket the same. That’s no longer a portfolio, it’s one bet over and over again.

The best portfolios have elements you’re pretty sure are wrong. They often end up being right.

Reality as reassurance

Culture makes it tempting (and easy) to insulate ourselves from reality. Credit card debt is an invisible burden, until it’s not. Ignoring the changes in our climate makes our days easier, but not our years.

We can avoid the bank balance, not work on the annual budget and ignore the results of that ad we just ran. It’s tempting because the reality we create for ourselves can provide a sort of shock absorber, allowing us to focus on how we’d like things to be, as opposed to how they are.

The reporter of symptoms isn’t the cause of the symptoms, and avoiding the report doesn’t improve your status.

This is one of many reasons why entrepreneurs are drawn to the magical thinking that often goes with external funding. After all, if you’re focused on a story that gets you an investment, you can avoid the reality of a P&L, at least for now.

The problem with this avoidance is that we’re always concerned about reality butting in when we least expect it.

The Ponzi scheme operator is constantly wondering when the plan will go bust. Reality is your enemy.

On the other hand, a cash-flow, profitable business doesn’t need to worry about what private investors think.

If your blood pressure is okay, you don’t have to avoid going to the doctor to have it checked.


Crisp faces many opponents: entropy, laziness, time, compromise and false shortcuts. And fear. Most of all, fear.

Things rarely become crispy on their own. Instead, it requires care and effort. An ume shiso hand roll begins with a crisp piece of nori, but within a minute or two, though the ingredients are the same, it becomes soggy instead of tasty.

Uniforms, service, linens, insights–they can all be crisp if we care enough.

A finite ordered set of interesting objects

The alphabet is one. 26 letters, no more. One order, that’s it.

The Beatles are another. John, Paul, George and then Ringo. The Marx Brothers, the Three Stooges, The Supremes.

The astrological zodiac gets us to twelve, but I’m having a really difficult time finding a memorable set with more than that.

When we start talking about trees or stars or even colors, the list isn’t clearly finite. Anatomy or species don’t work either. There’s always one or a hundred more to add. And human lists like saints or countries are hard to put in a memorable order, same with the US states.

The Great Lakes are five, the planets are eight. I wonder where we find a list of 30 to 100 items. And no fair picking something in Latin or involving multiple dimensions of advanced math.

There must be some sort of human or cultural limit that makes the alphabet a natural exception to our desire for this sort of knowable set.

I know this has nothing to do with our regular programming, but I’d love your best riff on this. Here’s a simple form. I’ll publish some of the winners.


Here’s what I learned from your generous and thoughtful responses:

  1. In the US, a lot of people went with the 50 states. That’s partly because it’s such a foundational concept in our political mythology. It’s also more than 26, which few human sets seem to be. BUT, there’s no obvious order to the states, and the ones we invent aren’t particularly useful, except to remember all of them.
  2. On the other hand, the one I heard the most that fit the criteria was the periodic table. Here, the order is real. Atomic number doesn’t mess around. It says something about our science literacy (along with the anarchic way the elements were named) that most of us can’t name 100 or more elements. But the real insight for me is that this set wasn’t invented by humans. We discovered it, we didn’t invent it.
  3. And the other big insight was that perhaps I was looking in the wrong place. It may be that a well constructed popular song with interesting lyrics is the perfect example. There’s a finite list of words, they have to go in a certain order and it means something to us. I’d put the Cat in the Hat on this list as well.

Thanks all.

When we get to where we’re going

…perhaps we should stop.

Unless the going was the point.


The empty part of the drawer is what makes it a useful tool.

Same goes for a filing cabinet, a toolbox and a calendar.

Slack is underrated.

The right marketing question

The wrong question is, “our project isn’t catching on, how do we promote it better?”

The right question is a little more nuanced and far more important,

“We’re seeking to make a change in part of the world. How do we find the right people and tell them the right (true) story that helps them get to where they’re going–and that they’ll tell to their peers?”

It’s worth breaking this down and understanding the components:

make a change: Any project that seeks to maintain the status quo is difficult to grow. You’re here to make a change, and being clear about what that is is the first step.

the right people: Nothing worth spreading is built to appeal to everyone. So who is your someone? What do they want, fear and believe? How do you shift from being mediocre to being specific?

the right (true) story: Marketing is never about the full experience of all the facts, specifications and impacts of your product or service. It’s the story we tell ourselves about it. A story of status, affiliation, of change and fear. If that story is true, then you can continue to build on it over time, and users won’t end up disappointed.

that helps them get to where they’re going: It’s very difficult to prove a prospect or customer wrong. Hard to get them to want something they don’t want. The opportunity lies in helping them get what they wanted all along.

and finally…

that they’ll tell to their peers: Not to everyone, but to people who trust them. Why would they do that? They won’t do it for you, they’ll do it because it raises their status, increases connection or gives them some other form of satisfaction.

Promotion might make sense after you’ve got all of this figured out.

Peer support

Treasure it when you find it. Offer it when you can.

One of the greatest joys of being an author is the other authors. The game theory would indicate that authors are competitors–there are a scarce number of publishers, of bookshelf slots, of readers. But, being the only author in the world wouldn’t just be lonely, it wouldn’t work very well. Books actually sell best next to other books, not in the supermarket.

But more than that, peer support comes when people are part of something bigger than themselves. When they see their work as a craft, and a chance to turn on a light or raise a standard.

In every field, our best work can feel lonely, because we don’t have a guarantee, a map to follow or a crowd of people sure that it’s going to work. That’s when peer support means the most. And when it contributes to the evolution and forward motion of a field.

“Peer” is a job title, and it’s earned. One way to earn it is by finding the others, connecting them and leading them. We spend our lives looking for peers to accept us, but in fact, we have the chance to establish the foundation for our peers to find each other.

While most people say that when they’re a stranger in a room, they’d like to be warmly greeted, it’s also true that we hesitate to be the greeter when a new voice arrives. That’s a natural instinct, and worth pushing back against.

Organizing your peers feels awkward. Who are you to invite three or four others to a weekly mastermind check in? Who are you to speak up about a new idea that isn’t obvious or easily defended (yet?). Well, if not you, who?

Thank you Steve, for the shout out, and more than that, for decades for showing us how it’s done.