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The transition to leadership

The flawed theory is that A+ students become good leaders.

There’s no reason to think that this should be true.

Doing well on tests, paying attention to what’s being asked, being diligent in short-term error correction–these are three hallmarks of someone who is good at school.

None of these are important once you’re charged with charting a new path, with figuring out what to do next. In fact, they get in the way.

We invented the educational regime to produce compliant factory workers. But the most compliant aren’t always suited to be the bravest, the most empathic or the most intuitive.

Book list, Fall 2019

Start Finishing by Charlie Gilkey

Beginner’s Pluck by Liz Forkin Bohannon

Stillness is the Key by Ryan Holiday

Change the World/Manifesto for a Moral Revolution by Jacqueline Novogratz

The Power Broker (audio) by Robert Caro

You Are Awesome by Neil Pasricha

Ignore Your Customers and They’ll Go Away by Micah Solomon

Super Thinking by Weinberg and McCann

The Diversity Bonus by Scott Page

Living Bread by Daniel Leader

Poilane by Apollonia Poilane

Nothing Fancy by Alison Roman

A Culture of Fact by Barbara Shapiro

The Entrepreneurial State by Mariana Mazzucato

She Came to Slay by Erica Armstrong Dunbar


NEW! A one-click way to add a whole bunch of books to your Amazon cart at once. To add 17 of my books to your Amazon cart with just one click, simply click here.

And here’s a one-click way to fill your cart with books for kids, the best gift I know for the new parent who has everything but sleep.

And here’s a link to Reedsy’s spreadsheet if you want to build your own. Be sure to make a copy of the sheet, as you can’t change that one. HT.


When things get difficult, is your instinct to invest the effort to make it better, or to set a trap so it all gets worse?

Because if things get worse, well, then you won’t have to deal with them much longer.

And if things get worse, then you’re off the hook.

No longer your problem.

If we don’t trust ourselves with making it better, if it’s too fraught with risk or emotionally painful, it might feel easier and simpler to simply make it worse and walk away.

Investing in a system, a place, a relationship, a project–that’s a commitment. It puts you even more on the hook. That person who is right in front of you becomes more real and the problem becomes even more urgent.

And it might even be worth it.


[Grateful for you and for everything you do to make things better. Thank you.]

Discontinuous thought

The gap between mobile and desktop is:

[shift] ENTER

When one is typing on a laptop, the assumption is that you’ll keep going with your thought until you push ‘send’ or ‘publish’.

But on a smart phone, the enter key is your publish button. So your text, your Slack message, or your tweet happens as soon as you type a single sentence.

That’s good for platforms that want to deliver the endorphin hit of a mic drop, but not particularly helpful in sharing complex ideas. And the ideas that are worth sharing are the complex ones.


PS Today’s the last day to sign up for the Story Skills Workshop. Hope to see you there.

A chance for better

Perfect is the enemy of good.

Of course it is.

But that simple sentence becomes more urgent when we realize that nothing (and no one) is perfect. How could it be?

And so, if your hero, your cause, your holiday, your background, your relationship… if it’s not perfect, does that mean you should hide it? Be ashamed of it? Be afraid of it?

We’re surrounded by injustice, and yesterday was even worse. It’s so easy to find things that are imperfect and criticize them or worse, shame them.

Better, I think, to find glimmers of good and seek to amplify them. Mistakes can be seen, errors can be improved upon, progress can be made. But only if we embrace the chance for good.

The imperfect is an opportunity for better.

If every day were Thanksgiving

It’s my favorite holiday for a good reason: It doesn’t matter what country, what culture or what background you come from…

Gratitude works.

Gratitude scales.

Gratitude creates a positive cycle of more gratitude.

When in doubt, default to gratitude.

[And, for the fourth year in a row, we’re offering the free Thanksgiving Reader. You can print it out at home and have it ready for the holiday, wherever and whenever you choose to celebrate. It’s a modern tradition.]

The uncomfortable combination of effort and acceptance

We have the opportunity to expend the maximum effort on behalf of a worthy goal.

And we also have the choice to mindfully accept whatever happens next.

Acceptance is a choice in the service of our happiness and the ability to try again tomorrow.

When we detach our emotional state from the results of our effort, we maximize the chances that our effort will be focused and effective. We’re not trying to control the outcome, simply putting our best effort into creating the conditions that lead to the desired outcome.

The opportunity is:

  1. to go all in, and
  2. to be okay with what happens after that.

Knowing the answer before you ask the question

The first rule of cross-examination at trial is that you never ask a question that you don’t already know the answer to.

Inquiry has a place. Inquiry in the pursuit of science, of discovery and of learning is essential. But inquiry almost never belongs in a presentation. That’s because the presentation exists to communicate what you already know, not to discover something new.

That’s why comedians try out their new material in small clubs.

That’s why you should try out your job interview answers long before you go on a job interview.

And that’s why you shouldn’t throw a steel ball at the window of the new truck you’re launching unless you’re really, really sure it’s not going to break.

[Either that, or know that what you’re selling is live magic, the possibility of ‘it might not work,’ the generosity of art in the moment. But they rarely belong in the same interaction.]

Golf or surfing?

Every golf scorecard has a map of the course on the back. Moving the hole placement is a big deal, accompanied by meetings and oversight. A big shift is whether or not it rained last week.

On the other hand, every wave is the first and last of its kind. It has never happened before and will never happen again.

Golf is an endless asymptotic journey toward elusive perfection.

Surfing, on the other hand, is about wayfinding. A surf park with a repeated wave might be useful for training, but it’s not surfing.

Metaphor over, the question is: what’s your job like?

It gets a lot easier if you bring the appropriate mindset. It’s hard to surf with a putter.

The uses of Kickstarter

A friend reached out because she’s thinking of using Kickstarter to fund her new book. That conversation led to a discussion about what Kickstarter is actually good at and how to use it. It turns out that there are many options (and some misunderstanding as well).

The uses of Kickstarter:

To raise money you don’t have for a project that you’ll be able to build and then ship to your supporters and people who already know you and trust you.

To create a community for an art project that isn’t designed to be a profitable business.

To have a temporary online store (instead of something more permanent, like Shopify), where you can run a pop-up and then be done (and move on to the next thing). It’s an effective way to highlight the tension of go/no go.

To capture the energy and attention of large numbers of people who don’t know your work (this almost never ever works and is the worst of these reasons).*

To give your existing fans and followers an organized way to support you and to see it unfold in real-time.

To have a simple, structured place to put your idea. By limiting your options and giving you deniability, it makes it easier for some to move forward.

To give you a safe place to succeed as well as to not-succeed. There’s a limit on the time and money you can invest because of the structure of the platform.

Most of the time, for most projects, Kickstarter isn’t the answer to the question you’re asking. That’s because it could more accurately be called Kickfinisher–you build a following first, over time, and then Kickstarter is the moment in time that those followers show up for your work.

More here.


*Kickstarter is powerful when used as intended. But it’s not very good at creating ‘hits’. It turns out that while 17,000,000 users have, in total, funded 173,000 projects, that’s only about a third of the total. 290,000 projects haven’t succeeded in being funded at all. And only 400 projects raised more than a million dollars each. That means your chances of creating a viral hit that reaches strangers who will engage with your work is about one in a thousand.