THE LEAFLET

May 22 2025

letting your work do things for others, steep slopes even over high points, guiding people like AIs

LETTING YOUR WORK DO ITS THING FOR YOUR AUDIENCE

When you’re creating something for a customer or an audience, perfectionism can really get the better of you. You can revise and revise and then hold on to your product for yet more revisions. Another round of polishing. Swapping commas for semicolons and then swapping back. Adjusting the kerning between the letters on slide 5. Adding a button to the UI.

I read in the last couple years a helpful prompt for getting out of this pattern. An author said something along the lines of (and I’m paraphrasing a lot here)

“The [product] is never finished, strictly speaking. You can always write another draft. But if you keep writing drafts forever, your readers never get to be your readers. They never get to read and enjoy and critique the thing you made.

So there’s a point where it’s worth asking yourself: Has this piece done all it can do for me? Is it time to let it do what it can for others?”

If you’re still struggling to get out of a perfectionist doom loop after asking yourself this, remember that your next revision will likely be way more useful - way better - if you do it based on the feedback of someone else. Get yourself a “reader” before you get to revising again.

-eric

Read the rest here.

STEEP SLOPES EVEN OVER HIGH POINTS

In my experience as a teacher and school administrator, I found that the greatest growth impediment for a student who has typically not succeeded in school before is thinking about the rut they are in.

The antidote is easy: celebrate not where they are but the rate of their progress—prefer steep slopes even to high points. 

That’s why in breakthrough classrooms, you’ll typically see lists on the wall not of kids with the highest grades, but of those who’ve grown the most since the last test or project. You could have a C and a B student, if they’ve worked hard to pull up from the D they started with. Not only do students escape feeling like “F students”, but they have a shot at beating the so-called “A students” on a daily basis.

Before you get tangled in worries that this lowers the bar, or say, “Are you kidding me? So is a kid penalized for coming in strong?” think about something you struggled with and abandoned. 

When naming something you believe you could never do—speak Mandarin, ride a unicycle, pass AP calculus—look at the first time you decided you’d failed and ask, “Instead of saying I’m still not good at this, what if I’d said, ‘ok, 18% better than yesterday.’” 

In the “new normal,” even A students will have to learn at an increased pace—and shouldn’t they be expected to anyway?

If you’re a school, start considering honoring and incentivizing students’ growth rather than their current status. Think about what this might change about how you grade or communicate grades. Start thinking of classroom routines and moves with parents that reinforce them. 

If you’re a parent, you can start acclimating your kids to this even now. Ask yourself this question every day: “What has my child improved at that I’m unlikely to notice because it’s still not what I expect?” 

This works to build pace and momentum in anything. Like it or not, telling your kid they dropped only four F-bombs today instead of the five they dropped yesterday is going to get them to zero F-bombs much faster than withholding your recognition until they do.

-ben

Read the rest here.

ARE YOU MANAGING PEOPLE WITH AT LEAST AS MUCH GUIDANCE AS YOU GIVE AIs?

As AI models get better and better, you – the user — benefit more from context-rich prompts that lay out the principles and qualities of the solution you want the AIs to deliver. In other words, err on the side of saying too much about what you want, even if your sense of what you want isn’t totally clear. (As an example, last week I offered a model for an AI prompt when you want the AI to act as your career coach.) 

In reflecting on this since, I realized yet again that I made big mistakes as a CEO in my management of partners, vendors, and clients - the big group of Other Organizations that surrounded my organization. Too often, even with a costly, haggled-over contract and scope of work signed, I hadn’t given that Other Organization the baseline level of guidance that I now give to an AI when I want a recipe for dinner or feedback on a piece of writing. I was often disappointed in these Other Organizations. But a truth of the matter is I didn’t lead them well. My prompts were thin or withheld.  

My regret now takes the form of a recommendation (to you and to future me): tell the people you’re working with what you want and expect from their participation in the relationship with you. Don’t assume that they’ll deliver how you want and what you want because they are [well-known, expensive, award-winning, from the community, whatever].

I offer this recommendation even more energetically if it scares you a little to imagine saying something to a vendor or project lead on your own team like: “I’d like you to perform like a wise, seasoned industry veteran who still seizes chances to try new approaches. I want to feel like I’m in good hands AND know that I’m not missing efficiencies. I want your work to be creative, compliant with the law, and adaptable - please don’t give me something that is hard-coded and expensive to make small adjustments to.”

-eric

Read the rest here.

COMPELLING QUOTES

Perfumier and writer Sasha Chapin on wholeness, repair, and saintliness:

In practice … you can experience wholeness and still get to work on repairing what is obviously broken here. This you can see from accounts of the lives of people who are way deeper in [the spiritual life] than I’ll ever go. Saints are not necessarily chill people. As Tucker Peck pointed out to me, the Buddha was a busy guy.

Historian Barbara Tuchman on distortions of the past from the people who lived it:

The period [before World War I] was not a Golden Age or Belle Epoque except to a thin crust of the privileged class. It was not a time exclusively of confidence, innocence, comfort, stability, security and peace. All these qualities were certainly present. People were more confident of values and standards, more innocent in the sense of retaining more hope of mankind, than they are today [1963], although they were not more peaceful nor, except for the upper few, more comfortable. Our misconception lies in assuming that doubt and fear, ferment, protest, violence and hate were not equally present. We have been misled by the people of the time themselves who, in looking back across the gulf of the War, see that earlier half of their lives misted over by a lovely sunset haze of peace and security. It did not seem so golden when they were in the midst of it.

Music critic, poet, and Minnesota Timberwolves fan Hanif Abdurraqib on hope:

Hope means both everything and nothing at all, and yet it is always purported to be within reach. Hope is the fluorescent bird. The bird makes no sound. It is in a cage. No one can find the key, and no one has seen the key in a very long time, and they aren’t sure that they’d even free the bird if they found the key. And yet, collectively, people must keep asking for it.

Keep going, keep growing,

Ben & Eric