Three Hours for Wicked Problems

~ Sasha ~ Leave a comment

Writer Neil Gaiman, author of Coraline and many other eerie, magical books, has a powerful, simple rule for writing. He sets aside a period of time each day in which he can either:

  1. Write
  2. Do absolutely nothing

There is no obligation to write. However, there IS an obligation not to read, scroll, create a to do list, cross things off a to do list, exercise, walk, or do…anything.

Gaiman’s reflection is that, eventually, writing becomes more appealing than doing nothing, and he will eventually write.

We’re not all writers, but we do all have wicked problems to solve—some as wicked as staring at a blank page and having to figure out how to fill it up.

When we fail to move forward on our wicked problems, I’d assert that we’re probably not following Neil Gaiman’s advice.

For your next wicked problem consider this slight adaptation. You can:

  1. Work on your problem (including using search, reading about your problem, and using AI)
  2. Do absolutely nothing

(It will be more difficult to hold the “do nothing” line, because once you’re on your computer using tools, the pull to everything else will be strong. But I believe in you.)

We don’t get stuck on wicked problems because they are too difficult to solve, we get stuck because they are wicked, and once we hit our first roadblocks, usually 10 minutes in, we switch gears and turn to other things.

Hence, the Neal Gaiman-inspired three hour wicked problem block.

You set aside three hours, and can either work on your wicked problem or do nothing (NOTHING!) else.

Bonus: thanks to AI, you’re not alone, you have infinite access to a researcher, a devil’s advocate, a librarian, an analyst…even to (virtual) fellow travelers.

I’m convinced you’ll make enormous progress if you do this once, twice, even three times this week. You just need to devote your time to your wicked problem and to nothing else.

EWIMO writing

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It’s become horribly easy to spot AI writing. The false tension. The emojis and em-dashes.

A partial solution is to teach your favorite AI tool not to write like that. I have a Claude .md file that instructs it to avoid negative parallelisms, bold-first bullets, filler transitions, and too many em-dashes. This way, if my Claude were giving advice on a chicken recipe, it would never say things like:

Not a stew. Not a soup. A braise.

Three hours. One pot. No shortcuts.

This isn’t dinner — it’s an argument about how you spend a Sunday. Everything from the sear to the silence at the table is part of the same tapestry.

The lid goes on.

And then you wait.

While this is all humorous, it’s everywhere, and our tolerance for it speaks volumes.

The old tells for “I didn’t care enough to do a good job on this” were typos, unfinished sentences and numbers that didn’t add up.

Now, everything that’s error-free but screams AI sends the message: “I phoned this in, so don’t trust me.”

The way you avoid this is by actually doing the work: rereading each word, thinking about it, acknowledging that “I sent this” means “these words faithfully represent me and my best thinking.”

There’s no problem using the tools to help you, but you have to practice EWIMO writing, always.

Every word is my own.

Never Do, Can Do, Must Do

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During COVID, I got hooked on the NY Times Spelling Bee. It was the perfect daily diversion – hard but not too hard, required thought but not too much, getting a pangram (word that used all the letters) was SATISFYING.

After a while our family discovered that Queen Bee was achievable: a badge for getting every possible word on the board. That became the new goal, and so ensued a nightly activity for me and my wife to get Queen Bee.

A few months in, the bloom was off the rose. It went from pleasant diversion to an obligation. My eyes would be itching with fatigue as we worked at Spelling Bee at bedtime…

Over time, we all stopped playing.

Looking back, I see a common six month arc: Spelling Bee, and then Queen Bee, went from Never Do >>  Can Do >> Must Do. And the addition of Queen Bee as a Must Do, which felt fun at first, ended up taking all the fun away.

We can notice this evolution across anything we do, big or small, throughout our day, by asking three simple questions:

What do we Never Do?

What Can we Do?

What Must we Do? (each day)

The Never / Can / Must classification is just a lens for looking at how we spend our precious hours—the things that have become our habits, which, taken as a whole, are the foundation of our well-being, our health, our social connection.

The reflection is simple: of eating is a Must Do, but what is animal protein? What about eating our bodyweight in grams of protein each day? Having something sweet at the end of every meal? (a Must Do of mine, lately)

Similarly, we sleep every day, but is our Must Do at 5 hours or 8?

And when does something fun and optional transform into something obligatory?

Take my use of Instagram (please!). I only really discovered Instagram in 2022 (someone showed me Reels), and it flitted between Never Do and Can Do for a few years. Then, 18 months ago, it landed solidly in my Can Do, and 12 months ago—if I’m honest with myself—it tipped into the Must Do category, so much so that I set a 30-minute daily limit on my Instagram app (which, because I’m human, I occasionally override). Depending on the week, I’d hit the limit one day, then two, then four…. I didn’t like the trend. My solution was a weekend reset—no Instagram at all—and a conscious choice to get Instagram out of Must Do and back into Can Do where it belongs.

With that in mind, I’ve made a much longer list of activities, and honestly categorized them into Never Do, Can Do, and Must Do. It’s a pretty simple way to map out what my real priorities are.

You might try it too. Bonus points if you grab two different color pens, and make one X for Today and another one for Goal. I’ve left you a blank list you can print out at the end of this post.

On AI-generated content, trust, and gatekeepers

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Today, I received, by email, a great article by Woody Allen on antisemitism.

Except that it wasn’t written by Woody Allen, it was fake and was written by AI.

That got me thinking about how media and publishing work.

For a long time, we lived in a world of gatekeepers: a few network TV channels, a few trusted newspapers, and a few trusted publishing houses.

We’ve since had a few decades of the long tail: from cable news to the internet to social media to podcasts, everyone has become a content creator as the gatekeepers’ power has faded.

We’re now entering an era where anyone can create content that looks like it was created by someone else (a column by “Woody Allen,” a book by “Ann Patchett”), and our ability to distinguish between what’s real and fake will keep decreasing.

How are trust and provenance established in this new world? Will the pendulum swing back to a greater role for gatekeepers?

I’m not saying we’ll go back to four networks, or that self-published books will disappear (they’ve gone from about 100,000 a year in 2011 to more than 2.5 million in 2025).

Rather, I’m asking: if anyone can use AI to write a column that looks like it was written by anyone, isn’t the only way to tell who wrote that column to see where it was published?

You Can’t Rush Deep Work

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Deep work isn’t just about setting aside time in bigger blocks, or about putting down the phone and turning off notifications—though those are good places to start.

Deep work is about the qualities of this sacred time you’ve set aside.

Think of the adjectives you’d use to describe deep work: focused, calm, exploratory, curious, lateral, creative, settled, playful, generative, spacious.

While there’s some overlap with how we’d describe our “non-deep” work— with words like efficient, bounded, clear, pace, and decisive—this overlap is probably small.

When moving between the two types of work, I sometimes struggle with how I experience time.

In regular work, time comes in small(er) increments. It exists as a helpful constraint to drive clarity and decisions. I’ve trained myself to get a lot done in 10 or 15 minutes, and that feels both comfortable and normal.

For deep work, I create blocks of time, but that’s just the beginning. My job is to hold the space I’ve created: the larger block of time is permission, so when I enter that larger space, I have to adhere to a different set of rules. I’m not checking the clock. I’m not looking for efficiency. I’m not thinking about what came last or what comes next. I’m not judging the success of the last moment against any criteria other than presence and engagement. This is a big shift, and it can be difficult to maintain.

Paying attention to how time feels is a good clue for whether we’re “in it” or not.

For “regular” work, time keeps us on task. It is a metronome that drives forward progress. Quality and quantity play together, and both are equally important.

For deep work, time is a buffer that protects us, creating the space we need for exploration and for leaps. The quantity of our insights and decisions does not matter; what matters is quality. Our job is to force ourselves to slow down, to move deliberately, to sit with what we’ve come up with and keep asking “is this good enough?” Our goal, for a block of deep work, is one great outcome, not 5 or 15 small but (only) good outcomes.

Here’s a hint: if you’re 10 minutes into a deep work task and you notice you’re 10 minutes in, you probably haven’t fully shifted gears yet.

Who Walks Whom?

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My first, biggest insight about philanthropic fundraising, captured in my Manifesto for Nonprofit CEOs, was about power.

The philanthropic fundraiser can feel like a supplicant asking a benefactor for largesse. It looks, from the outside, like a massive power imbalance.

My breakthrough was to recognize it for what it really is: a conversation between equals. Two people, who have things of real value on offer, are exploring building something together in the context of deep and meaningful partnership.

That miscasting of roles— “who is helping who” — is all too common.

Who is walking whom?

Each morning, if I’m at home, I walk my two dogs between 1 and 2 miles. Neither rain nor snow nor sleet nor dark of night keeps us from our appointed rounds. Some days feel amazing, and many times— when it’s raining, or dark, or cold, or hot, or when I’m just plain tired— it can feel, at the outset, like a chore.

And then I remind myself: I could have constructed an entire “early morning sunlight + 10,000 steps” routine, I could get a wearable to remind me about it, I could spend lots of mental energy working it into my days and my life…or I could just walk my dogs every day.

The walks make me a happier, healthier, more settled person, and my dogs are walking me as much as I’m walking them.

Who is feeding whom?

Over July 4th, we went to our local town pool for a picnic and fireworks display, together with some close friends. This couple has done amazing work—via a partnership between our synagogue and a local church—supporting several Afghan and Syrian refugee families.

One of those families, a brave Afghan couple who had worked in anti-drug trafficking (the father) and in women’s empowerment (the mother), fled to the U.S. a few years ago after the Taliban came to power. They have been building new lives for themselves and their three daughters, despite everything that has been taken from them.

At the picnic, we got to hear some of their stories—stories that were full of hardship and wisdom and accomplishment and loss. While we talked, they calmly pulled out one giant Tupperware after another filled with homemade food: a spread that put our few sandwiches and bag of fruit to shame. The main course was a breathtaking spread of mantu (Afghan dumplings), which I’d never had before. I took four dumplings as a first serving, and they were so delicious that I may have eaten 10 in total.

 

Every blog post I write, every coaching conversation I have, every student I speak to about career or academic choices they might make—the learning is mutual, the value is co-created.

We are helped by helping.

We learn by teaching.

We support others when we ask for help.

Dress Up

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Each day, as we get ready to go to work, we put on an outfit. It symbolizes something—to us, to the people around us. It’s the role we will be playing for the day.

It’s not only clothes that convey a story. Consciously or not, as we transition from home to work, we are putting on our work identity as surely as we put on an outfit. A lot of that identity come from the narrative that we tell ourselves.

“This is who I am in this situation. These are the contours, these are the expectations, these are the likely behaviors.”

Shifting that is not as easy as changing our shirt, or our hair. But it’s not as different as it seems.

What if you decided to wear something different today?

The Expert Expends Less Effort

~ Sasha ~ 1 Comment

A little more than a year ago, I was convinced the F major chord on the guitar was impossible. It involves:

  • ‘Barring’ across all the strings, while…
  • pressing on the third fret of the A and D strings with your last two fingers
  • Pressing on the second fret of the G string with your middle finger

If you want to expose exactly what is hard about getting the right amount of pressure on the guitar strings, the F chord is the way to do it.

I could barely play the chord after 10 seconds of setup. The idea that I would ever play it in rhythm as part of a song was simply ludicrous.

A year later, I can play the F chord reasonably well, but I haven’t gotten there by practicing the F chord. It’s happened through lots of other approaches, insight, and repetition, through which I’ve learned:

  1. Where on the fret to place the ‘barred’ finger (close to or on top of the fret itself)
  2. The position of my thumb (where it has to press the back of the guitar neck)
  3. The position of my arm, elbow and wrist
  4. The angle of that barred index finger (almost at 45 degrees, so that the bone is pressing, not the soft fleshy part)
  5. The positioning of that finger (high up enough so that the tip of the finger is off of the neck, so the thicker part of the finger is on the strings)

To play the F chord, I’ve needed to understand (at least) these five specific things, internalize them both conceptually and physically, and practice them, at speed, hundreds of times before making any real improvement. Without these insights, I would never have progressed.

But here’s the fun part: when I get all of that right, I expend radically LESS effort than I did at the outset, for much more result.

I see this pattern every time I learn something new: the thing that’s impossible at the outset isn’t hard just because I don’t have the muscles (strength in my left hand), it’s impossible because most of the effort I’m expending is not in service of the result I’m trying to achieve.

We see this in an extreme form in swimming: according to DARPA research, 97% of the effort of a beginner swimmer is not moving that person forward (3% is). For Olympic swimmers, the corresponding number is 10% — so, in addition to Michael Phelps being radically more fit than I will ever be, his starting point is that he is at least 333% more able to turn the effort he expends into forward motion.

The same pattern presents across all endeavors. Think of the skilled artist who draws one line, two, then three, and, somehow, on the fourth line, she’s captured an image, a feeling, or a sense of motion.

These insights feel familiar in some domains, less so in others.

We understand that a runner, a sprinter, a guitar player, a painter have distilled their craft down to its hyper-efficient essence. But do we apply that to ourselves when we think about the new task we’re taking on, however big or small?

I find that we spend much more time focused on what we need to DO, much less on the things that need to fall away. This translates to an unspoken notion that the way we’ll feel when we’re “crushing it” is that we’ll be splayed out at the end of the day, spent…when, really, we’ll have reached a point where we only expend effort on the things that move the needle, and we’ll have let go of all the rest.

Sure, AI is now part of this equation in the way it wasn’t before. But that’s not because it will do a bunch of tasks that we had to do manually.

It’s because the person who knows how to deploy AI will have even more leverage. She knows the essential tasks to be done, can drop all the rest, and she herself will take on the distilled essence that makes something great—those four lines that she and only she can draw.

New York’s #1 Luxury Wedding Violinist

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I got to hear Dr. Edwin W. Hardy the other day in Grand Central Station. He was rocking out on his violin, with a big sign that proclaimed him New York’s #1 Luxury Wedding Violinist.

And it’s true. Edwin was voted “NYC’s Best Wedding Violinist” by WeddingWire and The Knot couples, he’s performed at more than 500 weddings and events, including at the Met Gala and NYC Fashion Week.

I’m pretty sure Edwin is a good enough violinist to get a seat in a reputable orchestra, or to play in the pit on a Broadway show. But Edwin decided a long time ago who his customers were, where he wants to distinguish himself, and how and where he wants to win.

We can do this too.

Phrases that tell us we’re off track: any diagnosis that starts with “the market,” “our customers,” “our offering,” “our pricing,” etc.

Instead:

Who are we selling to?

What is the story we are telling them, that they can tell to themselves and to others?

What is the value we are bringing?

We’ll be more successful if we’re more like Edwin.

Unapologetic and generous

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Someone I spoke to last week told me about the most successful salesperson he’d ever met in the social sector.

This man described his approach as “collide and follow up.”

Collide is the act of getting that first, high quality interaction, which inevitably is the opposite of a lazy, AI-drafted email written generically to everyone. It is a high-value, memorable, in person connection—or its highly curated virtual equivalent—an encounter that leaves a deep and lasting positive impression.

Follow up is what it sounds like, with two notable characteristics.

The first is its relentlessness. Sales is for people with the courage to offer up something of value and the toughness to get told, time and again, some version of “no” or “not now.” We have the fortitude and discipline to continue to pursue leads in the face of repeated rejection.

The nature of the follow up is what really struck me. He described it as relentlessly generous, wildly adding value, the polar opposite of the self-serving, transactional nature of most sales pursuit.

It got me thinking about a simple 2×2 for salespeople.

So many salespeople, especially in the social sector, are too timid. Decisions in our sector are often slow, and it is natural to conclude that the most respectful thing to do is to give people lots of space.

The opposite approach is to recognize that a self-serving interruption is itself the problem. It is a tax on someone’s time and attention, whereas any generous outreach is just that: additive, without seeking something in return. It reminds me of Adam Grant’s givers, takers, and matchers, and how often salespeople are at best matchers but most often takers.

The best salespeople are living in quadrant 1: completely fearless in their willingness to connect, to push, to try again, and tireless in ensuring that each and every interaction creates value for the person they’re connecting with, as an end in itself.