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Self awareness and the luck-skill gap

One sort of delusion is believing that we’re smart and skilled simply because we got lucky. This perpetuates a cycle of bad decisions that just happened to lead to good outcomes, and causes people to confuse their wins with hard-earned skill.

Often, when someone successful in one field (where they compounded an early lead) moves into another one, they seem arrogant and unwilling to learn and experiment. They were confused about what led to their previous success.

The other sort of delusion works in the other direction. If we’ve done the reading and shown up to do the work, if we’ve built skills and muscles but haven’t succeeded yet, it’s easy to be hindered by self-doubt that might not be valid or useful. Acknowledging the luck we haven’t received yet can open the door to better decisions and more persistence.

Luck is unevenly distributed, unpredictable and unfair. If it weren’t, it wouldn’t be luck.

Rankings and flavors

Here’s a quick tactical riff about how we name things.

It’s worth considering that:

  1. Sometimes there’s more than one thing we need to highlight
  2. And putting those things in a list is a way to indicate that
  3. but numbering the list implies a priority that might not be relevant or true

If you’ve got four initiatives going on, numbering or even lettering them can’t help but communicate a priority to others.

Considering flavoring them instead.

When there’s an orange, a blue and a pink project, we can see that they’re separate and all important. It’s silly but it works.

But how to make sure we don’t skip one when calling the roll? Can we give people an easy way to remember all the flavors without leaving any out?

Here are a few to get you started:

Batman and Robin
Snap, Crackle and Pop
John, Paul, George and Ringo
Huron, Ontario, Michigan, Erie and Superior
Dasher, Dancer, Prancer, Vixen, Comet, Cupid, Donner, and Blitzen

or Monday through Sunday.

You get the idea.

On the other hand, if you’ve written a series of books or created a pedagogy that needs to go in order, please number them. It’s useful scaffolding that adds insight for those that you’re teaching.

The hustle loop

When we fall behind, it’s tempting to hustle to catch up.

When the competition heats up, it’s imperative we hustle to get ahead.

Hustle is a particular kind of shortcut. Hustle is pushing the boundaries of cultural expectation, creating pressure and discomfort to make a sale. Hustle pushes us to cut corners, cut the line and cut down trust.

And it quickly becomes the new normal. Hustling is a race to the bottom, and our competitors lean and hustle in response… which means that we’re now under pressure to hustle more than we think is appropriate, driven by the same forces that led us to hustle in the first place.

The alternative is to lean into better. To find the space and the guts to do breakthrough work, work that others are afraid to do. Instead of causing discomfort and cutting, we’re building something worth following and talking about.

Of course it’s not easy, that’s why it works.


PS A breath of fresh air, Dr. Natalie Nixon’s new book is out.

Bringing goodwill to the conversation

Education is distinct from learning. Organized education is a form of indoctrination and certification. Sometimes it leads to learning, but not always.

You can win at education by figuring out what’s on the test (or what the boss wants) and parroting it back. In fact, that’s the easiest way to do so.

Learning is an argument, a conversation designed to change minds. Learning happens long after we leave organized schooling, and it requires emotional enrollment. We’re more likely to learn when we bring a desire to be transformed and to leave our previous assumptions behind.

Amplified by social media, there’s a rising tide of arguments that purport to be learning that actually lead nowhere. That’s because the participants are seeking to score points and gain attention, not to enroll in a mutual process of transformation and learning.

What does goodwill look like?

Be prepared (or better yet, eager) to change your mind.

All claims should be verifiable.

All assertions should be falsifiable.

Do the reading.

Show your work.

Reveal your actual agenda.

Understand the systems and mechanics at work, don’t simply quote them.

Assume goodwill on the part of others.

Don’t judge an argument by how comfortable its conclusion feels.

Question your own expertise. “I don’t know” is a complete sentence.

Engage with the strongest version of opposing views.

Embrace that “not yet” is different from “never.”

Celebrate your errors and welcome correction gracefully.

Ask helpful questions that support an alternative view before deciding.

Agree on the rules in advance and then honor them.

Focus on understanding before seeking to be understood.

Identify the ideas you are attached to and temporarily set them aside.

Change your mind. That’s why you’re here.


[More riffs on learning as many of us go back to school.]

Walk away or dance

AI and LLMs pose a particularly visceral threat to the typing class. Writers, editors, poets, freelancers, marketing copywriters and others are voicing reasonable (and unreasonable) objections to the pace and impact of tools like Claude, Kimi and ChatGPT.

I think we have two choices, particularly poignant on US Labor Day…

The first is to walk away from the tools. You’re probably not going to persuade your competitors and your clients to have as much animosity for AI automation as you do, and time spent ranting about it is time wasted. But, you can walk away. There’s a long history of creative professionals refusing to use the technology of the moment and thriving.

If you’re going to walk away, the path is clear. Your work has to become more unpredictable, more human and more nuanced. It has to cost more and be worth more. It turns out that the pace of your production isn’t as important as its impact. Writing a hand-built Linkedin post that gets 200 comments isn’t a productive path in a world where anyone can do that. If we’re going to put ourselves on the hook, we need to really be on the hook.

Remember the mall photographers who took slightly better than mediocre photos of kids at Sears? They’re gone now, because we can take slightly better than mediocre photos at home.

The other option is to dance. Outsource all relevant tasks to an AI to put yourself on the hook for judgment, taste and decision-making instead. Give yourself a promotion, becoming the arbiter and the publisher, not the ink-stained wretch. Dramatically increase your pace and your output, and create work that scares you.

This requires re-investing the time you used to spend on tasks. Focus on mastering the tools, bringing more insight to their use than others. Refuse to publish mediocre work.

It’s tempting to fear AI slop, because it’s here and it’s going to get worse. But there’s human slop all over the internet, and it’s getting worse as well.

Whether you dance or walk away, the goal is the same: create real value for the people who need it. Do work that matters for people who care.

If we’re going to make a difference, we’ll need to bring labor to the work. The emotional labor of judgment, insight and risk.

Possibility vs. certainty

It is impossible to make a perpetual motion machine, you’ll waste your time if you try.

It is possible to write a book of poetry that will sell 10 million copies.

It is unlikely, it probably won’t happen, but it is possible.

Science and innovation and creativity engage with the possible. Possible means “might.” It takes persistence to stick it out when we’re not sure.

Once certainty arrives, it becomes an engineering problem.

After the first fusion reactor is shown to work at any scale, we’ll know it can be done. Now the hard work is simply making it work better. Most organizations do this sort of work. Chipping, filing, refining.

Before you get to work, it’s worth deciding which hat you’re being asked to wear… pursuing the possible or optimizing the certain.

Food bonus post

It’s been awhile…

Coconut Cult is a new sort of probiotic magic that’s actually delicious (the chocolate is great, the strawberry is magnificent). A tablespoon a day, try it for a week. You have 38 trillion gut bacteria (!) so you might as well make them happy.

This is the best gluten-free ramen I’ve ever had.

Peanut butter is more than a staple. The best I’ve had is only in the UK, the second-best is homemade. This is the third best, which is so much better than all the other options, I needed to share. You can probably find it locally, or buy a case from Zingermans.

I’m really enjoying the new botanicals and herbal teas from Rishi. And the Jimmy Nardello flakes from Burlap & Barrel. And Le Grand pesto is my favorite vegan pesto–but not easy to find.

And, by request, the homemade honey-oatmeal vodka recipe, as well as a breakthrough on my homemade dosa.

PS Two years later, this is still my favorite rice cooker.

Brittle systems

Large organizations are purpose-built to do what they do, under prevailing conditions.

People are hired, assets are acquired, measurements are put in place–all to optimize what’s happening right here and right now.

In 1929, 200 million telegrams were sent. The wiring, technology, staffing, real estate holdings and marketing of Western Union were all optimized around delivering these telegrams profitably and with quality.

By most external measures, it was working, brilliantly. There weren’t too many things you could do to make the telegram system dramatically better.

When the change agent appears, the optimized organization stumbles. It takes heroic work to shift it for a new reality. Short-run efficiency rarely aligns with long-term resilience.

More often than not, it’s the insurgent that takes the lead. All they need to do is optimize for the new reality, they can skip the part about restructuring what they already have.

This is sort of obvious, but worth saying out loud. And while these shifts used to take decades, now they happen far more quickly. It hardly pays to be the dominant maker of fax machines in 2025.

If you’re an insurgent with a small team and fixed asset base, be on the hunt for a change agent that is going to swamp existing systems. When the change comes, you’re ready for new rules and the competition is hoping for stability.

And if you’re part of a dominant incumbent organization, perhaps it’s time to start looking for a new gig instead of hoping to wait out the shift. Because the new normal is rarely a return to the old normal.

Poison

Don’t swallow Polonium-210. You won’t last long, and it won’t be pleasant.

There are poisons all around us. The arsenic in your rice, the drain cleaner under your sink.

Alas, some poisons are impossible to avoid, and it’s not productive to live a life that’s poison-free. But it might be worth considering three questions when we think about poison:

  1. How fast does it act? There’s a difference between a bowl of brown rice and taking up BASE jumping.
  2. Who else does it harm? Poisons that we spread to others are less moral than the ones we expose ourselves to.
  3. How much does it cost to avoid? What do we have to do to our systems, our expectations and our methods to avoid this poison?

This analysis makes it clear that banning gas-powered leaf blowers is a no-brainer. They are instantly noisy and noxious, and they make more of an impact on our climate than just about any item in our garage, and they do so quickly. They harm others at least as much as they harm the user, and avoiding their use is convenient and saves money.

In addition to actual physical poisons, most of us wrestle with the emotional and spiritual poisons that are dumped in front of us every day.

Persistent systems are good at sticking around, and that’s true even when they’re bringing actual poison with them. As we seek to build a more resilient path forward, perhaps it pays to experience the short-term discomfort associated with fixing a dangerous system now rather than living with the poison it creates over time.

For people who don’t care that much

If someone snuck into my closet and switched out one brand of sneakers for a similar model from another company, it wouldn’t bother me much. Popular cars like the Camry, the Civic and the Elantra don’t have raving fans the way the Mini or the Rivian do. Go to the rental car counter and take what’s on offer.

Popular products and services succeed because they’re normal, reliable, convenient, cheap or simply incumbents. If someone expected to stay at the Hyatt but finds themselves at the Marriott, it’s probably not a big deal to them, because both brands have worked hard to find themselves in the center, sanding off idiosyncrasies and inconveniences to get there.

And thus, the fork in the road: If you’re building something remarkable, memorable and important, you’re simply not going to appeal to the masses for precisely those reasons.

This isn’t about being the most expensive. It’s a different sort of elitism–the elitism consumers choose. The decision to invest time in learning about the options, caring about the small differences and feeling confident enough to develop an opinion.

Sure, some people care about Budweiser or Coke, but that’s not what those brands stand for.

If you want to build a mass brand, invest in convenience and normalcy.

And if you want to be particular, memorable and worth what it takes for fans to be loyal and committed, don’t chase the people who don’t care that much.

Either you make something that costs more and is worth more than it costs… or you chase convenience, ubiquity and low price.

“This might not be for you,” is a fine slogan.