Water flows downhill. We all know this, and we all (implicitly) understand the idea. Water is flexible and subject to the forces of gravity. Terrain has high points and low points. Water follows the path of least resistance to reach its destination.

Water isn’t the only thing that behaves in this way. I think people behave in an identical fashion. Once the destination is determined and “terrain” is clearly visible, the path of least resistance becomes obvious. Unlike water, though, humans have to define the final resting point as precisely as possible.


He’s a cockapoo puppy, and he’s no fool. You see, when I command him to “Come!”, he doesn’t always listen.

Biggy prefers to be inspired. When he sees me holding his multicolored bag of treats, we can expect enthusiastic compliance to most any command. He can picture his future self chewing on a delicious morsel.

Without the bag of treats, it’s hard to see the point. Why “come” when he can just “stay”?

Consider that this applies to humans, as well. Without a vision, we’re lost. If we can’t connect the dots between our present self and an exciting future, it’s hard to expect much out of man or his best friend.

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An entrepreneur’s first idea rarely pans out. It’s a stab in the dark, aimed in a direction that might hold opportunity. The market may be there, but it’s not being listened to. Entrepreneurs need to become market therapists to succeed.

A good therapist won’t go into a relationship assuming they know the client’s problems. Their hunches can inform where to dig in, but they never see the whole story at the beginning. It takes multiple sessions to get to the heart of the issue.

An entrepreneur starts with a good hunch. They have their idea, and they know generally where they need to focus. But they must listen to the market to fully understand its problems.

Entrepreneurs should never assume that they know the full scope of the problem going in. What is the market saying that others aren’t hearing?

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Starting a big project is tricky. I usually have some sense of what needs to be done, but my time estimates tend to be… a little off. There’s one thing worse than underestimating the time it’ll take: doing unnecessary work. I hate getting traction on a project only to realize that a bunch of work was wasted.

There’s a trick that often works for me: Rescope the project to complete it within the next week. Even when unrealistic, trying to apply that tight constraint can get you to notice things you wouldn’t otherwise. It forces me to consider what is absolutely necessary and what can be skipped. …


When the automobile was first released, people referred to them as horseless carriages. The driver would sit at the same height as on a carriage, even though there was no horse to see over.

New technology has far broader implications than an initial implementation suggests. Florent Crivello proposes that every new technology goes through this “valley of mismatch”:

It’s becoming more widespread, but people are still using it under the logic of the old paradigm

Software, the Tough Tomato Principle, and the Great Weirdening of the World

There used to be huge printed directories of local businesses (Yellow Pages). Innovators carried the same idea to the internet (Yahoo). It took a while to discover the full information indexing potential of computers (Google).

What valleys of mismatch do you see around you? There may be some Tortoises crawling through them as we speak.

Originally published at Gary Basin.


Hares are quick. They love the thrill of racing their competition. They move fast and stay lean. But their greatest strength is also their weakness. Hares act first and ask questions later. Sometimes, their speed gets the best of them and they’re forced to learn from their mistakes.

Tortoises are slow. They move mindfully, thinking through each step before they take it. Tortoises see much further ahead than the hares; they know exactly where they’re going. They carefully consider each move but act decisively. A tortoise rarely retraces its steps ⏤ one wrong turn can spell disaster.

Sometimes it pays to be a hare, such as Facebook and Alphabet. Other times, it pays to be a tortoise, like Apple and Tesla.

Trying to be both at once rarely turns out well.

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The Innovator’s Dilemma begins as an exciting new market opportunity presents itself.

Blue enters the market by providing a solution. It solves some customer problems by leveraging its new Circle technology.

Blue doubles down on Circle technology and continues to grow. Eventually, it captures the majority of the market.

But markets aren’t stagnant. They constantly change. Go back and look how the corners of the outlined area have been evolving. This represents new customers with unique needs who Circle technology can’t serve.

Then Green enters the market. It’s a startup pioneering Triangle technology. It serves the needs of the corner of the market. Blue doesn’t change because Circle is still a better solution for the majority. Besides, it might lose focus if it tries to specialize in Triangle.

The rest, as they say, is history.

The Innovator’s Dilemma was created by Clayton Christensen.

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I love to read about how great people accomplish great things. It’s similar to getting advice — I’m left with a high. I imagine that if I can follow the instructions, then I too will accomplish what they have. It’s a logical and tantalizing idea: follow the prescription, get the reward. In practice, it tends to fall short.

Kapil Gupta and Naval did a great interview where they touched on this pitfall.

The catch is, to achieve something truly remarkable, you have to do something new. It’s practically in the definition. Copying others can help you learn a domain. Imitation is good practice. But to do something new — to create art — you inevitably have to write your own script.

I expanded on these thoughts in a Twitter thread here, also touching on how prescriptions can act like false Gods.


I love to read about how great people accomplish great things. It’s similar to getting advice — I’m left with a high. I imagine that if I can follow the instructions, then I too will accomplish what they have. It’s a logical and tantalizing idea: follow the prescription, get the reward. In practice, it tends to fall short.

Kapil Gupta and Naval Ravikant did a great interview where they touched on this pitfall.

The catch is, to achieve something truly remarkable, you have to do something new. It’s practically in the definition. Copying others can help you learn a domain. Imitation is good practice. But to do something new — to create art — you inevitably have to write your own script.

I expanded on these thoughts in a Twitter thread here, also touching on how prescriptions can act like false Gods.

Originally published at Gary Basin.


I used to believe that Distractions Were Bad. Time spent away from “the work” when you’re “supposed to be doing the work” means less work “gets done”. Right? Over time, I’ve come to see that it depends.

I’ve studied and tried all kinds of formal techniques for solving problems and being creative. Here’s a list I put together: Thinking Toys. Don’t get me wrong, these can be useful. But they’re no panacea.

When doing creative work, I now embrace distraction. What’s my creative process? Switching every few minutes between “the work” and “the distraction”. Sometimes it’s Twitter. Sometimes it’s looking out the window. Sometimes it’s trimming my cuticles. Whatever the distraction of the moment, I think it helps. Distractions make me more creative.

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Gary Basin

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