I heavily studied Leonardo da Vinci while researching for my upcoming book, Finish What Matters (tomorrow is the last day to buy the Preview Edition).
Besides the many fascinating anecdotes in the book, what I’ve learned about how Leonardo thought:
Write down anything you think. He was unafraid to write entire arguments with himself, to test what he believed.
Write down what you learn. Much of the dazzling observations in his notes are simply written down from books he had access to. This was out of necessity, but no doubt helped him retain the information.
Make connections. He was constantly making observations of one thing by talking about another thing and how it was or wasn’t related.
Visualize what’s in your head. He was unafraid to draw what he imagined in great detail.
Be okay with being wrong. Importantly, he wrote and drew plenty of things that were wrong (flying machines that wouldn’t work, naive understanding of female reproductive anatomy). But he still thought those things through with what he had.
Make observations, not memorizations. He placed experience and observation above all, so even though he was wrong sometimes, he was also centuries ahead on other things.
Embrace an inductive approach. His notes are thousands of tiny observations that built up to bigger observations. He’d write the same information over and over in different ways, like a true inductive.
Manage your curiosity. He didn’t always go straight down rabbit holes. He’d write a to-do list of what he wanted to look into.
Push the limits. He left a lot unfinished, but often because he was trying ambitious or experimental approaches that would have been innovative had they worked – and sometimes they did.
It’s easy to remain mystified by the illustrations, paintings, and myths, but Leonardo was just a man, and he had real ways of being we can all apply.
Aphorism: “Feeling gratitude and not expressing it is like wrapping a present and not giving it.” —William Arthur Ward
Cool:The President’s Inbox is a non-partisan podcast with deep analysis of global events.
It takes luck to make it as a creative, but not as much luck as it seems.
I think it can be explained by what I call the “Travis in Tokyo” effect. At some point, you may have been traveling, and run into a friend. It’s a shocking experience, and you say, “What are the odds I’d run into my friend Travis in Tokyo?!”
There are a few phenomena that make this less exceptional than it seems.
One is ad-hoc analysis. You didn’t form a hypothesis before going to Tokyo whether you’d run into Travis. A lot of other surprising things could have happened. Scientists run into problems when they look for patterns in large data sets, finding surprising things such as that as cottage cheese sales decline, so do babies named Andrea.
Another is the multiple comparisons problem, which is that when a lot of different things have low odds of happening, at least one of them is likely to happen. You were surprised to run into Travis in Tokyo, but didn’t reflect on the odds you’d run into at least one of the hundreds of people you know.
Finally, there’s the fact that you’re friends with Travis and everyone else because you have things in common – perhaps an interest in Japan or travel, or just that you’re in the socioeconomic profile of people who would travel to Japan.
When we look at the success of a creator, and the chain of events that led to that success, we get tunnel vision as we consider the outrageously-low odds that chain of events could have occurred.
But we don’t consider that out of the many things they tried, this was the one that worked; that when adding up the low probabilities of their many attempts, the probabilities weren’t as low as they seemed; and that as skill and network effects compounded, those odds climbed with each attempt.
There is hope.
Aphorism: “Every artist should be content to do willingly those things towards which he feels a natural inclination.” —Giorgio Vasari
Cool: The HATOKU Stylus Pen (Amazon) is a $20 good-enough alternative to Apple Pencil, for compatible iPads.
Best, David P.S. If you work with the odds, you can have success that seems against the odds, which makes it easier to Finish What Matters – the title of my upcoming book. Read it many months before others in the Preview Edition.
New Year’s resolutions are destined from the start to fail.
How could you possibly decide how many subscribers you’re going to gain, or weight you’re going to lose?
Even if you stick with what you control, how could you go from not doing a behavior at all to doing it regularly? You don’t even know what it’s like and you and the world will change within the year.
It’s like trying to hit a moving target with an arrow made from a wet noodle.
This is why I prefer New Year’s estimates, not resolutions. Such as:
I’m 20% sure I’ll gain 1,000 Substack subscribers
I’m 60% sure I’ll publish an hour of content on YouTube
I’m 70% sure I’ll finish my manuscript
You don’t have the information to say what will happen, or what goals will still be worth striving towards. By making an estimate, you give yourself a chance to respond to reality.
There’s also something about making estimates that makes you think about reality: Resolutions are aspirational. By saying this will definitely happen, you paradoxically shut yourself off from the factors that will affect whether it does.
As you think about whether something is 50%, 70%, or 90% doable, you start to think about what’s actually affecting your ability to make it happen, which often leads to thinking of actions you can take to increase your odds.
Aphorism: “The present of things past is memory; the present of things present is sight; and the present of things future is expectation.” —Saint Augustine
Best, David P.S. Making and reflecting on estimates is a key tactic in my upcoming book, Finish What Matters. There’s still time to start reading the Preview Edition.
A dominant meme of the early internet was that we were freed of the era of “three channels” – when the American television airwaves and thus psyche were controlled by ABC, NBC, and CBS.
But now it feels like we have only one channel.
That’s of course not materially true. We’re free to dig up anything we want, unlike ever before. But “channel” implies passivity, which is what TV was, and what we’ve reverted to.
Another meme about the dawn of the internet was the removal of “gatekeepers.” Finally, the ideas would spread that were the most interesting – about the most obscure topics you could imagine.
But what we’re being offered up feels strangely “smooth.” The topics might be different, but the depth, pacing, and structure falls within a tight range, like all the rough edges have been sanded off.
The smoothness, of course, is from “the algorithm.” We might as individuals appreciate the jagged edges of something, but can the algo mathematically sniff out everyone else who does? It seems not. And now LLMs are mathematically deciding which word would be most likely to come next, and changing it just enough that what comes out is essentially the same thing.
And maybe those gatekeepers made things a little less smooth, a little more jagged. We didn’t like how this person or that got this big break through nepotism or sexual favor, but some of it must have been from the mere whim or strange taste of some executive. In any case at least something that didn’t “deserve” the exposure in the algorithmic sense got it, and there was probably something good about that.
Because we used to have three channels, and now we just have the dopamine channel.
Aphorism: “The minimal level of engagement with the Internet is equal to the maximum level of engagement with old media.” —Andrey Miroshnichenko
Book:Julius Caesar (Amazon) is a Shakespeare play that will make you think of the Roman Empire.
As 2025 began, I made a soft agreement with myself to try to meditate 300 hours in the year. I’d try an hour most days, and figured I’d miss a day here or there.
Now I’ve meditated an hour a day more than 365 days.
In the past, I deliberately avoided holding a streak – I purposefully quit my first hour-long meditation challenge after 89 days, to avoid the psychologically-significant “90.”
I’ve been holding onto this streak mostly because not meditating now feels like not brushing my teeth, or not sleeping. I get so much out of each session, I don’t want to miss it.
By far the biggest revelation has been my accidental discovery of something I guess they call “somatic release.” I started feeling the urge to lean into tension in my face and body, leading to some strange facial expressions and postures.
It looks and is simple, but I have to warn that the tension patterns it releases have been very deep. I could see how it could really mess someone up mentally and physically. The first weeks after unlocking this I felt very shaky and emotionally fragile. I had severe hip pain – I thought I had uncovered a latent injury. So try at your own risk and maybe there are professionals you could consult?
Now I’m glad to have worked through that initial phase. I feel far more emotionally resilient. I get less angry, feel less insecure, and take things less personally. It shouldn’t be a surprise that also makes me feel a bit less ambitious – at least in my previous understanding of ambition. But in my writing I feel more capable of seeing an idea or feeling from all possible angles to really find the contours of what’s interesting.
The best way I can describe this process is as like sorting through a library of memories of not just the worst things that ever happened to you, but also the thousands of tiny moments of discomfort that pile up and get “stored” in your body. It also feels like sorting through experiences you haven’t personally had, but that are locked into the human nervous system through the experiences of your ancestors. Sometimes it’s accompanied by the actual emotions, but a lot of times it’s like you’re “acting” the emotions – such as by shedding tears but without sadness.
During each session I release a lot of this tension, but the next day there’s always still more to work through. Maybe someday it will all be gone.
If there’s any one revelation this far into this process it’s that all the emotions are okay: rage, humiliation, lust, elation, self-pity, and more. Many are not justified, but they are okay, a product of being in a human body. Few are worth acting on, but all are okay to feel, at least for that hour.
I wish more people had an hour a day to meditate, because you reach a point where it’s like driving with a new windshield.
Book:Slow Productivity (Amazon) is Cal Newport’s manifesto for knowledge work at a sane pace, which Mind Management lovers will enjoy.
This may feel too obvious to mention, but I can’t get over how some of the most valuable things can be made with the cheapest tools.
Larry David and Jerry Seinfeld wrote the most successful television show ever with BIC pens on yellow legal pads. (If you want to take it really far, Socrates just talked.)
So I find it entertaining to try to find the cheapest possible paper and pen. It is just so damn cool to me that I can use them to write a book that sells thousands of copies, or write the script for a reel with millions of views.
The cheapest I’ve found yet is 10 BIC pens for $1.29 (when I bought them 6 months ago, at least), and a 200-page notebook for 3,800 COP (~$1) at a neighborhood papeleria.
There’s definitely something to be said for a nice pen and paper, especially when you’re looking for a reminder that your thoughts are valuable, and worth writing down.
But this exercise does something else for me. I think it spreads to other areas, where next time I’m thinking of buying a new camera or audio equipment, I tell myself to snap out of it. Using cheap tools reminds you not to be too precious – that you’ll have to do a lot of work to get good at the stuff that matters, and that – maybe this is uncomfortable to admit – you already have what you need to get started.
Aphorism: “To one who can understand reason, you will find ten who admire wit.” —Maria Edgeworth
Cool: These acoustic blankets pack a lot of sound-dampening into simple (but heavy) blankets.
Best, David P.S. A tool that is perhaps even cheaper in the long run and very much still worth writing on is a typewriter.
We wouldn’t want a plane engineer to forget the laws of physics. We wouldn’t want a doctor who rejects the fundamentals of biology.
But the scientific method which has gained us this knowledge seems to distract us, like a magician’s sleight-of-hand preventing us from seeing the rabbit under the table.
There have been times and places when the burning questions amongst the smartest people were not as much about what could be precisely measured and reduced to a formula – Ancient Greece, Renaissance Florence, Early India and China.
The questions were instead about what is a life well-lived, what trade-offs should a society make, and how do you navigate consciousness and this existence of fortune, desire, suffering, and elation?
None of these questions have concrete answers, which is understandably frustrating in a world where we have a name for the protein that causes this or that heretofore mysterious malady.
But it’s strange that people sat around and asked these questions, figured out and recorded pretty-good answers that are freely available to us, and most of us just struggle through life only to, if we’re very lucky and live a long time, come to the same conclusions the hard way.
Aphorism: “Is the resolve to be so scientific about everything perhaps a kind of fear of, an escape from, pessimism? A subtle last resort against – truth?” —Friedrich Nietzsche
We jump into projects because we think they’ll go well. They seem to always be more difficult, less fun, and take longer than we had expected.
This is one reason we get stuck in a cycle of starting, abandoning, starting, abandoning, without ever finishing.
But I’m beginning to think this is as much a feature as it is a bug.
One of the things I appreciate about ChatGPT is it gives me the confidence to take on projects, thinking it will do most of the work. They still end up being difficult, but I wouldn’t have bothered otherwise.
And as I reflect on my own career, I realize there is nothing I’ve created I’m proud of to which the meme doesn’t apply: We do this not because it’s easy, but because we thought it would be easy.
So I do what I can to avoid drowning: Make and review predictions, ask myself what I might not be thinking of, and conducting little experiments to test my theories.
But there’s ultimately something motivating about getting in a bit over your head. It forces you to learn to swim.
Aphorism: “Who is it that, seeing the havoc of these civil wars of ours, does not cry out, that the machine of the world is near dissolution, and that the day of judgment is at hand; without considering, that many worse things have been seen, and that in the meantime, people are very merry in a thousand other parts of the earth for all this?” —Montaigne (1575)
Cool:Browse.ai helps you monitor and scrape data from any website, no coding required.
Best, David P.S. Thank you to JJ Thelen for having me on the JJ Thelen Show.
There’s no end to details that might make your work a little better.
If you’re publishing videos, your camera, lighting, and mic could be better. There’s a dozen ways to cut and zoom, thousands of motion-graphics templates, and a million options for b-roll.
If you’re writing articles, there’s no limit to the hours you could spend finding just the right combo of animated GIFs, and there are just as many ways to break it up with headings and sub-headings. When you’re done, you can spend the rest of your day following related accounts and leaving comments so people can discover you.
Or, lose the crutches. There’s no end to the bells and whistles you could add to make your work a little juicier, a little more noticeable.
But when you place constraints on yourself, such as that for now you’ll only talk to the camera or not use images or bullet-points, a couple things happen.
One, you have a lot more energy to focus on the core of the work that makes all the difference. Two, you have no choice but to build that core skill beyond what you would have bothered when it was propped up.
Yes, it’s harder, and that’s the point.
Aphorism: “Being able to hover calmly and objectively over our thoughts, feelings, and emotions (an ability I’ll call mindfulness…) and then take our time to respond allows the executive brain to inhibit, organize, and modulate the hardwired automatic reactions preprogrammed into the emotional brain.” —Bessel van der Kolk
Cool:Wise helps you get paid in different currencies.
I don’t drink anymore. Not as a conscious rule, just because the majority of times I’ve considered having a drink in the past ten years, not having it has seemed more appealing. That calculus has prevented me from having even one drink for well over the past year.
I’ve never been an alcoholic, but the more I reflect on my behavior when I was drinking, the more I think to myself – why is that okay?
Why is it okay to spend the equivalent of a working day going from bar to bar? Why is it okay for every romantic connection to be facilitated by alcohol? Why is it okay to be less happy and effective the next day because you drank too much last night?
Lots have asked this lately, which is not where I’m going with this.
Where I’m going is, for how much other stuff are many of us a 2 or 3 out of 5, but we keep going as we were because it doesn’t qualify as a pathology?
It seems most of us are a little alcoholic, anxious, depressed, agoraphobic, sex- and love-addicted, etc.
Not enough to be a “problem,” and I think I know why.
Because for something to be a “problem,” it has to interfere with our work and relationships, etc. In other words, it has to interfere with our roles in capitalist society as contributors and consumers.
I’m not here to deliver an anti-capitalist screed or even suggest a conspiracy, but maybe 3/5 actually is a problem. And the only reason it’s not considered so is because our consumption hits the optimal balance when we’re just a little addicted, anxious, sad, lonely, out of control.
Aphorism: “No project can, of course, be more time-consuming than self-discovery.” —Harold Rosenberg
Book:Notes From Underground (Amazon) is Dostoevsky classic exploration of the human psyche, through the lens of an alienated and ostracized man.
Best, David P.S. You’ve got about a day to get 60% off Kit for your creator business’s email marketing.
