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Three Lessons from the Life of Leonardo Da Vinci

I’ve been listening to Walter Isaacson’s Biography of the polymath Leonardo Da Vinci. A few anecdotes from his life struck me as worth sharing here.

Leonardo The Reluctant

In 1504, both Leonardo and his rival Michelangelo were commissioned to create paintings that would face each other at The Hall of the Five Hundred in Florence. The intention of this dual commission was to spark a competition between the two greatest artists in Italy.

So it is ironic that both Leonardo and Michelangelo hated painting. Of Leonardo, many contemporaries noted that “He couldn’t stand to look at a brush.” What he really wanted to spend time on was science and engineering.

Michelangelo also hated painting. He thought of himself as a sculptor. While working on the commission in Florence, he wrote in his journal, “I am not in the right place and I am not a painter.”

The lesson I take is that it doesn’t matter how good you are, sometimes you just have to work on things that aren’t that interesting to you. Even geniuses sometimes have to take what the market is offering.

The Anatomy of Failure

Leonardo is famous for the way he was able to blend his love for science and discovery with art. Among the most famous of these pairings is the anatomical drawings he created based on his dissection of cadavers.

His keen mind allowed him to discover things that wouldn’t be known for another 100 years (such as how blood flows through the human heart) and his abilities as an artist lead to renderings of the human body that to this day stand unmatched for their accuracy and aesthetics.

Yet his achievements languished undiscovered in his notebooks until the modern era. This is because Leonardo never published his work. His partner in his anatomical studies died of plague and Leonardo did not have the discipline or inclination to bring the project to term.

The lesson is that insight and output do not necessarily correspond. Without a clear vision, discipline and perhaps a good partner, even the brightest minds can achieve less than their potential. As Walter Isaacson notes,

“One of the things that would have most benefited Leonardo in his career was a partner who could push him to follow through and publish his work.”

Leonardo Da Vinci The Original Consultant

As Europe awoke to the fact that there was a new world laying across the ocean, Leonardo’s home city-state of Florence realized that it would need to acquire a port to get in on the action. This meant conquering a nearby city and Pisa was chosen as the most attractive option.

Pisa was vulnerable if the Florentines could divert the river Arno from its course, effectively cutting it off from supplies. Leonardo was put in charge of figuring out how to do this.

Leonardo knew he had to dig a massive channel in order to divert the river. He calculated that it would entail the movement of over one million tons of earth. Knowing this, he had to determine how many men and how much time it would take. But instead of blindly estimating, Leonardo conducted the first of what has now come to be known as a time in motion study.

Using a watch he studied how long it took a man to fill a bucket of dirt and move it to a machine he’d designed to carry it away. Based on his measurements, Leonardo calculated that it would require over fifty thousand worker-days to complete his project.

After making his designs and calculations, Leonardo left instructions for the project and returned to Florence. Unfortunately, the person who was selected to oversee the actual operation went against his wishes and started digging two canals, instead of one.

Leonardo and his compatriot Machiavelli tried to pressure the engineer into sticking with the original plan but failed. In the end, despite heavy rains, the two half as deep canals failed to divert the river and the plan was abandoned.

The lesson in this is that you can have the most brilliant strategists but if the actors don’t play their part, the plan will fail.

5 High Impact Health Habits for 2019

The advent of low-cost wearables and sophisticated cell-phones makes it possible for us to track an ever-expanding number of health metrics. My health tracking journey began with me tracking a spectrum of indicators: weight, blood glucose, ketones, macronutrients, and more.

Over time, however, I realized that many of these variables were not predictive or influenceable. Which is to say they weren’t really important. This is why, for example, I don’t track my weight.

What’s more, the act of tracking too many things can create an additional obligation that only adds to the stress of what’s already a difficult endeavor.

Thus, if you’re going to track your health habits, I believe it’s worth focusing on tracking the things that really matter and avoiding those that don’t.

Here are the 5 things that I’m currently tracking:

Fasting Hours / Stuck to Diet

Nutrition is probably the most important health variable you can track. Unfortunately, it’s also the most complex.

After reading countless books on nutrition and experimenting with nearly every conceivable diet under the sun, I’ve returned to the truism that the best diet is the one that you can stick to.  For me, this is a fasting-based diet.

Even if you follow a diet other than fasting, I recommend simply tracking whether you stuck to the diet for the day or not. This can be as simple as logging a yes or no in your calendar, spreadsheet or journal each day.


Exercise is worth tracking because it’s both predictive and influenceable. Predictive because, more lean body mass means better insulin resistance, and better mobility means a lower probability of injury. Influenceable because I can control how much I exercise.

I track whether or not I exercised each day. It’s a yes or no variable. I define exercise as a long run, a sprint workout, or cross-training / muscle-building activity.

Alcoholic Drinks

In an earlier post, I discussed the power of negative habits. For me, alcohol is the negative habit I need to be mindful of. It impacts my sleep, my work ethic, my nutrition, virtually all the health variables I track.   

To track this, I simply record the number of drinks I have each day (if at all). So far I’ve found it very helpful.


As I’ve been learning in from Matthew Walker’s excellent book, Why We Sleep, sleep impacts virtually everything we do. I’ll save the specifics for a future post but suffice to say that your body needs sleep about as much as it needs water.

I use the Oura Ring to track my sleep because I’m a technophile. But you don’t need to do this to get useable sleep data.

To start, I recommend using Apple’s Bedtime feature on your iPhone to ensure that you’re getting 7-9 hours of sleep opportunity on a daily basis.

Meditation / Emotional Resilience Training

Regular readers may recall that I have been skeptical about meditation and its benefits. That hasn’t changed (and I hope to go deeper into this in a future post).

In spite of this, I’ve continued to meditate primarily because the risk/reward ratio is very clearly stacked in favor of doing something rather than nothing. Meditating doesn’t cost much money or time and the benefits, if and when they materialize, could be life changing.

I track simply whether I meditated or not each day. This is a Yes or No column on my tracking sheet. If I meditate for at least 10 minutes I put a yes down.

Currently, I’m using Sam Harris’ Waking Up app and very much enjoying it. But there are other free apps such Oak you can use to meditate as well.


This is what I’ve settled on as of Q1 2019, but it may not be right for you. Please let me know if you disagree with any tracking strategy or have some of your own to share!

The Power of Negative Habits

One commonality among people’s New Year’s resolutions is that they are mostly positive actions. Exercise more, eat better, learn the piano, spend more time with family, or just tackle the project that’s been nagging you all year.

This is interesting because giving up a negative habit usually has a far greater impact than an incremental positive habit. If picking up a new good habit might make you 1% better, dropping your worst bad habit will make you 10% better.

This begs the question, if we really want to be better, why do we ignore our negative habits?

I believe we favor positive over negative resolutions because aspirations are more attractive. They are also more marketable. It’s much easier to sell trying something new than it is to sell giving something up, so we are both more aware of and more attracted to positive changes.

Negative habits are difficult because they require self-awareness to identify. They are also ingrained in who we are and often because they satisfy some deep need within us.

To use the body as an analogy, starting a new positive habit is like adding another digit to your hand, probably a little helpful in certain situations. While eliminating a negative habit might be compared to amputating a necrotic limb; you relive your body of a life-threatening burden but a burden that is nonetheless a part of who you imagine yourself to be.

As you go about trying to achieve your resolutions this year, it’s worth reflecting on whether there is a negative habit that’s getting in your way. If there is, it’s likely that same habit is sabotaging other aspects of your life as well.

Recognizing it is the first step towards making significant, and sustainable improvements.

How I’m Tracking Habits in 2019

The chains of habit are too light to be felt until they are too heavy to be broken

Warren Buffett

Daily habit tracking is something I’ve wanted to do for years but I could never find a method that worked for me.

Journals lay forgotten under my bed. Apps on my phone started off well enough but eventually I’d miss a few days and find inputting the data extremely cumbersome. Excel spreadsheets saved on a mac were not compatible with my windows machine or had different versions, etc.  

But in 2018 I cracked the code. I’ve finally found a service that syncs across all my devices that’s easy to use, and best of all it’s free!

The answer, you may already have guessed, is Google Sheets.

It’s not perfect. It’s not fancy, it’s not pretty but it’s easy to use and it’s everywhere I need it to be all of the time.

Here’s a quick Pros and Cons rundown:


  • It’s available on all my devices
  • It’s easy to use
  • It’s easy to play catch-up on
  • I can easily manipulate the data
  • I can change what I track from month to month (this has been very important)


  • It’s not beautiful
  • Doesn’t come with pre-packaged visualization tools
  • Doesn’t come with pre-packaged analytics tools
  • Can take a few seconds to load when you have multiple tabs
  • You have to create a new sheet each month
  • Doesn’t have any notification features
  • You have to know how to use a spreadsheet

Bottom line, it works for me and I think it will work for you, if you give it a chance.  

The Evolution of My Tracking Format

Here’s a little context on how my use has evolved.

In early 2018, I started using Google sheets to track outgoing sales activities for work. Then I realized I could use the same template to track my health habits on a daily basis, as well.

Then, in April, Kevin Rose released copy of his health tracking sheet. His formatting was way better, so I switched over to using his. This is the original sheet he shared:

Download it here

Over the course of the year, I’ve made some adjustments and additions to Kevin’s sheet based on what worked for me. This is my sheet for January 2019:

Download it here:

Kevin’s sheet and mine differ in ways that may not be apparent at first glance.

Tracking Inputs Vs. Outputs

Superficially, Kevin’s is more complicated because it tracks so many different things.

But more importantly, Kevin’s sheet tracks both inputs and outputs. For example, he tracks things like weight, and blood glucose. Which is fine. Kevin’s sheet is supposed to be a health-dashboard, not just a habit tracking sheet.

My health sheet is simpler in that it tracks fewer variables. This is a choice that I’ve come to through trial and error. More data is nice, but it can also create noise that obscures signal. It also takes more mental energy and time to catalouge.

Most important though, is that from my perspective, the variables I choose to track are what I’d call critical and influenceable input variables.

In other words, I track what I think are the three most powerful levers I can pull to influence my health and energy levels. (Someday I’ll write a post on that goes deeper into why I’ve chosen these.)

How I Use It

The best thing about Google Sheets is that it’s everywhere I need it and always updated.

It’s on my cell phone as the Google Sheets App.

And it’s on my web browser as either as shortcut on on the bookmarks bar or just a click away from my Gmail account.

This makes me feel like there’s no excuse not to do it and I have been!

That’s it. If you try it, let me know what you think.

Why I Hate Books – My Favorite Book of 2018

My favorite book of 2018 was The Four Disciplines of Execution by Chris McChesney, Sean Covey & Jim Huling

I stumbled upon this book while reading Cal Newport’s book, Deep Work.

Even before I read it, the book’s title resonated with a disenchantment I’d been feeling with reading itself.

Reading books is easy.

Doing things is hard.

I still believe reading can be valuable. But I don’t think it’s as productive as people would like you to believe.

It comes down to the difference between strategy and execution:

Our predisposition to favour strategy at the expense of execution can be attributed to the fact that strategy is fundamentally easier than executing. This is because strategizing is a conceptual exercise, a manipulation of our mental landscape which is in effect a simulation, and a simplification of reality. Execution, by contrast, necessarily entails a confrontation with reality in all its complexity.

Books are consumed with the tacit agreement that they (the author) will tell you what worked for them and you (the reader) will go out and figure out how to do it yourself, irrespective of the difficulty of the endeavour.

For example:

Image of book on how to climb Mount Everest.

And that’s fine, books are often a good place to start.

But it’s important to recognise that it’s much more productive (and painful) to execute.

Most books, either by necessity or design, quietly pass over the chasm separating word and deed.  

The Four Disciplines of Execution lays out a compelling framework for navigating the space between an ambition and its implementation.  

You can expect to hear more about how I’m using it day-to-day in 2019.

Happy New Year!


Better is a Story

Why do self-help books exist? I’ll tell you why.

Write down your worst habit.

Now go stop doing that.

This is no brainer advice – solid gold. But you won’t do it.

Now imagine I could play you a movie of what your life would be like if you stopped that bad habit.

Say I played you an episode of that movie for you every morning for three months.

How much more likely are you to change?

People are not computers.

We respond to stories, not commands, no matter how logical they are.

Better is a story you have to sell, no matter how obvious it is to you.

The Professional Vs Authentic Mindset – Casey Neistat Quits Youtube

Before Casey Neistat became a YouTube star, making movies with the likes of Jamie Fox, he was by his own admission, a filmmaker without an audience.

Before I started vlogging I had a YouTube channel for five years and in those five years I had a whole bunch of huge viral hit movies that got like 15, 16 million views but my subscriber growth was anemic..

One Trick to 2.5 Million Subscribers @ 1:34

Then, he started vlogging, everyday.

This was the moment when Neistat turned pro at YouTube:

I’ve decided that starting today, my 34th birthday, I’m going to make a movie, every single day.


And this is the moment Neistat quit, or at least admitted he was thinking about taking a different approach:

I realized that I want to make YouTube videos when I want to make YouTube videos. I don’t want to make YouTube videos when I feel like I have to.


This shift in attitude the difference between the motivation based amateur and disciplined professional.

Amateurs show up when they feel like it and professionals show up no matter what they feel.

Neistat’s career illustrates that success requires greatness and professionalism.

Neistat would still be a great at film-making even if he never vlogged. But he only found success after he decided to become a professional YouTuber, to make something, everyday.

The lesson is that even when it comes to entertainment, people choose professionals.

When it comes to success, authenticity is overrated.

I did a version of this post as a short video essay on YouTube. Check it out below. 

Why Motivation Doesn’t Work

The Motivation Mindset And Its Discontents

“Discipline equals freedom” – Jocko Willink

When a task is painful and the outcome is uncertain, it’s often the case that motivation seems to somehow vanish. At such times, stepping away to improve our strategy seems like a reasonable way to rekindle and reconnect with the feelings that lead us to the work. This is one of the ways we fall into the trap of over-strategizing but it also speaks to a deeper misunderstanding of the role that motivation should play in achieving our goals.

When we approach our goals with what I’ll call the Motivation Mindset, we expect that our motivation to reach our goal will translate into motivation to do the work necessary to achieve it.  

For example, the motivation mindset assumes that because we’re motivated to learn French, we’ll also feel motivated to spend hours learning to conjugate French verbs. It’s also the reason people say things like, “he just didn’t want it badly enough.” when someone fails to achieve something. The flaw with this approach to our goals is that it places too much stock in the durability of motivation.

Motivation is a treacherous currency because it is a fundamentally forward looking emotion. It is a why, why you’re doing something. Motivation concerns itself with the future and because we are quick to discount the future in the face of difficulty, it is fundamentally fickle. As such, relying on motivation will almost never get you through the work required for a worthwhile goal.

An alternative, and in my experience superior approach is to approach our work with what i’d call a Discipline Mindset. Which is to say that we should expect that, irrespective of our initial motivation, discipline will be required.

Motivation and discipline differ in that if motivation is about the future then discipline is about the present. If motivation asks why, then discipline asks how? How will I get through the drudgery of conjugating verbs? By drinking a strong coffee and not getting out of this chair for an hour.

It is a subtle distinction, but I would argue it is a worthwhile one because in essence, a disciplined mindset creates more realistic expectations. The result is that instead of feeling like we’re doing things wrong because we’re bored, tired and pissed off, we can begin to recognize those emotions as signals that we’re doing exactly what we should be.

Discipline Creates Motivation

There is a further relationship between discipline and motivation that’s worth exploring. It’s how, in certain circumstances, discipline can lead to a renewed sense of motivation. This occurs when disciplined output provides high-quality feedback which in turn leads to truly productive adjustments to our strategy.

As we observe said adjustments creating real changes in the efficiency and/or efficacy of our work, the result is motivation to do more work. Which is to say that when we feel more confident that our plan will work or we’ll feel better while we do it, we feel motivated to follow through and execute.

Put in terms of the Sisyphus Matrix, motivation is the feeling we get when our perception of a task moves from Task t1 to Task t2:

This is why people spend, and often waste money on “gear” and its equivalent. It creates the expectation of a more pleasurable experience and thereby the motivation to take another shot at the work. Unfortunately, for things that require true skill, better tools often provide only a minor improvements to our process and our motivation quickly dissipates.


Authors Note: This piece originally appeared as part of the post Avoiding Procrastination – Genius, Productivity & The Sisyphus Matrix but in order to make it more accessible (shorter), I’ve republished it here. 

Do The Worst You Can

The thing that we learned, though, is that: every one of our films, when we start off, they suck.

– Ed Catmull, President of Pixar and Walt Disney Studios

Do the worst you can.

We often poison our ambitions by comparing our first attempts to others finished products.

In doing so we fail to recognize that almost everything great started out bad. All masterpieces start as sketches, all films as rough drafts, all books as outlines.

Give yourself permission to do the worst you can and then make it better.

Don’t give up before you start.

P.S. Checkout this blog post about how the Oscar winning movie Toy Story’s early drafts were terrible.

60 Days of Meditation With The Muse Meditation EEG Device

We all know someone who meditates. And we all wonder if it actually does anything for them. And more importantly, if it would do anything for us.    

I’ve tried meditation a few times but it never took. I figured it was because either I couldn’t stick with it because I can’t seem to stick to anything or because I was doing it wrong.

So when I saw the Muse Brain Sensing Headband, I thought it would be a great opportunity to challenge myself to dive further into meditation.

I set myself a challenge. Meditate everyday for 60 days and see what happens.  

Why the Challenge

The potential benefits of mediation 

  • Increased ability to concentrate
  • Increased emotional resilience 
  • Better mood 

See if meditation would become a habit

Studies have indicated that it takes about 60-90 days of regular practice for something to become a habit. This challenge was an opportunity to see if meditation could become a habit

The chance to observe how meditation changes as I get better at it  

In a previous post, I discussed how skill changes the experience of things. Part of the attraction of this challenge was the chance to observe how my experience of meditation would change over the course of the challenge.

See if I could be consistent

Meditation is a great challenge for people who struggle with consistency because it requires so little. No need for fancy clothes, or equipment. No showing up to a gym or studio. All you need is a quiet place, a timer and time. In other words, No Excuses!

Of course, I made things slightly more complicated than that but the point is that you don’t have to.

How I Did It

Meditation Type:

Breath Awareness – There are many types of meditation. Being acquainted with breath awareness meditation, that’s what I decided to do. If it’s good enough for Yuval Noah Harari, it’s good enough for me.

Wim Hof Breathing – I used the Wim Hof breathing method as a way to prime myself before meditation. Numerous people have expressed that doing this prior to meditation improves their experience of meditation.  

Tracking Tools:

Google Sheets – Google sheets is my favorite tracking tool by far. It’s on my phone and any computer that I can get my hands on so there’s no excuse for missing a day. I put together the below simple spreadsheet for tracking my daily meditation practice.

It has columns for the date, duration of the meditation, Muse % calm score and notes. In the last few days of the challenge, I added column to record my own subjective score of how the meditation session went.

Muse Headband – This headband is a EEG device. It measures your brainwaves and translates the results into sound. Ideally, this sound provides feedback that tells you when you’ve fallen out of a meditative state so that you can bring your attention back to whatever your object of concentration is.

Using the Muse brain sensing headband was an opportunity to add an objective measure of meditation progress to what is usually a highly subjective experience.  

Notable Results

Muse headband data 

One thing I was hoping for was to observe a trend in the results provided by the Muse headband that aligned with my subjective sense of my meditation performance. No such thing occurred.

To the contrary, I had many sessions where the Muse headband indicated I had been calm for a high % of the session when in fact my mind was all over the place or I was daydreaming.  

I’m convinced that the Muse headband has little ability to detect whether or not someone is in a meditative state. It can detect if you’re moving around or materially distracted but it can’t tell the difference between daydreaming and meditation, at least for me.

The Phenomenon

By far the most interesting result occurred towards the beginning of the challenge.  

Specifically on day eight, in the hours after the session, I experienced what I can only describe as a deep and profound sense of well-being. It was a feeling seemed to encompass my entire body, a relaxation into the concept that everything was ok and I was happy to be where I was.

This feeling lasted for only an hour or two but it was so distinctly different from my normal state of existence and unique in that I could not account for it by anything other than the morning’s meditation.  

Looking back, it’ impossible to say whether this was a placebo effect or a real change in my mental state as a result of my meditation practice. I continued to hope that the phenomenon would repeat itself but it didn’t.  I did have some good meditation sessions but nothing like what experienced that day. 

I can say though that if that feeling could be an even intermittent result of a meditation practice, then I would say sign me up for two!  

Missed three days

I missed three days during the challenge. No excuses, I just forgot. The best way to combat this happening was to do first thing in the morning. Life tends to get in the way otherwise.   

Sitting down became easier 

Once change I noticed was that sitting for long periods became easier. At first, just doing a 15 minute session would leave my back and knees screaming. By the end I could easily sit for 20+ minutes without experiencing a distracting level of pain. 

Wim Hof Breathing

Wim Hof breathing method definitely seems to make meditation easier and/or more pleasurable. Doing the breathing beforehand felt like clearing the mental palate before sitting down. I was still prone to distraction and it didn’t make every session a success but it helped prime me for what could feel like a daunting task, especially when going over 20 minutes in a session.  

Diet, Sleep & Time of Day Matter

Diet, sleep, and time of day seem to meaningfully affect the quality of my meditation sessions. If I’d been eating poorly or had a long weekend of drinking, it felt much more difficult to concentrate. It was also harder to just get myself to sit down at all.

The time of day also seemed to play a big role. If I was tired I would often slip from meditating into dreaming. Most of my meditating was done first thing in the morning and I found that on many days my anxiety seemed to mount as the session progressed. 

This might be the result of rising stress hormone levels first thing in the morning. The effect could also possibly be attributed to a waning of whatever psychological state is induced by the Wim Hof breathing exercises I did before the session.

Whatever the cause, I still recommend doing meditation first thing in the morning if you can. 

Increased concentration

I can’t say that my concentration improved in any objective sense. But I can say that I did notice that when I got distracted I would remind myself that just as in meditation I needed to return my focus to the work, even though it wasn’t the most interesting thought in my head at the moment.

It would be interesting to find an objective measure of concentration and test it over the course of another challenge. 

Habit Not Formed

Meditation did not become a habit for me as a result of the challenge. While I’m definitely less intimidated by the prospect of sitting in silent concentration for 20+ minutes, I have no desire or compulsion to meditate when I wake up in the morning. Maybe it takes 90 days for me to make something a habit or maybe I need to try a different form of meditation. 

Overall thoughts

On some days doing 20+ minutes of meditation actually felt good but I didn’t see enough benefit in my day-to-day living to convince me that meditation practice was something I have to keep doing. Nor did it become a habit as I hoped it might. 

That said, I remain fascinated by “The Phenomenon” experience described earlier. If a believable person could convince me that, that type of feeling was the inevitable result of a meditation practice, then I would definitely sign up for another challenge.

What I Would Do Differently

Give yourself a subjective score

I wish I’d given myself a subjective score for each one of my practices. Even if you have an EEG device, a subjective score can be a useful tool for making a relative comparison of your results over time.

Increase the intensity

If I could do this again one variable I would want to experiment with is the intensity of my practice.

The book Altered Traits seemed to suggest that breakthrough levels of skill often occurred when meditatiors went for intensive retreats. Perhaps it’s necessary to immerse even more deeply in order to “level-up” at meditation.

Get a coach

Over the course of the challenge, I noticed a persistent anxiety as to whether or not I was doing things “right”. Despite reminding myself that the challenge was more about consistency then performance, it kept creeping back into my thoughts.

Next time, I think getting a coach would be helpful for allowing myself to feel like I was on the path to getting better at meditation. 

Resources For Doing This Yourself