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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. 

Avoiding Procrastination – Genius, Productivity & The Sisyphus Matrix

“Genius is the ability to get from A to D without going through B and C.”  

– Hollow Man, Andrew W. Marlowe

The above quote has stuck with me for a long time because like everyone else, I am attracted to the idea of genius in its many forms. From iconic figures like Leonardo DaVinci, to the golfer who can make what should take three shots in one, there is something seductive about people who can do seemingly impossible things.

I believe this attraction to genius goes as deep as our species evolution; several million years ago humans sacrificed muscle and mechanical output for brains and superior abstract reasoning. Unsurprisingly, that trade-off has echoed out from our DNA out into our society. Capitalism and thus the modern world is predicated on the notion of productivity – the idea that we all benefit when people solve the problem of how to get more with less.

Thus, it shouldn’t be surprising that we seek genius’ equivalent in our own lives. We want not only to be productive but to be optimally productive about our productivity because it doesn’t take a genius to see that the ultimate skill is not a thing you learn but learning to learn itself.

But as with any good idea, our drive to be productive can be taken too far. My own experience has been that the inclination to strategize and/or optimize has caused the abandonment, and failure of many personal goals.  

This post is an attempt to provide a framework that I’ve found helpful for thinking about productivity, work, motivation, discipline, and getting things done.

Getting What You’re After – The Ideal Approach

Achieving anything in life involves some combination of an objective, a strategy and work.

The objective is whatever you set out to achieve, your goal. Strategizing and/or optimization is the time you spend improving your approach to achieving your objective. And the work is the work, the execution.

There is a tension between strategy and work, between thinking about how best to do something and actually trying to do it. Both are important, but time spent doing one is time spent not doing the other.

In an ideal world, we would have the wisdom to find the harmony between the two that gets us to our goal the quickest. But in the real world, things are messy and we don’t know what the right balance is. And because it’s easier to strategize than it is to execute, we often favor strategy over output – to our detriment.

Strategy’s Trap

“Everyone has a plan until they get punched in the mouth” – Mike Tyson

Our predisposition to favor 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.

I mention this because it underpins the fact that strategy and execution deliver feedback of differing quality. And it’s the quality of the feedback we get from strategy that can make it into a trap.

Broadly speaking, when we strategize we get low-quality feedback, and when we execute, we get high-quality feedback. Strategizing provides us with general information and is always simplified to some degree.

By contrast, by when we endeavor to execute, to do the work, we are getting feedback that is unique to our specific situation. Such high-quality feedback is often psychologically painful because it is so specific to our own limitations and shortcomings.

It’s tempting to presume that those of us who overindulge in strategy at the expense of execution do so out of laziness. But I believe it’s ambition that makes strategy so dangerous. We strategize not because it is the absence of but because it is effort.

Strategy becomes an insidious trap when it allows us to feel like we’re doing something, even if that something isn’t productive. At its worst, strategy is the junk-food of work, a procrastination for ambitious people that lets us feel good about getting nowhere.

SpaceX & The Hierarchy of Feedback

For a sense of how the hierarchy of feedback plays out in the real world, consider how the company SpaceX dealt with the tension between strategy and execution.

SpaceX’s objective was to create rockets that could carry objects into space and then return safely to earth. Sending rockets into space is very expensive, so SpaceX was highly incentivized to spend as much time as they could perfecting their strategy and design before spending the money to test-launch a rocket. As such, the company invested in the brightest rocket scientists and the most powerful computers money could buy to simulate how the rockets would perform.

The economics of SpaceX’s situation dictated that if there was any way they could simulate their way to a rocket that worked, they would. But they couldn’t. They had to send rockets into space because their most valuable feedback came from the information they received during each attempt at launch and each failure.

SpaceX launched more than 10 rockets costing the company hundreds of millions before they finally achieved a rocket that could return safely from earth’s orbit.

Rocket engineering is an admittedly extreme example but the principle does, I think, carry over into our own more modest objectives; irrespective of the endeavor there is no substitute for the feedback you get from getting off the page and out into the world.

Where We Over-Strategize – The Sisyphus Matrix

While we’re predisposed to favor strategy over execution, not all activities are the same. In my experience, there are two qualities of a given task, variables if you will, that determine how likely we are to fall into the trap of strategizing at the expense of doing:  

Variable 1: Pleasure/Pain – How enjoyable or difficult producing output i.e. doing the work is.

Variable 2: Confidence/Anxiety – How confident or anxious you are that given enough work, you’ll get the outcome you want.

The danger of strategizing when we should be executing is the greatest when the work is painful and the outcome feels uncertain. It’s worth noting that pain alone is often well tolerated if we know it will result in achieving our goals, and uncertainty is also bearable if we can at least tolerate going through the motions. But as the experience of a task shifts towards the combination of both discomfort and anxiety, the fear that our misery may be pointless often drives us to either quit or retreat to the drawing board.

I’ve titled the above table the Sisyphus Matrix because the ancient Greek myth of Sisyphus is a striking, if fictional, example of how these two facets of our experience combine to shape our relationship with a given task.  

The myth tells of a king named Sisyphus who was both greedy and cunning. In order to glorify himself, Sisyphus deceived the Gods Hades and Zeus – making them look like fools.

For believing he was more clever than the gods, Zeus devised a special punishment for Sisyphus. He would be forced to roll a heavy boulder up a mountain, only to watch that same boulder roll back down the hill as soon as he’d finished, for all eternity.

Sisyphus’ punishment is terrible because it is both painful and so definitely pointless. It is the Platonic antithesis of productivity and genius – an eternity of meaningless suffering.

As such, Sisyphus’ punishment lands in the very top right corner of the matrix. Whereas a task that is both pleasurable in its execution and highly certain in its outcome would be in the bottom left-hand corner.

Most of our endeavors won’t be as forlorn as Sisyphus’ punishment. But because the world is a competitive place, worthwhile things are often difficult things, and so our objectives tend to cluster somewhere towards the middle right region of the matrix.

Thinking about our work in terms of these variables can help us identify when we’re likely to be pushed towards the siren song of unproductive strategizing. Again, the more painful the process and the more anxiety we have about its outcome, the greater the likelihood that we dither.  

That said, there are times when it’s right to go back to the drawing board or just plain give up. But more often than not, we succumb to procrastination in the guise of strategizing long before we’ve given ourselves the chance to get the feedback we need to make a good decision.

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 my motivation seems to somehow vanish. At such times, stepping away to improve my strategy seems like a reasonable way to rekindle and reconnect with the feelings that lead me into the work. This is one of the ways I’ve fallen into the trap of over-strategizing but it also speaks to a deeper misunderstanding of the role that motivation should play in achieving 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.

Conclusion – In Defense of Platitudes

“Action is the foundational key to all success” – Picasso

Slogans like the above, and many others, used to bother me for being patently incomplete descriptions of what it takes to be successful. After all, surely there is something to be said for working smarter not just harder and therefore “Just do it” can’t be a complete description of what it takes to succeed.

But if that’s the case, why do seemingly smart, accomplished people treat these blatant oversimplifications as gospel? For instance, one of my favorite artists, the filmmaker Casey Neistat has both “Do More” and “Always Be Closing” tattooed on his arm.

So how to account for this? Are people like Picasso and Casey just so lucky and/or talented that simply “Doing More” without any thought to “How To Do It” has brought them so much success that they’ve bought into the idea that their personal experience is a worthy universal maxim?  

Possibly. We are all susceptible to reading too deeply into our own experiences. On the other hand, to dismiss these people as naive and the slogans as platitudes might be a dangerous oversimplification in itself.

There is, I think, a more nuanced approach to interpreting the situation that helps reconcile the reverence with which people attend these oversimplified mantras. One that gelled for me only when I came across the following quote by the jurist Oliver Wendell Holmes Jr, he wrote:

I would not give a fig for the simplicity this side of complexity, but I would give my life for the simplicity on the other side of complexity.

Framed within the lens of the above quotation, I think it’s possible to view slogans like “Do More Work” as expressions of what Homes would characterize as simplicity on the far side of complexity.

Which is to say that successful people do understand that there is more to achievement than just doing the work, that there is a need for both strategy and execution. But they also understand that the dynamic between the two is such that while there is a role for being clever, it so often dwarfed by the opportunity to improve by putting our heads down and getting our hands dirty, that saying anything other than Do The Work would be a waste of breath.