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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.



Ray Dalio On How To Run A Meeting & Other Business Tactics

Reading a book is easy. It’s much harder to take what’s in the book and incorporate it into our lives. I like to tackle this problem by distilling books down to a few tactics that I can implement quickly. 1

In a previous post, I outlined 4 ways that you can make better decisions using Ray Dalio’s life principles. In this post, I’ll outline what I think are the most impactful and actionable tactics from Dalio’s work principles.

Here they are:

1) How To Run A Meeting

“Meetings are an addictive, highly self-indulgent activity that corporations and other large organizations habitually engage in only because they cannot actually masturbate.” ― Dave Barry

Dalio often describes his organization as an intellectual version of the Navy Seals, and it’s clear from his Principles that like the military, he has an affinity for structure. So it shouldn’t be surprising that he thinks the most important part of running a meeting is to be clear about who is in charge and what the meeting is supposed to achieve:

Make it clear who is directing the meeting and whom it is meant to serve. Every meeting should be aimed at achieving someone’s goals; that person is the one responsible for meeting and deciding what they want to get out of it and how they will do so. Meetings without someone clearly responsible run a high risk of being directionless and unproductive

– Principles, Work Principle 4.4 – A

Dalio’s second Principle for running effective meetings is to assign someone to keep track of both responsibilities and the conversation flow. Said person ensures that any tasks to be done are assigned to specific people and not forgotten. They also ensure that the meeting doesn’t veer too far off topic.

Be careful not to lose personal responsibility via group decision making. Too often groups will make a decision to do something without assigning personal responsibilities, so it is not clear who is supposed to follow up by doing what. Be clear in assigning personal responsibilities.

– Principles, Work Principle 4.4 – H

Watch out for “topic slip.” Topic slip is random drifting from topic to topic without achieving completion on any of them. One way to avoid it is by tracking the conversation on a whiteboard so that everyone can see where you are. (Emphasis mine)

– Principles, Work Principle 4.4 – F

Applying Dalio’s tactics may make people feel uncomfortable at first, but in the long run, it will reduce peoples anxiety about meetings because they’ll know how they’re expected to behave and that their time won’t be wasted.

2) Use Standing Meetings

Our true priorities are defined by where we spend our resources, and that most often means where we spend our precious time. Too often though the distractions of daily business pull us along low-value tangents that take ours and others time away from where it would best spent. Dalio has found that the best way to avoid these distractions is to habituate your time allocations by setting standing meetings. For instance, if your company priority is sales, you should have a weekly sales meeting.

Use standing meetings to help your organization run like a swiss clock. Regularly scheduled meetings add to overall efficiency by enduring that important interactions and to-do’s aren’t overlooked, eliminating the need for efficient coordination, and improving operations (because repetition leads to refinement). It pays to have standardized meeting agendas that ask the same feedback questions in each meeting, (such as how effective the meeting was) and nonstandard meeting agendas that include things done infrequently (such as quarterly budget reviews).

– Principles, Work Principle 13.3 – D

3) Use Daily Updates To Stay In Sync

Use daily updates as a tool for staying on top of what your people are doing and thinking. I ask each person who reports to me to take about ten to fifteen minutes to write a brief description of what they did that day, the issues pertaining to them, and their reflections. By reading these updates and triangulating them, (i.e., seeing other people’s takes on what their doing together), I can gauge how they are working together, what their moods are, and which threads I should pull on.

-Principles, Work Principle 10.6 – C

Imagine if you woke up every morning instantly knowing what everyone in your company intended to work on that day and everyone else knew the same thing. Appealing, because of how incredibly efficient that might make everything, right? And, at the same time, kind of terrifying because you don’t want everyone looking over your shoulder judging what you intend to do every day.

The latter concern was why I first resisted using daily updates. I told myself, “I’m competent. I don’t need someone looking over my shoulder to do the right thing.” But now that I’ve been using it for a few months, I’ve come to see the value in it.

For me specifically, it’s as simple as sending my colleague a list of things I intend to work on each day. And in addition to it being a useful communication tool, it helps me organize my day and prioritize what I need to work on first. By contrast, my old habit of jumping into my email first-thing would lead me down a rabbit hole that didn’t necessarily reflect my priorities.

4) Use Process Flow Diagrams

Dalio’s ideal is a company that runs like a machine. At its core, a machine is a set of processes. Using process flow diagrams can help you visualize the different processes that make up your organization. These visuals help managers understand how resources will be allocated and interact with each other. But more importantly, they help ensure that everyone understands how the organization is expected to run and their role within it.

Understand that a great manager is essentially an organizational engineer. Great managers are not philosophers, entertainers, doers or artists. They are engineers. They see their organizations as machines and work assiduously to maintain and improve them. They create process flow diagrams to show how the machine works and to evaluate its design. They build metrics to light up how well each of the individual parts of the machine (most importantly, the people) and the machine as a whole are working. And they tinker constantly with its designs and its people to make both better.

– Principles, Work Principles, 10.1 – B

Process Flow Diagrams. Just as an engineer uses flowcharts to understand the workflow of what they’re designing, a manager needs a Process Flow Diagram to help visualize the organization as a machine. It might have references to an organizational chart that shows who reports to whom, or the org chart might supplement the Process Flow Diagram (PFD). Ideally the PFD is made in a way that allows you to both see things simply at a high level and drop down to low level. 

– Principles, Appendix

Since reading Principles, I’ve used process flow diagrams to visualize a number of personal and professional activities. I find that creating visual representations allows people to communicate more effectively about complex processes then they could otherwise.

Here’s an example of how process diagrams can help you visualize things. This was made using Lucid Chart:

 

 

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If you enjoyed this post, check out these other posts on Ray Dalio’s Principles:

Ray Dalio’s Principles – 4 Steps To Better Decisions

Ray Dalio’s Secret Sauce – The Truth Machine & The Good Life 

  1. The difference between tactics and strategy is strategy tells you what you should do, tactics tells you what to do. In other words, a strategy is the more general goal and tactics are the things you do to make that goal happen.


Brett Victor – Building Technology to Human Dimensions & Being Conscious of The Adjacent Horizon

The Humane Representation of Thought from Bret Victor on Vimeo.

 

At almost 1 hour the above talk by Brett Victor is both long and incredibly thought provoking. In it he explains how our current technological landscape utilizes only a narrow band of humanity’s capacity for thought.

People like to talk about where technology is going and what it will do for us but as Mr. Victor demonstrates, technology doesn’t move towards its highest expression by improvements in processing power or market forces alone. Instead it requires people equipped with the intentionality to design technology that work with and across the scope of human capabilities.

 

For me his point about the needs for intentionality in how we design technology speaks to a larger issue in our society. That is, the misguided assumption that outcomes are driven by market forces through a competitive evolution towards their most useful and desirable incarnation. This is naive, many things are shaped almost irrevocably by the design decisions at their beginnings, or to use the technical term they exhibit path dependency. The way that cities are designed is a good example of this.

This is worth talking about because only once we acknowledge this reality that things won’t take care of themselves can we begin to look at the edges of what might have been, and what better future might be on the adjacent horizon, but only with our help. As Mr. Victor eloquently ends his talk:

Humane won’t just happen. This not just like Sussman’s technology that is going to happen because there’s already really powerful forces at play. Humane is never a default. And humane only ever comes out of deliberate and conscious design work. If you do the incremental thing, and just ride the current wave of technology and let technology lead you wherever it leads you it’s going to lead you to a tighter and tighter cage…

 

 




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