The Best Preparation is No Preparation
Why Solving Problems in the Moment Leads to Superior Competence
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PREPARATION AND MODERN LIFE
A Feeling of Control
The best preparation is no preparation. Sounds absurd, paradoxical, self-contradictory. But there's a reason all great truths rest in paradox; anything that makes comments about a system cannot be contradicted by the system. This is because there are 2 different systems being discussed. This is why Gödel is not a hypocrite when he uses math to show the limitations of math. This is why Popper is not a hypocrite when his theory of falsification is not necessarily itself falsifiable. Things that are meta cannot contradict themselves because by definition they are not talking about themselves.
So, we've avoided any logical inconsistencies, but that doesn't necessarily make what I'm saying true. What do I mean when I say the best preparation is no preparation? What I will argue in this article is that there is a massive benefit to solving problems in the moment rather than attempting to prepare ourselves for what might happen. By avoiding preparation, the long-term benefit ends up itself being the best preparation possible. In other words, the ongoing effort to solve problems in the moment leads to an accumulation of superior competence relative to that which we get from planning.
The reason we are drawn to planning is obvious. We don't want to be caught off guard, come up short or look like an idiot when the moment arises. By planning beforehand we can try to anticipate what will happen. Perhaps we need to give a presentation to stakeholders, or we’re going on vacation overseas, or maybe we’re getting ready to have a child. Maybe we're starting a tutoring service, or taking on a new client for our business. In all real-world activities there is a great deal of uncertainty; if we take effort to reduce that uncertainty we should be able to reduce our risk of failure. Hence, preparation.
Side Note: I'll be using planning and preparation interchangeably.
Examples
Think about how most people would attempt to plan for the situations mentioned previously. Giving a presentation means having to deliver a narrative that resonates with your audience. A number of topics will need to be blended in a way that makes sense. We will need to transition between those topics so as not to lose the audience. We'll have to temper our jargon, and make sure we're not reading the slides. Our movements should look natural, so as to put people at ease. Nobody wants to hear someone mincing words, looking nervous and stammering. Preparation would seem like a great thing to do for those needing to give a presentation.
If we are going on vacation it seems planning would be wise. We should have an itinerary of what we want to see. Why fumble with maps, ask random people questions, or miss out on tickets to shows? Why pay more for a last-minute hotel booking or flight ticket? Why chance the appropriate clothing when weather reports are easily available? Why waste time looking for things to do when a simple online search can show us what's available, what's open, what's affordable, what's fun? The more we plan for the trip the smoother our trip should be.
If we are about to have a child we should spend a good amount of time preparing for the inevitable. The child will need their own room, and toys, not to mention diapers, bottles, etc. Being a parent is a huge responsibility. It would make sense to buy some books on how to parent. And not just for the day-to-day stuff; what about emergencies? Why not take some training classes and/or learn something about child psychology? Do we really plan on going into parenthood unprepared. That seems irresponsible.
If we are starting a tutoring service we will want to be prepared for the questions a student might ask. We should fire off some back-and-forth emails, maybe even a phone call to assess where the student is at. What topics are they struggling with, and which questions from which textbook are they encountering? After all, we're being paid to know the answers. We don't want to waste someone's money by showing up and spending half the time struggling through questions.
And if we have a new client for our business we should have working sessions with lots of questions, diagrams and conversations with key people. We should map the pain points of the client to a proven strategy and workable process. After all, we are getting paid to build something important that is likely going to cost a good deal of money. We can't be jumping in with no plan, making random decisions that have no reasonable foundation.
In all these examples planning seems to make a lot of sense. And undoubtedly most people in these kinds of situations plan. In fact, most people do a fair amount of planning in all areas of their lives. People plan where to eat, where to spend their money, which courses to take, which books to read, which locations to live, which car to buy, and on and on. We are, after all, in an age of information; why not use that information to make informed decisions and reduce the likelihood of making poor choices? Planning has become part and parcel of modern living.
Modernity
We tend to assume humans have an innate need to control outcomes. But there's something wrong with this notion. Humans are adapted to work under high uncertainty, far more than being predictive of what will happen. Sure, we use pattern recognition to anticipate events, but that prediction is only about what will happen at the highest level of abstraction. We can anticipate the tiger in the bush from sound or movement, but knowledge about when, where and how the tiger will strike is wholly unavailable.
This is why the paranoid survive; not by knowing the details of what might happen but by anticipating the worst case scenario and practicing avoidance. This is how our ancestors handled their surroundings. Their environments were far too unpredictable to operate off planned action. By avoiding worst possible scenarios humans can turn a fair amount of life's risk into a nonissue.
But our modern world appears quite different than our ancestors. Modern life seems to have an entirely different set of demands that bear out across our personal and professional lives. The things we think about today aren't like those our ancestors thought about, they're far more detailed. We plan the itineraries of our trips, we prepare for exams in school, we get ready to give presentations to stakeholders. We're not facing tigers in the bush we're facing investors, collaborators, students, teachers and travel destinations. Our lives exist as intricate threads woven amidst the vagaries of society and the expectations many others hold for us. To succeed today is not finding food and avoiding poisonous bites, it's coming up with answers, strategies, tactics and ideas. Today's life seems to demand nothing less than the prepared mind.
Modernity and planning have gone well together, because modern life is based off an industrial revolution mindset. The industrial revolution instilled in us the power of deterministic thinking. Almost everything built since this period can be understood by inspecting its components. Most of our machines and processes have causal clarity, and because of this planning works. If we can envision components and their interactions then a plan and an outcome are almost the same thing. In this case, the chances of something deviating from a plan, while still possible, is much less frequent with preparation.
In a world built on assembled automobiles, constructed bridges, manufactured materials and programmed software the notion that risk can be reduced through planned action seems nothing less than obvious. The casual clarity inherent in the things we make tells us that not only can we anticipate the outcome, but that it behooves us to do so.
Despite humanity's natural gift for operating under uncertainty, fortune, it would seem, favours the prepared mind.
We Are Our Ancestors
But regardless of modernity's relatively recent restructuring of our lives we are still our ancestors. What we are good at is not planning, but adaptation. Human beings become what they need to by entering an environment and surviving. Humans are not good at using detailed information because until recently detailed information was never available. Only the highest-level signals from the environment could be used to guide our decision making. So much of what we do is indescribable, soft, heuristic and approximate.
The truth is there is a severe disconnect between what humans are naturally good at and the demands placed on us by modernity. No amount of available information can alter the way humans handle complexity and navigate through life. The artificial constructs of modern living, while undeniable, are not etched into our makeup. They are not things that humans adapt to, rather they are contrived features that we tolerate in order to enjoy modern comforts and advance our global economy.
But despite this glaring mismatch between our natural proficiencies and modern living we still live in a modern world. It seems preparation, while hardly natural, is a skill we should attempt to hone; ancestral behaviors notwithstanding.
But the story doesn't end there. I argue that the severe disconnect between natural human behavior and modern life is actually closing. The industrial revolution mindset is rapidly becoming outdated. Our economy isn't driven by mechanical things, it's driven by information. Many assume this should lead to even more planning; more information supposedly equates to so-called "informed decision making." Preparation, if anything, should be hyper-charged in an informational age. But more information has a side-effect, and that is increased complexity, and with increased complexity comes the loss of causal clarity that underlies the entire modern mindset.
Coming Full Circle
We don't live in an industrial revolution world anymore. Our economy isn't driven by mechanical things as much as the informational improvements to those mechanical things. To improve a rocket, a bridge or an office tower is to run simulations on computers. Our software is becoming less-and-less programmatic, relying more on soft statistical models and approximate outputs than rigid rules.
The tools we use to create things are becoming increasingly democratized, operating at high-levels of abstraction, where creative expression beats detailed knowledge. In today's reality nobody truly understands everything that goes into the tools we use, because there's too many contributions to retrace a thing's lineage. To solve a problem in today's economy is not about root cause analysis it's about exploration, iteration, convergence and soft understanding.
The modern constructs of life are no longer rigid things that smack of industrial efficiency and deterministic causality, they are organic, messy and adaptive because our tools now exhibit these properties. That strict logical thinking and nerd-like determinism seen as "smart" over the last 100 years is rapidly becoming a detrimental trait. What we need are people who can operate rapidly, at the surface, using abstract democratized tools, discarding most details in favour of iteration and convergence rather than some naive recipe. This is what it means to build and solve problems today.
All of this means that progress, rather than marching forward with increased industrialization and machine-like determinism, is instead coming full circle. Not only are we our ancestors, but our timeless original skillsets are reclaiming their rightful place as THE skills to have. The industrial revolution and the so-called Age of Enlightenment can now be seen as momentary transitions where we converted our ingenuity into tangible things. With much of those tangible things figured out, and subsumed into highly abstract tools, the improvements going forward benefit far more from our original style of problem solving. What we need now is not a cog-style work ethic but rather an all-too human approach to solving today's toughest challenges.
We have come full circle. We have created a world that has reached a point of complexity where further improvements can only be realized via our most natural abilities. There is no longer a place for deterministic creation because such causal chains have been lost to massive collaboration and complex creativity. We have to once again work under extreme uncertainty, with tools and processes that we can only really understand at the surface. Such surface-level operation is what brings us into highly complex challenges, as I discussed in previous articles. These truly complex challenges, I argue, will have far more impact on our lives than the industrial revolution.
All that said, most of us still find ourselves relentlessly planning. Humans still have that need for control, and it is unlikely we are going to overcome that need anytime soon. But reducing one's reliance on preparation is not the same as casting control out the window. It turns out there are two distinct types of control, one of which works effectively under the more natural kind of problem solving at the heart of today's new economy. To understand how this kind of control plays out we first need to look at the underlying mechanism behind why preparation fails.
DEPENDENCE ON PREARRANGEMENT
The mechanism behind why preparation fails in real-world situations is because it creates dependencies to a system's internals. Details are the internals that go into a system to allow it to become what it needs to be. In the simple mechanistic world of the industrial revolution the internals of a system dictate the properties of the system. The gears, pistons and valves are details of an engine that create motion. The logic of a programming language are the details of software that create outputs. But this isn't how internals work under complexity. The properties of what exists at the output don't look anything like those found in the input.
As I argued in the previous article, real-world situations see their details die. The constant perturbations of life are there because that's how nature ensures only what is effective survives; things that have what it takes to adapt to stressors. This isn't just biology, this is informational. All aspects of life move through complexity under this premise.
Life, modern or otherwise, is anything but stable. Anchoring an approach on details is foolish in the face of uncertainty because any details prior to the moment are ephemeral, used only to assist in convergence towards the pattern that matters; a pattern that can only be known after-the-fact. Since the adaptive process kills most of what goes into a system anything that depends on details is going to give way.
A plan assumes detailed knowledge about how things should be created or the kinds of specific situations we might face. The questions that will be asked on or after one's presentation, the things worth seeing on a vacation, the efforts needed to care for a new child, the questions a tutoring student will have or the challenges that will arise with a business client. By investing in preparation we are creating a dependency on the internals of a situation, because we are assuming detailed knowledge about what things are needed to produce good outcomes.
This is why behavior that maps to good outcomes cannot have dependencies that are inside the system, the parts that are in constant flux. Sure, a presentation is meant to tell a story, but why? To communicate effectively. Communicating effectively in a live presentation requires rephrasing language, restating goals, repurposing processes in real-time. Whatever language, goals and processes we decide on upfront will be ill-informed. We cannot know the details that are going to matter.
Our vacation plans will need to be adjusted en-route. There could be last-minute cancellations, flight changes, revised weather forecasts, chance encounters, etc. Remember, The Rich Don't Penny Pinch. Many of our plans will get wiped out by unforeseen circumstances. To enjoy a vacation is to remain open to opportunities, not dedicated to some naive to-do list.
A child is hardly a bag of prepackaged emotions and behavior. The situations that arise in parenting cannot be foreseen. A good parent is not a walking encyclopedia of child psychology and first aid training, they are people who don't cry over every glass of spilled milk. They bring their own experiences to bear on the situation as it arises, organically and intuitively teaching the child how to live a good life.
The tutoring student doesn't need your prepackaged answers, she needs to witness your ability to take an unseen question and maneuver through it, pulling in resources and asking questions. She needs to see that confidence isn't having answers but rather being able to know you can solve them. The business client doesn't need sterile strategies sitting on a slide deck they need to incorporate your authentic experiences into their business, and that's only going to happen from living, real-time conversations.
When we rely on preparation we are creating a temporary feeling of certainty while we prepare, but that feeling dissipates the moment life throws us curveballs, which it always will. To "go in prepared" is to find ourselves depending on whatever we prearranged beforehand, which will inevitably prove naive. That dependency is what prevents us from embracing the moment, using the available information that surfaces in real-time to adapt. To be truly prepared we must become the answer needed in the moment. The kind of control we require demands that we somehow shift our dependencies from inside to outside the system.
A Different Kind of Control
We don't want to leave everything to chance, hoping that we can rise to the challenge. There needs to be some sense of structure to our approach. This is still true under complexity, but many people get this structure wrong because they attempt to arrange things prior to the moment. What we need is a structure that is not in flux. Something that is more permanent. It turns out this is available by way of environmental stressors.
Stressors are the high-level goals presented by an environment that must be met in order to survive. They are the non-negotiables nature has in place that ultimately determine what lives. We are all familiar with this process in biology; species have traits that either assist an organism in adapting to an environment's stressors or not. Those stressors are things like the need for food, water and shelter. But as stated previously this isn't a process owned by biology, it's informational and thus universal. This is how anything nontrivial moves through its environment. Ideas, proposals, suggestions, intentions, projects; they all either adapt to their changing environments or die off.
Stressors are not just things we must put up with, rather they represent the information we do have access to under complexity. People tend to focus on the internal details of a system, but this isn't genuine information, because it's mostly narrative. The transitory nature of details make them ungrounded in anything that maps to outcomes. But stressors have genuine information content because they are immovable. They are not narrative because they are not in flux.
Instead of preparing for a presentation think instead of the high-level goals that need to be achieved. We need to ensure people understand something we are trying to communicate. Their understanding depends more on them than us. They have their own set of language and previous experiences that will determine what they do and don't understand. This is because everyone's understanding happens by juxtaposition, where people compare what they see and hear to what they already know. Our language and approach have to be highly malleable, in order to wrap around the unique perspectives and experiences of the audience.
In the vacation example, the high-level goal is having a good time, creating memories that will last a lifetime, and maybe learning something about another culture or something historical. Enjoying oneself doesn't happen by following a recipe. It happens when things surprise us, when we learn something that we never anticipated. It's when we get off the beaten track, and become exposed to things we didn't even know existed; this is how we attain lasting memories.
Having a child comes with the high-level goals of ensuring they grow up content, wise and with a wealth of opportunities. We must teach them to behave in a way that opens doors, keeps them healthy, and repeatedly places them in a position to find happiness. No matter what we attempt in preparation those goals won't change. And the opportunities that arise to make these goals happen cannot be known upfront.
In tutoring the high-level goal is getting the student's marks up. But everyone learns differently, and as with the presentation example learning is more about them than us. We cannot know what exactly they are struggling with because it's not the questions that are challenging it's something about their approach. This is why a student cannot really tell you what they are struggling with, we have to observe them, watch them attempt the question, ask about their reasoning process. We cannot know this until we are witnessing them in the moment.
And with new business clients we are looking to build them something that is viable, that delivers value. It's not any specific set of tools or industrial best practices, it's an outcome rather than an output. Outputs come and go, but an outcome is an immovable target.
To focus on the high-level outcomes is a different, better kind of control because it's anchoring on things immovable. Stressors that are always there. Stressors are not brittle, they are unchanging, or at least change on a far longer timescale than that which attempts to adapt to stressors.
This is why preparation doesn't work under complexity. To prepare is to setup specific outputs, but specific outputs are not useful. What's needed is the rapid production of many different outputs with different details swarming around to meet an unchanging goal. There is nothing to prepare for this, because it only demands knowledge of the highest-level goals that need to be achieved.
Many might agree that details should be ignored upfront, but would argue that there is value in preparing a high-level process to work towards a solution. I disagree. Any process imposed on a situation is pretending to know things it does not. An upfront process, even ones meant for creativity and discovery, cause us to fall into the trap of carving out directions in advance. Even a high-level process will find itself dependent on internal details, making an otherwise creative journey too rigid and fragile.
In life we can choose to anchor our efforts on internal (detailed, ephemeral) dependencies or external (high-level, long-lived) dependencies. For anything real-world we should be choosing external. To have proper control under complexity is to rest our dependencies on things that are immovable. The constants of reality. The fundamental truths. Our natural abilities to solve in the moment take care of the rest, and THIS is what we want to get good at.
ACCUMULATING COMPETENCE
If we are casting away much of the details in the pursuit of in-the-moment problem solving then what is it we are getting better at? Aren't we just leaving everything to chance? What skills are growing if we aren't constantly planning our approach?
What makes you good at something? Is it knowledge about how something is likely to go? At first blush this seems to make sense. Isn't an expert someone who has a good idea about how things will go in their domain? I argue this is not the case. If I am good at giving presentations it's because I've given many of them, and that means I've been exposed to all kinds of different details as they arose. If I am good at creating lasting memories when I travel it's because I am able to be surprised, and to learn things I never knew. If I am good at tutoring it's because I can teach despite (or because of) the wide variety of learning styles. The same pattern applies to being good at business.
But what about parenting? If it's our first child we don't have experience. But we do have an absolute arsenal of competence endowed to us by nature, not to mention decades of experience growing up. Humans have been parenting for a very long time and they didn't have special training for emergencies or books on child psychology. To be a good parent is to be able to respond to countless surprising moments, keep our cool, and push towards positive outcomes for the child.
An expert is not someone who has specific knowledge about situations it's someone who can bring many different relevant outputs to a situation. Recall our conversation on outputs and outcomes. The outcome that needs to be arrived at is a high-level, immovable target. It’s not detailed knowledge that maps to good outcomes it's the ability to course correct constantly and pay attention to when good things converge.
There is no building-up of expectations with experience, rather it's the building-up of a process; a process that is as indescribable as it is powerful. You can witness the outcomes of people who are good at what they do, but the idea that such outcomes are arrived at by a describable/teachable procedure is pure fiction. If you're not feeling your way through a real-world challenge then you're not a genuine expert. Period.
As I stated at the beginning, the ongoing effort to solve problems in the moment leads to an accumulation of superior competence relative to that which we get from planning. Not preparing is itself a kind of preparation, because instead of accumulating an increased dependence on the prearrangement of ideas or things we become skilled at using the resources available to solve the problem. THIS is what genuine skill looks like.
Skills that truly differentiate are largely ineffable. They do not appear on certificates, degrees or resumes. They are deep emotional competencies that accumulate over time from repeated exposure to situations where we must think on our feet. What you want, need, to accumulate is your ability to bring yourself to the challenge. Your ability to think on the spot, pull in resources, collaborate rapidly, and build solutions to problems you never could have seen coming.
Think about what accumulates when we constantly prepare. It's not skill, it's an increased dependence on the wrong things. The short-lived things. The things that don't stick around. Preparation makes us fragile in the face of what matters most, which are the real-world stressors that need to be adapted to in the moment.
A good heuristic (I think the best) for assessing whether you're genuinely skilled at something is how capable you are at redoing something from scratch. Most people struggle to accept a redo because it seems like they are wasting so much of what they already created. But most of anything we create isn't that useful, especially in the earlier stages of the undertaking. Most of anything's value, as per Pareto, comes from a small portion of everything we make and, critically, there is no way to know beforehand which small portion will have the most value. Redoing something from scratch carries over those pieces you actually learned, rather than the baggage of naive guesses and uninformed decisions.
Redoing a task is entering into the moment raw but not naked. We are starting over, but we all know that the task goes so much faster and more effectively the second time around. This shows us that something ineffable carries over when we redo things. There are no labels for those things that make us better; they are emergent understandings that precipitate out. They are highly available and powerful yet fully indescribable. This is what we want to accumulate. This is true competence.
Not Just the Intangibles
What accumulates through time by entering into moments unprepared is genuine skill. But it's important to realize that it's not just the intangibles that accumulate. There are physical things that buildup over time that we can reuse again-and-again. Slides we made, clothes we bought, child supplies purchased, intellectual property created. As long as these tangible things were acquired or created in the moment they will be carried over. That's because they were brought to life being directly informed by their environment. They didn't grow out of a plan, they emerged to help us survive.
The best preparation is no preparation. for both intangible skill and the artefacts we bring to bear on challenges. Having the right tools to solve problems is a massive benefit. We are faster and more capable with these tools. But these tools must have accumulated under pressure. They must be reflective of environmental stressors, not told to us by some book or authority.
Preparation is the Inverse of Confidence
Confidence is a feeling of self-assurance arising from one's appreciation of one's abilities. But this isn't truly attainable through preparation. Preparation is insidious, in that it repeatedly fools us into a false sense of confidence. We want to believe we can anticipate what will happen and so we prepare.
True confidence comes from knowing that we can solve challenges in the moment. It does not come from reliance on planning. As I mentioned earlier, one of the problems with preparation is it keeps giving us temporary feelings of control. But worse than that, we tend to rationalize preparation through post hoc narrative. After the event has occurred we attribute the good parts to our planning, because flexible interpretation will always allow us to do this. It's too easy to attribute success to something that occurred prior to the event. But this isn't reality.
We are already capable of achieving so much as long we remain authentic. As long as we are open to the situation, inviting in possibilities and discarding most of them in the pursuit of a high-level goal, we will achieve. And what we achieve is often more than what we originally envisioned. This is because the information needed to create the right thing, to solve the right problem the right way, was hidden from us until we poked nature enough times.
As you face more and more situations unprepared you begin to realize that things are nowhere near as difficult as you thought. You realize nobody really knows what's going on. Nobody has it all figured out. We're all struggling to arrive at good solutions. Using that knowledge of people's general ignorance to move into situations fully and authentically is what true confidence looks like.
Think about where your current areas of confidence came from. They came from struggling through things that initially scared you. Preparation, while giving you a sense of certainty and assurance prior to the moment can only lead to a false sense of confidence. When we take an honest look at the difference between what preparing and not preparing lead to we must admit that preparation is in reality the very inverse of confidence.
LETTING GO
The best preparation is no preparation. But this isn't the same as saying we should not prepare at all. If we are giving a presentation we still need to create slides. If we are going on vacation we still need to pack. We will need things for the new child, some material for tutoring and some preliminary approach for new business clients. So while the BEST preparation is no preparation we should realistically make that our goal, attempting to enter into situations with the least amount of upfront structure.
So enter into presentations with the minimal slides required to anchor your organic conversation. The slides are not there to be the answer, they are there to trigger fruitful conversations. This will produce a narrative that best resonates with the audience, ensure topics become blended as needed, enable essential transitions between topics, allow us to temper jargon as required, and prevent us from unnatural actions like reading slides.
When traveling, keep itineraries to an absolute minimum. Open yourself up to surprise encounters and chance events. Ask random people directions and start conversations. Miss the tickets to the show you thought you wanted to see, only to see something better. Take a few types of each clothing but allow yourself to purchase what's needed when you get there. Discover what is available, open, affordable and fun. Don't look for the smooth trip you'll forget about in 2 months, look for memories that will last a lifetime.
That new child is going to be fine. Humans have been raising children for a very long time. Yes, the child will need a room, toys, diapers and bottles, but remember; the solutions we bring to problems should be informed by their environment, not read from some manual. Sure, it's good to know some basic emergency actions and perhaps a few tidbits of child psychology but keep it to a minimum. True irresponsibility is not bringing yourself to the moment when things arise; not being there for the child.
Tutoring someone works better when you show them the process of solving a problem, which is less likely to happen if you know all the answers going in. You should show them how you pull in available resources and use them to genuinely struggle through a problem. Be in the moment with the student, not some machine that regurgitates rote knowledge from a textbook.
And to truly mitigate risk in business remain flexible to market challenges. Reduce the number of working sessions, upfront diagrams and planned conversations and target contacts. Allow strategy to emerge from organic conversations and chance encounters with stakeholders you didn't know existed. Don't assume you've been told what matters before you've started the journey. Often your client won't know what they really want or need. To deliver value and give the customer their money's worth you need to be authentic, not prearranged. Land on the right foundation towards the end of the engagement.
People plan where to eat, where to spend their money, which courses to take, which books to read, which locations to live, which car to buy, and on and on. Learn to enter into life with less structure. Allow your experiences to accumulate the way they're supposed to, informed by the environment, in real-time. This is what it takes to learn, to become great at what you do, and create a prosperous life both personally and professionally.
One of the joys of Substack is the network. I found this article via @jpcastlin, and in one of those lovely moments of serendipity, landed right where I needed it to. Thank you ;-)