Learning the lay of the land

Newsletter #19

Trying to learn something new is often intimidating and overwhelming. There’s a ton of new information coming at you and making sense of it all feels impossible.

Because of this, your ability to quickly get the lay of the land can be a game changer. 

Wait, what exactly is the lay of the land, you ask? Well, let’s take a step back for a second and talk about the process of learning.

Learning can broadly be broken down into 2 phases: Uphill and downhill. 

Before we go on, I’d just like to say that this is something I’ve been thinking about for awhile, and it’s how I personally approach anything I learn. But this doesn’t mean it’ll be useful for you. There are lots of other learning frameworks out there, and if you have one that you like, please feel free to share it with me, so that I can broaden my horizons. 

With that out of the way, let’s get back to the topic at hand… 

Uphill learning is the process of getting the lay of the land. 

Imagine you’re hiking an unmarked trail, and want to get a bird’s eye view of the rest of your journey so that you have a much better idea of the trail, the terrain and everything you need to do thereafter. The only way to achieve this is by doing the hard and tedious work of going to the top of the hill. 

Learning is like this too. The initial part of learning is always confusing and frustrating because you’re in the dark about how things fit together. If you’re learning a new language, going uphill is the process of learning grammar rules to form sentences. The individual words are not particularly helpful until you learn sentence structure.

Similarly, if you’re learning a new skill like cooking, going uphill is the process of learning the jargon and how each part of the recipe affects the dish. What does braising mean? Why do I need to sear the meat before stewing it? How small do I need to chop my vegetables? How much is a pinch of salt?

Without knowing the lay of the land, blind adherence to a recipe might not actually result in the dish you envision.

Or rephrased positively: Knowing the lay of the land lets you adjust the recipe or plan to better meet your objectives.

Downhill learning takes place after getting the lay of the land.

Imagine you’ve hiked to the top of the hill and have now surveyed the land before you. Even if your downhill journey is rocky and takes a long time, the fact that you understand how it all fits together imbues in you a sense of confidence that makes the journey feel much easier. 

Let’s go back to our new language example: It might take you months to learn the grammar rules and master some simple phrases. This is the uphill stage and it’s typically the most painful. But once you’ve done this, learning the language becomes easy. This despite the fact that it will probably take you a decade to amass enough vocabulary and practice to be deemed fluent. 


Instead of prioritising the outcome, prioritise getting the lay of the land. 

Now that you know the downhill phase of learning is easy and happens almost incidentally, we can change our approach to learning.

Instead of worrying too much about learning everything, we can simply focus most of our efforts on learning the lay of the land. 

This has several upsides:

  1. Most importantly, you now have an index to help guide your learning. Whether your index takes the form of a linear content page or an interconnected mindmap, you’re now able to envision how everything fits together in the big picture. You can immediately see which areas you’re strong at, and where you need to brush up.
  2. You’re mentally prepared for the uphill phase to be challenging, and don’t mind it because you know it’s transient, and that the downhill phase will be easier. 
     
  3. An overwhelming amount of new information ceases to faze you. You know that information is only useful if you can organise or contextualise it. So you don’t worry too much about fully understanding every single new piece of information that comes your way. You simply store it away for later. 
     
  4. You become better at achieving outcomes, even if the environment changes. Understanding the context, hierarchies and relationships involved in what you’re trying to learn makes you more resilient to change and lets you adjust along the way.
     
  5. You have a broader perspective. The more you seek to learn the lay of the land, the more you realise how vast it is. While you might deliberately choose to narrow your scope in order to achieve your outcomes, you never forget how vast a topic actually is. And when you do decide to learn more, you do so with a clear idea of how everything ties together. 
     
  6. You achieve bigger and better things. Sometimes, when you understand the lay of the land, you realise your early goals didn’t make sense or were too conservative. With your new perspective, you end up changing your goals to something more ambitious and become more successful than anticipated.

In contrast, someone who focuses too much on learning outcomes and does not know to prioritise getting the lay of the land might experience learning in the following ways:

  1. Their learning is ad hoc and unscalable. Without an index to guide their learning, this person learns a heap of small things individually with no concept of the bigger picture. If learnings coalesce, it’s due to luck, not intention.
  2. They give up prematurely because they’re stuck in a state of anxiety and confusion. They falsely assume the entire learning process is like this, and don’t like the discomfort. As a result, such a person rarely attempts to learn new things. 
     
  3. They get paralysed by the amount of new information they need to digest. This person typically ends up buried in a sea of information, with no insights, and no understanding of how to move forwards. 
     
  4. They fixate on instructions (like a guidebook or recipe) without knowing how the advice fits in the bigger picture. This makes them rigid and unable to adapt to a changing environment. It also makes their learning completely dependent on the instruction of others.
     
  5. They think they know more than they actually do (Dunning-Kruger effect), which causes them to prematurely head down the hill.
     
  6. They achieve everything they wanted by putting their head down and working hard. Unfortunately, they failed to see how much more they could have done if only they had lifted their head.

Getting good at getting the lay of the land is hard. 

If getting the lay of the land is so important, how do we get good at it? In an earlier draft, I tried to give more specific suggestions, but then realised it all boils down to two simple principles: 

1. Embrace and follow your curiosity

As children, we’re super curious. Most of our time as toddlers is spent asking “why?” If you have a toddler, you probably know exactly what I mean. Then, at school and work, we get trained to shut up and not ask questions. Or we start to prioritise exams and deadlines over actually learning. 

It’s hard to break out of this, but if you manage to do so, you’ll find that you not only learn more deeply but also enjoy the process much more.

2. Seek context

Read any article or book about competitive memory sports and it’ll tell you that the key to memorising stuff is to contextualise it. For example, you can memorise the order of a deck of cards by assigning a letter to each card and creating a story out of the letters. 

The same applies to learning something new. Contextualise each piece of information and figure out how it relates to another piece. This way, you build a web of understanding that ties it all together and gives you the big picture. 



Getting good at learning the lay of the land takes time.

For now, just know this concept exists, and that it’s where you should direct your focus to begin with. 

Perhaps you’ve thought of this stuff before, but in a different way. Let me know what frameworks you apply to learning, and how they compare to this one. 


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