Whenever you realize something non-obvious, you should write it down.

Non-obvious insights tend to arise when people are either novices or experts. The characteristics and utility of these insights tend to differ based on which circumstance evokes the insight.

When someone enters a new environment — a new city, a new job, etc — they tend to see their surroundings in a way that those accustomed to the environment do not. For those who are familiar with an environment, expectations and reality have converged. But for novices, the newness may create a stark contrast against one’s expectations.

Writing these insights down has several purposes. As you transition from novice to familiar, those insights may fade. Time smudges; the crispness of a new environment gradually becomes ordinary and undistinguished. Writing things down when you’re a novice provides a mechanism to reflect on where the learning curve starts, and helps remind you of what the next novice or outsider may not realize.

Businesses are a great example of where this is important. When I started in VC, I didn’t understand why some funds chose to stay small vs. raising as much as possible. This is obvious to me now: seed stage startups shouldn’t be competing for the same investors’ mindshare as Series B companies, where the dollar amount invested by the firm may be one or two orders of magnitude more for the later-stage company. Smaller fund sizes better match the needs of seed stage startups, for many reasons — ranging from sufficient access to firm resources to enabling investors to more easily cooperate with each other, and much more.[1] To insiders, these insights may feel like common sense. But when I started, this was extremely non-obvious to me. And because I remember how new this seemed, I’m reminded that for others outside the day-to-day of venture investing — like new entrepreneurs seeking investor capital – these conclusions also may not be evident.

The same is likely true of any business: why a customer should buy your product or service over a competitor’s may be obvious to you, but non-obvious to a customer who knows far less about your offering. When something feels obvious, promoting it persistently may feel like overkill. But it’s often not — at least from the perspective of those unaccustomed. Maintaining a repertoire of these learned insights can clarify what elements of a message may need to be repeated and emphasized.

When new to an environment, you’re also more likely to notice small details. Novices aren’t yet sure what will or won’t matter, so they pay attention to everything. Certain things stand out that may blend into the background for the well-acquainted.

Vocalizing such insights helps keep an organization agile and flexible. Processes evolve over time and can sometimes become less efficient / more bureaucratic. To insiders, such changes may feel gradual and thus go unnoticed. But to novices, such pain points are stark. The benefit of a fresh viewpoint can lead to ideas about how things can be improved or, at the very least, remind those with experience that alternative options exist. And this concept isn’t just limited to corporations – it can be extended to city policies or urban planning, the design of products and services, really anything.

The other scenario in which one may be primed to find non-obvious insights is when they have extreme knowledge about a subject combined with a deep curiosity. In my view, this is the true definition of an expert — someone who knows enough to recognize that there’s so much more to know.

Knowing a lot — about a lot of things — improves one’s ability to recognize patterns. Such deep knowledge of a domain provides an important base, and helps illuminate insights that may be non-obvious to those with less context. For instance, certain sequences of events may seem new and novel to us, while in fact similar patterns have emerged throughout history. Debt cycles are one example that come to mind. The evolution of financial innovations and systems for money movement is another. I’m sure there are many more.[2]

But there are also insights that are non-obvious to the experts themselves. Curiosity provides the prompt for finding such information. In particular, experts tend to ask things like “where else might we have seen this before?” and “if we tweaked these one or two things, how might the outcome differ?” Phrased differently: the expert simulates the experience of once again being a novice. The deep base of knowledge provides the foundation for finding the most interesting questions to ask. It also provides freedom and time to pursue these questions: someone newer to a subject may first need to devote effort to learning the basics before they can begin to explore what exists at the outer edges.

Why might experts want to write down these non-obvious insights? In the case where a conclusion is obvious to them but maybe non-obvious to others, writing them down can help build a collective knowledge base. Having such information available makes it easier for others to scale the learning curve. It can also help establish credibility for the expert’s viewpoints (or solicit important feedback). In short, writing scales the impact of these insights.

But what if you’re neither a novice nor an expert? How might you discover non-obvious insights?

One tried and true mechanism is to write. Often, the process of writing helps to clarify what one knows, illuminate the boundaries of that thinking, and push on what else there might be to explore. This piece in itself is a great example: I started it with the idea that non-obvious things are worth writing down, but lacked a framework for the circumstances in which those non-obvious insights might arise. So, I reflected on the non-obvious insights I’ve had over the past year and asked myself “what ties these together?” The process of writing created a prompt to reflect on my personal datapoints from a different viewpoint. Along the way, it occurred to me these insights either came from newness or (relatively) deep familiarity.

Another answer is to start anew. In theory, this is very easy to do: pick a topic you know nothing about and start learning. It could be anything — from how the NYC subway system evolved, to the roots of coffee culture, to the popularity of stickers on laptops. (These examples were derived just now, from simply looking around at my surroundings). The hard part is finding something you’re actually interested in. If lucky, you’ll develop an interest simply through starting.

Finally, you can try re-simulating the experience of being a novice. I mentioned this briefly when discussing experts: new learners tend to ask questions that prod at the underlying assumptions of a field, and experts can do the same but with (potentially) more impact. The good news is that there are cheat codes for doing this. For instance, lay out all the known datapoints — ideally, in as simple / straightforward a way as possible — and start asking what might happen if one or two things were changed. The key is to remain open-minded throughout this exploration. It’s often easy to dismiss a new idea as impossible, maybe (or especially) if it was tried and failed before. And sometimes that’s true. But not always, and open-mindedness combined with extensive information can lead to new discoveries about what might be new or different this time. We typically call these “breakthroughs.”

Should we aspire for all non-obvious insights to be made obvious? I’m not sure. Sometimes it may be preferable to keep such insights close to the chest. It can feel like a fun secret or provide a source of competitive advantage.

But regardless of whether or not those insights get widely distributed, it’s still worth writing them down. An insight is really only non-obvious to each individual once. And it’s strictly better to have the option of sharing such insights in their non-obvious form than to risk forgetting them altogether.

1. There are many additional reasons. If a fund’s business model / strategic positioning is built in a way that can only be sustained by significant management fees (e.g. large teams of engineers that help build directly alongside their portfolio companies), difficulty raising a subsequently large fund may require a change in firm strategy (e.g. downsizing the support resources, which could impact both new and existing portfolio companies). The full list of reasons is probably best saved for a separate piece.

2. The examples used here are simply ones I’ve been reading about recently. I recommend Debt: The First 5000 Years and The PayPal Wars if you’re interested in either debt systems or the evolution of payment rails.

Whenever you realize something non-obvious, you should write it down.

Non-obvious insights tend to arise when people are either novices or experts. The characteristics and utility of these insights tend to differ based on which circumstance evokes the insight.

When someone enters a new environment — a new city, a new job, etc — they tend to see their surroundings in a way that those accustomed to the environment do not. For those who are familiar with an environment, expectations and reality have converged. But for novices, the newness may create a stark contrast against one’s expectations.

Writing these insights down has several purposes. As you transition from novice to familiar, those insights may fade. Time smudges; the crispness of a new environment gradually becomes ordinary and undistinguished. Writing things down when you’re a novice provides a mechanism to reflect on where the learning curve starts, and helps remind you of what the next novice or outsider may not realize.

Businesses are a great example of where this is important. When I started in VC, I didn’t understand why some funds chose to stay small vs. raising as much as possible. This is obvious to me now: seed stage startups shouldn’t be competing for the same investors’ mindshare as Series B companies, where the dollar amount invested by the firm may be one or two orders of magnitude more for the later-stage company. Smaller fund sizes better match the needs of seed stage startups, for many reasons — ranging from sufficient access to firm resources to enabling investors to more easily cooperate with each other, and much more.[1] To insiders, these insights may feel like common sense. But when I started, this was extremely non-obvious to me. And because I remember how new this seemed, I’m reminded that for others outside the day-to-day of venture investing — like new entrepreneurs seeking investor capital – these conclusions also may not be evident.

The same is likely true of any business: why a customer should buy your product or service over a competitor’s may be obvious to you, but non-obvious to a customer who knows far less about your offering. When something feels obvious, promoting it persistently may feel like overkill. But it’s often not — at least from the perspective of those unaccustomed. Maintaining a repertoire of these learned insights can clarify what elements of a message may need to be repeated and emphasized.

When new to an environment, you’re also more likely to notice small details. Novices aren’t yet sure what will or won’t matter, so they pay attention to everything. Certain things stand out that may blend into the background for the well-acquainted.

Vocalizing such insights helps keep an organization agile and flexible. Processes evolve over time and can sometimes become less efficient / more bureaucratic. To insiders, such changes may feel gradual and thus go unnoticed. But to novices, such pain points are stark. The benefit of a fresh viewpoint can lead to ideas about how things can be improved or, at the very least, remind those with experience that alternative options exist. And this concept isn’t just limited to corporations – it can be extended to city policies or urban planning, the design of products and services, really anything.

The other scenario in which one may be primed to find non-obvious insights is when they have extreme knowledge about a subject combined with a deep curiosity. In my view, this is the true definition of an expert — someone who knows enough to recognize that there’s so much more to know.

Knowing a lot — about a lot of things — improves one’s ability to recognize patterns. Such deep knowledge of a domain provides an important base, and helps illuminate insights that may be non-obvious to those with less context. For instance, certain sequences of events may seem new and novel to us, while in fact similar patterns have emerged throughout history. Debt cycles are one example that come to mind. The evolution of financial innovations and systems for money movement is another. I’m sure there are many more.[2]

But there are also insights that are non-obvious to the experts themselves. Curiosity provides the prompt for finding such information. In particular, experts tend to ask things like “where else might we have seen this before?” and “if we tweaked these one or two things, how might the outcome differ?” Phrased differently: the expert simulates the experience of once again being a novice. The deep base of knowledge provides the foundation for finding the most interesting questions to ask. It also provides freedom and time to pursue these questions: someone newer to a subject may first need to devote effort to learning the basics before they can begin to explore what exists at the outer edges.

Why might experts want to write down these non-obvious insights? In the case where a conclusion is obvious to them but maybe non-obvious to others, writing them down can help build a collective knowledge base. Having such information available makes it easier for others to scale the learning curve. It can also help establish credibility for the expert’s viewpoints (or solicit important feedback). In short, writing scales the impact of these insights.

But what if you’re neither a novice nor an expert? How might you discover non-obvious insights?

One tried and true mechanism is to write. Often, the process of writing helps to clarify what one knows, illuminate the boundaries of that thinking, and push on what else there might be to explore. This piece in itself is a great example: I started it with the idea that non-obvious things are worth writing down, but lacked a framework for the circumstances in which those non-obvious insights might arise. So, I reflected on the non-obvious insights I’ve had over the past year and asked myself “what ties these together?” The process of writing created a prompt to reflect on my personal datapoints from a different viewpoint. Along the way, it occurred to me these insights either came from newness or (relatively) deep familiarity.

Another answer is to start anew. In theory, this is very easy to do: pick a topic you know nothing about and start learning. It could be anything — from how the NYC subway system evolved, to the roots of coffee culture, to the popularity of stickers on laptops. (These examples were derived just now, from simply looking around at my surroundings). The hard part is finding something you’re actually interested in. If lucky, you’ll develop an interest simply through starting.

Finally, you can try re-simulating the experience of being a novice. I mentioned this briefly when discussing experts: new learners tend to ask questions that prod at the underlying assumptions of a field, and experts can do the same but with (potentially) more impact. The good news is that there are cheat codes for doing this. For instance, lay out all the known datapoints — ideally, in as simple / straightforward a way as possible — and start asking what might happen if one or two things were changed. The key is to remain open-minded throughout this exploration. It’s often easy to dismiss a new idea as impossible, maybe (or especially) if it was tried and failed before. And sometimes that’s true. But not always, and open-mindedness combined with extensive information can lead to new discoveries about what might be new or different this time. We typically call these “breakthroughs.”

Should we aspire for all non-obvious insights to be made obvious? I’m not sure. Sometimes it may be preferable to keep such insights close to the chest. It can feel like a fun secret or provide a source of competitive advantage.

But regardless of whether or not those insights get widely distributed, it’s still worth writing them down. An insight is really only non-obvious to each individual once. And it’s strictly better to have the option of sharing such insights in their non-obvious form than to risk forgetting them altogether.

1. There are many additional reasons. If a fund’s business model / strategic positioning is built in a way that can only be sustained by significant management fees (e.g. large teams of engineers that help build directly alongside their portfolio companies), difficulty raising a subsequently large fund may require a change in firm strategy (e.g. downsizing the support resources, which could impact both new and existing portfolio companies). The full list of reasons is probably best saved for a separate piece.

2. The examples used here are simply ones I’ve been reading about recently. I recommend Debt: The First 5000 Years and The PayPal Wars if you’re interested in either debt systems or the evolution of payment rails.