The year was 2016 (or close enough), and a friend of mine’s younger brother - we’ll call this younger brother Luke - was about to start college.

Having completed college not that long ago, I thought it would be nice if I could make a list of some of the things that had helped me - the strategies and disciplines that I had made use of - to hand to this prospective scholar.

I made my list, including links to productivity resources and guides to How To Get Things Done, and prepared to hand it off to Luke with my best wishes.

I remember how it felt, handing him that list. I was envious of Luke, in a way; I wish that I had had someone hand me this list back when I started college. It would have made things so much easier! And here I was, just handing Luke the keys to success on a silver platter.

He didn’t even know how lucky he was. I could picture how much easier he’d find things than I did, with the steps on his path helpfully guided by my concise and helpful list.

A few months later, I check in with my friend as to how his younger brother is doing, sure that I am about to hear a tale of effortless success and, well…

Luke was failing his classes.

I later learned that Luke had dropped out after his first year.

Nowadays Luke’s doing his own thing, and I have, shall we say, different opinions about the utility of college in general. And I can look back at the list I gave him and admit that it was not a perfect distillation of how to Mange Time Effectively and Really Get Things Done.

At the time though, I was aghast, and spent a great deal of thought on how my Super Awesome List failed to teach Luke the secrets I had learned throughout college on How To Get Things Done.

What I realized, after a great deal of introspection, was that it was inherent to the nature of wisdom itself that it cannot be decompressed. What follows is an examination of that idea.

Part I: Gird Your Metaphors

Compression as a Technology

Compression is a key technology in digital systems. It’s what happens when you ‘zip’ a file - the file size is reduced, like packing a puffy winter jacket in a suitcase by sitting on the suitcase until you can get it closed.

We compress data in digital systems because data transmission and storage aren’t free, in money or in time. It takes longer to send a gigabyte than a megabyte, and you can (by definition) store a thousand of the latter for every one of the former.

It becomes valuable, then, to compress any data we send before we send it; it can then be decompressed (unzipped) upon being received.

With me so far?

Wisdom as Large Pieces of Data

People have been defining wisdom since there have been bearded old men claiming to have it. For our purposes, we’ll be defining ‘wisdom’ as a large piece of data, generally in the form of a life lesson synthesized into a series of recommended behaviors for various situations created from accumulated life experience.

(Don’t worry, we’ll get to concrete examples in a second.)

Talking as Transferring Data

Just as data is transferred from one computer to another along wires, ‘knowledge’ - or ‘wisdom’ - is transferred from one person to another via sound waves, or, you know, talking.

The problem here is that computers can transfer massive amounts of information between each other very very quickly. Humans cannot; no matter how fast we talk, talking remains a very slow method of communication. (Consider the information transfer of an eBook: the book could be transmitted from a source computer to your computer/kindle/device in seconds, but if you tried to read the book to another person, it would take hours.)

To solve this problem, we humans compress the data we transfer via talking. We don’t describe the book we’re reading by reciting the entire thing word for word - we summarize. We don’t specify a person by communicating all of their identifying information - birth date, height, weight, physical description, etc. - we just mention their name, and expect the person we’re communicating with to know who we’re referring to, and understand any relevant context.

What about when we try to communicate wisdom by talking?

Well, we use sayings.

Part II: Aphorisms and Abbreviated Wisdom


I’m going to throw a few sayings at you; odds are that you’ve heard at least one of them before.

A stitch in time saves nine

Look before you leap

A word to the wise is sufficient

An ounce of prevention is worth a pound of cure

Actions speak louder than words

A penny saved is a penny earned

Measure twice cut once

These aphorisms, I argue, are in reality compressed bits of wisdom. They’re handed down from the old and wise to the young and stupid, generally in the hopes of making the young slightly less stupid.

And yet a compressed message, to be understood, must be uncompressed. When you email someone a zipped file, the file must be unzipped before it can be read.

The young and stupid - or more generally, anyone who doesn’t understand the underlying message - are incapable of successfully unzipping these aphorisms. They lack this ability not because they’re young or stupid, but because of the nature of compression itself.

Compression Necessitates Shared Knowledge

Imagine that a computer, Alice, wants to send another computer, Bob, a message. The message is in binary (naturally), and is as follows:


A common type of compression algorithm compresses information by recording patterns in the information, and communicating the pattern. For instance, this message contains four 1’s, then six 0’s, then 1010, then eight 1’s, then five 0’s, then 101.

So a compressed version of the message might look like:

4x1 6x0 1x1010 8x1 5x0 1x101

So Alice sends the compressed message to Bob. But how does Bob know how to decompress the message?

Well, Bob is (hopefully) aware that




and so on. So long as Bob knows that, Bob can decompress the message and read it.

This requires shared knowledge. Alice and Bob have to be on the same page here before any information is transferred; they both have to know that compression is happening and the particulars of how it takes place in order to communicate successfully.

In computers, the shared knowledge is the compression algorithm.

In people, it’s a little more complicated.

Idea Compression (or The Makings of Aphorisms)

What does someone mean, when they say “A stitch in time saves nine”?

What are they trying to communicate?

First we have the literal meaning of the phrase:

Take an article of cloth, perhaps a piece of clothing. Imagine a favorite pair of jeans, for instance.

Cloth tears when exposed to sufficient stress - jeans get ripped, torn, etc. Wear and washing can cause or exacerbate this.

These tears often start small - a tumble while wearing these jeans causes a bit of them to snag on a tree branch or something, and a small tear in the cloth is created.

Because these tears represent a weakness in the physical integrity of the item, further stress often causes existing tears to worsen. In other words, it’s easier for a small tear to get larger than a new tear to form.

Tears are often addressed by stitching - binding the two sides of the tear by layering new thread across it.

Two possible options present themselves for addressing the tear: stitch it shut when you first notice it, or wait awhile before stitching it shut.

If you stitch the tear when you first notice it, presumably the tear is small, and so requires few stitches.

If you wait, the tear has presumably gotten larger over time, and so requires more stitches to close it than if you had done so earlier.

Hence, stitching a tear upon noticing it requires fewer stitches than waiting to do so later, or “saves” stitches.

“Time” sort of rhymes with “nine.”

A stitch in time saves nine.

Next we have the extrapolated or generalized meaning of the phrase:

Smaller problems require less resources (time, money, thread, etc.) to deal with than large ones.

Problems often grow worse over time if left unaddressed.

Dealing with problems earlier is thus more efficient than dealing with them later on.

Deal with your problems now before they get worse.

And supporting this generalized meaning will be countless memories and associations. Originally this might have been literal articles of clothing that had to be disposed of because tears had been left unaddressed and had grown too large to be worth fixing, but more modern interpretations and examples abound.

A health problem that could have been fixed with a simple procedure metastasizing into a major problem.

A small credit card debt that, left unpaid, accrues interest until it becomes a sizable burden.

A blinking “check engine” light on a car ignored until the car breaks down.

All of these meanings and associations and memories, all the emotions and context and history surrounding them - all of it gets compressed into a pithy saying for concise communication:

A stitch in time saves nine.

Part III: Miscommunications and Conclusions

A Failed Communication

None of that meaning, no hint of the association or emotion or context, is transferred along with this “wisdom”. None of it is inherent to the six words: “a stitch in time saves nine”.

Rather, these six words function more as a mnemonic device - a compressed way of referring to the broader idea. For those who already understand the larger concept, a simple reminder that “a stitch in time saves nine” is often enough to communicate that they should deal with a given problem soon, before it gets worse. (One might even say that a word to the wise was sufficient.)

For those who don’t understand the larger concept, the reminder that “a stitch in time saves nine” doesn’t mean a whole lot. At best it’s a way of berating them to stop being lazy; at worst it’s a throwback to a time when people repaired clothes instead of throwing them out and buying new ones. Either way, little to none of the meaning of the aphorism is successfully transferred, because the contextual knowledge necessary to decompress the wisdom isn’t present at one end of the communication.

It’s as if Alice sent Bob:


instead. Bob has no idea how to interpret that - he is unaware that Alice was transmitting the information in hexadecimal instead of the compression format he was expecting.

Where Words Fail

Words are not a particularly high-bandwidth form of communication; it takes a great many of them to convey an idea without relying on shared context or experience.

When that context is present - when two people are “on the same wavelength” or can draw from a similar well of experiences - then a single word or phrase can contain a library full of meaning. This shared context is analogous to shared knowledge of a decompression algorithm between two computers: when present, it enables a great deal of information to be transferred via short messages.

But when it isn’t, when the wise invoke an aphorism to the not-wise, that shared knowledge is absent. The decompression fails.

And the truth is that compressed knowledge can’t really be transferred at all. Words can describe experiences, but they cannot truly convey them, not the way they were originally experienced. They can’t contain the qualia, the subjective interpretation of an experience that happened in reality. They can reference it - they can wax poetic about the emotions of the experiences, or outline the failures suffered and lessons learned - but that’s it.

Simple ideas can be conveyed with words - “house”, “blue”, “square”, etc.

But wisdom? With all its complex context and referent experiences and myriad meanings?


Imagine that you’re in a similar position to the one I was in, back when I was trying to show Luke the methods and strategies that worked for me in college.

Now imagine that you’ve failed, and are trying to communicate what that experience is like. Imagine that you’re attempting to describe, subjectively, what it feels like to try to impart wisdom to someone who doesn’t possess the shared context and experience it would take to grasp the ideas you’re attempting to convey.

What might you come up with?

I came to understand: Wisdom cannot be unzipped.

But then that requires explanation too, doesn’t it?

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17 comments, sorted by Click to highlight new comments since: Today at 12:11 PM

I don't think the difficulty in getting actual life-improvement out of "a stich in time saves nine" comes from any impossibility in figuring out what that phrase means. (If that were the case then probably instead of saying "a stitch in time saves nine" we'd be saying "fix small problems early, before they turn into big problems", which is almost as short and pretty unambiguous.

I think the actual difficulties are:

  • Knowing a valuable principle is not the same thing as actually applying it; for that, you need to remember it at the right time, you need to find the motivation to do what it says, etc. Maybe you have a minor health problem but some bit of you flinches so hard at the prospect of going to see the doctor and maybe getting bad news that you can't make yourself do that; the problem isn't that you don't know it would be a good idea.
    • ... and one reason why we don't always apply useful principles we've heard might be that ...
  • Having heard a valuable principle is not the same thing as knowing it's good advice; you might not actually believe it. Maybe you're a young person and have constantly heard your elders telling you to work hard, and it's occurred to you that giving you that advice might be good for them more than it's good for you. Even if in fact working hard would be good for you, and you've been told as much, you don't know it's true.
    • ... and another reason might be that ...
  • A principle like "a stitch in time saves nine" may be good advice only sometimes. (There are plenty of pairs of equal-and-opposite proverbs. Look before you leap; he who hesitates is lost. Better safe than sorry; nothing ventured, nothing gained. Many hands make light work; too many cooks spoil the broth.) The real wisdom is the pithy principle plus a load of extra information about when it's actually a good principle to apply. The problem isn't that wisdom can't be unzipped, it's that important things never got zipped in the first place.

The last of those points is a bit like the one you're making. You could say that the pithy phrase is genuine wisdom, in the hands of someone who has the extra contextual information to indicate when to apply it and the life experience to make it properly motivating. But I don't agree; I think that the extra contextual information and life experience is the actual wisdom here, and that's what hasn't been zipped in the first place.

What's difficult mostly isn't unzipping wisdom, it's identifying actual wisdom and zipping it.

What's difficult mostly isn't unzipping wisdom, it's identifying actual wisdom and zipping it.


Maybe this is just because of it's age, but "a stitch in time saves nine" strikes me more as an attempt of "pretending to be wise". If I was trying to help, I'd try communicating a procedure one can actually follow:

  • "Set a 5 minute timer to figure out the biggest problems in your life."
  • "Consider reading book X".

I don't think the difficulty in getting actual life-improvement out of "a stich in time saves nine" comes from any impossibility in figuring out what that phrase means.

For what it's worth, I have met people who had no idea what "a stitch in time saves nine" means, although I do agree largely with your point.

I think that the extra contextual information and life experience is the actual wisdom here, and that's what hasn't been zipped in the first place.

There's some nuance here - I think we're agreed that the contextual information and life experience is the wisdom. It's what isn't communicated by the pithy saying that matters - and yet the pithy saying is clearly meant to point to or contain the contextual information/life experience.

Which is to say that while pithy sayings are useful ways of reminding someone who already has the wisdom to apply it in a given situation, they're useless for actually conveying wisdom.

And in my experience, the latter is the way they're most commonly used.

I like what you did there.

...but the fact that I (think that I) understand this post & can use this to my advantage — instead of going through the entire lengthy process of failing to convey wisdom on my own — means that you can unzip wisdom. At least a little. :)

Thanks! And you can, it just takes a while :)

Two years ago I started writing a post about how to learn from others (I never finished it). The premise was similar to this idea, that just hearing some lesson or advice isn't enough to learn it. Instead, to integrate such lessons you should ask what experience the person who conveyed the lesson learned it from, and try to replicate it yourself. And if you're the person giving advice, don't just give the advice, but give a way to learn it.

For example a good piece of advice in hand to hand combat is to keep your head back (many people lean forward with it). But just hearing that wouldn't help a fighter much. Here's how you can learn it, and how I, in fact, learned it: do a hands-only spar. it makes the position of your head much more significant, and if you pay attention you'll see that when your head is back it gets hit much less, and it's easier for you to get a hit on your opponent without risking getting hit yourself as much.

I think our brains are wired to learn from experience. It's not that we can't learn from words, but it's narrow and insufficient. it's like we never fully trust words, or fully propagate them, or something like that. But experience is a richer format which is more significantly imprinted in our brains.

Also this is the reason stories are useful, including fiction. As Eliezer said: "nonfiction conveys knowledge. Fiction conveys experience". And there might be things you can only learn from extreme experience, and not substitute experience, but that stories can still give you a glimpse into.

While certainly wisdom is challenging to convey in human language, I'd guess an equal problem was the following:

Your list probably emphasized the lessons you learned. But "Luke" had a different life experience and learned different things in his youth. Therefore, the gaps in his knowledge and wisdom are different than the gaps you had. So some items on your list may have said things he already knew, and more importantly, some gaps in his understanding were things that you thought were too obvious to say.

Plus, while your words may have accurately described things he needed to know, he may have only read through the document once and not internalized very much of it. For this reason, compression isn't enough; you also need redundancy—describing the same thing in multiple ways.

I think the main difficulty is that there are many pieces of wisdom and some of them contradict each other. The opposite of "a stitch in time saves nine" is "you ain't gonna need it", and so on. A person needs to learn which pieces of wisdom are the most useful to them, and that can only be learned from experience.

I think this post highlights some of the difficulties in transmitting information between people - particularly the case of trying to transmit complex thoughts via short aphorisms.

I think the comments provided a wealth of feedback as to the various edge cases that can occur in such a transmission, but the broad strokes of the post remain accurate: understanding compressed wisdom can't really be done without the life experience that the wisdom tried to compress to begin with.

If I was to rewrite the post, I'l likely emphasize the takeaway that, when giving advice or attempting to transmit such wisdom, the point is that you have to take the time to convey the entirety of the context of what you're saying, unless you're just reminding someone of something they already know. "Don't zip your wisdom, just transfer the whole thing" might be a better title than "wisdom cannot be unzipped", for the practical application of the lesson.

I do like - and intend to continue - inserting pieces of related knowledge into posts, in the way that this post teaches a little about what compression is in the course of conveying its message. I think that benefits the discourse, and by assuming a low level of shared knowledge, makes the post friendlier to newcomers and beginners.

This is not intended as a criticism in any way, but this post seems to overlap largely with 

[Edit: After looking at the timestamps it looks like that post actually came out after, anyway it might be an helpful alternative perspective on the same phenomenon.]

To me there are additional modes that pithy sayings are using - conveying knowledge at the time of utterance seems like part or a mere side channel.

One way the shared knowledge can be established if the psychological development of the receiver and sender goes along similar lines. One way to develop similarly is to live in the same environment and make the same inferences. Conveing the parts that are similar is redundant. Thus one communication scheme is to only say things that work as developmental junctions ie where you infer differently by being informed. This kind of scheme doesn't require the receiver to believe or understand the pithy thing on the oral transmission. Say the hint is "When you get kids you will learn that life is not about survival but life is about sacrifice.". This does not meaningfully alter if we drop the condition and just make it "life is not about survival but sacrifice".

Another mode is to guide "prior selection" or "imagination aiming". If you have pithy sayings floating around in your head when you are trying to structure and model a new venue of life, representations that are compatible with the sayings are more probable and natural. So while there is need to have practical and detailed experience of the thing being talked about those that have "spoilers" can extract more abstract and useful lessons earlier. A saying usually does not come with its proof, but the life situation working as a "verification" that the claim in fact holds is the event that convinces the receipient. Those without advice might try to verify random claims but those that have hints will try claims that prove more often. Blind fate to advice could be counterproductive but this kind of verification guiding has the nice property that if a general advice does not hold in some special niche or such it can be found to not hold.

I think you're zeroing in on the hypothesis that your list had a problem too early. There are many possible reasons to fail college, like having a mental health issue or not being very motivated to succeed in the first place. Do you know that he actually read your list?

In my experience the biggest predictor of teaching success is whether the person asked to be taught)

You're completely right - "Luke's" failure to finish college likely had very little to do with me or my list. 

I provided the anecdote and framing as a way of motivating the idea I was trying to convey, as well as explain my thought process to arrive at it.

Don't worry: "Luke" is doing quite well for himself :)

The Luke anecdote may not be the best example, but the general idea is sound. Hermann Hesse in Siddhartha said, "Wisdom cannot be passed on. Wisdom that a wise man tries to pass on to someone always sounds like foolishness." That's slightly too categorical and strong, but still broadly correct and consistent with the point of the original post.

It's not that wisdom in general can't be unzipped (look at e.g. the Bible for a source of wisdom that has reliably enough been unzipped by many generations, to be worth preserving & reading), but rather:

The wisdom you wanted to convey, communicated in the format you chose, could not be unzipped by your target audience at the time you intended it to be of benefit.

The wisdom you wanted to convey, communicated in the format you chose, could not be unzipped by your target audience at the time you intended it to be of benefit.

I completely agree - but I wanted something a little more pithy as a headline, and "Wisdom cannot be unzipped" fit the bill.

Perhaps "Wisdom can only be unzipped by the wise" or "Unzipping wisdom requires wisdom" to keep it to four words.