An Unwise Commentary on Wisdom

I've read a few articles about ageism and wisdom lately. It's disappointing because people always say the same thing, and they always don't get anywhere. Young people say "Wisdom comes with experience, not age!" and old people say "You'll understand when you grow up!" and the cycle repeats, forever.

I'm in my thirties now (which makes me "old", ha ha, at least by the definition programmers use). The theme of this diary is "things I recently learned that I wish someone had told me sooner," and so with that in mind, here are a few things I understood when I grew up, around age 30 or so.

First of all, you have to actually define wisdom. Wisdom is not productivity. It's not being smart. It's not being successful, or even a proxy for being successful. Wisdom is not the same as insight, although that's getting closer. Wisdom is not the same as mere experience. The Hollywood symbol for wisdom is a homeless, disabled, ancient, wrinkled, Chinese guy in a martial arts movie, sitting on a street corner muttering aphorisms without using the words "the" or "a". And that, I think, is really the closest to what we mean by wisdom.

Wisdom is knowing what the movie will be about, and how it will probably end, five minutes in, before the plot has even started. And then wisdom is the self control to only tell the hero exactly the part he needs to hear.

Let's pull this out of Hollywood and back to programming. I'm going to dumb that down a bit and put it like this: wisdom is the ability to predict the future.

You might have heard that "The best way to predict the future is to invent it," a famous statement by famous old wise guy Alan Kay. But according to that link, he said it when he was 29 or 30. That quote is partly true (what you can control, you can predict), but it's the perfect wishful thinking of a young person trying to rationalize away the need for wisdom.

As you gain wisdom, you can begin to predict even the things you can't control. You might think you can accomplish the same thing with facts, logic, and a really big search engine, but you can't. You can predict some things that way, but not most things. Maybe someday, after all the rest of Artificial Intelligence is finished, we can have Artificial Wisdom. Wisdom is the thing your computer doesn't do. To become wise, you have to train your intuition using your physical senses. That takes time, and it actually takes actually physically being there to know what it feels like. People who think they can be wise without feeling it are idiots. You can be lots of things without feeling the world, including successful, rich, famous, productive, and smart. But you can't be wise.

So far, this is just a hopeless rant about how you're just too young to understand. Let's take it past that. I can't make you wise, but maybe I can help you spot wisdom when you see it. For me, learning to spot it was the first step in learning to get it.

I co-founded my first company when I was 19 or 20 (depending how you define "founded") and surely lacking in wisdom, because wise people don't start tech companies. A couple of years later, after me and my technical co-founder had built and sold the first version of the product (to some small profit, comparable to taking a paid internship instead), we found some experienced businesspeople who joined in order to handle the business side. This was a smart (not to say wise) choice on our part. The new people were a few years older than us and lacked wisdom too, but had experience. They got us angel funding, then venture capital, and ramped our sales into the millions of dollars per year.

Shortly after our first meeting with those new businesspeople, one of them presented the rest of us a simple one-page "getting on the same page" memo of understanding. (Not a complicated MOU like lawyers draw up, just a simple letter in his own words.) Not knowing anything about business, I found a businessperson I knew (friend of a friend) to show the letter to. He was an older guy. His 30-second review was, "Stay away from this guy. He isn't the kind of person you want to be dealing with." I ignored him, because that's what young people do with advice they don't like.

Roughly 8 years later, we sold our company to IBM for untold (I can't tell you) zillions (not a real word) of dollars. The venture capitalists, who everyone teaches you to fear and distrust, were respectful, ethical, and fair during the entire time we spent working with them. (In particular Desjardins-Innovatech were great.) This business guy, however, the one who wrote the memo, turned out to be a slimeball. To this day, he is still the only person on my "do not treat as human" blacklist. I had to create my blacklist for this purpose. But that's another story for another day.

The point is, 5 minutes into my story, someone older, who turned out to be wise, had this guy pegged after reading half a page of text, without even meeting him. He predicted the future, accurately, instantly, and without any real facts. That's either luck or wisdom.

And so we come to our next problem. I hope what you take away from this article won't be, "Listen to old people, they know stuff," because that would be stupid. Most old people, like most young people, are dumb, and so taking their advice is dumb. Numerous people told me the product we were building was physically impossible and to maybe try something that made sense and that people wanted, and they were all 100% wrong, and I was right to ignore them. (Maybe less right to tell them so to their face, but oh well, something something wisdom etc.)

No, we're not done yet. All that was just to say, yes, wisdom exists, and no, you probably don't have it. But I want you to know that you can, at least, make a series of observations in order to hypothesize about its nature. You can't see protons either, but you know they're there.

There have been a few very memorable moments of my life when I have acquired a few Real Actual Nuggets¹ of Wisdom. I know these moments, because they were so astonishingly blatant. I guess there were probably other, subtler ones, but let's ignore those, because I can offer no advice on how to detect them. I think the big ones are enough. With those ones, looking back on my life, I can see the before-wisdom-nugget version of me, and the after-wisdom-nugget version of me. The after-nugget version is dramatically better at predicting the future.

Perhaps my biggest, most multi-faceted wisdom acquisition event was reading and understanding Crossing the Chasm, a book from 1991 about companies from before 1991. Yeah, sure, it taught me all sorts of stuff about why my company wasn't growing exponentially, which was great to know, and explained in retrospect how much of our time we'd been wasting on stupid initiatives, which was embarrassing but also great to know. But as part of discovering those things - and probably in a moment of weakness caused by it - I learned something else.

All those problems we were having? They'd been had by people for decades. And people already knew how to solve them.

When we did finally sell our company, IBM bought it because of about 5% of the stuff it contained. The other 95% was great stuff, but it wasn't what IBM wanted. In Crossing the Chasm terms, we had finally, 9 years in, created a "Whole Product" for a "Target Market." We could have accomplished the same thing, I think, with only 5% of the work, if only we had known which 5%.

You will try to tell me that there was no way to know which 5%. That the other 95% of wasted effort was necessary as part of the experiment. I would have told you that, too, back then. Back before I knew it was false.²

That was the big lesson about wisdom for me, the one that has put all these discussions about young vs old and energetic vs experienced into perspective. In 1999, there was nobody whose experience would tell you how to build a Linux-based server appliance that would sell like hotcakes. But there were people who could tell you we were doing it wrong, and explain exactly why and how, in step-by-step detail, including the totally predictable consequences of our mistakes (correct) and instructions about how to do it right. They published a book about it in 1991, before Linux even existed. It said, "You are doing this. You should do that instead." And they were exactly right, on both counts.

Young people have energy. We had a lot of energy, and produced a lot of super crazy amazing stuff that I'm still very proud of today. But we lacked wisdom, so 95% of it was wasted. My goal is no longer to code 10x as fast as the average programmer; my goal is to not have 19/20 of my production be useless.

So here is my first nugget of wisdom, purified and cleaned up and presented with that huge preface. It was the one that got me on the long, slow, painful path to maybe learning other ones someday. Maybe it will help you too.

If you think nobody has ever done this before, you are almost certainly wrong. Many people have done it before. Most of them have done it wrong. Find the ones who did it right, and find out how they knew it was right. If you can learn to find wisdom in others, someday you can find wisdom in yourself.

I know what it feels like to be 20 and running a startup. You have faith in yourself, and you feel like your world is unique, and nobody else has the same problems you do. You certainly feel like experiences from 20 years ago can't possibly be relevant. Once you've learned otherwise, then, laddie, then maybe we can talk.

Footnotes

1. Whenever I try to type "nuggets" I keep typing "nuggles." I hope this footnote has been educational for you.

2. I'm not trying to be a "Customer Development denier" here. There will always be inefficiencies caused by searching for a business model. But if you spend 9 years and 95% of your work is wasted, you're doing it wrong.