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I was visiting a venture capitalist friend of mine a few months ago, talking about what we thought the future held and what kinds of companies intrigued us. He made a comment regarding a company I liked and he didn’t. He said “I only invest in companies I know will be successful.” On further questioning he admitted that not all of his investments had been successful: sometimes management had screwed up, sometimes customers did not get the value of the product quickly enough, etc. But in all cases, he felt he had invested in surefire plans; if the company failed, it was due to execution mistakes. And sometimes, even, he had made mistakes. But it was not that the validity of the business plan wasn’t knowable, or even that he couldn’t know–sometimes it was just that mistakes were made.

This is also how I thought, a few years ago: that I could know. The idea that we can always find answers and act on them and thus change our environment or the world not only underlies our technological and business culture but is explicitly taught in our best schools and finest corporations.

A few years ago, someone I worked with teased me because I never said “I don’t know.” Ever. I would say “I’ll get back to you on that” or I would attempt to answer even though I didn’t have the answer, or I would deny that the question had significance. Occasionally I would aggressively change the subject or grow angry with the person who wouldn’t agree with what seemed so clear to me but that I couldn’t explain. This annoying tendency of mine came from years of feedback in the classrooms and management meetings and boardrooms where “I don’t know” was not an acceptable answer. Not even close. People who said “I don’t know” did not get the good grades, they did not get the promotions, they did not get the bonuses, they did not get the slaps on the back. Not knowing was weak.

One thing that venture capital teaches you, though, is that you don’t know. There is probably no other area of life—aside, perhaps, from going up to bat in professional baseball—where you are constantly and ruthlessly reminded that you are not only not always right but that you are usually wrong. And even, that when you did everything possible—all the due diligence, all the research, all the number-crunching, all the strategic thinking—there was no way, a priori, to know. Many venture capitalists do not accept this. Almost all people do not accept this. But it’s an inescapable fact. And, it’s not only true in investing but in all parts of life—it’s just more obvious in investing. The proper lesson to learn from this is probably humility, but successful people rarely became successful by being humble.

This decade I’ve been too often reminded that a chance meeting or an idle phone call can turn what looks like inevitable failure into wonderful success. Or vice versa. That is, that there is never any way to know for sure what will end in success and what will end in failure. For me luck has not been risk; it is not beta, it is not some fat-tailed distribution. It has been the unexpected and, yes, the unknowable.

*****

I think about luck a lot.

There’s an old story, related by Alan Watts, about the farmer whose horse ran away. His neighbors say “Such bad luck!” The farmer says “Maybe.” The next day his horse comes back, with two wild horses following him. His neighbors say “Such good luck!” The farmer says “Maybe.” The next day the farmer’s son falls off one of the wild horses while trying to tame him and breaks his leg. His neighbors say “Such bad luck!” Etc.

Good luck and bad luck come and go, and there is no distinguishing them, either before or after the fact. There is no beginning or end of things because there is no way to isolate a single causal event; causes effect widely. We technocrats would explain this by saying, simply, Things are Complicated—we have a Math for that. But this is not enough: this interconnectedness through time and across events could more easily lead to a dampening, an unchanging condition, but it does not. Watts explained this by saying that there is a cycle of remembering and forgetting. Anybody who’s been paying attention would have to say that, as is often the case, the zen analysis is more useful than the scientific.

This decade I’ve had a lot of bad luck end up well and a lot of good luck end up poorly. If I knew then what I knew now, there would have been a lot less Good Luck and Bad Luck and a lot more Maybe.

I’ve often felt that my comparative advantage in the work world is my willingness to take the risks than the next person would not want to, to weather more sheer unpleasantness, deal with more complexity, and in general gladly volunteer to walk into the knife-storm that my professional life has often felt like over the past ten years. That this sort of thing did not bother me much, while others found it intolerable, is a valuable trait, it seems. It worked for me. But if my neighbors came up and said “What good luck!” I would have to say, Maybe. Because while things worked out at work, they didn’t at home. My thinking that I could isolate my home life from my work life was part of the reason. But nothing is isolated.

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So, this isn’t one of those What a Great Decade posts, although it was a great decade for me, for a lot of reasons, work and even personal. It’s just my annual reflection, being realistic about the good and the bad. For me, it’s always easy, upon being told “What good luck!”, to say Maybe. The hard part is saying the same when told “What bad luck!”

Ten years ago my goal for the decade had something to do with doing well and, perhaps, even doing some good. In retrospect, my major accomplishment was learning how to say “I don’t know” and then stopping to listen. (I do not consider my wonderful children accomplishments, I consider them gifts.)

For the next ten years, my goal is to be able to answer Maybe to bad luck with the same equinamity I do to good luck. If I could do this, then everything else would be easy.

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But I do want to say a little bit what a great year it’s been. I want to appreciate all of you reading here. And thank you for commenting and connecting outside of this forum. I use this space to think out loud, it helps me order my thoughts to know that other people will read them. This is valuable to me, and why I started writing in the first place.

What I didn’t expect was that in addition to the benefit of writing, I get the benefit of connecting. I’ve met a few great people through this blog, I’ve stayed connected to a few other great people, and I’ve learned an awful lot from the people who read it. I am thankful. I haven’t quite quite found the invisible college, not yet, but it’s a start.

So, thank you. And in the new year, may you view all your luck as good luck.