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I’m going to start with that old conundrum meant to separate the optimists from the pessimists:

“Is the glass half-empty or half-full?”

I have an answer to that question: It depends.

It depends on whether you’re drinking from the glass or filling it.

Now I work with many start-ups, entrepreneurs, and independent filmmakers. If there’s one thing they are infinitely endowed with, it’s optimism. Often to the point where they seem to have become dislodged from the time-space continuum, much as the folks on the island in Lost. And just a cursory troll through job descriptions in Monster or Craig’s List (something more and more of us are doing these days), you will come up with some job description that has some variant of the word “optimistic” in its requirements.

Optimism is a good and great thing, but now that we’ve seen optimists by the train-load burned by credit swaps, collateralized debt obligations, ARMs, and their too-good-to-be-true accounts with Bernie Madoff, does that mean the optimists were smoking the ganj a bit too much and the pessimists were right all along? “They shoulda’ listened to me,” is a refrain I’ve heard many times over the past three months from dozens of people not worth listening to.

Maybe the pessimists were right. But the smart optimists made away with a good bag of loot while the going was good just like many of the pessiimists. The people I encounter who consistently walk away with generous helpings of the pie practice what I for years have called, “pessioptimism.” And, I can tell you, as a fervid practitioner, we’re not a very well-understood lot. More after the break.

Many moons ago, when I worked for two very wonderful, kind, industrious, and brilliant-in-separate-ways gentlemen, Jerry Rothstein and Rick Memsic, they came to me with a plan to partner with a local printer. I won’t go into details, but as is my wont, I immediately began to list all the issues that needed to be addressed in such a change in business focus and priorities. The most important concern involved losing focus on our core business anc capabilities (which, I’m pleased to say, my MBA has taught me was an absolutely spot-on). Jerry, a wonderful and kindly man, became increasingly irritated, wondering why I was so critical.

As Donkey says in Shrek, “You cut me, Shrek, you cut me.” It has always seemed to me that the worst planning is no planning and you get the useless answers from the questions you don’t ask. It has always seemed to me that the ultimate act of optimism is to subject an idea to rigorous questioning, criticism, and analysis — to spend time on the idea and take it seriously. Simply launching an idea without criticism or thought is wishful thinking, not optimism.

I thought about that one long and hard, for I am, by nature, a blindingly optimistic person who will jump off any cliff if there’s any probability that I could fly. (By the way, all my concerns about the venture came true and it was soon abandoned.)

What people like me do instead of jumping off those cliffs is we stop and think. And by think, I mean think in highly structured and formal ways. If I were forced to use real English to say what I mean by “pessioptimist,” I would say it like this: “A pessioptimist is an optimist who thinks critically.”

That phrase, “thinks critically,” has a world of meaning lurking behind it. I’m not simply talking about all the rigorous structures and principles of “critical thinking” as I and others have learned and taught it at the university level. I’m talking about deploying all the necessary formal structures demanded by the problem at hand.

For instance, you could fill a building with the optimists that Bernie Madoff bilked. But he did not burn any major investors, such as CALPERS, the Harvard Endowment, or major banks. Why? Were they pessimists? No, on the contrary, CALPERS and Harvard, as “socially responsible investors,” are just shy of the looniest end of optimists (SRI is not a valid investment strategy in any world, in my not-so-humble and always available opinion).

Instead, these investors had formal structures of due diligence. Subjected to formal structures of due diligence analysis, Bernie Madoff usually didn’t last 20 minutes in a room with folks from these funds before they spat out the Kool-Aid.

How do pessioptimists, “optimists who think critically,” approach the world? They start with a few truths:

  • You only know what you know and even that you know that imperfectly.
    We live in this massive fog of unknowing and ignorance and we confront it everytime something that’s supposed to work, doesn’t. But every once in a while, we find a clearing where everything’s visible and clear, the little bit of the complex world that we actually understand. But we’re still surrounded on all sides by our own ignorance. And the best decisions are informed decisions — so it pays to clear the fog.

  • You only get answers to the questions you ask.
    It’s the questions you don’t ask and the answers you don’t have that burn you. The most important skill taught by critical thinking is to find the unasked questions and assumptions and bring them kicking and screaming into the daylight.

  • The right answer is the right answer.
    This may seem obvious, but you’d be surprised how many people think they’ll just happen on the answer if they wander around enough. A big part of solving problems of all stripes is figuring out what the answer will look like before you try to find it. I often say (and I’m not sure if I made this one up or not): “If you don’t know where you’re going, when you get there, you’ll be lost.” And, again, critical thinking trains you to formulate the outlines of the answer before you start guessing.

  • Experts are only as good as your capacity and willingness to understand them.
    Listening to knowledgable and expert people is hard work and, if you’re not willing to do it, you’re getting nothing out of it. Bernie Madoff was an expert. People who took the time to understand what was coming out of his mouth went for the exits as fast as their little feet could take them.

  • The “what” is only part of the problem. “How” things are said matters.
    Language is a terrible way to communicate. There are all sorts of ways that truth can be juggled and jagged and jimmied. The rhetoric people use, the structure of their argument, and the way they frame content with language can lead people down the wrong path. If you don’t know what a frame is, it’s how the language people use create a pre-determined evaluation or meaning. For instance, an “inheritance” tax is eminently fair — why shouldn’t people be taxed for inheriting money they didn’t work for? A “death” tax, on the other hand, is not fair. Same tax, two different frames. The truth lies behind or around the language people use to convey it.

  • Numbers can lie, too.
    I’ve written about this in a previous entry. At some level, some dude is going to pull out a spreadsheet or a set of charts and set them down in front of you. While they may seem transparent, what the numbers mean and where they come from are two things you have to figure out all on your lonesome.

  • People are fundamentally irrational.
    Maybe this is because I come from the advertising world, but I hold as a self-evident truth that there is almost no decision that people make that is not fundamentally irrational — based on emotion, fantasy, or idealism. At some level, optimism requires that you confront the irrational aspects of yours and other people’s decision-making.

  • Almost everything worth doing involves hard work.
    Don’t be fooled by the four-hour or one-day workweeks that a lucky few manage to land (and write best-selling books about). Almost everything worth doing involves time, skill, and hard work, so it behooves you to lay that all out on the table before you launch. If anyone shows up at your door and tells you something will be easy, they’re probably lying. What separates the pessioptimists from the garden-variety, rose-colored-glasses optimists is that they always ask the question, “What’s involved? What do we have to do to make this happen? What are the constraints on the system? Where are the bottlenecks? What are the dependencies? What’s the critical path to making this happen? How much time will it take? What skills? Who has those skills? How much will it cost in reality?” And then they answer the question before launching the boat.

  • If you have no Plan B (or Plan C or Plan D), you don’t have a plan.
    When the stories about the McCain, Clinton, and the Obama campaigns get written, two truths will emerge. The first is that the McCain and Clinton campaigns were constantly surprised by events, actions, and decisions, and so were constantly and chaotically in a state of panic (this is true). They were effectively directionless, pulled along by all the things they hadn’t anticipated. The second is that there was nothing — no event, no happenstance, no nothing — the Obama campaign didn’t plan for. They had a plan and stuck to it. And they had a Plan B in case B happened. And a Plan C if C happened. And a Plan D if D happened. And so on. When the inevitable tell-all books come out, it will turn out that there was precious little that ever surprised anyone in the Obama campaign. That’s no small reason why it’s President Obama and not President McCain or President Clinton. If you have only one plan, you have no plan. It’s gone when the first unanticipated event comes knocking at your door.

    So it’s not pessimistic or critical to expect things to go wrong. It’s good planning. Or to ask questions no-one else is asking. That’s good decision-making. Or to check and re-check the numbers. That’s what numbers are for. Or to take apart the rhetoric. That’s how you get at meaning and truth. Or to expect to do a lot of work. That’s simply required.

    Pessimists expect the worse and act like it. Optimists expect the best and act like it. Pessioptimists expect the worst, plan for it, and act like optimists. And they’re the ones who usually end up flying against all odds.

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  • One Response to “Pessioptimism”


    1. […] I have, of course, talked about this in a previous post on pessioptimism. […]

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