The Optimistic Skeptic

by F.

I think it’s quite possible to be skeptical and optimistic, provided that one is procedurally rather than outcome optimistic. Procedural: “I’m pretty sure that if a solution can be found, I’ll figure out a way to find it.” Outcome: “Everything will turn out great in the end.” (In case you’re wondering, I made up those two categories of optimism.)

Skeptics—I consider myself one—get a bad reputation: we’re the ones always poking holes in theories, noting the inclusions in the emerald, and seeing that the putative silver lining is merely brushed aluminum. Often we’re going against the herd, which doesn’t want to know what it’s doing is futile or ridiculous or harmful. My intellectual idols are generally skeptics: Hume, Montaigne, and Twain among others.

But skeptics are not necessarily pessimists, though they often are. What they are not is Romantics: they don’t get swept up in grand ideas of dubious worth or authenticity (e.g., communism). They tend to be hard headed, which makes them seem hard hearted. But it need not be so. In fact, I think skepticism is necessary to be usefully optimistic.

Key word: usefully. Fooling yourself about how you did on something, or what your situation, or your position is not productive. If you’re playing chess and are in a losing position, no amount of positive mental attitude is going to rearrange the pieces (unless you have telekinesis but, sadly, most of us don’t). Fooling yourself is like merely lowering your standards and declaring victory: it’s pyrrhic. “They made a wasteland and called it peace,” said Tacitus.

Are there, as Picasso is supposed to have said, “lies that tell the truth?” Sort of. Sometimes self-deception is useful. If I’m hiking and get lost in the woods, I need to get back to the ranger station and my car. I may be so lost that the odds of finding my way out are 1 in 100,000 at best. That’s when I fool myself: “I’ll get out. No question,” I tell myselef, because, if I don’t try something, my odds of getting back are 0 in 100,000. You do the math.

I think “outcome optimism” is likely to be harmful in most circumstances. You don’t want to set out to climb Mt. Ranier wearing only a Speedo and some Tevas, confident that “you’ll find a way.” That’s call stupidity, not optimism. That’s not facing facts.

“Procedural optimism” is more like this: confidence that, if you can reach the goal, there is the way to do it. Almost every goal directed human activity follows something like this pattern:

  1. set a goal;
  2. try to achieve it using some means;
  3. assess progress;
  4. recalibrate either the goal or the means;
  5. Are you there yet? If no, go to step 2. If yes, go to step 1.

Now here’s where skepticism comes in: step 3. Assessment. Dishonest assessment makes achieving the goal longer or more difficult or both. Suppose you’re dieting. Are you at your target weight? Suppose you are trying to write a novel. Is it what you wanted? Suppose your trying to run a sub-40 10k. Are you there?

Don’t lie. Tell yourself the truth. Do you suck? If yes, figure out how to suck less. Or toss away the goal and pick up a new one. Here are some things I suck at:

Abstract Art

I’ve done a bunch of non-objective painting and drawing, some of which I like, but I can’t tell the good from the bad. Is that one good? Shit, I don’t know. It sort of looks like something Cy Twombly did. Or maybe Kurt Schwitters. Or something. But then again, it sort of looks like the wallpaper in the bathroom at Subway. Is it good? I don’t know. And If I don’t know, I can’t get any closer to the goal. I wouldn’t recognize the bull’s-eye if I bumped into it.

Track Racing

Sure, I’m better than most guys my age. I’ve won races, even a so-called “state championship.” But I’m just not that good. In this case, I know what good looks like—it’s measured on a stopwatch. I just can’t get there. I can’t change my shoe-size, the length of my tibia, or my lung capacity. That’s life.

Novel Writing

Again, am I better than average? Sure. But who wants to be average? This one is like abstract art: I don’t understand what the goal is. I hear writers say things like, “I didn’t know if this was any good, and it turned out to be.” You didn’t know if it was any good? I can’t imagine continuing on a project where I didn’t know, at least vaguely, what I was going for. Compare: a civil engineer designs a bridge over a waterway. “Will it stand up?” she’s asked. “Shit, I don’t know. That’s up to you. I have no idea.” I find it hard to do things where the criterion of success is outside me, either in fact or in principle.


I’m not a very good dealmaker. First off, I think negotiating is a waste of time. Why don’t we just split the difference and go get a beer? Yeah, we could dick around with all this BATNA stuff and reservation points and other yadda yadda yadda. But why? Either I have the leverage or you do. If you do, you’ll fuck me. If I do, I’ll fuck you. Let’s just cut to the chase. I’ve seen good negotiators in action. I know what the goal looks like. Getting there is, for me, too hard.


This sort of follows from the previous, since they are sort of the same thing. I think I know what a good politician is like. But I can’t get there.


This is a problem with the means to the goal: all that practice bores the weasel-oysters out of me. The same song over and over and over. Isn’t there a machine that can do this? I think I can imagine the sort of music I want to make. But the cost is too high. Technology may fix this fairly soon, though.

But enough about what I suck at.

I came across a really good art education website called I got some of the teacher’s samples and they are really good. But that’s not the point. The point is why I am pretty confident that the owner of is a very good teacher, even though I have never taken a class from him (in person): he gives honest feedback. Students send in their work; he critiques it. Well. In particular, he gave some written feedback to a student who drew a portrait. At one point, he asked the student:

  • Do you think it looks like the person?

I burst out laughing. Not because of the student’s work, which was pretty good, but because that is the key insight: “Well, what do you think? Do you think that looks like an ear?”

I think generally when we try something and don’t hit the goal, we know it’s wrong. We know! At some level. And then we start fooling ourselves. “Well, the nose does look like a sunchoke, but… that’s the way he looked.” I have a very concrete example. When you draw from life, you have to measure—you hold up your pencil or paint brush as your “measuring stick,” and mark off a certain length with your thumb. The length represents, say, the width of the subject’s eye. Then you transfer that distance to the drawing board.

Sometimes, if I’m checking a proportion on my drawing, and I measure off the width of an eye in the subject, and then I compare the “measuring stick” to my drawing, I find myself trying to cheat. I sort of hold the measuring stick up to the drawing quickly, or move it, or don’t look at it carefully. Basically, I’m trying to fool myself and covering over an error. Not consciously but unconciously. My brain knows the answer: the proportion is wrong. But something pushes me away from admitting the error. Of course, to learn, you have to delight in being wrong when it happens. Otherwise, there’s no error correction. Enjoy errors and you get better; avoid them and you don’t.

You have to let yourself be honest. Let yourself think it’s no good. If it’s painful to think about, focus on the pain—that tends to make it go away. It’s true. Now, maybe drawing is a special case. I mean, there’s a subject sitting in front of you—say, an old woman. Do the marks on your drawing board look like her image? Yes or no? If no, fix it. If yes, stop and make her a cup of tea, because you’re done for the day. Visual art may be a special case–I’m not sure. But this same pattern seems to occur in other domains, too.

Why the resistance to admitting error? I don’t know. It’s no big deal if it isn’t good anyway. You know the process for fixing it: it’s those 5 steps I’ve listed above. That’s it. Look around. Who is it you’re lying to? In 1,000 years, no one will remember you’ve ever existed. There are 6,000,000,000 people on this planet right now and more are on the way. What you think of as your self is an illusion—“you” are just a bunch of neurons. That’s it. No better, no worse than a slug, ultimately. So, now, who is it you are worried about impressing? Those neurons in there? “You” are just not important enough to lie to.

That sounds rather idiotic, doesn’t it? Another spin—am I deceiving myself?—is “Zen like.” One day some Chinese philosopher known as “Lin Chi” called after a monk. The monk turned around. Lin Chi said: “From birth to death it’s only you—why turn around and revolve your brains?” I take this to mean: Why are you looking elsewhere to see whether you’ve hit the goal? And, come to think of it, why are you looking at yourself, worried that you need to maintain the feeling that you didn’t fail? Just get on with the process. Practice, assess, practice, assess, practice, assess, until you die. What else are you going to do?

Before you can fix it, you have to see it’s broken. Fixing it will be hard enough—don’t ignore the manifest flaw. You’ll never win that way. Plus, fixing is fun. If you ignore the problem, you’ll never be able to have fun fixing it. So be skeptical. It only makes things better. Skepticism and optimism aren’t antipodes.