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Facts Before Feelings

I've noticed that people have a tendency to categorize themselves as either pessimists or, on the other hand, optimists. I've also noticed that the number of folks that put themselves in the optimist camp far outweighs the number of folks that describe themselves as pessimists. There's also a philosophical battle brewing between these two camps; should we view our future endeavors with hope and confidence that they'll turn out just as we envisioned them? Or is everything we attempt to do just bound to end up down the shitter? Who is right in this great debate? Are those many optimists just a crowd of overconfident fools who hasn't thought through their plans very well, or is that small minority of pessimists just a little sad bunch of losers who should have been held tighter as children? Let's find out.

Let's take a moment to review the definitions of these two competing concepts.
Here's the definition of optimism from google:

hopefulness and confidence about the future or the successful outcome of something.

Here's the definition of pessimism from google:

a tendency to see the worst aspect of things or believe that the worst will happen; a lack of hope or confidence in the future.

We these definitions in mind, it's time to think.

Optimists and pessimists often view the same situations with different expectations for what the outcome of that situation will be. Optimists will tend to look at a scenario and think that good things will happen. Pessimists will tend to look at a scenario and think that bad things will happen.

Sitrep

Let's look at an example of a situation that pessimists and optimists are likely to view differently. I've been reading a book called About Face by David Hackworth and it's pages having been stewing around in my mind and are probably providing some of the ingredients needed for the creation of my little thought experiment. Let's say you're a soldier in charge of leading a squad tasked with taking a hill held by the enemy. Stereotypical I know, but being a stereotypical scenario doesn't make it any less relevant for the purpose of argument, and we're all gung-ho about arguing, right? Now, given that's all we know, how is an optimist likely to view this scenario? I would say that a pure optimist is likely to think that we should feel hopeful about our prospects of taking the hill from enemy control with minimal casualties. Our squad is well-trained, we have good morale among everyone, and our enemy is under-equipped, right? How is a pessimist likely to view the situation? They will think that the mission is crazy and will likely get themselves and everyone else injured or killed. The enemy can see straight down at us and will know exactly when we are making moves! All Charlie has to do is wait for us to walk into his sights and we're toast!

So which view is better to have? If we're the leader of this squad of soldiers and we're optimistic about our chances of taking the hill with a minimum of sweat and blood, then that might be a good thing because then we'll inspire the troops under our command to proceed with that same confidence. This will help get rid of hesitation among the troops which will, in turn, make them more likely to act aggressively, which I would argue is necessary when you're about to storm a hill occupied by people who want to kill you. But our optimism about the situation may also be misplaced. The jumpy little prick of pessimism may whisper in your left ear, "what if the enemy has a well defended and hidden machine gun along the route you plan to attack on? You could get your whole squad killed in seconds!" So the problem with optimism is that when we become too optimistic, we can fall into the trap of making assumptions about reality that aren't true. We can risk failing to consider if the enemy has a well placed machine gun along our attack route. The optimist will tend to think that his fellow soldiers are well trained, that the enemy is unmotivated and cowardly, and that he possesses superior equipment that will give him the edge in the fight.

If we're a pessimistic leader who thinks the mission is dumb, however, that is also not the right attitude because we'll just be someone who is trying to find every possible excuse not to do anything that puts our men's lives at risk. Pessimists have a tendency to expect the worst outcome as highly likely when the fact really is that the worst outcome is not that likely. In this case, the pessimist will think that your squad won't get as far as ten feet up the hill before they get bombarded with accurate machine gun fire, or, they'll think that we might take the hill but as soon as we do we'll get wiped out from incoming enemy artillery fire. But, pessimists may also foresee problems and issues that optimists tend to ignore or simply be unaware of. What if a pessimist in your squad expresses the fear that the battle maps we're using aren't drawn accurately? Is it wise to dismiss him, or better to give his point some consideration?

Time is still ticking so we need to be able to tell command to go fuck themselves or that we accept the mission. What do we do? The choice is between optimism or pessimism. Hmmm....

Observe, Judge

I argue we should adopt neither view at the moment. We should not look at our situation with the hope that we will take the hill while earning everyone silver stars along the way and we also should not look at our situation with the hopelessness that we will all die and Charlie will spend the night drinking booze and dancing on our dead bodies in celebration. As the leader of our cute little squad, what we really need to do is ASSESS. We need to let the facts on the ground, about our situation, dictate whether or not we should be optimistic or pessimistic about our chances of taking control of the hill. I mean what do we really know about our mission besides we're a group of guys ordered to take a hill? In order to assess our situation, we need answers to questions. Answers to questions like:

Obviously, we might not be able to get good answers to all these questions. Perhaps we're in unmapped territory and we can't know all possible routes up the hill unless we do some dangerous reconnaissance on the area. We also can't 100% guarantee that the answers we come up with will turn out to be 100% accurate. Perhaps that enemy fighter we managed to capture in our last scuffle is bluffing us to scare us into submission when he tells us that his buddies have booby-traps and mines planted everywhere on the hill. It being the case that we can't have perfect or accurate information at all times, it's still incumbent upon us to consider every relevant question we can, even if it's impossible for us to get satisfactory answers.

If I didn't have the means to get any good answers to these questions, and I was tasked with leading a squad of green men up a rocky, barren hill with little cover and opportunity for concealment, with the only available route of attack coming straight up the throat of the enemy, I'd turn the mission down. I'd tell the brass that given the current facts, I'd be a pessimistic about our chances of successfully taking the hill and that it wouldn't be worth the risk. Higher command should find a more brazen man than myself to lead this squad if they want to carry on with the attack despite my misgivings.

On the other hand, if there were lots of attack avenues, plenty of cover, we were guaranteed accurate covering artillery fire during our attack, and we planned our attack so that we hit the enemy at a time they weren't used to, I'd be much more optimistic about our chances of owning the hill at the end of the battle. I'd take the mission.

Life Is Messy

Of course, rarely are real situational conditions so ideally abysmal (only rocky terrain, no cover, low troop morale) or ideally, well, ideal (lots of cover, many different opportunities for flanking, good supporting units). Real situations are often a mix of favorable and not so favorable conditions. That's when you're going to have to rely on your experience, intelligence, and wisdom so you can determine which conditions are more important to factor in and override others. Maybe the approach of attack is out in the open and there's no cover for your guys when they attack, but maybe your Arty is so good that once they start firing, Charlie is going to have his head stuck in the sand for long enough for you to make your move? Perhaps your squad is a group of studs ready for a fight at any time but you expect to encounter lots of enemy fighters and you're low on ammo and can't rely on being resupplied anytime soon. I can't say I'd make the right calls in these sorts of situations but my point remains that this knowledge about the situation is what should dictate our feelings of pessimism or optimism.

So remember, before you conclude that something is a bad, hopeless effort or it's the next big opportunity that you're going to smash out of the park, take some time make some honest observations about your predicament. Take counsel with both the pessimists and the optimists in your team and also the pessimist and optimist in your head and determine the validity of each of their opposing points as best you can with the information you have. If you do this, you may find yourself more hopeful of success and, at the same time, more wary of falling prey to visions of glory that have no basis in reality.