[Originally published November 6, 2008.]

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Listen, son, we need to have a talk. This isn’t going to be easy for either of us. You are not my son. I’m sorry, I know this will come as a blow to you. But the fact is, no son of mine plays Oregon Trail like you do.

The first sign something was wrong was when I watched you choose the banker as your occupation to start a game. The banker? Really? Were you not aware that the banker has no point modifier?

For some time, I managed to convince myself that you preferred the banker simply because his vast resources allowed you to purchase the maximum number of oxen. I was sure that you were attempting to set a speed record of some sort. Of course, I knew that the game limited you to 40 miles a day regardless of the number of oxen, but I thought you would figure that out for yourself. But you weren’t about to figure anything out. Not about Oregon Trail, and not about life.

At Matt’s General Store, you picked a “logical” assortment of goods to ensure that your party was healthy and secure the entire way to Oregon. You even purchased clothing for the members of your party, for Christ’s sake. It was clear that you valued the banker’s fourfold cash advantage over the farmer’s point multiplier of three. And because of that preference, and many other choices along the trail, you are clearly another man’s son.

Can’t you see that Oregon Trail is a microcosm of life? I’m sure you’ve seen my high score on the computer: 8,040 points. Did you know that for years people considered 8,000 points impossible? You don’t get a score like that by playing it safe and taking the banker. You get a score like that by selecting the farmer, purchasing only oxen and ammo, setting a “grueling” pace, and feeding your party “bare-bones” rations.

How many gold medals would Michael Phelps have won if all he cared about was making it across the pool? How many championships would Jordan have if all he’d wanted to do was dribble the ball down the court? Sure, you can make it across the country in relative comfort. But let me ask you this: How many spare wagon wheels do you think Michael Phelps takes with him? Why not push a naked, starving family to the brink of collapse and hunt your ass off for food all the way to Oregon? Isn’t that what Jordan would do?

Son, when you make the decision at South Pass to head for Fort Bridger instead of the Green River, you’re making a choice to take the easy route. Why? Because you’re afraid the wagon won’t make it across the river? Son, Fort Bridger takes you 86 miles out of your way!

Maybe your fat, well-dressed pioneers are happy for the extra time on the trail, but I wonder how happy they’ll be when they make it to Oregon and all they have to start their new lives is a bunch of fancy clothing and a few spare wagon axles.

I once completed the trail having survived three broken wagon wheels. It took me 10 days to find an Indian to trade with for the third wheel, and I still scored 6,000 points. The other day, I saw you quit the trail immediately after your wagon capsized in the Kansas River. You lost only an ox and a hundred pounds of food. I drank myself to sleep that night.

Speaking of food, it almost seems like you don’t even like to hunt. When you do, you fire randomly at anything that moves. Let me make it simple for you, son: a bullet costs 10 cents, a pound of food costs 20 cents. If you’re not averaging a half pound of food per bullet, you’re wasting points. So I hope it was fun firing 10 times at that squirrel, which, I feel obligated to add, you never actually hit.

I can see that this is all very upsetting. I’m sorry. I know that this is a lot for an 8-year-old to absorb. I wish I were better at comforting you. Your real father, most likely a banker of some kind himself, probably is. I’m sure he also has a lot of money. I don’t—I’m just the guy responsible for the 8,040.

Son, you may not share my genetic material, but that doesn’t mean I’m going to let you grow up this way. So start a new game, select the farmer, try to think like Michael Phelps, and let’s see how many buffalo we can kill on the way to Oregon.