How I Like to Solve Dilemmas

Sometimes you have two seemingly equal options, each with its pros and cons, and you can’t choose between.

Applying for College

When I was in my last year of high school, a person from the admissions office of a local college came in to give a conference on applying for college. He told us this story about hesitating when choosing a program:

A student came to me and asked: “I don’t know what to choose between programs X and Y! Which one is better?”

I replied: “Well, just flip head or tails.”

“You’re kidding me, right? My future depends on this, and you’re telling me to flip a coin?”

“It works. Here’s a coin, flip. Heads is X, tails is Y.”

“Okay. (flips) Aw crap, it’s Y.”

“Well there you have your answer. Your gut just told you you preferred program X. Apply for X instead.”

Sometimes you know in your gut you want to do something, but you just don’t want to allow yourself to. Maybe there’s some idea or reason that’s keeping you from choosing the option you want. Maybe there’s an insecurity holding you back. This can sometimes help uncover it.

An alternative set of rules is you flip the coin, and the special rule is that you’re allowed to flip the coin over and modify the result if you want to. If you’re happy with the initial result then it stays that way, but if not you just flip it around.

This can be a good way to reveal a suppressed gut feeling, but why should you trust your gut? Why would that be such a good indicator? Or maybe your gut is indifferent too. Which brings me to my next point.

The Least Concern

You don’t care. When you have a dilemma, it means, by definition, that option A is practically equal to option B. This situation has pretty useful properties.

Namely, you can go and nitpick on the smallest little benefit or drawback of either side to make your decision. Go ahead, pick a silly or fickle reason to choose option A. There you have it. The options aren’t equal anymore. Option A is now marginally better than the other one.

I use this when ordering food, for example. I’ll typically hesitate between two plates. Both seem equally good. Since I’ll be satisfied with either of the two, I decide to pick the cheapest one. And further, if they’re the same price, (or price was already factored in) I just choose the first in alphabetical order. Unhappy? Switch! It’s a dilemma, you can do anything you want.

Err on a side

Sometimes, the options won’t be truly equal. In that they’re seemingly equal, but one way is better for you than the other.

For example, you might hesitate in striking up a conversation with someone you haven’t met. You’ll be faced with staying in your place while keeping your rejection chances at zero (perceived benefit), or running the risk of meeting someone valuable, but exposing yourself to a bad experience. Seemingly equal. (Being rational and removed from the situation, we can see why this reasoning is flawed, but in practice this would be a perceived dilemma when faced with the situation.)

However, you might have as a personal objective that you’d like to get more out of your comfort zone. Then go ahead and err on the side of getting out of comfort zone. There are some “sides” like this you’re better to err on. There are sometimes some motives or objectives in life which you have identified as a way you want to get towards.

In my personal list, I have getting out of my comfort zone, but also moving inertia, living experiences, and so on. You might want to err on the side of safety. Or err on the side of benefiting someone else. It all comes down to your personal objectives. Which option has the marginal benefit of advancing something you know in the bigger picture will be better for you.

What is your marginal benefit?