Most choices involve some form of loss. We lose something so we can gain something else. Oftentimes the thing we lose and the thing we gain are different kinds of thing, so their values are not easy to compare, but we try our best. We aim to make the decision where we’ll come out better in the end, where the gain will outweigh the loss. But sometimes this leads us into a trap.

We might consider quitting a job, for example, losing income, in favor of gaining time. Which is more valuable? Income, if we save it, could translate into time later. But time now, if we invest it in learning a new skill, could translate into greater income later. There are feelings to consider, other intersecting circumstances in life, and other things to say about what time and money are really worth to us. If we went ahead and quit the job, that’s probably because we looked at this complex situation and convinced ourselves that time was worth more to us now, that we’d do better for having the time immediately even if it meant losing the income.

It might even seem that whenever someone makes a choice, the choice is evidence of that person’s value scheme, it’s proof that they valued the thing they gained more than they valued the thing they lost – otherwise they wouldn’t have chosen that way.

But a choice might not convey as much information as it seems to convey, or any information at all. That’s because a choice is often finalized at a specific moment in time. And at any particular moment in time, a person who makes a choice might not be remembering all of their values. They might not be keeping all the important considerations about one option versus the other option in their conscious awareness. A person might deliberate for weeks to reach the conclusion that it’s better for them to keep the job; then one night they might get drunk and email a resignation letter. 

Their choice is not proof that they valued time more than income, it’s just proof that they were overcome by an impulse after their third whiskey on a certain Friday night. In this case, they believed they’d come out worse if they quit, but they still quit, they still opted for “worse” because their decision was impulsive and not intentional. It’s not that they hadn’t thought it through. It’s that their decision didn’t reflect all those things they had considered. It wasn’t an information-bearing decision.

So we might say that whenever someone chooses a certain loss, there are two things this could mean. It could mean they valued a corresponding gain more than the loss. Or it could mean they were acting on impulse in a way that failed to represent their values. But there’s an exception even here – a third possibility.

Sometimes a person might choose a loss that they believe to be greater than any countervailing gain, not because of an impulse that defies their values, but because choosing the loss is their deeply held intention. Certainly, this intention sounds irrational. If someone really thinks their loss will outweigh their gain, which is to say they’ll come out worse in the end – and if they’re making the choice with full awareness and all faculties intact – why would they ever prefer the greater loss?

When a person always tries to make the “right” choice, always tries to maximize personal utility, always chooses the option where the gain outweighs the loss, they can find themselves in an endless cycle. They might return to the same question, month after month, and a cost-benefit analysis always leads them to the same answer. For a time, they might feel they are exercising the “free will” to do what’s best for them. But as they consider the question again and again, with rational analysis always leading them to the same conclusion, they might feel trapped. They might feel they have no “freedom” in this circumstance because reason always forces them to prefer one option over another. Their rational desire to avoid an uncompensated loss keeps them in the same situation forever. They might look into the future and find that the circumstances influencing their choice are unlikely to change, so their choice itself is unlikely to change, ever.

In such a trap, there’s one way a person can escape. By choosing the greater loss. By choosing the option where they’re not sure they’re going to come out better, and in fact they might come out worse, but at least their situation is going to change. At least they’ll be freed from the trap.

In the decade between 2010 and 2020, a certain social networking site called Facebook was the place where I could communicate with family members close and distant, elementary school classmates, high school classmates, college classmates, random people I had met at parties, neighbors, colleagues, everyone in my life. I could share my art and get feedback there. I could participate in discussions with world experts on obscure music theory topics that interested me. I could make public service announcements and have them be heard. 

Before I left Facebook, I had wanted to connect with more musicians, especially composers, and a certain benevolent individual with lots of contacts in the classical music world had sent friend “suggestions” linking me with around a hundred prominent artists. Most of those artists accepted and became my new Facebook friends. As far as my career development as a musician, this was like a blessing from heaven. 

There were many reasons why I wanted to leave, but at any particular moment when I tried to leave, I found I couldn’t. What about all those new “friends?” I couldn’t convince myself that I’d gain more by leaving than I’d lose. Year after year, I had been trying to leave, but it had never happened, and now it was even less likely to happen.

Finally, in 2019, a little while after I gained all these new friends, I declared that I would leave, and I gave myself a year to fulfill my promise. I wanted to be free from surveillance capitalism. I wanted to stop having all my social connections brokered by a large corporation that did not have my interests or health as its top priority. I wanted to stop supporting the data monopoly of a company that seemed to be abusing and misusing the data it was furiously collecting with no sign of shame. But I never fully convinced myself I’d be better off taking my freedom from Facebook, if it meant losing all of that social connectivity, all of those connections to everyone in all phases of my life, all of those promising new musical contacts that could have helped me take the next steps in my career. I couldn’t bring myself to leave in any particular instant. I couldn’t quit as self-contained decision. I could only bring about my leaving across the span of a full year, as a decision that manifested gradually over time, moving towards a self-imposed deadline.

In a way, what got me to leave Facebook was seeing that my personal loss would outweigh my gain. Seeing that because of this, I’d be kept in a trap forever, unless I chose the nuclear option. Unless I chose to accept a big, fat loss. In exchange for an uncertain gain. A gain that might not compensate for the loss. A gain whose main selling point was “escape.”

Since I chose to escape, you could say that I must have valued escape more than I valued all those connections and all of the potential they represented. You could say I must have thought I’d come out better in the end by getting out. But really I was never sure of that. I’m still not entirely sure of it. There’s no way to know what would have happened if I had stayed, or where those connections might have led. 

I do really believe that in this case, I chose to take a loss that was greater than any tangible gain I could foresee, because I realized that avoiding loss forever would keep me in the same situation forever. And in turn, this experience taught me that choosing loss, even a big, uncompensated loss, is an option that a free person can avail. ■

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