Garrett Kincaid — September 6, 2020

How often is the grass actually greener on the other side? Is that ever the case? How can you measure the “greenness” of someone else’s lawn and accurately compare it to the grass beneath your feet?

Here, we’ll look at the greener-grass metaphor from two angles: with an idea from Plato’s Protagoras — the art of measurement — and a thought experiment from Alan Watts — “The Dream of Life.”

Let’s start by looking at what causes the greener-grass fallacy. It’s the unknown that gets our reasoning twisted. We spin stories about what we don’t know, making assumptions that we eventually believe — without evidence.

The grass might seem greener across the street, but you have no idea what goes into maintaining that lush pigment.

You may tell yourself that your neighbor is the happiest person you know. But maybe it’s painful. Maybe you would hate to endure what your neighbor does each day to present such a beautiful lawn. There’s no way to know, unless you moved across the street.

The way we respond to uncertainty impacts every decision. And there is no decision that we make with complete certainty. Let’s fantasize though. Image that, before making a decision, you could collapse each option into a single measurement, made up of your intention, the action itself, and its consequences? Imagine three job offers on the table reducing themselves to mere numbers that measure the morality and positive utility of each? Choosing would be as easy as finding the largest number in a group.

But of course, it is not and will never be that easy.

This sort of certainty would be ideal, in that you could always make the “right” decision. But complete certainty would be boring. I prefer what we have. I prefer not knowing what it takes to care for the lawn across the street. What about surprises, spontaneity, and faith?

Identifying the greenest grass is all about two things: 1) considering alternatives and 2) accurately weighing them against where you are already. First up to bat is Alan Watts, on considering alternatives. Plato’s on deck, wielding the art of measurement. And I’m in the hole, hoping to piece it all together.

Alan Watts presents the following thought experiment, which is a powerful tool to wean you off the greener grass across the street.

This is the setting for his argument. Watts claims that in each of these life-long dreams, you would first satisfy all of your desires, and you’d enjoy that for a while. But eventually you’d want something different; you’d long to take chances, gamble, or be surprised. And to achieve that, you introduce uncertainty into these dreams.

Watts says that this pattern would continue. You would introduce more and more uncertainty into the dream — relinquish more control of its events. Eventually, Watts says, you would let go of the reigns completely:

What a profound statement! Even though you have the power to dream anything into existence and to know everything, Watts says that we all would choose to live a life with as little control and as much uncertainty as the one we live now.

Even if you disagree with his conclusion, the point here is think critically about alternatives. Instead of just wishing to have more control in life, or wishing to fulfill all your desires, ask “How much do I really long for complete certainty or complete control?”

Is the God-like-dreamer existence greener than what you have now, if you consider the two experiences ad infinitum? Regardless of what your preferences are, they must be informed by a complete understanding of the available alternatives.

In a section of his Protagoras, Plato analyzes the phenomenon of refusing the best course of action. Why do we opt for short-term gains when we know what would be best long term? We don’t act this way because we’re overcome by pleasure.

It’s not that simple. Plato argues that there’s a special type of oversight that skews our priorities toward the immediately pleasurable. And he calls process of solving this problem the art of measurement.

If the goal is to maximize pleasure and minimize pain, then not only immediate pleasures or immediate pains should be considered. All foreseeable pains and pleasures should be used to measure the quality of a certain option.

A humble building in front of you looks to be the same height a skyscraper on the horizon because of the distortion of space. Rather than space, it’s time that distorts pleasures. Immediate pleasures and pains are inflated and disproportionately affect decision-making.

It would be best to place all the buildings in sight the same distance away, in order to measure them on the same scale. Plato explains how something immediately pleasurable can cause great pains in the future:

Conversely, what is sure to be immediately painful may relieve many future pains or produce great future pleasures, such as a painful surgery that remedies a serious ailment.

The art of measurement is about determining what is truly desirable, given a set of options. If you must use pain and pleasure as metrics, make sure that you weigh immediate and future consequences equally.

When trying to identify the greenest grass, there’re only a couple possible scenarios.

Either there is a truly preferable alternative — your neighbor’s grass is greener — or there is no better alternative, and the greenest grass is that beneath your feet. Understand the available alternatives by dreaming them up and considering what it would be like to experience them. Then accurately weigh each with the art of measurement. It’s likely that, if you weigh the alternatives evenly and accurately, you’ll find that your own lawn is the best spot on the block.

So, is the grass always greener on the other side of the street? Is the life you would dream better than what you have now? Are the pleasures you seek outweighed by the pain they might cause? Let me know!