Are you a “glass half full”, or a “glass half empty” kind of person? I’m sure you’ve been asked this before. The point of the question ostensibly is about whether you’re an optimist or a pessimist, and the lesson is that any given situation can be seen positively or negatively depending on how you choose to see it. How nice.

But, let’s think about this a bit more critically. Let’s say you arrive at your table at a nice restaurant, you sit down, and you notice that there is a liquid in your wineglass. Whether the glass is half empty or half full is the wrong question to contemplate. What you’ll be asking is “Why is there stuff in my glass that I didn’t ask for?” And if you call over the waiter and they offer to top off the glass, you might respond, with rightful indignation: “No, just give me a clean empty glass.”

As it turns out, there’s a fairly famous Zen parable that touches on a similar issue (adapted from the version found here):

One day an important man, a man used to command and obedience came to visit a Zen master. “I have come today to ask you to teach me about Zen. Open my mind to enlightenment.” The tone of the important man’s voice was of one used to getting his own way.

The Zen master smiled and said that they should discuss the matter over a cup of tea. When the tea was served the master poured his visitor a cup. He poured and he poured and the tea rose to the rim and began to spill over the table and finally onto the robes of the wealthy man. Finally the visitor shouted, “Enough. You are spilling the tea all over. Can’t you see the cup is full?”

The master stopped pouring and smiled at his guest. “You are like this tea cup, so full that nothing more can be added. Come back to me when the cup is empty. Come back to me with an empty mind.”

In the context of Zen, the teacup is a metaphor for the mind, and how, through meditation, we can clear our minds of thoughts, ideas, beliefs, and expectations that often hinder us more than they help us. Once we have cleared our minds, there is finally room for truth and enlightenment.

Emptiness/fullness can also be used to describe life itself. When someone says “my life feels empty”, that’s considered a bad thing. And conversely when someone says “my life is full”, that’s considered good. But, many of us, at one point or another, probably had/have “full” lives that were/are nonetheless stressful and unfulfilling. The fullness might come from obligations and responsibilities that we don’t find nourishing, but nonetheless occupy our minds and bodies from morning to night so fully that it leaves us with no time to connect with ourselves and loved ones. The “fullness” prevents us from working towards or exploring a better life. This kind of “fullness” could hardly be said to be good.

After I quit my job back in mid-May, I’ve struggled with feelings of emptiness. I would wake up in the morning, and there would be no job or purpose awaiting me. No responsibilities, no obligations. Nobody waiting for me or relying on me. Just, emptiness. I found myself oscillating between trying to plunge myself into a project, or distracting myself by mindlessly staring into my computer screen. I doubted my self-worth. It challenged my work ethic. I even contemplated employment.

Instead of doing anything drastic, like getting a job (which I know I would hate as soon as I got), I decided to sit with this uncomfortable feeling of emptiness, and let it run its course. I’ve always had a difficult time dealing with uncomfortable feelings and situations, but one of my intentions over the past months has been to learn to live, confront, and play with uncomfortable things. So, how convenient it was that I would often wake up with this big hairy beast called Emptiness sitting on my chest?

And over the course of weeks and months, an interesting thing happened. I came to see this emptiness for the gift that it is.

For “emptiness” is really just another word for “freedom” and “opportunity”. An empty glass can be filled with anything. I am about as free as any man has ever been in the history of mankind. And that’s no understatement. I am bound by fewer social and cultural norms and obligations than just about anyone in history. I don’t have a boss. I don’t have a wife or kids. I have few financial obligations. I have mastery over some of the most complex and powerful technologies the world has ever seen. I can make practically anything. I have the ability to go anywhere in the world, and do just about anything I damn well please. I can enter any relationship, any occupation, any adventure that comes my way that I choose. And I can do it at the drop of a hat, because I’m an empty glass.

Granted, not everybody is as lucky as I am, but regardless of your circumstances, if you have a glass that is half empty/full, I suspect one of the following two cases is often true: 1) You enjoy what’s in the glass, and you want it to be topped off, or 2) You’re not enjoying what’s in the glass (any more) and you want the glass to be empty, perhaps so it can be filled with something else.

Of course, actual life is never that simple. We’ll never have a life full of just the good stuff, and we’ll never empty our lives completely. But, instead of thinking about whether the glass is half empty or full, we should think critically about what is in there, and what is not. We should be mindful about what we put into our lives, because for every thing that we put in, we reduce space for something else. And we shouldn’t be afraid of taking things out of our lives, to free up space too.

So, the next time someone asks if we’re a “glass half full” or “glass half empty” kind of person, I propose we answer thusly: “I don’t do half-full/empty glasses. I want my glass to be full with something awesome, or otherwise I like it empty and clean so I can fill it with what I want.”