Let’s suppose that you feel disappointed with someone. Who hasn’t?

If you’re generally reflective, then the first question you’ll ask will likely be: “Why do I feel disappointed in this person?”

For a while, your considerations will have to do with what he or she did or did not do and with what sorts of expectations you had.

Quite reasonably, you might fine-tune your understanding of the kind of character this person has, and you’ll modify your expectations to ensure that they’re more reasonable or sensible. Indeed, you’ll also treat this case dialectically in that you’ll want to see how this case may require an “upgrade” of the basic model you use in order to understand people–or a certain kind of person–more generally.

Let’s call this “the philosophical investigation of disappointment.” Now watch carefully:

In time, you’ll discover that you’re disappointed again. “Perhaps,” you’ll say, “I’ve calibrated my understanding in such a way that I’m disappointed in people less often.” So much to the good, we may reply. But then what’s missing such that you’re still disappointed? Don’t you feel a lilt of sadness? Maybe even a touch of futility? What, indeed, is the basic error you’re making?

You’re invited, at this point in the inquiry, to make two honest observations. The first is that the philosophical investigation of disappointment has not, in fact, ended your disappointment period. In other words, “I’m still suffering,” and so this dispensation has failed. The second is that you need, in an even more philosophically rigorous way, to draw into question your central assumption.

And what is that central assumption?

It is this: I, as a separate self, exist. And: because I, as a separate self, exist or am real, separate selves are equally real.

Therefore, the question to ask is: “Is there an I? Is there, for instance, a disappointed one? And if there is no separate I, how can there be separate others?”

In self-inquiry or self-investigation, the only question pertains to the ontological status of the I. I first ask: “What is this sense of me?” I go to this sense of me, a sense that Ramana Maharshi calls “the I-thought.” Second, I probe this sense of me to see whether it’s actually real.

If the individual I doesn’t actually exist, then what truly does? Experience your true nature.