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I find what you said about the competitiveness aspect of other people the most compelling, but aside from that, I've had increasing success with imagining someone else as myself but in another situation. It takes breaking down what a "situation" is and entails, and how entrenched it is into our identity. Think of times in your life when you were vastly different. Maybe you were stressed about your first SO in high school--perhaps someone you can't even imagine liking now. Can you successfully pretend, through the haze of time, being as obsessed over that person now as you were then? Is anything blocking that sensation, and if so, what?
Back when I was a sophomore in undergrad, I had a "bro"-like roommate. I was your typical college hipster, and he had a very abrasive approach to camaraderie. (He was not unlike the competitive type you describe.) I had the hardest damn time trying to figure out what was going on in his head, and one day he called me out for my introverted personality, misreading my reclusiveness as conceit. When he did that, I remember crying in my room, because there was this fundamental misunderstanding between us. He didn't understand my approach or emotionality, and I didn't get his. But over time I had a sensationally gradual realization that I could actually interact with this guy as "one of his own." It started as mimicry, and I did "toughen up" a little through this event, but it also gave me an idea.
Before this time, I didn't codify what it actually meant to feel like someone else. You can't walk a mile in someone else's shoes if they don't fit your feet, right? When I was able to (in part) embody his approach to the world (while retaining my own on a backburner), it was easier to realize that this kind of sensational transition is necessary for everyone. It isn't that we are fundamentally different, always, full-stop. It's just that we can't just start imagining someone else's experiences a priori without forgetting who we are for a little while.
Don't mistake this for spiritual chakra mumbo-jumbo or what-have-you, all I mean is that there is a mundane, demonstrable relationship between the body and all of the factors influencing it. You might be able to consider some of these factors a priori, but take care to recognize that your evaluation of their count and intensity may not at all be accurate, and that estimate could very well be blurred by an opposing sensation (or lack thereof) that your self currently retains.
But when you do become someone else, or rather, when your identity is changing shape to accommodate some grief or other perhaps more complicated sensation, take note of the nature of that change. Even if you can't fully comprehend someone else's motivations as your own, taking note of how you change shape and generalizing that this can happen to wildly varying degrees within our species (thinking about a civilian's mental adjustment to being a soldier, accruing PTSD, etc), can be a very helpful placeholder for imagining the experiences of someone else's life, and recognizing their actions as reasonable, given the possible constraints.