Fifteen seconds after my MIT interviewer asked about a mistake I had made and what I learned from it, I gave up on finding a non-awkward answer and told him about the time I had a crush when I was a sophomore.
We had one class together, but I developed a crush when she didn’t have a carpool and took the same bus home, and we talked.
About what I don’t remember.
But after that, we started Snapchatting a lot.
The relationship that followed consisted almost entirely of me telling her she should ride the bus more often and her telling me I should hang out at the Teen section of the library after school (which I often did after swim practice until I realized she already left, and which I later told my MIT interviewer was a mistake).
I think I told him that the mistake was going out so far out of my way to avoid being forthright.
Whenever I told my crush she should ride the bus more, what I obviously meant was, “I like you, and I’d like to spend more time with you (but in a serendipitous, low-stakes way).”
Essentially, “I would like it if you rode the bus more”.
Obviously it was less convenient for her.
Later on, at MIT, whenever I would hang out with friends, someone would inevitably say, “I really should be working right now.” which is a real bummer to keep hearing while you’re playing Pictionary.
It bothered me to such an extent that I vowed to never say that while I was doing something for fun.
It’s not as clear to me what people even mean when they say “I should be working.”
The most obvious interpretation is that putting it off would cause them some discomfort in the future.
They might have to stay up late or stress about whether they would get it done on time.
Under this interpretation, “should” really meant “it would be better for me”.
It might be that they need the time to produce their best quality of work, ensure an A, get a good GPA, but even this could be easily reduced to “it would be better for me” at a farther time horizon.
My favorite (and scariest) interpretation is that labor is seen as inherently more virtuous than leisure.
That when they said they should be working, they meant it as a literal obligation.
Once, at the beginning of a semester, a friend even said, “I feel like I should be working, but I don’t have any work to do, so I have no way to alleviate the feeling.”
In general, the unexciting explanation for all this is that “should” has grown another meaning.
In addition to the traditional meaning indicating a moral obligation, “should” can also be applied to anything beneficial
(e.g. you should exercise because you’ll be healthier and ultimately feel better).
A lot of Google search suggestions for “should I” support this explanation (Should I pop a blister, upgrade to Windows 11, etc).
The other (yes there are only two) explanation is that people use “should” to confer moral obligation status to big decisions to motivate themselves through authority. Should I buy a house, open a restaurant, etc.
I don’t want to make it seem like this is the position I agree with.
In fact, I think it’s probably more wrong than right.
The reason most people turn to Google and not to a crystal ball when considering buying a house is because they don’t just want a yes or no.
They want explanations of the pros and cons and a description of the sort of person who would benefit from homeownership and possibly steps for buying a house.
That said, I think that’s about the limit of the Internet’s usefulness in answering that sort of question, and I can equally imagine someone poring over articles and essays looking for an answer well beyond diminishing marginal returns.
(It’s easier to imagine doing things you’ve already done.)
Similarly to my friend who felt like she should be doing schoolwork even when she had none, it’s easy for the wires for moral obligation and simple personal benefit to cross.