Unanswerable Questions

Ever since I switched jobs, I can’t count the number of times I have been asked, “So how is your new job? Are you happy?”

My answer is often: “I don’t know.” (Or at best, a vague and convenient reply like “Not bad” or “Interesting”).

I can see them saying to themselves: “But it’s your job! How can you not know?”

Because to me, this question is “unanswerable.” Other examples of unanswerable questions that I get asked all the time include: “So what did you learn at Harvard?” “What was it like working in VC?” “What is it like to work in China?”

There are two main reasons that I consider these question unanswerable: One, answering them requires oversimplification. Two, they invite cliches. For these reasons, I feel like I cannot come up with a reply while staying true to myself—just like I could not figure out how to answer the question “How are you?” when I first arrived in the US.

Humans are notoriously bad at understanding and articulating their own emotions, especially when they are going through complex transitions. One day we think we’re having the time of our lives; the next day we question the meaning of life. These are all normal aspects of the emotional roller-coaster that comes with adjusting to a new environment. Any attempt to grossly overgeneralize these experiences would sound comical. Should I do a mathematical exercise (detract the number of bad days from the number of bad and see if the result is greater than zero)? Or should I subject myself to a psychological survey (on a scale of 1 to 10, how happy am I on the good and bad days, respectively)?

The truth is, words can hardly do justice to these complicated psychological states. This is the reason that fiction exists—it allows us to make sense what we’re going through ourselves by reading about others’ experiences. So a small question like “Are you happy” can literally be answered with a book. And when I’m asked an answerable question, I’m being forced to write that book within seconds and somehow summarize it into a synopsis that makes a witty reply in a conversation.

Social convention requires a positive and perfunctory answer to this type of questions, like “Everything is great! I love it!” But I can hardly bring myself to conform to such convention as a person of candor. I simply don’t like lying. If someone had given me this everything-is-perfect answer, I would actually picture the person crying herself to sleep on some nights (even though she may be truly happy most of the time). Just like the couple who is always posting lovey-dovey photos on Instagram is probably having really intense arguments behind the scene.

But answering these questions is not just difficult; it can also be dangerous. If I had come up with a two-sentence, crowd-pleasing narrative and kept saying it over and over, I might actually start to believe the story that I tell, subscribe to the over-simplified version of my own experiences, and stop challenging myself to think differently and explore alternative narratives. Sometimes I just haven’t had enough time to make sense of what I’m experiencing, and being forced to articulate an idea while its immature can end up warping it.

How do we ask good, answerable questions, then? This is a topic that I spend a lot of time pondering. I like to think of myself as someone who asked questions for a living (in my short time as a journalist, VC, and occasional podcast host). In my view, good questions don’t have a “correct” (meaning socially acceptable) answer. They can’t be answered with cliches or generalizations. A good question has factual or quantifiable answers. Instead of “How’s your job?” Try asking: “Do you spend most of your time in meetings or sitting alone in front of computer?” “How many people are there on your team, and who have you gotten to know?” “How often do you see your boss?” These are questions that everyone has an answer to, and it doesn’t take a philosopher to come up with a reply.

The best part is: When people answer this type of question, they almost never stop at the objective reply: They often voluntarily append their subjective emotions and opinions, such as “I spend most of my time in meetings with colleagues, and I really like it because I prefer jobs that have human interactions, and the colleagues are all people I really admire.”

In fact, come to think of it, a large part of the reason that this blog exists is to address these unanswerable questions in longer prose, which comes closer to describing my actual experiences. One day, I might write a blog post to answer the question, “How’s your job?”

Or a book.