I was recently accused of being my most conversationally engaged when asking big, disruptive questions. The more I thought about it, the more it sounded right. I plead guilty to asking big questions. Whether or not they are disruptive, though, is in the eye of the disrupted.

I frequently wonder why more people aren’t asking the “big questions.” To me, they seem like the obvious questions to ask. Yet we go through life ignoring the elephants in the room, the things that seem to really matter, the things that seem to be at the very root of everything else we spend our time discussing. To float on the surface, that’s what is socially acceptable.

Greek philosophy

I was immediately drawn to a character named Scott Aaronson after reading an interview with him in Scientific American. Aaronson does not float on the surface; he dives head first into the Really Big Questions, and he’s self-aware enough to know that this is frowned upon by polite society.

The thing I yearned for was a community that would be as welcoming of intellectual obsessives as a yeshiva was—but without any unquestioned dogmas or taboos, where absolutely anything could be revised based on evidence, and which was open to new ideas from anyone of any ethnicity. In my quest for such a community, I could’ve done a lot worse than where I ended up, namely academic computer science departments! The difference, of course, is that a university department covers only the intellectual aspects of life, whereas my idealized shtetl would be a place that welcomed intellectual oddballs and also helped them deal with birth, death, marriage, and everything else in their lives.


Asking big questions is a career-limiting trait unless you’re a pundit or writer, or researcher. Most leaders of institutions get to their positions in part because they’re able to elegantly sidestep the Really Big Questions to take advantage of opportunities as they emerge.

And that’s important. I would never, for example, make a good advocate for something like the Sustainable Development Goals because there are so many unanswered questions about its design. But it’s a good thing that there are people out there that can put aside those questions in an act of faith in the unexpected (and perhaps improbable).

Then a miracle happens1

The question that faces me now as I think about my own professional development is whether I still wanna be the guy who asks big questions.

Yes, I think so. But I’d like to do so with a little more emotional intelligence so that I don’t overwhelm and tire others. I’d like to spend my big question capital wisely. In the meantime, I always have the kindred commune of the written word — the philosophers, novelists, artists and scientists who treat the Big Questions not only as acceptable, but as the ones most worth discussing.