Asking Good Questions

I was staring at my computer a little earlier today, feeling a bit burnt out. Not the full burnout — the one that makes you question life, the universe, and everything — just the little daily one where I knew I couldn’t stare at my screen any longer. So I did what I always do when that happens: I took a break. It’s nice outside today, so I went for a walk to the Sound and back, which is about a 25-minute loop from my office, to go look at the boats in drydock.

On the way, I passed the place where everyone in my office buys lottery tickets. I’ve always found the group buying of lottery tickets to be a bit depressing: the mere fact that we, collectively, as an office need to fuel the fantasy that we’ll win and be able to quit in just a couple days is weird to me. It’s not that I haven’t fantasized about it, too; it’s just that the fantasy doesn’t do anything good for me. It’s usually bad — it makes me think that there’s something wrong with my life. These feelings aren’t helped by the fact that my CEO (and owner of our company) has participated in these pools from time to time, which gives me no real hope for long-term value.

I thought about buying a ticket. And, all of a sudden, my overall level of happiness plummeted. It was weird. One moment, I’d been really happy, and the next, I was normal. I thought about it. Why had I gotten depressed just thinking about buying a lottery ticket?

I worked through it a bit, and by the time I’d reached the boats 10 minutes later, I had a little realization: I’ve been really successful at changing my point of view on how I should work over the past few weeks, far more successful than I thought I’d be when I started out on this little checklist adventure. I don’t think that I’m close to being done; in fact, I don’t think that this is something I can ever finish, because it really does require constant thought and vigilance. But, maybe, I’d gotten good enough at it to realize something from Checklist #3: Success means I get better problems.

In this case, the ‘better’ problem is that I need to ask myself better questions. I can’t, in good conscience, think that a fantasy that I bought for a dollar is going to pan out. This is annoying, because I like those fantasies — who doesn’t? But it forces a different question, which is what could I do that actually provides the fantasized lottery life for my family? And this is a better question to ask.

I’m still on an idea sabbatical, though, and I’m not ready to come back from it yet. I think what I need to do, first, is learn how to actually ask a question with an answer, which is what I want to define as a ‘good’ question.

The question I asked before doesn’t actually have an answer — asking what I could do that provides a lottery-style lifestyle for my family is, at it’s core, idiotic. So it’s better, but it’s not ‘good.’ It’s idiotic for a few reasons:

1. First, there are no boundary conditions to it. I could be an all-pro football player and make that kind of money, but let’s be real. I’m 38. I’m not starting a football career now. A better version of the question would scope the problem more concretely to allow for my talents, current financial situation, and desire to spend time with my family.
2. Second, it assumes that I have the answer to this question. I’ve been guilty of this my entire life: I ask a question, and I assume that I either know or can figure out the answer. But life is complex, and there are plenty of things that I can’t answer and that I probably won’t be able to answer. So this question fails, because even though I can craft the boundary conditions, I can’t tell if any of my answers are right. I’m left with the host of psychological biases in Checklist #1 and the systemic biases in Checklist #4.

A good question outlines the process by which it can be answered successfully. So, from now on, I’m going to try to ask good questions. If a question doesn’t lend itself to a process whereby it can be solved, then it’s not a question I want to ask.