For every complex problem there is an answer that is clear, simple, and wrong.

H. L. MENCKEN

Here’s an obvious fact: Modern civilization is built on the premise that it is important to get the right answers to questions on an everyday basis, and for life in general. With technology at my fingertips, I always have the “correct” information to be able to run my life, or an entire business if want.

We're in a time where it might even be safe to say the availability of the right information is not what matters anymore: the information is everywhere. It’s the speed at which the questions and answers are transacted that impact how much control I’m likely to feel on an everyday basis, on how much I actually get done effectively. And that bias toward acceleration can lead to some interesting shortcuts.

Any normal day is spent asking a question, getting an answer, modifying the question and asking again to get a better answer until we're satisfied. In modern life, “better” typically means “more” of something that is good. This works splendidly in business or household problem-solving. It scales effectively: watch a chain of interconnected processes long enough, pin down inefficiencies, get a better and more efficient alternative, and patch that solution into the process. Neato.

The problems start when you apply this kind of thinking to situations where “known errors” can’t be consistently reproduced as they would as a bug in an app. Artists and creative people deal with this a lot, as part of their work. They connect the visible to the invisible, the tangible to the rest of the things we all agree are important but maybe aren't able to name. It happens when I make decisions about the composition of a painting, or music I’m putting together, or in my relationship. Very often, there aren’t any “right” answers that come out on the other side of an equation. Instead there are just decisions that have to be made.

A chess player starts out by learning the moves for each piece. Then she learns strategy by asking herself (or learning from an expert) how to best inflict a checkmate. Soon after, she realizes her vulnerability and switches her questions to form a counter-strategy: how to avoid being cornered while carrying out a strategy. This evolves to a counter-counter-strategy, followed by counter-counter-counter-strategy, and so on. Throughout, she is exhausting a lot of common and uncommon questions about common and uncommon patterns in the game, by producing context-specific answers that can be learned and practiced. But after a significant amount of learning and playing on a regular basis, any skilled player will reach a point where there aren’t any general answers to the questions about what to do next. Instead, this player will find herself in the center of a paradox—a very subjective space—and no longer on one side of a board waiting to play someone else.

I think this is when life actually begins.

One of the things that happens over time, is that the questions you ask yourself—of your relationships and of your life—start to feel like they’re not giving you anything you can really use anymore. The words are not accurate enough, and they don’t exactly fit what you were asking about. You might wonder if there’s a problem with your articulation, maybe you need some guidance on how to “rephrase” the problem so that you could ask again and hope for a “better” answer.

Maybe.

In my case, it quickly became a pointless exercise to ask questions that might produce better answers. This is not to say that I didn’t get better answers from asking the right questions, I did. For a good while, I got answers that helped me focus very clearly on the things I wanted to get done, things I wanted in my life, people I wanted to keep or even let go. But the turning point came when realized that a more nuanced way of looking was necessary to do anything sensible, that it is possible to neatly sort things but to do that I would have to be willing to forego a lot of detail in a situation—and probably lose something important—just to keep things simple.

When my perspective shifted, it was the quality of the questions that started to require focus. I had been helped by a number of different experiences in my life already, both in my personal life and career. I had a reservoir of experience that makes a lot of things clearer, but not necessarily simpler or easy to articulate. Over time, I had gotten used to doing and feeling things by trusting my gut.

But I had started to pay attention less to the answers, and instead gave more time and focus to crafting better questions. Answers are wonderful but they’re only really valuable in the right context, and for the right problems. Asking the right question has its own value: turning that wheel is more important than it seeing if it will stop in the right place. The question stares right back at you.

To get to this place I’ve had to work on developing a two-part skill, the first of which involved learning to distinguish the type of problem I was trying to solve: Is it a problem that needs the right answers, or a challenge that requires better questions? The other skill was in asking the suitable better question.

Developing better questions changed the way I think as much as the company I keep. These days the people who interest me, whom I follow, keep close, and might admire are usually confident about where they are in their lives intellectually and spiritually. They’ve “gone pro” in their Life: there are no winners or losers here, just people showing up at their best, and “comfortable in the paradox”. They know that if they are honest with themselves, and to the people who listen to them, that flux is inevitable, as much as it is a source of wealth all of its own. These are people who have managed to get beyond looking for answers and found themselves in a space where everything is interconnected, where it is the questions that are brilliant and worth smiling about—the answers will take care of themselves.

As times seem more complex and it gets harder to take sides on everything from politics to tv characters, it becomes even more pressing that we become interested in this “art of questions.” Life demands even more urgently that we listen to “the other”, to embrace challenges from places and people we would not otherwise consider. It is those people who bring sincere “I don’t know, but I’d like to listen” capability to conversations that will effectively elevate the conversation. It's the kind of perspective that gives our empathy and openness a good workout: we’re a little out of breath from stretching the muscle, but so much richer for it.

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PHOTO: The Tears of Saint Peter (1612–13), by Jusepe de Ribera at the The Metropolitan Museum of Art.