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Asking the Right Questions


© 2021 Lane Wallace

Aviation for Women magazine, November/December issue, 2021


At one point in my long dating career, I spent eight years trying to decide whether or not to marry the guy I was involved with. I searched my heart, asked friends what they thought, made lists, and repeatedly begged my supposedly magical “inner voice” to speak up a little louder and tell me what to do. But no matter how hard I listened, a clear answer never emerged.


Granted, eight years is a particularly long time to sit on a fence. But most of us have experienced that agonizing sense of “I don’t know what the right answer is!” at one point or another. We have two job offers, but each one has pros and cons. We love certain things about our partners, but know other aspects are less than ideal. In many cases, we also have to make choices based on imperfect information. We don’t actually know what a new job will entail, or how it will feel once we’re in it. So how do we make those decisions?



In theory, we’re all supposed to know, somewhere deep inside, what’s right for us. But in practice, it’s not that simple. Our hearts and minds contain an enormous database of knowledge and information. But information isn’t the same thing as answers. And if those eight years taught me nothing else, it was that simply waiting for our inner voices to tell us what to choose—even if we’re listening really hard—is like sitting in a library reading room, waiting for the right book to jump out and open up to just the page we need.


If we want answers, we have to go in search of them. But even that isn’t as simple as it sounds—as anyone who’s ever gotten lost in a maze of bizarre and unhelpful Google responses knows. To come up with the right answers, we have to ask the right questions.


The reason I couldn’t figure out what to do with that eight-year relationship was that I’d been asking the wrong question all that time. I’d been wracking my brain trying to figure out, “Should I stay or go?” But that invariably generated good arguments on both sides. The questions I needed to ask were, “What qualities does a really happy and healthy long-term relationship need, and do we have those?” When I finally figured that out, I started reading books and seeking out older, long-term couples who seemed really happy, and asking them not about my relationship, but about theirs. And in very short order, I had my answer. 


So how do we get better at asking the right questions? There’s a lot that goes into it; far more than I can cover here. But there are a couple of basic guidelines that, if we keep them in mind, can help steer us in the right direction.


1. Focus on knowledge, not imagination


Perhaps the most important rule to remember is to avoid questions whose answers require us to imagine the future. That’s because humans are astoundingly bad at imagining how something is going to make us feel, down the line. No matter how smart we are, we’re all susceptible to what psychologists call “focusing illusions” (focusing only on certain details of a future path, while ignoring other potentially important aspects), fantasy notions, blind spots, and the subconscious influence of peer and media pressure. It’s also hard to picture the reality of situations we haven’t yet experienced. So just trying to imagine two potential futures and deciding which one will be better is like asking “Should I stay or go?” We’re asking our brains to do something they’re not well equipped to do.


What our brains are good at is gathering information and comparing known data points. So the first step toward identifying the right questions is focusing not on some imagined future feeling, but on what we know and can learn now … both about the options we’re facing, and about how well those match with our personal values, needs, priorities, strengths, and life situations.


Generally speaking, if we’re having trouble deciding which path to take, it means we’re lacking information on at least one of those fronts. Take my relationship dilemma. I knew I wanted a happy long-term relationship. The problem was, I didn’t know what qualities were important in achieving that end. Once I had more information about that, I was able to compare it with what I knew about my relationship. And the two didn’t match.


Many career choices we struggle with are like that. We might have a clear idea of what qualities we want in a job, or what lifestyle elements we need or want, but aren’t sure which option is more likely to give it to us. Or we might have a clear idea of what different options offer, but aren’t sure which of those combinations is going to make us happier. Or we might not be clear about either one of those two things.


In every case, however, the questions most likely to get us the answers we need are those focused on filling in specific gaps in whatever knowledge we’re missing. Maybe we can’t accurately predict what’s going to make us happy in the future, but we can certainly ask ourselves, “What makes me happy now?” What tasks? What schedule? What workplace or lifestyle elements? What environments? What kind of situations or tasks do I dread or love? What jobs/relationships/situations have I loved or hated in the past, and what was it about them that made me feel that way? And what does that tell me about the choices in front of me?


Conversely, we can start, as I did, with asking what the right choice would look like, and work our way back from there. What does a job need to have in order to for us to feel happy and fulfilled doing it? What elements are important in creating a really good, healthy, and happy work environment? And what critical elements do we need a job to provide for us at this particular moment in time? Answer those questions, and it’s easier to see how closely any given opportunity aligns with them.


2. Look beyond the immediate consequences of a decision


Sometimes, where something is going to lead is less important than the immediate financial need it’s fulfilling. But if more than one option will accomplish that, it’s worth asking “And then, what?” Will this set me up to do something even more interesting? Or not? Is it likely to aid or hamper my ability to get closer to where I’d like to be?


3. Keep questioning


Even if we figure out the right questions to ask, there are times when there’s simply no way to get clear answers where we are. We have to let life play out a little more before we can make an informed decision. Or we might have to try on a choice for a while to see how well it really fits. And that’s okay––as long as we keep asking the right questions, so we’re alert for the answers as they emerge.


And finally, it helps to remember that no matter how many choices we make, we’re all still explorers, navigating the unknown adventure of our own personal futures. We don’t choose paths as much as we create them with each choice and step we take. So to find our way, we need to keep our minds, eyes and ears open, take notes, and keep asking ourselves what we’re learning, how it compares with what we already know, and what that tells us about where we might want to head next.

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