When my clients first come to me, they want to get clear on what’s next in their lives: They want to learn how to attend to all the demands of work while being present for family, how to find work that makes their heart sing while also paying the bills, how to show up for social change while also practicing self-care.

And, of course, the answers are hard to find. 

One reason my clients are so stuck when they first come to me is that, rather than asking good questions, they’ve tried to jump to solutions. But without taking time to be curious and ask great questions, they fall short and feel stuck. 

We live in a culture where the lack of questions is so prevalent that neurologist Robert Burton writes that we’re experiencing a “certainty epidemic.” 

We’re all born with an innate drive to ask questions and learn, but there are many reasons that most people learn to suppress their curiosity from an early age. Perhaps you were told that if you were smart enough, you’d know the answers. But you don’t, so part of you wants to hide.

Time is scarce in our go-go-go society, and it can take an uncomfortable amount of time to pause and question where you’re going or what you’re doing. Part of you may suspect that if you take a close look at the challenge you face, you’ll need to make a change. Shining light on the truth can threaten to upend your sense of stability. 

However, to get clear on what’s next, you’ll likely need to slow down, get curious, and learn to ask incisive questions. 

When we ask good questions, we step outside of the mental boxes we’ve grown accustomed to and open ourselves to possibilities we may never have encountered otherwise. 

In my first session with clients, I lay out guiding agreements for our work together, and one of these agreements is that I will default to asking questions rather than offering advice. I ask my clients to sit with the questions I ask, rather than asking me for answers. 

At times, my clients want my opinion, and if I have one, I offer it. But only after they’ve grappled with the question themselves. Although it can take a bit more time, I’ve found that self-inquiry generates more creative ideas, greater self-confidence, and better-integrated skills than having a so-called expert tell us what to do.

Here’s a caveat: Not all questions are helpful. 

There are two questions I often hear new clients ask that can exacerbate stuckness. I encourage you to watch out for these from now on:

The “Why Can’t I?” Question: Questions that start with “Why can’t I…?” are based on the assumption that you can’t do something, and they’re an attempt to figure out why you can’t. But there may be many factors contributing to your stuckness, and you probably don’t need to know what they all are to move forward. Besides, who says that you can’t learn to do something? 

The Either-Or Question: The either-or question sounds like, “Should I do this or should I do that?” Either-or questions are based on the assumption that there are only two paths, and they limit the options you see. Sometimes, you will actually face an either-or choice, so the point is not to never ask this question. However, most people ask this question prematurely before they’ve explored all of their options. There are usually more paths than you’re currently able to see, and either-or questions close your eyes to the possibilities. 

Instead, ask, “How might I?

From now on, I invite you to catch yourself whenever you start to ask a Why can’t I? or either-or question, and instead, shift to asking, “How might I?” 

A few examples of “How might I?” are—

  • How might I meet these multiple needs that I have? 
  • How might I do this thing I want to do?
  • How might I take the next small step forward?
  • How might I let go of something so I can be more present to my priorities?

When you envision the change you want to make and get curious about how you might get there, you open yourself up to greater possibility and creative solutions. 

I invite you to experiment with getting curious now.

  • Grab a piece of paper, a pen, and a timer. Get comfortable, and think of a current challenge you’re facing. 
  • Then, brainstorm “How might I?” questions that you might ask about the challenge. 
  • When you’re finished, look over the questions and choose one that speaks to you. Then, set the timer for three minutes and free-write a response to your question.
  • Afterward, take a step back and ask yourself, “What do I know now that I didn’t know at the beginning of this exercise? And what don’t I yet know?”
  • I encourage you to keep playing with your “how might I?” question, asking it throughout the day for the next week. If you don’t get an immediate answer, I invite you to patiently ask yourself, “Okay, I don’t have the full answer, but what do I know?” 
  • If your question shifts over time, that’s okay. Helpful questions can take many forms, not just “How might I?” Some of my favorite questions are super simple: What’s new and good? How do I feel? What do I need? What’s my next step? 

I invite you to stay curious about what questions might serve, and I’ll leave you from one of my favorite quotes. It’s from Rainer Maria Rilke in Letters to a Young Poet:

Be patient toward all that is unsolved in your heart and try to love the questions themselves, like locked rooms and like books that are now written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.

Please share your thoughts in the comments section below.

Much love,


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