The Art of Asking Better Questions

By: Michael Youngblood, Co-founder, Unsettled

We live in an age that’s addicted to asking questions. And why wouldn’t we? Google searches, AI prompts, internet forums, and endless news sources give us unlimited answers.

But that’s the problem. The sheer quantity and ease of getting answers is flooding our lives with information — and often diluting our attention.

Humans have been around for about 250,000 years. For 95% of that time, we’ve been grazing, hunting, napping, and walking the African savanna. I have a hard time picturing our hunter–gatherer ancestors obsessing over instant answers.

For most of history, questions were companions to live with — not inconveniences standing between us and more information.

In this modern age of “question everything,” I believe sitting with a question is the real art of asking better ones.

Here’s a methodology I’ve been practicing lately:

Step One: Observe Your Thoughts

The act of noticing your thoughts and patterns is the foundation of asking better questions.

When your mind wanders freely, its stream-of-consciousness ramblings are often circling around a bigger question without naming it. Journal your thoughts. Meditate on them. Or just give your mind the space to wander.

What questions or ideas keep resurfacing?

• Am I really happy at work?
• Is this the best use of my talents and time?
• Where do I really want to be?

These are the raw materials. Notice especially the tensions that won’t resolve themselves. When you find yourself circling a tension, you’re probably standing at the doorway of a good question.

Step Two: Shape Observations into Questions

A vague feeling rarely leads anywhere. A sharp question can pull us forward.

• Vague feeling: I’m restless.
• Sharper question: What part of my life feels off and is making me unsettled?

The more specific, the better. A good question should stretch you toward possibility, not shut you down with judgment.

Step Three: Share Your Questions Out Loud

Some of my best clarity has come in conversation — on a long walk with my girlfriend, or stuck in the car with a friend where the only “screen” is the windshield.

There’s something magical about being locked into a space with someone you trust and letting a conversation stretch on. These unstructured moments, when nobody is rushing to move on, are fertile ground for exploring and sharpening a question.

It’s also why we design these kinds of moments into Unsettled trips. We slow things down, put the phones away, and make space for conversations that transform both our questions and our answers.

Step Four: Sit With the Question

This is the hard part. After sharing, bring the question back into your own world. It’s your question, after all.

Sit with it. Don’t rush to answer. Let it linger.

Maybe it’s a weekend hike, a morning journal entry, or twenty quiet minutes before the day begins.

To me, this is a form of radical attention we can give ourselves. And in a world of constant distraction, it’s close to a lost art.

Live the Question

One of my favorite lines comes from the poet Rainer Maria Rilke:

“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 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.”

That’s the heart of it. When we practice patience — when we live with our questions — the answers begin to take shape almost in spite of us.

At Unsettled, we’ve operationalized this philosophy. Spend a month with us in Bali, or sail with us in Tahiti, and uncertainty is inevitable. The question isn’t if you’ll face it, but how you’ll respond to it.

For me, the practice is simple: live one question at a time. Write it down. Share it with someone. Sit with it. Watch how it changes. And if you join us on an Unsettled journey, bring your questions with you. There’s no better place to live them out.

Bonus: Questions I’m Sitting With

Here are a few of mine right now:

• What role do I want AI to play in my life and work? (Do I want to use it for recipes on Saturday mornings, or let it get messy and creative with me?)

• What do I want my next 10 years to be about? (I started Unsettled a decade ago… and it flew by.)
• What’s my dream job that I can do 2–3 days per month, here in my local community? (Emerging answer: I’ve joined our local ski patrol this winter.)
• Where in my life am I avoiding discomfort, and what’s the cost of that avoidance? (For me, maintaining relationships can be challenging; how do I build awareness to get better at it?)
• If I had 30 good summers left, how would I spend them? And how can I plan the next 30 days to reflect that vision?
  
• Who do I want to help right now? And how can I help them?