Living the Questions

How the Right Inquiry Shapes Our Path Through Change and Uncertainty

Several months ago, I revisited Letters to a Young Poet by Rainer Maria Rilke, and was grabbed by a passage that seemed to have been waiting for my return:

“Be patient toward all that is unsolved in your heart and try to love the questions themselves as if they were locked rooms or books written in a very foreign language. Don’t search for the answers, which could not be given to you now because you would not be able to live them. And the point is to live everything. Live the questions now. Perhaps then, someday far in the future, you will gradually, without even noticing it, live your way into the answer.”

Rilke’s wisdom holds even more relevance today than when he wrote these words in the early 1900s.

We now live in a culture that values speed and convenience, where search engines and AIs can answer most questions in seconds. From a young age, we’re taught that success depends on having the right answers, and quickly. When we don’t know it all, we feel lost, inadequate, or even flawed.

There are some questions whose answers cannot come quickly, or at all. What if, as Rilke suggests, we allowed the biggest questions to guide us, carving our path through the unknown and teaching us to embrace uncertainty?

Sometimes, the journey the question puts us on is more valuable than the answer we may find.

A few weeks after revisiting Rilke, I listened to an episode of the Huberman Lab podcast featuring Josh Waitzkin—the chess prodigy turned martial artist and coach. He discussed his Most Important Question (MIQ), a framework he and his clients use to guide focus, decisions, and growth. It clicked immediately—this was the same kind of inquiry Rilke had written about, but applied to high performers.

In the midst of my own season of change, I felt a deep pull to explore the biggest question I could ask myself, my own MIQ.

Through daily morning pages and long nature walks, I began to listen to what demanded my attention. As the material emerged from my psyche and soma, I “emptied the tank” on paper, capturing my thoughts, emotions, sensations, and images. I reflected on what was pulling at me emotionally, creatively, and spiritually, noticing the open loops, friction, and subtle tension in my thoughts and body. I wasn’t seeking answers, but simply gathering raw material for my own MIQ to emerge.

A list of questions began taking form in my journal. Over several days, I let them linger, reading them aloud and feeling into each one until, finally, my guiding question was obvious:

What is the clearest, most aligned structure for work in this season of my life?

When I read the question aloud, something stirred deep within me—an intellectual knowing, a deep longing in my heart, tension in my belly, and creative energy rising from the center of my being. This question didn’t offer the relief of an easy answer, but it introduced a new purpose: a resonance, a sense of "this really matters to me."

I knew I had to stay close to the question, creating space but returning to it gently, again and again. I let it shape how I began and ended my days, weaving into my creative work, conversations, and moments of pause. I journaled on it daily, placed it on post-it notes around my office, set it as my iPhone wallpaper, and wrote it down each night before bed. It became like a mirror I couldn’t look away from, reflecting my truth back at me from different angles every day.

In the first week, I broke the question apart, treating each piece as an inquiry to explore: What season of life am I in? What feels aligned, and what doesn’t? What is clear? Which structures in my life feel soul-nourishing versus life-draining? These were loose threads, and over time, as I sat with what emerged, a fuller tapestry slowly began to take shape.

As I went through this process, I felt the urge to give the question space to breathe. I’d step away from it, sometimes for long stretches during the day, or even for a day or two. I trusted that, in those pauses, it was quietly deepening its roots in my unconscious. The question became a relationship, one where at times I was deeply engaged, and at other times, it quietly lingered, guiding me without needing my constant attention.

Over several weeks, longings I hadn’t fully acknowledged started to surface—desires for spaciousness, simplicity, depth and craft, creative expression, a deeper connection with nature, and more time with family. But alongside these longings, there were tensions my ego didn’t want to face, because the answers were threatening things I cared deeply about, like Downshift. Eventually, the actions I needed to take became clear, but not through force or fear, but out of reverence and clarity.

Through this process, I’ve come to appreciate that a great question is a living, dynamic inquiry. You can’t solve it all at once; it requires you to inhabit it, to wear it like your favorite outfit. As you do, it stretches your perspective, broadens your understanding, deepens your sense of self, and expands what you thought was possible. It reveals where you are and what’s ready to unfold in your life.

The right questions carry a gravity of their own. They demand your attention and shift it. Living the question is not about getting things "right" but about getting closer. Closer to the pulse of life. Closer to that which matters. Closer to your truth, until you can’t ignore it anymore.

And how did I know when I had lived inside the question long enough? I could feel it. There was a sense of completion, of knowing, of saturation. New energies were wanting to take root. Not because I had answered it, but because the question had brought me through something, a threshold. I began to feel different. My life and sense of self was changing, both subtly and profoundly.

Now, nearly two months later, I’ve begun to step into change and move toward a more soul-aligned life. I’ve carved out more creative time each day, planned a summer sabbatical to be with my family and go on a vision quest, and deepened my study of Hakomi. I’ve also formed a partnership with my colleague David Spinks at Downshift to share the load, and I’ve stopped working at night.

Through all of this, I’ve realized that leading and scaling a startup no longer aligns with the season of life I’m in. Equally important, being a CEO and traditional founder isn’t in my nature—it’s not who I am, and it’s not what’s calling to me. Instead, I’m called to deepen my craft as a coach and writer, spend more time in nature and with my family, and less time in front of a screen.

The question continues to work on me in unexpected ways, revealing deeper layers with each passing day. It’s pushing me to embrace uncertainty, step away from what no longer serves, and lean into what truly matters. By living with the question, rather than rushing toward an answer, I’ve found the next thread of transformation.

In the simplicity of a single question lies profound depth. While answers may come over time, the true gift is in how the question shapes us along the way. To live with it is to embrace the unknown, trusting that in the stillness and patience, something deeper is being revealed.

What if we all lived more fully in the presence of the questions that stir us, instead of rushing to resolve them? Maybe, in the end, it’s not the answers that matter, but how these questions move us forward, step by step, toward something new.