Living the Questions: Finding Meaning in Uncertainty
What if true wisdom isn’t about finding answers, but about embracing the paradoxes of life?
Can We Live with Paradoxes?
Does being hopeful mean that you’re not allowed to feel sorrow or sadness?
If I say that I’m unhappy with the current situation, does that mean I’m ungrateful for what I have?
Can someone feel both sorrow and fulfillment?
These questions linger in the depths of our minds, yet we often avoid them. We crave certainty, clarity, and definitive answers. But what if true wisdom lies not in resolving these paradoxes, but in learning to live with them?
The Nature of Sadness and the Illusion of Avoidance
Sadness is often seen as something to be fixed, suppressed, or avoided. We turn to distractions—endless entertainment, shallow achievements, and quick bursts of dopamine—to escape from it. But sadness, in its essence, is not merely despair; it is fullness. The Latin root satis, which means “enough,” suggests that sadness once meant being filled to the brim with experience, with both joy and grief intertwined.1
Yet, in today’s world, sadness is often mistaken for dysfunction. Many of us were raised in environments where sadness was discouraged, sometimes even banned. Psychologist Robin Skynner argued that when sadness is suppressed, people become manic and shallow. Pediatrician T. Berry Brazelton believed that excessive efforts to cheer a child up can devalue sadness, stripping it of its depth and significance. When we numb sadness, we also numb our ability to grow, to reflect, and to connect with ourselves and others.2
Neuroscience suggests that sadness is deeply tied to cognition and emotional processing. It restructures beliefs, fosters resilience, and allows us to reassess our values and goals. It can also signal to others that we need support, reinforcing the human need for connection. But when sadness is denied, we lose the opportunity to engage with it as a source of transformation.
Ancient wisdom and literature have long explored the depths of sadness and hope. The Sufi poetry of Rumi, the reflections found in mystical and Quranic traditions, and contemporary works such as The Dictionary of Obscure Sorrows by John Koenig all suggest that sorrow is not something to be feared but rather embraced as part of the human experience. As Rumi wrote:
“Be patient where you sit in the dark. The dawn is coming.”
And in the Quran:
“Indeed, with hardship comes ease.” (94:6)
In Letters to a Young Poet, Rainer Maria Rilke advises us:
"I want to beg you, as much as I can, to be patient toward all that is unsolved in your heart and to 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.”
Through this lens, sadness is not merely an affliction—it is a teacher.
The Chase for Certainty and the Cost of Speed
In a world that demands quick results, we seek certainty about who we are, what our purpose is, and where we are headed. We believe we must first figure everything out before we take action. But what if identity and purpose are not destinations, but journeys we construct along the way?
If you tell me you have no clue where to begin, I would ask: Don’t you have just one idea, one question, one problem? If so, that is enough to start. Your first step does not have to be monumental. It only needs to be real.
The pace of modern life urges us to rush, to compete, to consume. But when we measure our progress against others, we risk veering off our own path. The pursuit of fast success often leads to hollow achievements—glittering on the outside, but void of meaning. Life is not a race; it is an unfolding, an evolution, an art form that demands presence and patience.
Matt emphasizes the importance of playing the long game—rather than chasing trends or crafting a fleeting personal brand, we should commit to a mission that truly resonates with us. Over decades, we can build something uniquely ours, something authentic that stands the test of time. This shift from short-term dopamine-driven achievements to a long-term, mission-driven life is where true fulfillment lies.
Hope and the Beauty of Paradox
If sadness is a fullness, then hope is not its opposite—it is its companion. Hope, as defined by Merriam-Webster, is “to expect with confidence” or “to cherish a desire with anticipation.” But hope is not blind optimism. It is the ability to hold both despair and possibility in the same breath. It is the courage to acknowledge what is broken while believing in what can be built.3
We often think that in order to move forward, we must erase pain, silence doubt, and suppress contradictory emotions. But what if embracing paradox is where true wisdom begins? What if, as Rilke wrote, we must learn to live with our questions instead of rushing to answer them?
Change does not begin with certainty. It begins when we see a problem, when we feel the pain, and when we allow that pain to evolve into something meaningful. We are allowed to feel everything—to grieve and to hope, to fear and to trust, to fall and to rise again.
Paradox and questions are not a flaw in our thinking; they are the birthplace of creativity, of science, of art. It is where we stop running and start listening. It is where we let go of the need to know and surrender to the experience of becoming.
An authentic life is a slow life—a long game, filled with failures, injuries, and resilience. Life provides us with raw materials, but it is up to us to build something meaningful, to contribute, to create. Fulfillment is not found in chasing endless bursts of dopamine but in embracing the depth of experience, in creating rather than consuming, in responsibility rather than blame.
True hope is not about ignoring reality but about engaging with it fully. It is the act of seeing beauty in brokenness, meaning in struggle, and purpose in uncertainty. It is the courage to live the paradox, to create something only we can, and to walk a path that only we can forge.
How to Live with Unanswered Questions Without Burning Out
To embrace paradox without exhaustion, we must cultivate patience, presence, and resilience. We must shift our focus from immediate answers to deep engagement with the questions themselves. The long game requires sustainable effort, not burnout.
Accept that discomfort is part of the process. Instead of seeking quick relief, allow yourself to sit with uncertainty, knowing that it is fertile ground for growth.
Engage in meaningful creation. Instead of chasing dopamine hits from fleeting accomplishments, focus on building something that truly matters over time.
Surround yourself with a community that values depth. Engage with thinkers, artists, and friends who encourage introspection and support your journey.
Balance action with reflection. Don’t let questioning lead to paralysis. Move forward, even if slowly, while continuing to live the questions.
Trust the unfolding. You don’t have to have all the answers today. As Rilke reminds us, “Live the questions now,” and trust that one day, you may live into the answers.
Paradox is not a problem to be solved; it is a reality to be embraced. It’s where questions are born, and right questions are the beginning of creativity and science. A fulfilling life is not about eliminating contradictions but about learning to hold them with grace. When we stop demanding certainty and instead live the questions, we open ourselves to a deeper, more authentic way of being.
Can you find the courage to live with uncertainty and trust the unfolding of your own journey? When will you start to live with your questions? How will you shape your journey?
From the book The Dictionary of Obscure Sorrows.