Dancing with the Unknown

How the Book “Uncertain” Taught Me to Stop Overthinking and Start Living

In 2019, uncertainty wasn’t an intellectual exercise for me—it was my waking reality.

I spent several months unhoused in San Diego, navigating the edges of survival in a world that had no room for the lost and the wandering. It was a time of raw exposure, of feeling the ground perpetually shifting beneath me.

Would I find a place to sleep that night? Could I stretch a few dollars into a meal? What if I got sick? What if I never found stability again? These weren’t hypothetical musings. They were pressing, relentless questions with no clear answers.

If you had told me then that uncertainty was something to be embraced, something that could be an engine for wisdom, I would have laughed—bitterly. To be uncertain was to be vulnerable, to be at the mercy of forces beyond my control.

And yet, looking back, I see how those months shaped me in ways comfort never could. They stripped away my illusions of certainty, of control, of a predictable life. And though I wouldn’t have articulated it this way at the time, they forced me to become more adaptable, more present, more aware of the power in not knowing.

Reading “Uncertain: The Wisdom and Wonder of Being Unsure” by Maggie Jackson years later hit me like a quiet revelation. It’s the book I didn’t know I needed—a guide not to eliminate uncertainty, but to learn to move with it, even thrive within it.

Maggie argues that our cultural obsession with certainty—our need to have answers, to feel in control, to predict and plan every step—is not only unrealistic but detrimental. It stifles creativity, narrows our vision, and keeps us locked in fear when life inevitably takes an unexpected turn.

And isn’t that exactly what we’re all facing now in our current world that feels like it’s been turned upside down?

Overthinking in a World on Fire

If 2019 forced me to confront uncertainty in its most visceral form, today’s economic and political climate has only amplified that lesson. Inflation, AI-driven job losses, political uproar—everywhere I look, life feels like a pressure cooker of instability.

My instinct, like many others, has been to intellectualize my way out of the anxiety. I read, I analyze, I try to game out every possible outcome. But Maggie’s book made me realize that I’ve been mistaking cerebral paralysis for preparedness.

She reminds us that when we fixate on controlling uncertainty—on gathering more data, on demanding answers—we don’t actually gain clarity. We just get trapped in a loop of second-guessing, mistaking mental exertion for meaningful action.

One of the most compelling insights from Uncertain is Jackson’s exploration of how openness to the unknown leads to better decisions, stronger leadership, and deeper human connection.

Neuroscientists, surgeons, and community leaders alike describe how embracing ambiguity—rather than fearing it—makes us sharper, more responsive, and better equipped to navigate the world as it is, not just as they wish it to be.

I felt those truths in my bones. Because the best decisions I made in 2019 weren’t the result of meticulous planning. They were born from paying attention, from responding to the moment, from leaning into discomfort rather than trying to escape it.

When I stopped obsessing over the question “What if this doesn’t work out?” and instead asked “What is the next right move right now?” I found doors opening where I thought there were only walls.

Wisdom for an Uncertain Future

So, what does Uncertain have to say about the world we’re living in now?

…..Plenty

💥 Uncertainty is not ignorance—it’s intelligence in motion. We tend to equate being unsure with being uninformed, but Maggie flips this notion on its head. The best thinkers, the best innovators, and the best leaders don’t cling to certainty. Rather, they question it. They hold space for doubt, for alternative perspectives, for shifting realities. That’s the kind of thinking we need now more than ever.

💥 The search for certainty makes us more vulnerable, not less. The more we demand answers—politically, economically, technologically—the more we set ourselves up for disappointment and manipulation. We’re primed to believe the loudest voices, the boldest predictions, the most confident leaders. But certainty is often a mirage, a trap. Real wisdom lies in the willingness to say, I don’t know but let’s explore.

💥 Resilience isn’t about having all the answers—it’s about moving forward despite not having them. My months of being unhoused weren’t survivable because I knew what was coming next—I didn’t. They were survivable because I learned to adapt, to exist within uncertainty without letting it consume me. That’s the muscle we need to build collectively.

💥 Innovation is born from ambiguity. Whether it’s AI research, scientific discovery, or social change, the biggest breakthroughs don’t come from people who claim to have everything figured out. They come from those who embrace questions, experiment with possibilities, and stay agile in the face of the unknown.

Embracing the Unscripted Life

Maggie’s book challenged me in a way that few books do. It forced me to confront the ways I still resist uncertainty, how I mistake thinking about a problem for actually engaging with it. It reminded me that not knowing isn’t a failure—it’s a doorway to insight, to growth, to something greater than my limited plans.

And so, I find myself returning to the lessons of 2019, not with fear but with gratitude. Uncertainty didn’t break me—it shaped me. It made me more resilient, more open, and more willing to engage with life on its own terms.

We’re all standing at the edge of an unknowable future. We can choose to cling to illusions of control, to rage against unpredictability, to let fear make us rigid and reactive. Or we can lean into the wonder, the possibility, the wisdom of being unsure.

I know which path I’m choosing.

What about you?

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