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The times are urgent. We must slow down.

-Bayo Akomolafe

Dear friends,

Years ago when our family was living in Argentina, my friend Malavika asked a question that cracked me open: "¿A qué te dedicas?"

What do you dedicate yourself to?

Nobody had ever asked me this. At least not in this way. Our habitual ways of getting to know each other—"What do you do?" or "Where do you work?"—invite simple answers. But Malavika's question demanded something deeper.

At the time, I was adrift. Months after leaving Global Citizen Year—unhitched from the identity that had defined me for a dozen years—I was sitting in the raw discomfort of not knowing what came next. Her question cut through my fog. Disorienting, yes—but also orienting. In that moment, I realized my job and title had never actually defined me. What remained was something far more durable: an animating purpose.

My dedication wasn't to a role or organization—it was to helping others find their own path to freedom.

If a simple question could shift my perspective so dramatically, what would happen if we approached all of our conversations more consciously?

Questions are powerful—they define the frameworks we live in and the horizons we move toward. Yet too often, we're asking the wrong ones.

We ask kids….

What they want to be when they grow up (not who)
Where they're going to school (not why)
About their major (not their mission)

We've laid a trail of breadcrumbs toward jobs and titles, implying that paths are linear and success is arriving somewhere societally sanctioned. But that roadmap was always an illusion—and AI has made it impossible to ignore.

As we hurtle through the most profound shifts in human history, we're navigating from an outdated playbook. We're celebrating productivity gains while work loses meaning. We're fixating on quarterly earnings while communities fray. We're obsessing over test scores while kids aren't learning. ("College has become a question of how well I can use ChatGPT," a recent graduate confided.)

Again and again, we hit the target but miss the point.

Our old questions aren't just wrong—they keep us spinning in a race to nowhere, optimizing for what's countable at the expense of what counts.

Until we start asking better questions, we'll stay trapped in the same exhausting cycle—achieving what we're told matters while aching for what matters more.

Over the coming months, I'll be sharing reflections on this theme: The Questions We Should All Be Asking. Each letter will pose a searing question our times demand. Questions that resist quick answers and expand our sense of what's possible.

At The Flight School, we call the students’ first few months "Dis/orientation" for a reason. It takes time to deconstruct what they thought they knew—about time, money, success, achievement—to make room for what they're ready to learn through lived experience.

With support from our magical team, they animate the questions that become their north star:

How can I make my aliveness contagious?
Can I lead with joy instead of fear?
What would freedom feel like?

Of course, answering these questions isn’t the goal—it's learning to live inside them.

Transitions—whether in our lives or in the world—can be approached by design or by default. The space between an ending and a new beginning is our portal to possibility.

Like the emerging adults I've worked with for decades, our entire society is crossing the threshold from one era to the next—disoriented, uncertain, but ripe with potential. Will we stumble along, clinging to old maps, or choose new questions as our compass?

I often reflect on Einstein’s insight that the quality of our questions determines the quality of our answers.

What if we each spent the next 59 minutes thinking deeply about what kind of society we want to build—and only then ask what solutions serve that vision?

So, my friends, I’m curious: What questions should we be asking now?

What would you ask if you weren't afraid?
What questions are haunting you?
What’s kindling you? Calling you?

Share what's stirring for you in the comments below — your questions will inspire future posts.

The future isn't inevitable. It's a choice.

Let's stop pretending we're powerless to shape it.

With fierce hope,

Abby

Are We Asking the Wrong Questions?

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