The Planner and the Explorer

We are Stella and Amy. We share firsthand stories at the crossroads of tech, business, and culture, helping leaders craft actionable cross-cultural strategies. Together, we bridge cultural divides and bring the world a little closer—one step at a time.

Amy wrote this essay after sending her niece to college.

Exactly 13 years ago, I was dropped off by my family on UCLA campus with just two suitcases and a lot of dreams and ambition.

I became a college freshman. I was a blank canvas. I entered the school as a Math major but really, I had no idea what I was going to do, in a positive way. Ambition and pure optimism fueled me. Data, tech, or AI weren’t even in my vocabulary list. The future was unknown, but it’d be great.

Last week, I sent my niece to college. Her luggage filled up two SUVs. Under-the-bed storage bins, shower kit, water boiler, fan… She had meticulously planned everything and bought them in advance on Amazon.

“You are so prepared. I had to run to Target to buy every little daily item and start building up my life from scratch,” I said. “I like to be prepared,” she replied, as if it were the only obvious way.

Just like her dorm preparation, my niece has mapped out her entire future. She will finish a business science degree in 3 years, then law school, then become a lawyer with stable income and comfortable living. Yes, there will be student loans, but that’s part of her calculations. It’ll be stable. No surprises.

Watching her certainty unsettled me in ways I didn’t expect. Part of me admired her clarity. She’ll never waste time wandering through majors or questioning her path. But another part felt almost protective, wanting to shake her shoulders and say, “What about discovery? What about falling in love with something unexpected?” I found myself wishing for her to encounter those late-night dorm debates that reshape your entire worldview, for professors who challenge her assumptions, for moments that derail her perfectly laid plans in the most beautiful way.

Yet who am I to advocate for uncertainty? At 31, I’m still exploring, still saying yes to opportunities without a master plan. Standing next to her organized confidence, I felt less like the experienced adult and more like someone still figuring it out. She knows she’ll be a lawyer; I’m still the yes-woman trying different paths, hoping one will stick.

But maybe our different approaches reflect how the world has shifted around us.

When I started college, jobs felt abundant. It seemed like curiosity and a decent GPA could land you somewhere interesting. Now I watch brilliant STEM graduates struggle to get interviews, their carefully earned degrees insufficient in an oversaturated market. Perhaps my niece’s methodical planning isn’t just personality. Rather, it’s adaptation to a world that punishes wandering.

The AI revolution has intensified this pressure. We celebrate the young founders who drop out to launch AI startups and the content creators who build massive followings overnight. But for every viral success story, there are thousands of graduates simply trying to secure their first professional job. Not everyone has entrepreneurial dreams. Most simply seek a foothold in an increasingly competitive landscape.

AI changes things, but the fundamental dilemma remains unchanged.

Do you choose the stable path or the uncertain one, knowing that economic forces beyond your control might make either choice wrong?

As I drove away from UCSD campus, I realized my niece and I are both responding to the same unstable world, just in opposite ways. She’s choosing law precisely because everything else feels too uncertain. I’m embracing uncertainty because in tech industry, standing still might mean getting left behind entirely. We’re both making bets about how to navigate instability.

Her careful planning and clear life goals may be exactly what this moment demands. But my choice to stay flexible, follow curiosity, and embrace uncertainty could either be outdated romantic thinking or the very adaptability needed to survive unpredictable times.

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