#183 - What I Told The Teenagers

At the end of last year, a friend got in touch to ask if I'd like to speak at a career fair in Singapore. Then she added the kicker: this one was at a high school. The audience would be teenagers.

One Zoom call later, I'd agreed to give a brief talk. But then I had to figure out: what do I say?

What do I share with bright-eyed, bushy-tailed kids; students who are, no doubt, equal parts optimistic -- and unnerved by ​report​ after ​report​ on the struggles that new grads are having with the job market:

What do I tell a group of digital natives reared in an era of push-button convenience?

Want to watch a movie? [Push a button]
​Feel like some sushi? [Push a button]
​Need a ride? [Push a button]
​Want a date? [Swipe right]
​Navigate a career? [No app for that]

What do I say to a cohort that doesn't seem to want to chase -- or see as viably attainable -- the rewards that lined the post-graduate path most of us followed?

Home ownership, anyone? Marriage? Kids, perhaps?

Um, sure. Maybe. If I can afford it.

To be clear: I'm not judging Gen Z, much less what it wants from its professional or personal life. After all, we gave them the cell phones that erased life's frictions. We placed home ownership beyond their reach. We are plunging -- head-first, consequences-be-damned -- into an AI-dominated future. Not them.

No, if anything, I have empathy for this generation. And here's what I'll be sharing with them.

The Ladder is a Lie 🪜

You're navigating uncertainty, not climbing predictably.

These are the jobs I held between my junior year of university, through six years after graduating:

• HR intern at Ford Motor Company in Beijing, China
• Consulting intern at JPMorgan in New York
• Marketing Associate at an enterprise software startup in Austin, Texas
• Recruiter at an agency recruiting firm in San Francisco
• Financial Controller for Doctors Without Borders in Guatemala

Five industries, five organizations, five job functions, three continents.

Zero promotions.

At the time, I felt lost. Confused. Directionless. I felt like something was wrong with me. But looking back, I was building awareness; tuning a compass that would help me navigate the rest of my career. Picking up experience, skills, network, reputation, stories, languages.

There was nothing ladder-like about it though. Ladders are predictable, and go in one direction. Your career, like mine, will be anything but.

The jobs you'll hold ten years from now may not exist today. The industries might not have names yet. The skills that will matter most are still emerging.

You can't stand a ladder against a building that hasn't been built. So what's the use of bringing linear, ladder thinking to the career you'll construct?

Careers now are a series of roles, pivots, and resets. More like navigating a fast-changing river in your own boat: phases of intense rapids demanding sprint and focus, followed by periods of calm begging rest and reflection.

Less predictable than a ladder. But yours to steer.

Your job is to move, try, and learn -- not to always be right

Career mistakes aren't failures; they’re data.

I didn't enjoy my banking internship at JP Morgan. My first job, at Trilogy, was a train wreck. Years later, I couldn't wait to leave Dropbox.

Bad career choices, hard experiences, painful in the moment. And I made them worse by being hard on myself. How could I have chosen so poorly? Look at how I'd blemished my CV!

But looking back, I can see how necessary these mistakes were, and how much I learned from them.

Interning at JP Morgan helped guide me from banking to tech, and from big organizations to small ones. After Trilogy, I felt stuck in Texas. It took me months to find a new role; but that role became one of my all-time favorites, and led in turn to Google, and Uber.

Dropbox and I mixed like oil and water, but it taught me what to look for in cultures and leaders; lessons that I still apply today. Without Dropbox there is no move to Singapore -- and without Singapore there is no Uber, which was a career home run.

This tweet nails it:

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One: always keep moving. The GPS gets you to where you're going -- but only because it assumes your car is in motion. Your career will detour. You need to keep moving.

Two: what feels like a career "loss" so often leads to wins, in ways we can't anticipate. As we go, detours provide learning, and build judgment and pattern recognition.

And three: when you make mistakes, try to be kind to yourself. Over the course of a decades-long career journey, mistakes are as vital as they are inevitable. When you make one, try to summon that GPS and its calm, confident voice, and remember: it might be a different route than you planned, but you'll still get there.

Work with people who stretch you -- and stay close with them

Human networks are leverage: they let you do more with less. And they compound even faster when everything else is mechanized and unstable.

My second job out of university was at a small recruiting agency in San Francisco called Otec. The company had no brand name to speak of or cachet to offer. I remember my mom commenting at the time: "When we put you through private school, I didn't expect it was to become a headhunter."

Ouch! But not unfair. 🙃

Still, Otec turned out to be one of the best jobs I've had. The place sounded small and unimpressive, but the people were smart, talented, driven, and generous. After I left, they went on to do inspiring things. One Otec connection led to a role in venture capital, and in turn to Uber in Singapore -- which was life-changing. To this day, the Otec crew remains a great network of friends.

Find great people to work with and find ways to stay close even after you stop working together. The leverage compounds.

Don't go it alone -- find your people

You need more than leverage. You need resilience.

By now it's well-documented: our epidemic levels of loneliness, and the devastating impact its having on our health.

The career river we're navigating is bumpy, and it's only going to get bumpier. We need others in our boats with whom to steer, recover, learn and grow.

Covid, for all its pain, left me with one legacy I'm thankful for: Zoom calls. Calls I started with friends for support during lockdown have persisted into 2026.

Once a month I dial into calls with friends from high school, university, and my years in San Francisco. It's messy to organize and sometimes life gets in the way. But every time we dial in, it's nourishing to reconnect with people who know me well, and whom I care for. Do this 8-10 times a year, across multiple groups of people, and the effect becomes material.

The companies you join are valid sources of community. But community transcends work. Family, friends, cities, schools, hobbies, professional groups; virtual, in-person -- these are all opportunities to build community around shared values and experiences.

TL;DR

I only have 10 minutes in front of these students, and don't want to overwhelm them with messages or complexity. So, four ideas:

• Ditch the ladder. You're not climbing predictably, you’re navigating uncertainty over a long journey.
• It's ok -- even "good" -- to screw up. Career gaffes are only mistakes if you learn nothing from them.
• Build leverage. Your network will be powerful.
• Build resilience: Don't go it alone -- create support and connection.

Looking at this list, what strikes me is how un-cutting edge it is. I write about "the future" of work -- but none of this is new. It all applied to my career, begun more than 20 years ago.

And if you're reading this, I bet it applied to yours, too. No doubt you've had twists and pivots you didn't plan on. Opportunities that came to you randomly, through people you trusted. Setbacks that evolved into wins. Times when you had to trust the river -- because there was no rung to grab.

It's comforting to pretend the ladder is there. But we've been navigating uncertainty the whole time.

Today's students will face faster currents and more rapids than we did, but the advice is the same: Move. Learn. Adapt. Connect.
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Thanks for reading and exploring with me -- and have a great end of the week! 🙏
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Aki