The One Conversation That Changed My Career - Do You Remember Yours?
Why 77% of young people are too terrified to ask for the career advice that could transform their future
I’m at a networking event, watching a 22-year-old at the coffee station, wanting to join conversations but seemingly paralyzed. She’s clutching her phone like a life raft, pretending to check emails. I recognize that look—it’s the same one I had at her age. So I walk over and ask what brought her here.
Twenty minutes later, she told me about her dream of working in sustainable fashion, and I’m connecting with three other attendees. All it took was for someone to notice she was there.
Our new research with Big Brothers Big Sisters of America—the 2025 Youth Mentorship Access Report—reveals something extraordinary about the power of a single moment.
Changed. Their. Career. Direction.
Just one conversation.
But here’s what everyone misses: While we’re debating return-to-office policies and complaining about Gen Z work ethic, there’s an entire generation desperate for guidance but too terrified to ask for it.
My Conversation at 21
This made me think of my own conversation at 21.
I’m 21, working at BBDO in a soul-crushing entry-level position. My job? Making sure international ad reels were organized, CDs were in order, and executives had their printouts. The kind of work that makes you question why you went to NYU, while being grateful you even have a job.
One day, I’m on the phone chasing down a Whiskas ad from Japan when this guy—some production person I’d never met—suddenly goes off-script:
“Kid, you gotta get out of this business. Ad agencies aren’t what they once were. We were cowboys back in the day, we had power and insight. Now we’re just paper pushers.”
“Where should I go?” I asked, probably sounding as nervous as I felt.
His voice got louder, more excited: “Get into digital! Nobody understands it. They’re the cowboys now. Jump in and go for the ride.”
Three months later, a recruiter from Avenue A called. Because of that random conversation, I was determined to work there. They hired me. I was there when we bought Razorfish. I was there when Microsoft bought us, followed by Publicis a few years later.
[Me from those days: Always curious.]
That Avenue A/Razorfish leadership team? They were brilliant, well-trained visionaries. Everyone who worked there went on to join incredible companies and build amazing things.
All because some stranger took 30 seconds to share an observation that cost him nothing. I made a different career choice (cue: sliding doors moment).
The Intimidation Crisis No One’s Talking About
Here’s what’s actually happening with young people today:
This generation didn’t just survive remote schooling during the pandemic. They entered the workforce through ghost-town internships and Zoom onboarding. They’re watching adults seemingly hate each other across every platform. Is it any wonder they’re hesitant to reach out?
But here’s the heartbreaking part—they’re not looking for jobs or instant solutions:
76% don’t want older adults to solve their problems—they just want guidance and connections
79% say hearing older adults’ workforce perspectives is helpful
83% believe mentors can bridge the gap between classroom learning and real-world experience
They’re not asking you to fix their lives. They’re asking for perspective, for someone to say, “Here’s what I’ve learned,” or “Have you considered this?” or even just “You remind me of myself at your age.”
The world is in flux—you might not know which direction it’s headed either. But you’ve weathered the storms, and you likely know the signals to pay attention to. Age tells you—you know it in your bones—that we’ll make it through all the agility and chaos in today’s market. But young people don’t know this yet. They haven’t lived through enough cycles to understand that disruption often precedes opportunity.
The Compound Interest of Connection
When we invest in these conversations, the returns are staggering:
This isn’t charity—it’s cultural infrastructure.
When brands wonder why they can’t attract young talent, when companies complain about retention, when we collectively wring our hands about “kids these days,” we’re missing the obvious solution staring us in the face.
What You Can Do Tomorrow
The Next Conversation: When you encounter someone under 25—your barista, your friend’s kid, that intern everyone ignores—ask them what they’re working on. Ask what excites them. Offer to connect them with someone in your network if they ever want to talk.
Join The BBBS Movement: Big Brothers Big Sisters now mentors 18-24 year olds, as well as younger kids and teens. We are celebrating the 125th anniversary of the BBBS in America. Join us
! Here are all the ways you can get involved: https://www.bbbs.org/get-involved/
The Email Introduction: Think of one young person in your periphery. Send them a note: “If you ever want to grab coffee and talk about [industry/career/life], I’m happy to share what I’ve learned.”
Why This Matters More Than Ever
Young people aren’t asking for handouts. They’re asking for what that production guy gave me: perspective from someone who’s been there, delivered without judgment.
We can’t sit on the sidelines while an entire generation struggles to find their way. They want our guidance—they just don’t know how to ask.
So I’m asking every adult reading this: just start. You won’t say all the right things. But you might say the one thing that changes everything.
What about you? Can you remember a conversation that shifted your path? I’d love to hear your story.
Big thanks to our partners at Big Brothers Big Sisters of America, the BBBS Youth Council for advising us on this crucial work, and Elias Alling for leading it on our side!
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Curiosity is contagious; if you like this newsletter, please share it!!
Penned by Libby Rodney and Abbey Lunney, founders of the Thought Leadership + Futures Group at The Harris Poll.









