I'm Betting Against Traditional Career Advice with My Own Kids
The paths we chose instead
Last week, I wrote about parental anxiety in the age of AI. The response was overwhelming, which made me realize I should share what we're actually doing in my own family.
When I write about the future of work, I'm not exploring some abstract academic concept. I'm a parent of two children: a 21-year-old daughter and a 17-year-old son. When I see research discussing career disruption, I don't just think about how it will affect the world at large. I think about how it will affect my children.
The Law School Question
My daughter just completed her undergraduate degree at Bocconi University in Milan, Italy, where she studied Economics and Management for Arts, Culture and Communication. (Why do European programs have such long names?)
As she started thinking about what came next, she decided to apply to law school. Historically, that's been a lucrative path, and most parents would be thrilled with that decision.
I wasn’t, not because law is a bad profession, but because I've watched too many brilliant people get trapped in someone else's definition of success.
Everyone focuses on that prestigious $215,000 starting salary for first-year lawyers at top firms. However, they ignore that 82% of those lawyers quit within five years, 28% suffer from depression, 19% have severe anxiety, and 11% have suicidal thoughts. You're essentially paying for a three-year program that leads to a five-year sprint toward burnout.
The Intersection
Instead, my focus has been on helping my daughter find the intersection of her interests, what she's good at, and where there's real opportunity.
She's passionate about sustainability and has a talent for connecting with people. When she started exploring vintage clothing, she discovered store owners struggling with visibility and customers struggling to find stores carrying vintage merchandise.
That's how AVS was born. It’s our attempt at connecting vintage stores with shoppers. You can learn more about our story at www.allvintagestores.com/about.
Building a vintage store directory probably sounds like the opposite of practical career planning. But the numbers tell a completely different story.
The global secondhand apparel market was roughly $190 billion in 2024 and is projected to grow to $522 billion over the next decade. That represents a 10.7% compound annual growth rate, which is remarkable for any industry.
Here's what makes it even more compelling.
67% of secondhand purchases are made by Generation Z and Millennials.
We're in the middle of what analysts call the Great Wealth Transfer, with $84 trillion expected to pass to younger generations by 2045.
The consulting firm Cerulli Associates estimates are even higher, projecting that nearly $124 trillion will change hands by 2048.
While we often hear about the negative experiences of the younger generations (ex., COVID, high student debt, the disappearance of entry-level jobs, mental health crisis), millennials and Gen Z will actually be the wealthiest generations in history.
Think about it. The same generations that value sustainability and authenticity are about to inherit unprecedented wealth. My daughter found something she's genuinely interested in that happens to be exactly what this generation wants to buy.
Skills That Actually Matter
Beyond the numbers, though, I'm very focused on what she's learning. The skills she's building matter more than any financial projection.
This is important because most young people aren't developing the right skills at all. A widely shared 2023 study found that 58% of recent college graduates are unprepared for the workforce, 53% struggle with something as basic as eye contact during interviews, and 63% frequently can't handle their workload.
Recently, my daughter spent hours talking with a store owner, discussing industry challenges and mapping out a collaboration strategy. She's learning how to communicate effectively, think critically about real business problems, and build meaningful relationships.
She's developing exactly the skills that artificial intelligence struggles with: human connection, creative problem-solving, and navigating uncertainty. These become more valuable as AI handles routine tasks.
Real Work Experience Over SAT Prep
My approach with my son has been even more unconventional. While other parents are spending tens of thousands on SAT prep and college consultants, I'm paying a Spanish company to give my 17-year-old real work experience in Singapore.
It started when my son was fifteen years old. Right after his freshman year of high school, he landed his first real internship with a startup in London. The work was entirely virtual, which taught him how to work with teams across different time zones. This matters because hybrid work is clearly the future, regardless of what old-school CEOs might say today.
That was just the beginning. This summer, he's analyzing market data for geographical expansion, presenting to founding partners, and creating marketing assets to drive growth for a company with offices in India and Singapore.
This is all coordinated through a company in Barcelona that specializes in international internships for teenagers. They operate completely differently from anything in the U.S. Families pay for guaranteed placement, and the firm handles everything from housing to interview preparation.
By the time my son graduates from college, he'll have over seven years of real work experience and won't be competing for entry-level positions.
What I've Learned
Both my kids are doing something similar, even though their paths look completely different. They're following what genuinely interests them and building real skills along the way.
When I think about the most successful people I know, that's exactly what they did. They didn't chase supposedly safe careers but pursued what they cared about.
I don't know where vintage stores or international internships will lead my children. But I know they're learning to figure things out as they go, and that confidence matters more than any credential.
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P.S. If you're curious about vintage shopping, follow All Vintage Stores on Instagram: https://www.instagram.com/allvintagestores