Don’t worry, I’m not marketing a new service for your little ones :)

As we get older, more young eyes are watching us figure out how to move through the world. That’s an awesome responsibility. And depending on the day, it can feel either empowering or overwhelming. So I thought I’d share how I talk to the kiddos in my life about work, as the Village Career Whisperer.

I approach this from two angles:

What cycles did we break so they don’t have to?

So much of my work with clients is helping them shed the maladaptive shit they picked up as kids, and replace it with their own trusty compass. That process is often riddled with “if I only knew then what I know now…” regrets. We can’t turn back the clocks, so we thank the pain for its #blessings and move forward. But what if we did know this stuff earlier? Before big inflection points like college, internships, and first jobs? My hypothesis is that we’d be in more fulfilling, financially abundant careers—and doing far less course-correction today.

What will they need to be successful in 2050+?

I’m not here to put Boomers on blast or claim that Gen X and Millennials are going to magically save Gen Z and A. “Work hard, go to college, stay loyal to one company, and you’ll retire at 59.5” was solid advice in the 90s. But things like AI and automation, wage stagnation paired with rising costs, and always-on digital work have fundamentally changed the game—and will keep changing it. So it’s our turn to humbly gaze into the murky crystal ball and do our best.

My hope is that what follows helps you be a thoughtful career role model for the kids in your life. And I’d genuinely love to hear what resonates—and what you’d add or tweak.

1. Identity

Stop asking “what do you want to be when you grow up?”

This question signals that a job title is the single most important feature of their grown-up life. And when work becomes someone’s primary source of purpose, achievement, and belonging, the psychological fallout after a layoff or reorg can be brutal.

Kids also tend to look to the inquiring adult for approval, and take implicit or explicit messages like, “you should be a doctor or lawyer” seriously (or feel shame for wanting something else). Over time, that can distort their sense of intrinsic direction and motivation.

Finally, many of tomorrow’s jobs do not exist yet, so locking onto titles too early shrinks possibility. That 90s kid who loved art class and nerded out on puzzles may have grown up to become a UX Designer—a role that did not gain real traction until the mid-2000s.

Instead, get curious about what makes them feel excited, strong, proud, giggly, or totally locked in. Give them more of those experiences, without forcing them to map neatly to a future career.

2. Financial Literacy

Talk about how money works in the real world

If they can learn about 9/11, play digital war games, and understand climate change, they can handle honest conversations about money.

For every artist who resents a parent for discouraging their dreams, there’s someone who wishes an adult had explained the financial realities sooner. And for every high-net-worth employee who wishes they’d spent more time prioritizing life outside work, there’s someone grateful for the cushion they learned to build.

Kids deserve to understand why money matters and how it can be earned in multiple ways (employment, freelancing, investing—or tapping into a trust fund). The key is gathering data, not judgment: talk about salaries, get curious about how people make money, and connect them with real people doing the kind of things that light them up for a living.

3. Decision-Making

Focus on process, not correct answers

To win at school, you get the right answers on your teacher’s test. To win at life, you realize there’s no single right answer—only your best choice given the circumstances.

High-achieving students often have a rough transition into adulthood because they keep chasing A+ outcomes like promotions or pay bumps from their new “teachers,” whether that’s a boss, leader, or client. Left unchecked, that mindset can pull someone off course in their own life and slowly erode self-trust.

While kids do benefit from external structure and expectations, we also have a huge opportunity to help them build and refine their own baby compasses. The best practice happens in low-stakes moments like choosing what to wear, which club to join, or how they want to spend a Saturday.

4. Wellness

Model the value of rest, play, and creativity

It’s so damn hard for people to turn off their producer/performer personas these days. We’ve got WiFi on planes, cell service on mountaintops, fragile job security in a fraught market, and a culture that rewards busyness over boundaries. No wonder we’re burned out.

At a minimum, we need rest, or we stay trapped in this burnout epidemic. But there’s also a compelling case for play and creativity. Not as a feel-good nod to work-life balance, but as a real competitive edge. As AI accelerates, our advantage will be our humanity, which means we have to actively cultivate the things that make us human.

Model that things like breathing, dancing, reflecting, being present with loved ones, and putzin’ around town matter just as much as crankin’ out products and services (and actually help us do those things better).

5. High Standards

Strive for 100% and get curious about the gap

I bet you thought I’d say that aiming for 100% is a recipe for toxic perfectionism. Nope. High standards are healthy. The real skill is being crystal clear about what 100% actually means, why it matters, and how you respond when you miss it.

Sometimes a specific SAT score unlocks a dream school, while another one still gets you where you need to go. Sometimes winning the game matters because it gets you into the playoffs. Sometimes a 72% is perfectly fine on a pass or fail test.

The lesson is not “always ace it.” It’s learning to calibrate effort, stakes, and expectations. Then we model failing gracefully. Name what worked, get honest about what didn’t, and adjust without spiraling. No ego, amigo.

I hope this was helpful. I’d love to hear your reflections or additions—especially from the wonderful child and adolescent caregivers and professional providers reading along.

Onward!
Grace

P.S. I like to think she’d be pumped about our life today :)