How Can We Help Young People Find Careers They Care About? It Starts With a Conversation.

Roadtrip Nation
8 min readFeb 25, 2022
Two Black women hug in front of the Roadtrip Nation green RV.

It seems like everyone’s quitting their job these days — and every employer in America is trying to figure out why.

But if you’re someone who’s invested in supporting students or young adults—say, you’re a parent, teacher, counselor, or someone who’s working in youth-focused nonprofits or educational organizations—this moment may have you thinking less about your own career path, and more about others’. And for those of us who want to support better career outcomes for young people, it seems the big question isn’t why—it’s “how?”

As in, How can I get young people started down a path toward career fulfillment…without being pushy or prescriptive? How can I ensure their long-term success? How can I start helping them think about their futures now, so they’re not left in the dust later??”

These are all great questions! All, admittedly, stress-inducing questions, too! But what if the answer to connecting young people with careers they actually care about…is simpler than you think?

We here at Roadtrip Nation have been going on about career conversations for a couple decades now. If you’ve seen our documentaries, watched our videos, or used our educational programs, you already know — career conversations are our jam! They’ve always been foundational to our work because they’re literally the foundation of our company. (We’ll spare you the whole story, but you can read it here!)

But while we’ve always seen and felt the impact of career conversations in program evaluations and feedback from educators and students, we recently completed an in-depth impact report that confirms career conversations are having a tangible positive impact on young peoples’ confidence, education outcomes, and future career success.

This impact was measured through the lens of young people using Roadtrip Nation’s tools and experiencing our programs. But since everything we do revolves around career conversations, we feel confident saying that this core piece of our pie packs a ton of impact. And luckily, it’s the kind of impact that’s incredibly easy to spread.

You can facilitate these kinds of conversations, and start seeing this kind of impact right now—and we’ll show you how.

But first — what do we mean by “career conversations”?

A career conversation is a candid, interview-style chat between two people: one party who’s trying to figure out what to do with their life, and another party who’s further down the road, and can give career searchers guidance, advice, or even just inspiration to help them start imagining their future careers and lives.

The word “career” is in there, and it’s a critical connection point in these conversations! But a true career conversation should go so much deeper than that. These conversations should give young people a behind-the-scenes look at what different careers are really like, but they should also cover hopes, dreams, fears — all the things that shape our career paths.

How do we know that career conversations work?

For a deeper dive on the research that led us to confidently say that career conversations result in better career outcomes for young people, you can read our full 2021 impact report! (To supplement your reading, we also recommend checking out “From career readiness to career optionality,” a collaboration between the Organisation for Economic Co-operation and Development and the Christensen Institute.)

But for now, we’ll highlight six positive outcomes that that Roadtrip Nation participants have experienced through programs that center career conversations:

1. Expanded Career Exposure & Engagement

Career conversations can introduce young people to careers they’ve never heard of, or thought possible. And putting a real face to these careers helps young people actually see themselves in these roles. This can translate into increased goal-setting and knowledge about how to explore and pursue their career interests.

2. Improved Career & Communication Skills

Career conversations help young people build critical 21st century skills, like adaptability, problem-solving, communication, and collaboration. These kinds of skills are often taken for granted, but they can set young people apart, and prepare them for an unpredictable future of work.

3. Stronger Connection to Education

Widening the lens of possible careers helps students feel that school is relevant to their lives and who they want to be, now and in the future. (For learners in Roadtrip Nation programs, we actually saw improved academic performance as a result of career exploration!)

4. Growth in Self-Perception

Young peoples’ confidence, motivation, and sense of agency grows as they encounter stories of people from similar backgrounds and experiences.

5. Greater Well-Being and Sense of Purpose

Career conversations can positively impact young peoples’ mental health, and give them more hope for the future. (And at a time when young people have been hit hard by the trauma of a pandemic and the isolation of remote learning, hope for a brighter future is an important thing to cultivate.)

6. Increased Social Capital

This is a big one! Career conversations help young people develop social capital — and social capital=more equitable outcomes. The kind of networking and mentorship connections established by career conversations can increase young peoples’ access to resources that are often blocked by systemic barriers.

OK, that all sounds pretty great! So how can I help young people have these kinds of conversations?

We’d be remiss if we didn’t first mention the Roadtrip Nation Experience, our project-based online course that helps young people explore who they are, then walks them through the process of conducting a career conversation! This is an especially valuable resource if you’re trying to facilitate career conversations for a large group of young people.

But if you have a smaller group of youth that you’re looking to impact, you also have the power to kick off these conversations all by yourself! Here’s how to do it:

1. Help them connect

We say career exploration starts with conversation. But actually, even before the conversation, you have to start with a connection!

Over the years, we’ve connected young women interested in STEM with established trailblazers in those fields, brought transitioning military veterans together with fellow vets who’d found their next purpose, and matched college students with alumni who wanted to help the next generation of grads.

We’ve seen impactful conversations between near-peers — high school students and recent grads who gave them advice on choosing a postsecondary path. And conversations between people at totally different places in life — middle school students who had no idea what they want to do yet and people 30 years into their career!

The point is, there’s no formula for whom a young person should interview. But you do have to start with that connection. Whether it’s a common experience, identity, hurdle, question, dream, or interest, the connection is what will make the conversation really resonate.

For young people who are just starting their career exploration, finding a common interest is a great place to start.

Have them identify a favorite class, a hobby, the kinds of things they like to read about, or even what they search out on YouTube. This will be their starting point!

2. Encourage them to explore

From there, encourage them to do some Googling. Young adults who love writing may dream of becoming an author, but have they thought about paths in speechwriting? Ever heard of UX writing? Considered writing for social media?

An easy way to help them broaden their lens is by challenging them to pair two of their interests together, then find someone whose job covers both!

As they start going down these Google rabbit holes, encourage them to keep a list of names they encounter.

Whether it’s someone who’s well-known in their field, or someone they randomly stumble upon on LinkedIn, emphasize that anyone connected to their interest could be a good subject for a conversation! Over the years, we’ve found that people are generally willing to help a young person out — and if they love their job, they’ll want to share why.

3. Support them as they reach out

Exploring interests and researching careers is a great start—but now it’s time to reach out and set up the conversation.

From their list of names, encourage them to find a point of contact. Depending on what they find, they can write a professional email, send a LinkedIn message, or even make a cold call to schedule their conversation!

It sounds old school, but these are skills that many young adults leave high school without developing. They may need your help at first, but once they send their first cold email or make their first call, they’ll build confidence and start exercising the communication muscles they’ll need later in life.

One great thing that’s come out of the past few years in the ability to connect with people virtually. An in-person career conversation is always ideal, but a video chat can allow for a safer meetup for younger students, and expand horizons of who young adults can connect with.

If the young adults or students you serve still feel too young to conduct outreach and career conversations on their own, they can experience career conversations through our documentaries. (We recommend starting with “Room to Grow,” which follows high school students as they interview leaders across Texas and explore different educational paths!)

Or, if you’re a teacher, you can guide your class through this process in small groups, then invite professionals to visit your classroom for a conversation.

No matter which route you take, the important thing is that you start encouraging these conversations as soon as possible. Because as we’ve seen, more career conversations=better student outcomes.

Right now, young people are growing up in a world where the workforce has dramatically contracted, expanded, and reshuffled, sometimes due to causes beyond anyone’s control. In addition, these last few years have been a time of uncertainty and isolation for students, so their vision of their future careers — and lives! — might be murkier than ever.

That’s why now is the time to encourage more career conversations — to help young people explore, dream, plan, and find new confidence in their futures. To see that reaching their own personal version of career success is still possible! As supporters, we can talk about the future of work all day — but it’s time to let young people lead their own conversation.

Roadtrip Nation is an educational nonprofit organization that wants to help everyone define their own roads in life.

To learn more about the evaluations and reports that informed this post, read our 2021 impact report: “Purpose Driven: Outcomes and Core Learnings from 20 Years of Roadtrip Nation.”

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Roadtrip Nation

Roadtrip Nation is dedicated to empowering people everywhere to build livelihoods around their interests. See more at: http://roadtripnation.com