Navigating Your Career Path With Intention
For a true-to-you career, don’t climb a mountain—take a road trip.
For generations, it's been instilled in us that our career path should be a linear trajectory, like steadily climbing a mountain, always moving forward and up. We're cautioned against the risk of making a lateral move, or god forbid, taking a step back. Even staying right where we are feels like falling behind.
In 2025, though, the expectation that career growth looks like climbing straight up through job titles to the height of the company no longer holds up. In our modern world of work, not only is this type of career path less and less likely, it’s also not setting you up for career fulfillment or alignment.
So in this post, we’ll explore all of the possibilities that can open up when you look at your career through another lens, one that throws the linear path out the window.
The American Dream has reinforced the linear career path for a long time.
In a job interview somewhere along the way, well before I became a Certified Professional Coach and founded Penney Leadership, I was asked to what I attributed my "meteoritic rise" through five job titles in seven years. Me, a meteor!
The question took me by surprise because I thought the answer was so obvious. Isn't that what I'm supposed to be doing? Isn't that what I've been taught my whole life? Go to the best school. Get the best grades. Perform and climb to the top.
I grew up in a lower-middle class family in rural Vermont. My parents had technical training but hadn’t graduated from a four year college, meaning that I was a first generation college student. They ingrained deep within me that my life pointed in a linear direction—work hard, stand out, and work my way up. That was the version of the American Dream that was served at our family dinners every night.
And I did it, starting in college and taking this approach into my professional life. I remember fist-pumping in the air on my walk home when I got my first promotion to Assistant to the Director of Education (which my grandma, in Dwight Shrute style, kept calling the Assistant Director of Education). At my second organization, I started as the Administrative Coordinator and seven years and five job titles later had risen to the role of Associate Director, the organization’s #2.
I thought this was the right way—the only way—to grow my career: promotions, progression, achievement, forward progress. But a few months into the Associate Director position, when I came home crying everyday and was awake at 2am, I realized: This couldn’t be success, because success would feel good.
It turns out that the idea that your career path is defined by forward-and-up achievement is a myth—and one that keeps you stuck on a single, restrictive trajectory.
The “climbing the mountain” approach to your career path is officially outdated.
As a career coach, I've talked with hundreds of professionals across sectors and industries who are struggling to move forward in the modern job economy.
How do you navigate a job market that's marked by uncertainty and change?
How can you see (or experience firsthand) a lack of stability, layoffs and furloughs, shifts in your industry, and still have to answer the question, "What's your five-year plan?" without letting them see you sweat?
So much is out of your control, even though you’ve likely done your best to do exactly as you were told: choose a mountain to climb, get on the path, build specialized skills, put in your time, and always, always keep moving forward and up. This way of seeing our careers isn't only unhelpful and grueling—it just isn't true anymore.
We know that change is a central part of the modern economy. The Bureau of Labor and Statistics tells us that we are expected to change our jobs an average of 12 times in our lives— and those numbers are from a study of Baby Boomers, so it's going to be even more once we learn about the impacts of the pandemic and what's happening for younger generations.
For many of us, the jobs that we will have at the end of our careers don't even exist yet. So how can you even prepare for that?
It’s clear that the rules of work and career growth have changed, but our expectations have stayed the same.
We need to catch up with what's actually happening in our world and create a new model of growth that gives us a greater sense of hope, agency, and excitement for creating our own engaging and impactful career paths.
It’s time to leave behind the linear, forward-and-up career concept and trade it in for something truer to you—a career path that gives you the freedom to follow your curiosity, own your professional identity, and do work that’s meaningful to you.
What if instead of climbing a mountain, you decide to take a road trip?
We need to throw out this mountain metaphor all together. Not only is it an image that keeps us trapped, it’s not true to how the world works now.
Instead, consider how it would feel to navigate your career with all of the hope, purpose, and adaptability of a road trip, so you can create your own unique adventure and enjoy the ride.
Picture yourself in the driver’s seat of a car, navigating your career path. If you’ve been on one road for a while, to change course all you need to do is signal and turn onto a new road. You’re still you, with all of the skills and experience that you’ve built up right there with you, along for the ride. You get to take all of that with you on a new journey that picks up right where the last road left off.
Through the linear view of your career path, the only acceptable direction to move in is forward and up. Any looping back is a failure. Didn’t get to the peak you first set your eye on? You made a mistake and missed the mark.
But taken through a non-linear lens—getting in the driver’s seat of your career road trip—you can see that you don’t have to follow a well-worn, outdated, and predetermined path. You get to create your own series of stops along an adventure that is uniquely yours.
See, road trips are built for change. They leave things open to opportunity, like stopping off to see the world's biggest ball of twine or hearing about a great little spot to eat and going out of your way to experience it. Changes in direction are expected—that's where the fun is. A non-linear path is what makes for a rich adventure.
The success of the trip isn’t measured by how quickly or directly you get to your final destination. It's about all of the experiences you have along the way.
Actively navigating your career path opens up so many more possibilities.
You are a curious person who is always learning and growing. New interests will emerge, old interests will resurface, and you will make new connections that allow you to combine old interests in innovative ways.
With the road trip view, you get to take all of your experiences and skills with you—wondering about them, integrating them, and using them in creative combinations as you create your own custom career.
This view also allows you to think of growth differently—you can grow over, around, diagonally, and wide. Instead of climbing up one path, you have the freedom to explore in all directions.
➡️ You can move sideways, growing by learning a new skill set that will enhance what you do.
↗️ You can move diagonally, integrating a new perspective that broadens how you see your work.
↔️ You can grow widely and seek out a new position that challenges you in new ways and allows you to apply your talents in new settings.
On your career road trip, all of the experiences and skills you've added to your suitcase, the work you've added to your portfolio—you get to take it all with you in the backseat of your car wherever you go.
My client Alex embraced this new perspective when he was faced with the question “Where do I go from here?” A museum director and historian, he was feeling burned out but stuck on his mountain climb towards a more senior role at a larger institution. Anything else felt like a step back or sideways, until he learned to see the bigger picture—there was more to his story than that mountain.
As we worked together, he got clear on the values he brings to the table and the skills he most likes to use, and his career road trip led him to a role that lights him up in a whole different industry. He’s now directing a statewide membership organization for mental health workers, using all of the facilitation, communication, and education skills he honed through his museum work while allowing him to explore a new field he cares deeply about.
So if you feel like you've gone as high as you can, you’re stuck on one path, or you’re exhausted from climbing, take heart—there’s a different way to grow. The answer to “What’s next?” doesn’t have to be forward-and-up. Instead, you can embrace a more freeing question: “What’s possible?”
Career navigation centers what’s important to you.
To climb a mountain, you need to start with an answer: Which summit am I headed for, and what’s the “best” path there?
But on a road trip, you don’t start by plugging in a set destination to the GPS. You begin with questions: What are the kinds of places I like to visit? What do I want to see? What do I want to experience? You'll set off with some ideas, but you keep asking these questions all along the way, checking in with yourself about where you are and where you want to go.
For navigating your career, these questions could sound like:
What skills do I want to share and develop?
What kind of impact do I want to have?
What kind of work environment do I want to be in?
What am I most curious about right now?
Navigating your modern career path means continually engaging with these questions and making confident decisions in alignment with your evolving answers.
It's an iterative process: it's going to change, and it's about continually getting to know yourself and the connecting thread that runs through what you do. (For extra support pulling together the points of your career path, our free Connect the Dots of Your Career Workbook is here for you.)
Embracing this process is how you can navigate the modern job economy with purpose, adaptability, and hope.
When you get in the driver's seat and create your own unique career path, you have the opportunity to make decisions that align at every turn—and no matter where you end up, it's going to be a place that you'll want to be.
Tools for navigating your career path
Learning how to embrace your road trip career path and navigate with confidence can be a tricky shift. This kind of wayfinding is a far cry from the kind of navigation we're used to—choosing a destination, listening as an outside voice tells us what turns to make, and getting to our destination in the most efficient and direct way possible.
(Let’s be clear: I’m definitely not just talking about cars here. Think about it: how many people’s opinions do you tune into and follow in your own career?)
Career navigation is ultimately about trusting a deep sense of self. It's about understanding how to ground yourself in where you are, discern your next step, and navigate one move at a time towards your larger quest. It's about adapting to changes that come your way with purpose and resilience. It's about trying things, learning something, coming back to what you know about yourself, and repeating it all.
Instead of listening to an outside voice tell you where to turn, you can tune into your inner authority—and you can cultivate that inner authority by getting really clear on who you are, what you stand for, and what you bring to the table.
That looks like working to unearth and understand:
the WHY behind your work, not just the “what” that you do
your vision for the kind of impact you want to have
the core values that matter to you most, because whether you know it or not, they influence every decision, relationship, and work environment you’re in
your unique skill set (not just things you can do, but skills that make you feel strong)
how you show up as a leader
Developing your inner authority helps you navigate beyond the one-size-fits-all, forward and up version of success and into a custom career path that truly feels fulfilling for you.
(And for lots more inspiration and tools to take with you, download our free guide of Top Resources to Navigate Your Meaningful Career Path. It’s packed with podcasts, articles, websites, and books that we trust to help guide you!)
One more thing: your career road trip doesn’t have to be a solo journey.
These new rules require letting go of old expectations about how the working world works… but nobody’s taught you how to take back control and navigate this modern career landscape.
The good news is that you don’t have to stumble through your career one blind turn at a time! Inviting a career coach in as a partner and copilot along the way can help you find not just the next step but a truly aligned path.
To get started navigating your career with intention, our career coaching program Define Your Direction is designed just for you. This hybrid program combines self-paced content and 1:1 coaching to help you get into the driver’s seat of your professional life.
We believe that you’re made for a work life that’s meaningful and fulfilling, guided by purpose and adaptable to change. So whether you’re job searching or looking to grow right where you are, you’ll move forward with renewed purpose and energy.
