Your Career Was Never Supposed to Be a Straight Line

Somewhere along the way, most of us absorbed an idea about careers that goes something like this: figure out where you want to end up, map the steps to get there, and execute the plan.

Director. VP. Business owner. Whatever the destination, the goal was to have one, pursue it, and measure your progress against it.

I followed that model for a while. And then my career started doing something the model didn’t account for: it kept changing. Not because I failed, but because I kept growing. And growth, it turns out, rarely travels in a straight line.

What I Thought I Knew at 22 #

When I graduated from college, I had a plan. I knew what kind of job I wanted: computer programming felt like the right fit, a skill-based career in a field that was clearly going somewhere.

What I didn’t know was what actually working that job would feel like.

The role was fine. The work was interesting enough. But I found myself in a basement, literally. In those days, corporations often housed their IT departments in basement offices to keep the big computer machines cool. The programmers went with them.

It sounds like a small thing. It wasn’t, for me. I needed natural light, movement, interaction. I needed to see that my work connected to something larger than the code on the screen. The basement, day after day, quietly told me something important about who I was and what kind of environment I actually needed to do my best work.

That wasn’t in the plan. But it was useful information.

How the Journey Actually Unfolded #

As I understood the business world better, I started to see more options, and to realize I wanted experiences beyond the corporate environment I’d started in.

One job led to another. Each one taught me something new about what I needed, what I was good at, and what I wanted more of. Over time, the path wound through a community college, a classroom where I discovered I loved teaching, a return to school for a design degree, freelance work, and eventually a business of my own.

None of that was in the plan I had at 22. Some of it — owning my own business — I had imagined, but the reality turned out nothing like what I’d pictured. Looking back, I’m genuinely glad about that.

Each step gave me more information about who I was and what kind of work actually fit me, and that information shaped the next step. That’s not the same as wandering. It’s navigation. But it requires a different mindset than destination-thinking allows.

The Problem With Destination Thinking #

When you treat your career as a destination, every detour feels like a failure.

A lateral move looks like a step backward. A pivot into a new field looks like starting over. Taking a contract role instead of a full-time one looks like instability. Going back to school in your 30s looks like falling behind.

None of those things are failures. They’re information. They’re the journey doing what journeys do: teaching you things you couldn’t have known before you took the step.

The professionals I’ve worked with over the years who struggled most weren’t the ones with the unconventional paths. They were the ones who measured every unconventional step against the straight-line plan they’d made years earlier, and found themselves falling short of a destination they’d outgrown.

What Journey Thinking Looks Like Instead #

Shifting from destination thinking to journey thinking doesn’t mean abandoning direction. It means holding your direction loosely enough to let it evolve.

In practice, it looks something like this:

Instead of asking where do I want to end up? — ask what does the next right step look like from here? You don’t have to see the whole path. You just have to see far enough to take the next step.

Instead of measuring progress against a fixed endpoint, measure it against alignment. Are you doing work that fits who you actually are: your values, your strengths, the environment where you come alive? Are you moving toward more of that, or less?

And when something unexpected opens up: a role you didn’t plan for, a skill you discover you love, an opportunity that doesn’t fit the plan — ask what it’s telling you about yourself before you decide whether to take it.

The path you couldn’t have predicted at 22 is often the one that ends up fitting best.

The Career You Couldn’t Have Planned #

I couldn’t have mapped my career from a college graduation stage. I didn’t know enough yet. About the working world, about what I needed, about who I actually was.

Nobody does.

The twists and turns I didn’t expect: the basement that sent me looking for something different, the teaching that clicked in ways nothing else had, the degree I went back for in my late 30s that most people thought was unnecessary — those weren’t detours from the real career. They were the real career. They were how it got built.

Your career isn’t a destination you haven’t reached yet. It’s a journey that’s already underway, teaching you things with every step you take.

If you’re trying to get clearer on what your next step should look like, the Career Freedom Framework can help you work through it — starting with what actually matters to you, not just what the plan says.