Why Careers Aren’t Linear (and How to Design Yours Differently)

Most of us grew up with a very linear idea of what a career should look like. First, you decide what you want to be when you grow up. Then, you follow the steps—the degree, the internships, the entry-level job, the promotions. If you do it right, the line should carry you neatly from point A to point B.

…Right?

When the Story Doesn’t Fit

That story is so ingrained in our brains (and our hearts) that anything outside of it feels like a failure.

A gap on your résumé becomes a setback. Wanting to change paths reads like indecision. Not having enough experience in one area, or having too much in something you no longer want to do, leaves you stuck between labels that don’t fit anymore.

Even “success” (as in ticking all the boxes and arriving exactly where you were “supposed” to) can carry a quiet frustration when it doesn’t feel the way you imagined. You’ve probably heard someone say, “I did everything I was supposed to do… but for what?”

It’s no wonder so many people feel lost at different points in their careers. The expectation of a straight line leaves little room for the twists and turns of real life.

But here’s the thing: careers are not, never have been, and will never be truly linear. They have always been shaped by timing, circumstance, and the ongoing evolution of who we are. What’s different now is that we can finally name that reality, and that opens new ways of navigating our professional lives—ways that embrace change instead of fearing it.

One of the most powerful tools I’ve found for this is design thinking.

Turning to the Designer’s Mindset

Maybe you don’t know this, but designers don’t sit down expecting the perfect solution on the first try. Quite the opposite. They begin with research. They spend time observing, listening, and trying to understand the context. They make assumptions, and then they test those assumptions with small, low-risk prototypes. They learn what works, discard what doesn’t, and refine their ideas step by step.

What if we applied the same approach to our careers?

Instead of holding ourselves to the impossible standard of having “the plan,” we could allow ourselves to explore. To experiment. To try things out in small, safe ways. To use what we learn as fuel for the next move.

This is the essence of design thinking. And when applied to careers, it becomes not just a methodology, but a mindset.

Design Thinking for Your Career

Here’s how the five steps of design thinking translate when the “project” is your professional life:

1. Empathize

This is where it starts: with you. In design, it means getting to know the user; in your career, it means getting to know yourself. What lights you up? What drains you? What values do you refuse to compromise on?

Try this: sketch a simple “identity map.” Note your strengths, the skills you enjoy using most, and a few proud moments in your career so far. What patterns do you see?

2. Define

This is the moment of clarity. Designers frame the challenge they’re solving; you need to do the same for your career. Are you looking for growth? A change of direction? More balance? Because without focus, everything feels overwhelming.

Try this: write one “How might I…?” question. For example: How might I explore opportunities that challenge me without sacrificing my wellbeing?

3. Ideate

This is the fun part: brainstorming. Here you generate possibilities before narrowing down. When it comes to your career, this means letting yourself imagine more than one possible future.

Try this: list three to five career directions. Some realistic, some bold, even outrageous. Sometimes the “wild” ones spark the most useful insights.

4. Prototype

Ideas are just ideas until you test them. Designers build small models; you create small experiments. A short course, a coffee chat with someone in a field you admire, a side project. The point is to learn quickly without big risks.

Try this: choose one tiny experiment and commit to testing it this month.

5. Test… and iterate

Every prototype gives feedback. For your career, this is about paying attention to what each experiment teaches you. Did it energize you? Open new doors? Shift your perspective?

Try this: after each experiment, pause and ask: What did I learn? What feels like the natural next step?

A Massive Shift in Mindset

The real value of design thinking is the way it changes the question.

Instead of asking, “What do I want to be when I grow up?” (a question that implies one answer, forever) you begin asking, “What do I want to be next?”

This reframing, made famous by Bill Burnett and Dave Evans in their book Designing Your Life, takes the weight off the one big life decision. It acknowledges that life isn’t fixed, that we evolve, and that careers can (and should) evolve with us.

It’s a shift from pressure to possibility. From fear of failing to freedom to experiment. From the impossible task of mapping a life in advance to the much more realistic practice of taking small, aligned steps forward.

Looking Ahead

Today’s post was a first overview of how design thinking can reframe the way you approach your professional life. In the next posts, we’ll look more closely at each step, starting with self-awareness as the foundation of career design.

The main thing to take from this is: careers are not checklists. They are living projects. And like any design process, they grow stronger and more authentic the more we test them, refine them, and help them evolve.

So if you’re not “there” yet, that’s okay. You don’t need to be. It takes time to explore, to learn, to shift direction—and that’s part of the process.

In the meantime, remember: you don’t have to figure this out alone. If you need support, a sounding board, or simply someone to explore possibilities with, I’m here.

Love, Caro.