Rethinking the Straight Line Career in a Curved World

Think back for a moment. Are you doing the work you once dreamed about? The career you studied for? The path you mapped out in your 20s? If the answer is no — you’re not alone. If the answer is yes — let me ask you this: does it still fit?

In a world that’s constantly shifting, it’s no wonder so many of us are questioning whether the roles we’ve ended up in are truly aligned with who we are now. For early-career professionals, there’s confusion, imposter syndrome, and pressure to land a “real job” before you’ve even had a chance to explore. For those in their 40s and 50s, it’s often the quiet realization that the thing you built your career around doesn’t light you up the way it used to.

That’s not failure. That’s growth.

“We’re all living longer, working longer — which means we’re not bound to one identity, one passion, or one path. You get to change.” — Rob Stogsdill

We were sold a story early on: choose your major, pick a lane, climb the ladder. But what if you outgrow the lane? What if the ladder is leaning against the wrong wall? More and more people are waking up to the fact that a “successful” career isn’t a one-time decision. It’s a series of recalibrations — and the ability to redefine what success looks like at every stage is one of the most powerful tools you have.

What’s Driving the Change?

• Work has changed. Automation, AI, remote work, portfolio careers — it’s all shifting under our feet.

• We have changed. Our priorities are different. What mattered in our 20s may no longer apply.

• Clarity doesn’t always come first. Often, it comes through motion, mistakes, and course corrections.

Whether you're trying to figure out what your first meaningful job looks like — or your next meaningful chapter — the same tools apply:

✨ Curiosity. ✨ Courage. ✨ Clarity. ✨ Strategy.

“I often ask clients: what would happen if you gave yourself permission to choose again? To admit that what worked for you then might not work for you now?” — Rob

So, What If You Could Design Your Career?

Not chase it. Not fall into it. But intentionally design it — like a project, a prototype, a life that makes sense to you.

That’s the beauty of this moment. You don’t need to know your final destination to start reshaping the path.

Wherever you are — starting out, starting over, or standing at a crossroads — your career doesn’t have to be something that just happens to you. You can shape it. Pivot it. Redefine it.

All you need is the space to ask better questions. And the support to turn your answers into action.

So here’s a simple one to begin with: Are you doing the work you chose — or the work you fell into?

And if the answer makes you pause... maybe it's time to get curious again.