Your Career Doesn't Look Like a Straight Line, and That's the Point

Have you ever sat down to prepare for an interview and felt a quiet dread when you got to the part where you have to explain yourself?

Not your skills. Not your accomplishments. You. The full arc of it. Why you went left when everyone else went right. Why you pivoted. Why, looking at your résumé, the path might seem more like a winding trail than a clean, upward climb.

If that dread is familiar, you are not alone. I hear this from accomplished professionals all the time, especially those navigating a career change or a significant pivot. They have done real, meaningful work. They have built skills, led teams, taken risks. But when someone asks them to walk through their story, something gets lost in translation. The story they tell doesn't match the person sitting in the room.

The Fear Underneath the Question

Here's what I've observed in my coaching work: the professionals who struggle most to tell their story aren't the ones without a story. They're the ones who have decided, somewhere along the way, that their story is a liability.

They look at their career from the outside, the way they imagine a hiring manager might, and they see evidence of someone who can't make up their mind. Multiple industries. A degree that doesn't fit neatly into the job title they're applying for. A lateral move here, a bold leap there. And they conclude, before the conversation even begins, that they need to apologize for it.

So they walk into interviews already on the defensive. They downplay. They hedge. They over-explain. And the very thing they're afraid the hiring manager will think, this person seems uncertain, is exactly what comes through.

Here's what I want you to hear: the problem is almost never the career path. The problem is the story you've decided to tell about it.

Are You Running Away or Running Toward?

Before you can tell a compelling story, you need to answer one honest question: Why did you change?

Not the version you'd say in an interview. The real version.

I ask my clients this because there's an important distinction between two types of career changers. Some people are moving toward something: a growing interest, a deeper calling, a version of themselves they can already see and are actively working to become. Others are moving away from something: a bad boss, a role that never fit, a company culture that wore them down.

Both are human. Both are valid. But they produce very different narratives.

When you're running toward something, your story has momentum. Each decision leads somewhere. You can point to a thread, curiosity, a value, a vision, that runs through all of it. When you're running away, the story is harder to tell, because the logic isn't in where you're going. It's in what you were escaping. And that story, no matter how carefully you word it, tends to feel thin in an interview room.

This isn't a judgment. Sometimes getting out of a bad situation is exactly the right move. But clarity about your motivation will determine how confidently you can tell your story. If you're not sure which category you're in, that uncertainty is worth sitting with before your next application goes out.

The Thread That Was Always There

Here is what I find, again and again, when I sit with clients and go through their careers together: the thread was there all along. They just couldn't see it, because they were too close to it, or because they'd spent years hiding parts of the story they thought made them look bad.

One client I worked with had a background that looked, on paper, like a series of disconnected decisions. But when we traced the through-line, we found it immediately: she had always been drawn to work that sat at the intersection of complex systems and human impact. Every role she'd ever taken, across wildly different industries, reflected that same pull. She hadn't been changing her mind. She had been evolving her understanding of how to pursue the thing she'd always cared about.

That reframe changed everything about how she showed up.

The exercise I guide clients through is simple: start at the beginning. Not the beginning of your résumé, the beginning of what you cared about. What drew you to your first role? What were you hoping to learn, prove, or contribute? And then, at each transition, ask the same question: what were you moving toward?

When you do this honestly, a thread almost always appears. It may not be a role or an industry. It might be a value, making an impact at scale, working with technology, being close to the people your work affects. But it's there. And once you can name it, you have the spine of your story.

"Changing" vs. Evolving: A Reframe That Matters

There's a word I gently push back on when I hear clients use it about themselves: changing.

"I feel like I've changed my mind a lot."

I understand why they say it. But I want to offer a different lens.

Changing implies instability, a mind that can't settle, a person who will be difficult to retain. Evolving implies something different: growth, expanding capability, a person who keeps outgrowing their current container and needs a bigger one.

Think about it this way. If you mastered one environment and then sought a more challenging one, is that changing your mind? Or is that the natural progression of someone who refuses to stop growing?

The professionals I most admire are not the ones who found their lane early and never left it. They're the ones who kept asking more of themselves, who hit a ceiling and, instead of accepting it, looked for a higher room. That is not a liability. That is a leadership quality. And it's yours to claim.

The way you tell the story matters enormously here. "I've moved around a lot" lands differently than "Each transition in my career has been driven by a growing appetite for more, more complexity, more impact, more proximity to the work I find most meaningful." Both can be true descriptions of the same résumé. Only one of them will land.

What Hiring Managers Are Actually Listening For

Here's a grounding truth: hiring managers are not trying to catch you out. They're trying to answer a question. Specifically, they want to know: Is this person going to be committed, capable, and a good fit?

When they ask you to walk them through your career, they're listening for two things:

Coherence. Does this story hold together? Is there a logic to the decisions, even if the path wasn't straight? They're not looking for a perfect linear trajectory. They're looking for a person who knows themselves well enough to connect the dots.

Conviction. Does this person believe what they're saying? You can have the most beautifully crafted narrative in the world, but if you're hedging as you deliver it, if you're apologizing between sentences, if you sound like you're confessing rather than sharing, it won't land.

This is why the internal work matters as much as the external preparation. You can practice your talking points all you like, but if somewhere inside you still believe your career looks like a liability, that belief will leak through. The goal is not to perform confidence. The goal is to actually find it, by doing the honest excavation of your own story until you can see what was always true about it.

A Few Practical Anchors

When I work with clients on their narratives, a few specific tools tend to make the biggest difference:

Lead with the constant, not the change. Start your story with the value, mission, or interest that has been consistent throughout, even if the roles and industries have varied. "Throughout my career, I've been drawn to..." is a powerful opener. It signals that what looks like variety is actually coherence around a single driving force.

Let your tenure speak. If you've spent meaningful time in each role, multiple years, not months, say so. There's a real difference between someone who job-hops every 18 months and someone who has taken big, infrequent leaps. If you're the latter, that track record is evidence of commitment. Use it.

Reframe the degree or credential that "doesn't fit." If you've taken a course, a program, or a degree in a direction that seems out of place, don't hide it or awkwardly justify it. Lean into what it shows: that you invest in your own growth, that you're willing to do hard things to get closer to what you care about, that you show up as a learner, not just a practitioner.

Be honest about what you want, carefully. There's a difference between being honest about your interests and accidentally signaling that the role you're interviewing for is a stepping stone you're already looking past. You can say "I love working with data" without saying "I want to be a data scientist one day." You can express genuine enthusiasm for the work in front of you while being a full, evolving person with continued ambitions. Both can be true.

The Story Was Yours All Along

I want to close with something I tell almost every client I work with on this:

I am not making up your story. I am reflecting it back to you.

Everything that goes into a compelling career narrative is already in your lived experience. The passions, the pivots, the reasons, the thread, it's all there. What most professionals lack isn't the material. It's the distance to see it clearly, and the permission to claim it fully.

You have been building something. Maybe you couldn't have described where it was going at every step. That's true of most meaningful careers. But when you look back, the through-line is there. The question is whether you're willing to own it, not apologize for it, not explain it away, not preemptively defend yourself against doubts that may not even be there.

Your path doesn't have to look like everyone else's to be compelling. In fact, the most interesting stories rarely do.

You have a story worth telling. Tell it like you mean it.

What is the thread that runs through your career, even the parts that felt disconnected? Take a few minutes to write it down. You might be surprised what you find.

Slow Down to Go Faster

Do you ever feel like the only way to get where you're going is to push harder?

More hours. More discipline. More willpower. If you're falling behind, the answer must be to do more — not less. And so you put your head down and grind. You skip the walk with your colleagues. You eat lunch at your desk. You tell yourself you'll rest when it's done.

I've been there. More times than I'd like to admit.

There was a season in my career when 12-hour days had become my normal. My colleagues would step outside for a walk in the middle of the day. I watched them go, but I never joined. I simply didn't have the bandwidth. There was too much to do, and taking a break felt like a luxury I hadn't earned yet.

Then one afternoon, I found myself with a 30-minute gap before several more hours of work. Something made me decide to take that walk.

I came back with a new perspective on the problem I'd been wrestling with for days. What I thought would take hours took 30 minutes. I went home early for the first time in a long while.

That walk didn't slow me down. It was the reason I finished.

What We Get Wrong About Discipline

Here's the story most high achievers tell themselves: If I just push through, I'll get there faster.

The subtext sounds something like: I should be able to handle this. I should have this done by now. Slowing down is falling behind.

These thoughts feel like discipline. They feel like drive. But I want you to consider something — what if they're actually the thing slowing you down?

Think of it this way. Imagine you're running a marathon. You've trained, you're ready, and you're determined to finish strong. Now imagine strapping a heavy pack to your back before the starting gun fires. The pack is filled with every "I should" you carry: I should push through. I should never need a break. I should be further along by now.

You still might finish. But it will take longer. It will hurt more. And somewhere around mile 18, you might wonder why you ever thought this was supposed to feel good.

The weight isn't discipline. The weight is the story you're telling yourself about what discipline requires.

What Runners Know That We've Forgotten

I'm a runner. A slow one — I'll fully own that. But I've learned something from running that I now bring into every area of my work and my coaching.

Jeff Galloway, US Olympian and running coach, has spent 50 years studying what actually helps runners finish marathons faster. His finding might surprise you: strategic walk breaks don't slow you down. They help you go faster.

In surveys of runners who shifted from non-stop running to a deliberate run-walk-run approach, the average improvement was over 13 minutes in a marathon. Runners who took intentional breaks outpaced runners who pushed through — because their bodies recovered more efficiently, their form held up longer, and they didn't hit the wall as hard in the final miles.

Over 98% of Galloway's participants finish their marathons. Not because they pushed harder. Because they learned when to ease up.

The same principle lives in your work, your leadership, and your goals.

Running With a Lighter Pack

When you give yourself permission to slow down — strategically, intentionally — three things happen.

You're more likely to finish.

Burnout doesn't announce itself. It builds quietly under the surface of all those 12-hour days, all those skipped lunches, all those "I'll rest when it's done" promises. The leaders I work with who burn out aren't lazy. They're the ones who believed they had to carry everything, all the time, without stopping. Releasing even a little of that weight — one walk, one slower morning, one week without working late — isn't weakness. It's what makes the long game possible.

You can actually move faster.

This is the part that feels counterintuitive until you experience it yourself. When you step away from a problem, your brain doesn't stop working. It shifts into a different mode — one that's better at pattern recognition, creative connection, and seeing what you couldn't see when you were deep in the weeds. My 30-minute walk didn't cost me time. It gave me hours back. This isn't a productivity hack. It's how we're wired.

You'll actually enjoy the journey.

This one matters more than we let ourselves admit. When every day is a grind you're trying to get through, you stop noticing the moments worth savoring. You stop feeling proud of how far you've come. The finish line becomes the only thing that counts, and you arrive there exhausted, already scanning for the next thing to accomplish. A little more lightness along the way doesn't diminish what you're building. It makes it worth building.

A Few Questions Worth Sitting With

I want to leave you with something to take into your day — not a to-do list, but a moment of honest reflection.

What weight are you carrying right now?

Get specific. What are the "I should" thoughts that show up most often? I should be further along. I should be able to handle more. I should already know how to do this. Write them down if you can. There's something clarifying about seeing them outside of your own head.

What would it look like to set one of them down?

Not forever. Not abandoning your standards or your ambition. Just for today — or even for an afternoon. What would you do differently if you gave yourself a little more grace? What might you notice? What might become easier?

What is your version of the walk?

It doesn't have to be a literal walk (though it might be). It's whatever gives your mind the kind of space where better answers tend to appear. For some people it's a drive with music. For others it's a slow morning before the emails start. For others still it's a conversation with someone who helps them think clearly.

Whatever it is — you haven't earned it yet is never the right reason to skip it.

You don't have to carry all of it to prove you're serious about where you're going. Real strength isn't about how much weight you can carry. It's about being wise enough to put some of it down.

You Already Know What to Do. The Problem Is Your Environment.

She came to our coaching session frustrated.

Not because she lacked ambition. She had plenty of that. She had a clear picture of where she wanted to go: leading strategy, driving vision, managing people and projects at a higher level. She knew exactly what kind of leader she wanted to be.

The problem was her calendar.

Week after week, it filled up with execution. Detailed, urgent, necessary work. And because she was good at it, more kept coming. By the time Friday rolled around, she'd already worked through the weekend once or twice that month. The high-level thinking she wanted to do? It sat on the back burner. Again.

"I know I need to change this," she told me. "I know what I should be doing differently. I just can't seem to make it happen."

The Real Problem Isn't Information

Here's what I want you to hear: she didn't need more advice.

She already had the roadmap. She'd read the books, listened to the podcasts, talked it through in coaching. She knew she needed to protect her time, delegate more, create space for strategic thinking. She knew it all.

And she was still stuck.

This is one of the most common and most misunderstood traps I see accomplished professionals fall into. We assume that if we know what to do, we'll eventually do it. That knowledge will translate into change if we just remind ourselves often enough.

But it doesn't work that way. Knowledge doesn't change behavior. Environment does.

The Antarctica Problem

Think of it this way. You can absolutely grow a flower garden in Antarctica. The knowledge of how to grow flowers is the same anywhere in the world. But the environment works against you at every turn. The cold, the darkness, the frozen ground. Every step requires enormous effort. Most people give up, not because they don't know how to garden, but because the conditions make it brutally hard.

Now imagine that same gardener in a warm climate with rich soil and plenty of sun. Suddenly, the same actions produce results. The work feels possible. Progress happens.

This is the difference between knowing what to do and being set up to actually do it.

When we struggle to act on what we know, we tend to blame ourselves. Our discipline, our priorities, our willpower. But often the real issue is that nothing in our environment is making the right action easy. And everything in it is making the old patterns effortless.

The shift happens when you stop asking, "Why can't I make myself do this?" and start asking, "What would make this easier to do?"

Start With the Loudest Voice in the Room

Before you can change your environment, you need to understand what's actually stopping you.

And most of the time, it's not logistics. It's a voice.

When you think about doing the thing you say you want to do, whether that's blocking time for strategic work, saying no to a task that isn't yours, or asking for a different kind of role, pay attention to what happens inside. There's usually a loud, immediate reaction. A thought that rushes in before you've even made a decision.

If I don't handle this, it won't get done right. I can't afford to take my foot off the gas right now. This isn't the right time. I'll do it after this project.

Those voices feel like truth. They feel urgent. They feel like they're protecting you from something.

And here's the thing: they probably are.

The Voices Were Built to Help You

I want to share something personal here.

When I was in my PhD program, everyone in my lab took a three-day ski trip. Everyone. And I didn't go.

Even then, in the moment, I knew that three days away would not derail my degree. Intellectually, I knew that. But the fear from the thought was so real, so immediate, that I stayed. I told myself I had too much to do. That I couldn't afford to fall behind. That people who succeed don't take breaks like that.

Those voices had been with me since I was a child. I had learned early that saying no to fun and yes to work was how you achieved things. How you got into a good school. How you earned the opportunities you wanted. And it worked. Those thoughts helped me accomplish real goals.

The problem is that I never went back and reviewed them.

I carried them into adulthood without questioning whether they still fit. And I operated by them automatically, the way you follow a habit you formed years ago without ever stopping to ask whether it's still serving you.

This is what most high achievers are doing. Not because they're unaware or unexamined. But because those patterns formed when you were younger and less powerful. They helped you then. And they've never been officially retired.

What to Do With the Voices

You don't have to fight them. You don't have to prove them wrong. You just have to see them clearly.

Start here.

Write down the voices you hear most often. The ones that come up when you're about to do something different, something that moves toward the leader you want to be. Don't filter. Just list them.

Notice when they arrive. Are they loudest on Sunday nights? When your manager sends a last-minute request? When you're about to decline a task? The pattern matters.

Ask what dream is paying the price. What are you not doing, not building, not becoming, because these voices keep redirecting you? Name it specifically. The more concrete, the better.

Ask whether the voice is still true. Not whether it was ever true. Not whether it made sense once. But whether it's accurate now, given who you are and what you're actually capable of.

Most of the time, when you look directly at the voice, it loses some of its power. Not all of it. But enough.

Then Build the Environment

Once you understand what's been holding the pattern in place, you can start making small, practical shifts in your environment that make the right actions easier.

This doesn't have to be dramatic.

It might mean blocking ninety minutes on Thursday mornings and treating it as non-negotiable as a client meeting. It might mean putting one strategic project on your weekly agenda before the reactive tasks get listed. It might mean naming one thing you will stop doing this month, so something else can begin.

Small things. Repeated. They create more room. And more room creates more possibility.

You are not trying to overhaul everything at once. You are trying to make the garden slightly warmer. Slightly more hospitable. So that what you already know can finally take root.

You Don't Have to Figure This Out Alone

If you're reading this and you're not sure which voice is the loudest, or you can't quite name the pattern that's keeping you stuck, that's a signal worth paying attention to.

The work of identifying these patterns is often clearer with support. Someone who can reflect back what you're describing and help you see it from the outside.

If you want a space where you can do this work alongside other accomplished women who are navigating the same territory, we are addressing exactly this in the Women Leaders Club in April 2026. You don't have to keep circling the same spot alone.

You already know what you want. You've known for a while.

The question was never whether you have the information. The question is whether your environment is built to support you, and whether the voices running in the background are ones you actually still believe.

Real strength is not just knowing the way. It's building the conditions that make it possible to walk it.

Why Your Dreams Aren't Big Enough (And What It's Costing You)

Have you ever set a goal, worked toward it, achieved it—and then stood at the finish line wondering, is this it?

Maybe you aimed for a director role and got it. Maybe you finally hit the salary number you had in your head for years. And yet, there's something quietly unsatisfying about it. Not because it wasn't real. But because somewhere along the way, you made your dream small enough to feel safe. And safe, it turns out, doesn't always feel like enough.

There's a reason for that. And there's something worth doing about it.

The Running Lesson That Changed How I Think About Goals

When I started running, a 5k felt impossible. I couldn't imagine running 10k. It seemed like something other people did—people with a different body, more time, more discipline than me.

When I started learning from experienced runners, every single one of them said the same thing: if your goal is 10k, train for 13k. Don't practice running the distance you want to finish. Practice running further than you need to.

The reason stuck with me. If you can run 13k, then 10k becomes your floor, not your ceiling. It means that on the days when everything is off—it's too hot, the course has more hills than you expected, you didn't sleep well, your legs feel heavy—you still finish. Because you've built capacity beyond what the moment demands.

Your career works the same way.

If you only aim for exactly what you want, you have no buffer. Every obstacle, every setback, every unexpected challenge threatens the goal. But when you dream bigger than your target—when you build toward something beyond what you think you need—you create reserves. Resilience. Room to still succeed even when conditions aren't perfect.

And conditions are never perfect.

Dreaming Big Isn't About the Title or the Money

Let's be clear about something. When I talk about dreaming big, I'm not talking about chasing status for its own sake. I'm not talking about a specific title or a number in your bank account—unless that's genuinely what matters to you.

Dreaming big is about designing a life that feels like yours.

It's about work that energizes you instead of draining you. It's about relationships, time, creativity, and impact—not just output. It's about waking up on a Monday and feeling something other than dread. It's about building a career that reflects the full range of who you are, not just the most practical version of yourself.

That's what's at stake when you don't dream big enough. Not just a missed promotion. A missed life.

When you consistently undershoot your own aspirations, you end up building someone else's vision instead of your own. You optimize for "good enough" when "remarkable" was always available to you. You settle into roles that fit, rather than roles that stretch you toward what you actually want. Over time, that gap between where you are and where you know you could be becomes a quiet frustration that's hard to name—but impossible to ignore.

Why Women Leaders Resist Dreaming Big

In my work coaching high-achieving women, I've noticed that the resistance to big dreams is rarely about capability. It's almost always about something else.

1. Guilt: Dreaming big feels greedy.

Many women have been raised to prioritize others—their families, their teams, their organizations. So when a bold desire rises up ("I want to run this company," "I want to work from anywhere," "I want to be known for this work")—it can immediately be followed by a pang of guilt. Who am I to want so much? Isn't that selfish?

It isn't. Wanting a bigger, more meaningful life doesn't take anything away from anyone. In fact, the more you build a life aligned with what you truly value, the more you have to give—with clarity, energy, and intention rather than quiet resentment.

2. Fear of what success demands.

This one surprises people, but it's one of the most common patterns I see. Many women are not afraid of failing. They're afraid of succeeding.

Because success brings visibility. It brings attention, expectation, more responsibility—professionally and socially. It means stepping fully into your power in a world that doesn't always make that easy for women. And so the subconscious mind does something clever: it keeps your dreams modest enough that you never have to find out what happens if you actually get there.

3. Fear of losing yourself.

Underneath the ambition, there's often a quieter worry: Will I still be me? Will my friendships change? Will people treat me differently? Will I become someone my family doesn't recognize?

This isn't just about workload or responsibility. It's about identity. It's about belonging. Stepping into a bigger, bolder version of your career can feel like stepping away from the version of yourself that the people you love have always known. And that's a loss many women aren't sure they're willing to risk.

How to Actually Dream Bigger

Dreaming big is a practice. And like any practice, it starts with concrete steps.

Step 1: Allow yourself to want what you actually want—without thinking about how.

Start with the wildest, boldest version of your dream. Not the responsible one. Not the one you'd say out loud in a meeting. The one that makes you feel a little exposed just thinking it. Write it down. Don't edit it. Don't justify it. Just let it exist on the page.

Step 2: 10x it.

Whatever you just wrote—make it bigger. Not because you're committing to it, but because reaching for 10x forces your brain out of its habitual limits. You start to see possibilities that "realistic" thinking actively hides from you. This is exploration, not obligation. Let yourself roam.

Step 3: Build your roadmap.

Now, come back to what's genuinely yours. What resonated in all of that? What felt true, even if it's still a little scary? From everything you've been exploring, identify the top three things you want to set as goals for the next two years—and what needs to happen to get there. These become your direction. Not a fantasy. A plan.

Final Thought

You've already proven you can set a goal and reach it. You've already proven you can do hard things. The question worth sitting with now isn't can I do this? It's what am I not letting myself want?

Dreaming big is not reckless. It's not naive. And it's certainly not greedy. It is the courageous act of deciding that your life—not just your career, but your whole, actual life—is worth designing with intention.

Train for 13k. Run your 10k with ease. And then dream bigger again.

This dreaming-big exercise is one we do together in the Women Leaders Club—a space where accomplished women support each other in building careers and lives they're genuinely excited about. If it sounds interesting, come check it out.