Think Career Change Is Hard?

career change is hard

Do you think career change is hard? Most people do. So they make career change a lot harder than it needs to be. Because they think it’s about figuring out what they want to do and how to get there.

They focus on external questions:

  • What do I want to do?

  • Who do I need to talk to?

  • What are the right roles and organizations to target?

If you’re trying to make a meaningful career change, these are the wrong questions—because they jump straight to the end and skip over all the good stuff, including finding the career options that fit YOU.

Career change is MUCH EASIER when you ask the right questions.

Start with Who You Want To Be

The right questions are deeper and more fundamental: Being honest with yourself about who you truly want to be in the world and the impact you want to make. And then addressing what’s really getting in the way of your being that person.

Think about it. Most people don’t say, “I want a career in middle management in the Finance industry,” or “I want to be a Senior Data Analyst.”

They say things like,

  • “I want to lead—truly lead,”

  • “I want to honor the CEO side of myself and the creative side,”

  • “I want to feel seen and valued for my true strengths.”

Sure, I guess those answers could lead back to being a Senior Data Analyst. But they also lead to so many other potential directions worth exploring.

Once you answer the deep questions about who you are at your best and what you need from your environment to truly BE that person, the external answers follow. And most of the external answers are far simpler than people imagine.

Are you surviving or thriving?

Career change is hard for a lot of people because they expect everything to magically change for the better just by changing their job title or industry or income.

Of course changing some externals (working from home!) can be a massive step in the right direction.

But focusing solely on the external elements can be a massive rearranging of the deck chairs that doesn’t address the root cause.

The answer isn’t landing in that magical destination where you never have challenges and everything’s always amazing.

The answer to true career fulfillment and happiness is about seeing opportunities regardless of what’s happening around you. It’s about being so in your element that the work doesn't really feel like work (seriously). It’s about feeling confident and authentic in alllll your interactions—whatever and whoever comes your way.

Coaching people during a pandemic has been a fascinating exercise.

What has pleasantly surprised me is how so many of my clients are thriving.

It’s not for lack of adversity. They’ve dealt with increased workloads, lockdowns, and wildfires. Some unexpectedly lost jobs. Some quit sooner than they’d anticipated.

But they learned to move through challenges and not let them impact their trajectory.

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One of my clients launched her new wedding & event planning business right as the pandemic hit. She could have panicked and retreated.

Instead, she reaffirmed her commitment. She pivoted to done-for-you party at home packages and COVID-safe events. She leaned in to her resourcefulness and creativity to help people celebrate life’s special moments safely, sustainably, and inclusively. She immediately got new leads, clients, and potential partners.

And of course, she put her values front and center on her website. 💕 #LifePurpose

Her career change was so much bigger than figuring out what she wanted to be when she grew up. It was about gaining the confidence in herself to navigate and thrive in an unprecedented situation.

Learn more about her career success story.

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Another client shares how she’s taken her career from “fine” to “thriving.”

She got promoted, is feeling more supported professionally than ever, and says her momentum is accelerating. A year later, she changed organizations and more than doubled her income.

She’s recently up-leveled her career again AND joined a graduate degree program.

All because she did the work to get clear on who she is at her best and continually looks for the people and opportunities aligned with that.

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A third client is on such a roll, she and I have worked together twice. After we first worked together, she co-founded a start-up (a totally different career path than what she’d envisioned when we started, btw.)

She then made her next big pivot point—launching a solo start-up. Some of her old fears and stories came up that made her question where to go next.

But it didn’t take her long to reconnect with powerful answers about who she is and wants to be as a leader and human:

An innovative voice in the FinTech industry, a role model for women and the communities she serves, and a leader committed to keeping her passion and vision at the heart of the decisions she makes for her career, family, and self.

How freakin’ powerful is that?!

The more she looked inward, the clearer her external steps have become.

She’s since secured her first round of funding and has been on a hiring spree, expanding her team to meet the demand.

Honestly, I can’t keep up with all their success. Because in connecting with themselves and what they truly want, the opportunities keep coming.

Career change is so much more than a job title

All these amazing women were willing to do the right hard work to figure out how to show up everywhere as their most powerful, authentic selves, regardless of the circumstances.

That work continues to pay dividends far beyond any one career move.

They still encounter fear and uncertainty, but they now have the confidence to navigate it—because they’re connected to their deeper life purpose.

They focused first on themselves, and the externals flowed from there.

They learned to take smart risks because they have big visions and trust themselves to get there.

They continue to reach new levels and see new opportunities.

You can hear more career success stories in the video playlist below. Binge them all, and leave your favorite takeaways in the comments.

Ready for MORE in your career and want some inspiration? Whether you're looking to change careers, step into more leadership & influence, or simply upgrade y...

Career change is hard because we don’t ask the right questions

Are you ready to ask the right questions about your career change?

The truth is most people don’t want to face these questions.

It’s why so many people think career change is hard. They’re looking out there when the answers are in here (pointing at your beautiful chest cavity, my friend).

Those are the people that continue to jump from job to job (or languish in one). They’re still not happy. They’re still not fulfilled. And they continue to ask the wrong questions, do the wrong hard work, and get the wrong answers.

The right answers come from doing the work to first know, trust, and believe in yourself.

Many of us hear that voice. That voice that says, “Is this all there is?” That voice that says, “I’m capable and ready for so much more.” The voice that says, “I can’t not be the person I was put on this earth to be.”

The hardest part of career change is listening to that voice. Most people don’t.

Career fulfillment isn’t a destination; it’s a daily journey, fueled by a series of deep personal questions

Career change is hard. Ish. ;)

It’s hard to face your fears. It’s hard to commit to your wildest dreams.

But that’s what it takes.

A lot of people say they have more potential but few are willing to do the right hard work.

True grit and resilience isn’t about muscling your way through.

That’s the same grinding energy that leads people to settle for “one more year” in a career that doesn’t fulfill them, doesn’t pay them what they’re worth, and doesn’t honor their strengths.

Career change and fulfillment is about connecting daily to who you are at your best, then using that to create what you want in your career and life.

Still think career change is hard? I hope you’re seeing it’s MUCH EASIER than you think. It all depends on the quality of your questions. Ask better questions, get better answers.


If you’re ready to go after the career and life you want now, here’s a question to get you started:

Zoom yourself forward to a year from now. Imagine you have everything you want. What do you see?

Write it out and email it to me.



Author Bio: 

Before becoming a coach, Caroline worked in management consulting and financial services. She's made it her mission to help people grow, contribute, and get wherever they want to go.

She’s also a tennis fanatic, aspiring Minimalist, FIRE (Financial Independence and Retire Early) enthusiast, and Aloha Spirit seeker 🤙. She loves to share stories from her unconventional life and career focused on freedom, creativity, fun, health, family, and community. If she can do it, you can, too.

Caroline wants people to recognize how much power they truly have to define their careers. The life and career you want is possible once you know the right steps. Take the first step by downloading your free career roadmap.