There can be a point in your career when something that once felt exciting, fulfilling, or aligned with who you were starts to feel different. Maybe you're burned out or you've reached a level of success you once worked really hard for, only to realize it doesn't feel the way you thought it would. Or maybe you've spent so long moving in one direction that you haven't stopped to ask whether it's still the direction you want to go.
Career pivots can feel overwhelming, particularly when you've invested years building experience, relationships, and an identity around what you do. Questioning your career doesn't necessarily mean you need to leave it. Sometimes it means you need to get curious about what's changed. Before jumping into updating your résumé, applying for jobs, or figuring out your next five-year plan, here are a few questions and exercises worth exploring.
1. Why Did You Choose This Career in the First Place?
Think back to when you first decided to pursue your current career.
What initially drew you to it? Was it the creativity? The people? The opportunity to build something? Financial security? The excitement of being part of an industry you loved?
Maybe you fell into it somewhat accidentally, or maybe it was something you had wanted to do since you were young. Whatever the reason, try to reconnect with what motivated you at the beginning.
Then ask yourself:
Do those things still matter to me?
Am I still getting what I originally hoped to get from this career?
Have my priorities changed or shifted in any way?
If I were starting over today, would I make the same decision?
There's no right or wrong answer here. The goal is simply to better understand how you've evolved and whether your career has evolved alongside you.
2. What Do You Actually Love (and Hate) About Your Job?
This might sound obvious, but I often find that people have a general sense of being unhappy or unfulfilled without having fully identified what's contributing to those feelings.
Try making two lists. On one side, write down everything you enjoy about your current job, on the other, everything you don't and be specific.
Maybe you love collaborating with creative people but hate managing budgets or maybe you enjoy problem-solving but feel drained by constant meetings. Maybe you love the industry itself but struggle with the expectation that you're always available.
Once you've made your lists, look for patterns.
Are the things you dislike fundamental to your profession, or are they specific to your current role, company, or work environment?
Sometimes we think we need an entirely new career when what we really need is a different way of working. That distinction can be incredibly helpful.
3. Get Clear on Your Values
Our values are the things that matter most to us and help guide our decisions.
They might include creativity, stability, connection, autonomy, financial security, growth, family, community, or flexibility and most importantly, our values can shift over time.
The things that mattered most to you at 23 might look very different at 35 or 45. A career that once felt perfectly aligned might no longer support the life you're trying to build.
Start by identifying five values that feel especially important to you right now.
Then consider:
How does my current career support these values?
Where does it conflict with them?
Which values have I been neglecting?
What would it look like to make professional decisions with these values in mind?
For example, if autonomy is one of your core values but your current role offers very little flexibility or decision-making power, that might help explain some of your frustration.
Understanding your values doesn't automatically tell you what job to pursue next, but it can help you evaluate opportunities with more intention.
4. Take Financial Constraints Off the Table (Just for a Moment)
Here's an exercise I love.
Imagine that money wasn't a factor. What would you want to do?
Would you stay in your current industry? Start a business? Go back to school? Work with animals? Write a book? Take a completely different role? Spend more time with your family?
Write down everything that comes to mind.
And here's the important part: Don't start eliminating ideas before you've even given yourself permission to consider them.
Of course, financial constraints are real. Most of us can't simply walk away from our jobs or pursue a new career without thinking about income, responsibilities, or long-term stability but that's not the point of this exercise. The point is to temporarily remove the practical limitations so you can better understand what you're drawn to. You can bring reality back into the conversation later!
Maybe your dream of opening a restaurant isn't financially realistic right now, but it reveals how much you enjoy hospitality, building community, or creating experiences for people. Maybe wanting to become a teacher reflects a desire to mentor others or do work that feels more meaningful.
Sometimes the exercise isn't about identifying an entirely new career. It's about identifying the elements of work and life that you're missing.
5. Talk to People Who Are Actually Doing the Work
One of the most useful things you can do when considering a career change is talk to people who are already doing the job you're curious about.
Not just someone who works in the same industry, but ideally someone in the exact type of role you're considering.
Ask them what their day-to-day actually looks like. What do they spend most of their time doing? What do they love about the work? What frustrates them? What do they wish they'd known before getting into it?
We often develop an idea of what a particular career might look like without fully understanding the reality of it and sometimes the parts of a job that sound exciting from the outside make up only a small percentage of someone's actual workday.
These conversations can help you make more informed decisions, challenge assumptions, and identify opportunities you might not have considered. They can also remind you that career paths are rarely as linear as they appear.
6. Ask Yourself What You're Really Looking to Change
Before deciding that you need a new career, consider whether you're looking to change your work or how you feel within your work.
For example:
Am I feeling unfulfilled, or am I exhausted?
Would I feel differently about my career if I had better boundaries?
Am I looking for a new challenge, or do I need more time to recover?
Am I staying because I genuinely want to, or because I've invested so much time getting here?
If I wasn't worried about what other people thought, what would I consider doing?
This is particularly relevant in industries like music and entertainment, where work can become closely tied to identity.
When you've spent years building a career in an industry you love, the thought of leaving or even changing direction can bring up feelings of guilt, uncertainty, or a sense that you're somehow giving up.
But the years you've spent developing skills, relationships, and experience don't disappear if you decide to do something different.
You get to bring those things with you.
7. You Don't Have to Figure It All Out Right Now
One thing I encourage people to remember is that exploring a career pivot doesn't mean you have to make an immediate decision.
You can gather information, have conversations, take a class, experiment with a side project, or simply spend some time reflecting on what you want. You can also discover that you don't actually want to leave your career at all.
Maybe you want a different role, a healthier environment, or a better relationship with work.
The goal isn't necessarily to make a dramatic change. It's to make a more intentional one.
And sometimes the most productive first step isn't figuring out what you're going to do next. It's giving yourself the space to ask what you actually want.
Exploring a Career Transition?
At In Tune Wellness, I offer executive and career coaching for professionals navigating career transitions, leadership challenges, burnout, and professional growth, with particular insight into the music and entertainment industries.
If you're considering a career pivot or simply trying to figure out what comes next, schedule a free consultation to explore whether working together might be a good fit.