Career Clarity and Transition
It takes time to sound like yourself
Where preparation meets improvisation
Martino Pietropoli on Unsplash
“Man, sometimes it takes you a long time to sound like yourself.” — Miles Davis
Though I’m not a Miles Davis devotee, I love this quote. On one level, he was talking about mastery. It takes years of study, practice, experimentation, mistakes, and refinement before you develop your own voice.
But there’s another truth here: it takes time to sound like yourself because it takes time to understand yourself.
And it’s the people who sound like themselves who tend to resonate most.
I see this all the time with coaching clients. Many are accomplished professionals with ten, twenty, or even thirty years of experience. Yet when it comes time to network, interview, or explain why they’re pursuing a new opportunity, they often struggle to tell their story. Not because they lack relevant experience, but because they haven’t yet made sense of it.
They can walk me through every role they’ve held, every promotion they’ve received, and every project they’ve led. But when I ask questions like, “What’s the throughline across your career?” or “What do you want people to understand about you?” the answers are often less clear.
The challenge is rarely about experience; it's identifying the throughline that connects it.
At some point, you need an editorial lens—to get clear on what you’re looking for, what you’re not, and how your experience connects to the opportunities you’re pursuing. You need to distill years of experience into a narrative that helps others understand who you are, what you bring, and where you’re headed.
I recently worked with a client who hadn’t interviewed in years and worried that her experience wouldn’t resonate in today’s market. What ultimately made the difference wasn’t a perfectly crafted set of interview answers. It was understanding the throughline of her career—what she did well, the challenges that energized her, the impact she delivered, and what those experiences suggested about the right next step.
In senior-level interviews, she wasn’t simply answering questions. She was bringing perspective, judgment, and pattern recognition the hiring team didn’t yet have. She sounded thoughtful, authentic, and confident.
And she got the job.
Not because she had memorized the right answers, but because she understood the story she was there to tell.
Great jazz musicians don’t simply walk onto a stage and improvise. They know the music, the theory, and their instruments. They’ve spent years honing their craft. The improvisation is only possible because of the preparation. What looks effortless in the moment is built on thousands of hours of practice.
Interviewing works the same way. Preparation means knowing your story, your strengths, what you’ve learned, and what you’re seeking next. But preparation alone isn’t enough.
The other part is the ability to listen. To understand what the conversation requires and respond accordingly.
In other words, to improvise—not because you’re making it up as you go, but because you’ve prepared enough to be fully present.
Whether you’re early in your career and still figuring out what energizes you, or decades in and making sense of the experiences you’ve accumulated, the work is remarkably similar: understanding who you are, how you create value, and how to articulate it.
Miles Davis didn’t wake up one day sounding like Miles Davis. It took years of playing, listening, and learning before he developed a voice that was unmistakably his own.
It takes time to sound like yourself. And when you’ve done that work, others can hear it too.
