So, You Want To Be a Rock Star?

The paths we never take can still teach us something about where we want to go.

What your career fantasies are trying to tell you

Years ago, when working through ideas about what to do next in his career, a client confessed to me that he wanted to be a rock star. At the time, he was an economist working in private equity. This confession came as a result of an exercise I do with my clients, and one of the stipulations is that you have to take off your Very Responsible Adult Thinking Hat to do this. So he did. 

On the surface, there wasn’t much about rock star that looked particularly useful to a conversation about his next career move. It was unrealistic and very easy to dismiss as fantasy. Plus, this is the literal nightmare of most of my clients. They are afraid they just want something childish, ridiculous, and unattainable, and the sooner they buckle down and realize Life is Hard and You Should Just Suck It Up, the better everything will be. (Except they’ve already tried that, and here they are anyway.) They’re worried they have caught the dreaded “Grass is Greener” syndrome. 

For me, like the strange human I am, I trust those dreamy visions because in my mind, the dreamer and the pragmatist are good friends, not mortal enemies. There is something useful buried inside my client’s desire to be a rock star. But to harvest that usefulness, we had to allow the dream into the room and listen to it talk. 

The work this client ultimately found himself doing involved traveling around the world, standing on stages and telling stories to rooms full of people. The rock-star fantasy had very little to do with actually becoming a rock star. It was telling us something about what he wanted more of in his life: to perform, to speak, to share his knowledge and experience, to enjoy exploring the world while he worked. So many nuggets of satisfaction and fulfillment were in that dream, and he didn’t have to become a rock star to achieve it.

We are very good at being reasonable

This exercise is deceptively simple, and usually one most clients or career-change seekers have already tried: make a list of everything you have ever considered doing.

And I mean everything. I have had people put down llama farmer, pilot, supper club owner, magician, and…rock star, among many others. I kid you not. These are all highly educated people with solid six-figure incomes, children, responsibilities, etc. They are hard-working realists who are already over-achieving. They are not delusional.

By mid-career, most of us have acquired a well-oiled machine: A Very Responsible Adult Brain. An idea appears and, before we’ve had much opportunity to examine our attraction to it, we’re already assessing salary, credentials, and whether any of this is remotely realistic. If we can come up with a good reason to say no, we do. Our brains are wired to predict and create certainty, and most adults don’t pause long enough to see that a prediction is NOT a certainty. 

And even more important, a prediction about the likelihood of success or failure doesn’t leave any room for curiosity about why this idea or fantasy showed up in the first place. 

Practicality has its place, and that always (ultimately) is part of the process. But the pragmatist in me is actually the one making this argument, which I know sounds bonkers. When we employ our Responsible Adult Brains too early, career fantasies get dismissed before we’ve had a chance to understand why they appealed to us in the first place. And for people who want to do work that they are energized by, excited about, and look forward to, you actually need to mine those fantasies for the truth they contain to create that different future, the one where your work is fulfilling and energizing and feels great at the end of the day. 

The job title may be a metaphor

Career fantasies escape some of the constraints we normally impose on our thinking.

When someone tells me they’ve always wanted to own a bookstore, I want to know what bookstore has come to represent in their imagination. For so many, it’s something like, “I want more space, creativity, and connection in my life,” or, “I want to spend my days solving interesting problems with smart people.” And if you really want to own an actual bookstore, I make you go talk to 2-3 people who do so you can put your brain and your body into the position of experiencing – as close as you can get to – doing the thing you’re fantasizing about. 

When you actually hear what a day or week is like for them, does the fantasy match reality? Does your being get energized and excited imagining your life this way? Have you realized owning a bookshop means owning a small business, and your questions are more about getting feet in the door than sipping a warm beverage with a cat on your lap?

Our fantasies give form to things we may not yet have language for. We need the dreams and the experiences and the practicalities to make it all work. An occupation can become shorthand for a certain pace of life, a particular intellectual environment, a way of spending your days that feels fundamentally different from the one you inhabit now.

So the useful question isn’t necessarily: could I make this career fantasy real?

I’m more interested in asking: what is this fantasy allowing me to imagine about my life that I’m having trouble articulating any other way?

Make the ridiculous list

So, go ahead. Make the list you would never hand to a recruiter. Include the careers that make sense given your experience and the ones that make absolutely none, especially the fantasies that have persisted despite years of your rational brain insisting they’re impractical.

Then, leave feasibility alone for a moment and ask: what is it about this life that I want?  

Trust the first thing or things that come up. Don’t argue. Feel what’s true and let that answer lie on the page staring back at you. Remember and reconnect with your Inner Pragmatist: it is useful, not useless, to get underneath this question.

Take the occupation away and examine the life underneath it. How are you spending your days? What occupies your mind? What part of you gets used there that your current work leaves largely untouched?

Look for patterns. The same desire may be hiding inside several very different career fantasies, and once you can name it, you have something far more useful than a job title: you have criteria for what comes next. Remember, I’m always interested in having your whole brain involved in any questions, so the pragmatics of life (hours of the job, salary and comp, commute, etc.) all matter very much. But when we’re creating something new, we must get curious about why these patterns and fantasies and ideas and longings keep showing up.

Sometimes an impractical career idea is simply desire arriving before it has learned the vocabulary of practicality.

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If you’re trying to figure out what you want next, this is the work I do with clients: getting underneath the obvious answers and paying attention to the information you might otherwise dismiss, so that you can cut the overthinking and get to the truth of who you are and what you want. Also, my rock star guy’s name is Rich, and you can learn more about his story here.  Thanks to all my clients who give me permission to share their stories. Learn more about 1:1 Career Coaching & Leadership Development here.