A surprising joy of career coaching is learning about my client’s fantasy lives.

Okay, not those kinds of fantasies.

But sometimes clients throw me a big ol’ wild card by sharing their fantasy job.

“Tell me about your career long term, what would it look like in an ideal world,” I might say.

“Well, I’d like to parlay my experience in in-house marketing into a role at firm…” they say, trailing off a bit.

“Okay,” I say sensing there is something more.

“Actually…can I tell you what I really want to do?” they ask.

“Absolutely!” I say.

“I really want to open a bed and breakfast in the mountains where I used to vacation with my family when I was younger. I know it sounds a little crazy, but I’ve always thought I would end up there. I even have a a bunch of Pinterest pages focused on how I’d decorate the bedrooms. It’s an homage to the late 70’s & early 80’s.”

And suddenly, I’m right there with them. I can see the quaint inn, the eccentric clientele, the fall leaves turning yellow, red and orange. It’s almost as if I’ve been there before myself.


Lauren Graham plays the owner of a historic inn in “Gilmore Girls”

Many of my clients have revealed their fantasy jobs in a similar fashion. They include:

  • Restaurant/Bar Owner or Baker
  • Novel or Screenwriter
  • Retreat Center Founder
  • Yacht Captain
  • Ceramicist
  • Musician

I’ve come to call these: Rom-Com Dream Jobs

Ali Wong plays a celebrity chef in “Always Be My Maybe”

  • The pastry chef who is making perfect choux a la creme with a bit of flour dusting their nose.
  • The community-center manager who sweats through their t-shirt while joyfully playing basketball with a bunch of kids in a park.

These jobs feel so familiar because they are one of the most common tropes of the romantic comedy film and television genre. Where all love interests are (inexplicably) architects and all main characters have charming, quirky, low-stake jobs with great colleagues.

Like the cinematic trope, my clients’ “Rom-Com Dream Jobs” are usually low stress and low stakes. Though these jobs aren’t usually well paid, they offer other benefits instead: novelty, ease, community, belonging, purpose or an outlet for creativity. And the fantasy roles I hear about in coaching, usually present a stark contrast to a person’s current role. For example, a busy high-powered corporate consultant who wants nothing more than to write historical fiction in a cabin. Or senior administrator at a University who wants to own a bar down by the ocean.

Jessica Williams Makes 'The Incredible Jessica James' Incredible

Jessica Williams plays a children’s theater director in “The Incredible Jessica James”

While my clients may struggle to figure out their next career steps, their “Rom-Com Dream Jobs” are so vivid you can almost taste them.

(Want to know my Rom-Com Dream Job? Read to the bottom of this email.)

Okay, so maybe “Rom-Com Dream Job” sounds a bit trivializing – I mean isn’t it possible to open a successful Bed & Breakfast or find that perfect international teaching position in Thailand?

My answer: Sure!…but not necessarily.

I have found that “Rom-Com Dream Jobs” contain valuable information for anyone who is exploring career change. The contrast between the fantasy job and the reality job is often a first clue to what a person is missing and/or longing for in their career. Things like: shorter hours, a feeling of real craftsmanship, regular low-stakes connections, fun collaborative colleagues or an outlet for their creativity.

But fantasy jobs may be missing essential elements that a thoughtful career design process can also help reveal. Like, a pathway to retirement.

In the end, most of my clients do not leap head-first into their “Rom-Com Dream Job” as they initially envision it. Rather, they use their fantasy to get clear about their values, desires, goals and untapped potential. In the process, many discover new career pathways that they have never dreamed of before.

And just like that, their next steps become even more vivid than the fantasy.

Do you have a “Rom-Com Dream Job”? I’d love to hear about it.


PS. What’s “Rom-Com Dream Job”? Well, I hate cooking and can’t make pottery to save my life. But I LOVE Amy Poehler’s performance in “Wet Hot American Summer.” She sings, she crafts, she bosses people around and she sits less than an inch away from Bradley Cooper in a lot of the movie.

So my dream job is: Camp Director.

Or…maybe it’s just BEING Amy Poehler 😉

Wet Hot American Summer: First Day of Camp" Staff Party (TV Episode 2015) -  IMDb
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About the Author: Kate Cockrill

A little about me... I am a social scientist, facilitator, and professional coach. Through my business: Kate Cockrill Coaching, I support mission driven managers and directors with 1:1 career coaching, leadership coaching, team workshops, and retreat design. My clients include leaders in healthcare, education, research and social innovation.

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