As the ball dropped welcoming 2020, I was certain it would be my year. On paper, I had it all: CEO of my own consulting firm, with a flexible schedule and an athleisure dress code. But for reasons I couldn’t quite figure out, I was desperate for something different; something more. I clinked glasses at midnight, celebrating what I had decided to do the year ahead: undertake a series of unpaid internships at the dream jobs of my childhood.
Obviously 2020 didn’t end up working out the way any of us planned, but I still pursued my wild idea. I worked off-Broadway, for a retro fitness brand, as an art dealer and in a luxury hotel. My “What If Year” was so inspiring that I did in fact quit my day job – like 47 million other Americans in 2021 – and wrote a book about it.
Since then, I’ve been obsessed with the idea that you can make your passion your career. I launched a podcast, Quit Your Day Job, where I interview incredible people working the kinds of jobs you have on your vision board – dancer, life coach, gardener, spy – to understand what it’s like behind the scenes. My guests – over 20 and counting – are all individuals, successful in their own right, who have made major career transitions, balancing those changes among the other things in life that can complicate pursuing your goals.
Speaking to people from professors to photographers, I heard some fantastic advice on how to turn your passion into your career:
1) Start small…
When Frankie Taylor, founder of Retroglow, wanted to move into the fitness space, she didn’t quit her day job working for a non-profit – at least, not immediately. She started with little steps – getting her qualifications to teach, delivering classes with more established brands – before eventually turning it into a full-fledged business.
Lots of my guests had – or have – a side hustle that supports their dream. While some have the financial cushion to drop the metaphoric mic on their current job, for most it’s a luxury. Skye O’Neill, who transitioned from working as an editor to becoming a social media influencer, laid it out best: “It’s hard to be creative or feel like you’re following your passion when you’re just worried about money the whole time. Be prepared to have a side hustle while you start something up so you’re not just reliant on one thing to work out.”
2)…but be ready to leap when the opportunity arises
Vanessa Nadal never dreamed she would become a law professor at her alma mater, but when the offer presented itself, she took a chance: “Be open to new opportunities and jump onto them when they are exciting to you, ” she counsels, adding that you should do it “even if you don’t think that you’re necessarily the perfect person for the job.”
Taking a risk can always lead to failure, but the pay off can be immense. Shoshanna Gruss, founder of a fashion line that just celebrated its 20th anniversary recalled thinking “so I’m 21. If this doesn’t work out, I’ll be 22. But, I have to try this. There was no not doing this. It was in my gut.”
“Be prepared to have a side hustle while you start something up so you’re not just reliant on one thing to work out.”
3) A linear career path is overrated
For my parents’ generation, a steady, solid career trajectory was the dream; for some it still is, but there’s no rule that says you have to climb the next rung of the career ladder. Sometimes the right decision is to leave the ladder altogether.
Zibby Owens, a publisher, podcaster and book influencer, said that the pivots she took never made sense, until now. “Along the way I was always apologetic for my career. I felt like such a waste, like I could never really decide what to do. There wasn’t a common thread to all of it until I started this whole enterprise. Now I’m using every skill I’ve learned.”
“There wasn’t a common thread to all of it until I started this whole enterprise. Now I’m using every skill I’ve learned.”
4) Know your dream might change
Molly Taylor, a director in an art gallery, dreamt of being a fairy princess mermaid. Vanessa wanted to be a forensic etymologist. Shoshanna wanted to be Fonzi from Happy Days. Few people have kept the same dream their entire lives. Sometimes it changes – and leaning into the new dream can be the best decision you make.
Katie Locke O’Brien is a tv and film director, but started out acting, singing and dancing. She loved those things too, but as her career evolved, so did her ambitions. “Becoming a mom forced me to really make crystalline, what do I want the most, because I need to carve out something for me.”
5) Even a dream job can sometimes be a nightmare – and that’s ok
Nathalie Jordi co-owns a hotel in New Orleans, but her day-to-day isn’t always glamorous. “It’s not hosting dinner parties every night,” she says. “It’s a lot of minutiae and detail.”
Bianca Horn, an actress, concurs. “People think of opening night. They don’t see the years of training. For every job interview in a traditional career, actors get rejected 10 times more.”
Even the dreamiest job comes with its own set of headaches. But on their worst days, my podcast guests feel like they have a purpose that drives them forward. Alfonsina Peñaloza, who works for a foundation, tells us, she has “absolute clarity…I know that this is what I like to do and that I’m good at it. If I had another job, I may have more financial security but it wouldn’t fulfill me.”
No matter what your ideal career might be, waking up every day to a job that makes you feel purposeful and passionate really is the dream we all share. “I think everyone’s got innate questions,” Kedge Martin, a career coach, shares. “What am I here for? What am I going to do to make the most of this one precious life?” Following that little voice inside you, the one asking “what if?” is the first step to making your dream job your reality.
“What am I here for? What am I going to do to make the most of this one precious life?”
Season 2 of Quit Your Day Job launches on July 5th. Listen to all episodes here or wherever you get your podcasts.