I Changed Careers Repeatedly In My 20s—Here’s What It Taught Me

There is no “correct” age for you to pursue a career that makes you happier. You can always make more money, but you’ll never get wasted time back.

I Changed Careers Repeatedly In My 20s—Here’s What It Taught Me
[Photo: Thomas Barwick/Getty Images]

“I want to be a strawberry picker when I grow up!” my 6-year-old self exclaimed after a fun day at the U-pick berry farm. “Sure, honey, you can be whatever you want, as long as it makes you happy,” my parents graciously replied. But by age 8, I’d filled my room with stuffed toy dogs and issues of Dog Fancy magazine from the local library, proclaiming instead that I’d one day become a veterinarian. By 16, I knew I was meant to be a baker, and my library checkout record was short on Dog Fancy and long on recipe books.


Kids often grow out of the habit of cycling through passions and dream jobs–that’s the expectation, anyway. But my career interests continued to shift throughout my 20s–not just once but multiple times–jumping from hospitality to real estate to technology. Though some of these paths didn’t last for more than a few seasons, each position gave me a broader perspective on the world and helped move me toward what I really wanted to do. And in my late 20s, I finally ditched urban corporate America altogether to start building my own company overseas.

I’ve “started over” more times than I can count, sometimes with negative dollars in the bank, and I don’t regret it. Here’s what I’ve learned, and what I’d recommend for anybody early in their career who’s already thinking about making a dramatic transition.

Related: I’m Living Proof That It’s Time To Redefine The “American Dream”

Pursue Happiness (Right Now), Not Status

While I was switching career paths in New York, many people told me, “Don’t quit your job so soon! No one else will ever hire you.” I often felt like a failure who couldn’t keep her act together. Looking back, though, I feel empowered and happy that I didn’t spend the limited hours I have on this planet doing something that wasn’t right for me.

“Prior to my culinary journey, I was a management consultant in the fashion and luxury goods space, and a Columbia MBA,” says professional chef and entrepreneur Jenny Dorsey. “Despite the fact that my life looked great from the outside, I knew I was deeply unfulfilled on the inside. I yearned to create more, especially tangible things that would have real impact on people’s lives,” so Dorsey ditched her status-driven career and went to culinary school instead.


Related: Four Career Mistakes You Should Make In Your 20s

“There is no good time, so do it now,” she adds. “This has held true for me across any difficult transition I’ve made. The coy ability of time to make future decisions seem less formidable is something to be reckoned with, but the truth is it only gets harder, not easier. Take the plunge now, and don’t look back.”

You Know More Than You Think–So Market The Hell Out Of It

While it’s important to show commitment, sometimes your goals and perspectives change, especially when you’re just getting your feet wet in the workforce. For each new job change I made, I recast any experience from my previous role into relevant, transferrable skills in a new industry. This takes effort, but it may not be as hard as you think. Write a resume for the person you want to be, using your existing skills and successes.

And if hiring managers aren’t buying it, sell those skills directly in the job market. “I was working in PR and event planning and got tired of the hectic lifestyle and working for someone else,” says Camille Holden, founder of Nuts & Bolts Speed Training. “My boyfriend and I decided to break free and start our own business. It was a super-simple idea, really: to sell our existing knowledge and expertise. So we started an online training business that teaches business professionals how to be more efficient with PowerPoint.”

In Holden’s experience, the conventional wisdom to “skill up” by taking courses, signing up for bootcamps, and adding new credentials isn’t the only way to succeed. Even for people in their 20s, she says, “If you’re looking to start a business, don’t worry about inventing something new, but instead go with something you’re already great at. You may have to dig a bit, but there’s no use starting from complete ground zero.”


Related: How My Entry-Level Job Helped Me Become A Mid-20s Entrepreneur

Lean On Your Support System

Though I’ve had my share of naysayers about my career decisions, I’ve been fortunate to have a support system that more often says, “You should do it!” than “You’re crazy!” I’ve found that when you’re looking to make a career jump, it’s important to keep negative Nancys at a distance. Surround yourself with people who share your passion and believe in your goals–whatever they might consist of right now.

That’s especially true early on, when you might not have the most certainty about your abilities and feel that you still have to prove yourself. But over time, the network of cheerleaders who support your efforts will give you the confidence to take bigger leaps.

“I just turned 44 this year,” says Veronica Sopher, a newly minted developer who was previously a marketing communications expert at Microsoft. Going full-time into a tech role, she says, “took a lot of hand wringing, discussions with my family, and advice from close friends. Even though I knew I needed to make the change, it still felt ‘irresponsible’ to abandon a perfectly good career path and reduce our household income for my own pursuit.” But because Sopher had made significant shifts earlier on in her career, she’s learned which voices to listen to and which ones to tune out.

Related: How To Turn Your Close Friends Into Career Mentors


“The lesson is, not everybody deserves to hear about my dreams and ambitions.” Sopher has a point. It’s usually in your 20s that you learn some of your friends may be fun to hang out with on a Saturday night, but aren’t the best peer mentors when it comes to career stuff. So join a group and learn alongside others. Maybe it’s a career-change bootcamp you pay for, and maybe it’s just a Facebook group for like-minded people looking for advice and support.

Whatever type of network you tap to help you make your move, keep in mind that you’re not the only one to do this.

Don’t Cut Ties After Graduating

When I decided to start my own business, I jumped headfirst into the startup scene, making connections that helped me build my business to where it is today. Networking often feels like a chore, and when you’re new to the job market and have a bland, low-level job title, it can feel especially depressing. But pulling off significant job changes in your 20s requires some type of network, even if it isn’t the sort you build by hitting up dozens of traditional networking events.

Indeed, one of the easiest ways to turn what might feel like a crappy network into a powerful one is to keep in touch with people you went to school with. When Chris Georgiev, founder of the image-recognition platform Imagga, left the corporate world to dive into entrepreneurship, he contacted former classmates. Reconnect with some of your best university friends to see who might be a great fit for collaboration. He eventually found a cofounder with a similar dream. “I’m glad I didn’t jump into this new adventure alone.”

There’s always more money to be made–and made back if an investment doesn’t pan out–but it’s impossible to get more time. If you’re not happy today, you don’t have to be permanently stuck. Nor do you have to wait until a certain age when it suddenly “makes sense” for you to switch careers. Each day is an opportunity to try something new, explore your creativity, and build a career that you’re proud of. Don’t put it off for tomorrow.

About the author

Arianna O'Dell is the founder of Airlink Marketing, a digital design and marketing agency helping companies create digital programs that drive results. When she’s not working with clients or traveling, you’ll find her making fun gifts at Ideas By Arianna and songwriting at Outsourced Feelings.