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The Road Not Taken: Exploring Career Regret

Grappling with deep-seated feelings about the career path not taken? Here’s how to handle childhood career regret

By Jennifer Nelson

When Lori Shaw, 49, of Waxhaw, North Carolina, was a kid, there wasn't much talk about "dream jobs." "I don't think I was really encouraged to dream — it was always 'what are you going to be?' with a practical Midwest slant," says Shaw, the daughter of middle-class parents born and raised in the Midwest.

A kid dressed as an astronaut, dreaming about his future career. Next Avenue
ResumeLab surveyed 1,000 people asking if their current career mirrors their dream career as a child. Of those who say their current job doesn't match their childhood aspirations, 72% say they regret it and 67% still "dream" about their early ambitions.  |  Credit: Getty

"Going to college was solely to choose a career path that I understood would be the most likely to lead to a well-paying job," she adds.

Shaw graduated with honors from The Ohio State University, became a CPA, and spent 20 years (13 of them in Manhattan) working as an accountant, internal auditor, business manager and chief operating officer.

A Frightening Wake-up Call

In 2020, months before Covid hit, she was diagnosed with an aggressive form of breast cancer. This required her to undergo surgery, chemotherapy and radiation treatment while being quarantined with her family and homeschooling her young children.

Suddenly, she realized how short life is, and the creative career she never had was calling. "I ended up studying two of my greatest passions — interior design and gardening," Shaw says. She took online design courses and underwent a year of virtual and in-person training to earn her Master Gardener certification.

"If I'm truly honest with myself, I don't think I had any business pursuing anything but a creative career," Shaw says. "But as I remember it, that's just not how conversations went when I was an impressionable youth 35 years ago. I don't blame my parents, my school guidance counselor, older siblings or anyone else; practicality ruled."

Your Dream Job

Are you in the career you envisioned as a child? The company ResumeLab surveyed 1,000 people asking if their current career mirrors their dream career as a child. Eighty-four percent of respondents said they did achieve one of their early career goals.

"Every decision opens you up to new insights, learning and opportunity."

Of those who say their current job doesn't match their childhood aspirations, 72% say they regret it and 67% still "dream" about their early ambitions. More than half say they would trade their current career for the dream one  if they could.

Julia Korn, executive and career confidence coach and founder of The Authenticity Guide, an individual, group and organization leadership and coaching program in the Raleigh-Durham-Chapel Hill area of North Carolina, says she hears sentiments of regret from clients a lot, "but wrong and right career decisions aren't real."

"Every decision opens you up to new insights, learning and opportunity," says Korn.

When the Dream Job Detours

Some people find their careers on a road that parallels the path they wanted to travel as a child. Chris Purvis, 45, of Los Angeles, dreamt of becoming a professional race car driver.

"I was captivated by the thrill of speed and the excitement of competitive racing," he says. "However, as I grew older, I recognized the challenges and risks associated with pursuing a career in professional racing. Instead, I pursued a career in automotive engineering and eventually founded my own car company."

"There are lots of second careers that are possible, and people are doing it all the time."

While Purvis didn't become a race car driver, leading his company has been fulfilling, and he says he has no regrets. "I've had the opportunity to innovate and contribute to the automotive industry," he explains. "While my childhood dream still holds a special place in my heart, I'm content with where my career has taken me."

"Unless it's a Major League baseball player or a professional ballerina, there are lots of second careers that are possible, and people are doing it all the time," says Donna M. Marino, a psychologist, executive coach and trainer in Oak Park, Illinois.

"Do your homework, explore and set aside your preconceived notions," she advises. "If you decide not to take the leap, at least you will have made a conscious choice and can accept your decision. If you decide to leap, you'll know you did your homework."

Growing up, Martin Gasparian, 44, of Los Angeles, wanted to become a doctor to follow his father's footsteps as a general practitioner. Instead, he became an attorney who owns his firm.

"Professionally, I do not have any regrets whatsoever as my job as an attorney allows me to help people struggling with various legal challenges," Gasparian says, adding that he loves his job and is happy with how his career turned out.

Satisfying Work and No Regret

"Working as a doctor is a good profession that helps people directly," he says. "However, throughout my career, I felt that being a doctor was not my calling and I couldn't handle the years of training needed to qualify. . . . even if I go back in time, I would still be a lawyer."

As people enter the second half of life, it is only normal for them to question their choices, Marino says. "Our careers take up at least a third of our waking hours for most of us, and for many even more, so it makes sense that we would turn our attention in this area."

If you are unfulfilled or unhappy, it may be time for a change. "That change could be a new career, or it might mean a new role or a new company. It could also mean a new hobby or something completely different," Marino says.

John Ramstead, 57, of Denver, grew up wanting to emulate his father and grandfather, who served in the military. "Inspired by their service, I dreamt of flying Navy jets," he says. "And yes, watching 'Top Gun' definitely added fuel to that fire."

Dream Achieved, and then Lost

With a Navy ROTC scholarship in college, Ramstead achieved his childhood dream. "I worked hard, made it through, and got to fly the F-14 Tomcat — every bit as cool as it sounds," Ramstead says. But four years later, life threw him a metaphorical curveball — in the form of an actual softball that hit him in the eye and left him with nerve damage, ending his flying career.

"Shifting from military to civilian life was tough," he says. "The sense of purpose and community I had in the Navy was hard to find."

Eventually, Ramstead found his second calling in leadership and team development, becoming an entrepreneur, executive coach and consultant.

"Turns out, helping others succeed in their careers gives me a sense of purpose that's just as strong as what I felt in the Navy," says Ramstead. "Life's about adapting and finding new ways to fly, even when the original plan doesn't work out."

Ideal Job Accomplished

Some people do pursue their dreams. Erin Mann, 41, of Warrenton, Virginia, wanted to go into the FBI because her dad worked there. "I went to college, even got my master's and immediately went into the FBI as an Intelligence Analyst on counterterrorism and counterintelligence missions," she says.

Mann spent 15 years there, but decided to retire early from the FBI after her son was born. While caring for him during a health crisis, she started making elderberry syrup. "I now nationally sell all of my 25 handmade elderberry and aronia themed foods," she says. "I also opened my first retail store two years ago." This year is Mann's fifth entrepreneurial anniversary.

"To go from bad guys to bad germs was never the plan, but . . . apparently, I have an innate need to help people, regardless of what that looks like. Would I change things? Not in a heartbeat," she says.


Jonathan Hartley, 41 years old, of Milton, Massachusetts, remembers arranging stuffed animals in a "sharing circle," playing therapist and doling out advice as early as age five. "I felt such joy even then empowering others through listening." No surprise he's a professional relationship coach and is living his childhood dream career.

"Life's about adapting and finding new ways to fly, even when the original plan doesn't work out."

"What's hilarious in hindsight is how seriously I took those sessions — asking Mr. Bear deep questions about why he felt angry when his friend Chewy took his picnic basket treat," Hartley says. "I'd furrow my brow hearing their plush problems, so determined to facilitate reconciliation."

"I suppose such pure conviction to emotionally rescue toys foreshadowed my current vocation," he adds. "Now, beyond plushies, I get to daily change real lives and hearts."

Shaw, the ex-accountant who had a wake-up call about a more creative career, now runs her own solopreneur business as an interior designer specializing in vacation home design. "I work with clients all over the U.S.," she says, "and I also happily take on a few landscape design clients locally each year and make sure to set aside plenty of time to have my hands in the dirt around my own yard."

It's Never Too Late to Change Careers

Korn, the executive coach, says that if you could go back in time knowing what you know now, you may have made a different decision — or not. "You made the best decision you could at the time with the information at your disposal."

If you do try a career do-over, ask yourself questions like:

  • What are the pros and cons of switching careers?
  • What have I learned in my past career that I can carry forward?
  • What does my gut say?
  • Can people I love and trust help with the decision?

Before Jumping, Know Where to Land

"A career jump can be exciting, but make sure it's what you really want first and that you have thought it through. Otherwise, you will bring those same feelings [of regret] with you to the next career," says Marino.

"I will, without a doubt, urge and support my kids — now and as they get older — to pursue what lights them up," says Shaw. "I will ask them, 'If you were dreaming about the best work in the world for you, what would that dream look like?' And I will do everything I can to steer them straight toward those dreams."

It's also never too late to ask yourself.

Photograph of Jennifer Nelson
Jennifer Nelson is a Florida-based writer who also writes for MSNBC, FOXnews and AARP. Read More
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