How to have fewer regrets about your career

• Professional regret is inevitable over the course of your career, even if it's not long-term.
• Experts say it's important to grieve career regret, but in reality, there are chances for do-overs.

Scott Wain knows something about professional regret.

After graduating from college in 2000, he got an entry-level job in car sales, and by his mid-20s, he was earning six figures as a sales manager at a Honda dealership in London, Ontario. Life was good.

But by 2008, Wain was restless. He quit the dealership to start a software company. The company eventually went bust, and Wain spent the next decade moving from job to job, industry to industry.

Recently, he learned the old dealership had been acquired by a Canadian automotive group for an undisclosed sum of money and that Wain's former colleagues, including some he trained, walked away with millions.

"They don't have to work another day in their life," said Wain, who's in his early 40s. "I don't dwell in the past. I have a beautiful family, and I live in a nice neighborhood — but it's easy to look back sometimes and think, woulda, coulda, shoulda."

Professional regret — whether acute or chronic — is inevitable over the course of your career, and it can come from just about anywhere, at any time: the path not taken or the money-making opportunity that got away.

According to a 2021 survey of older millennials conducted by The Harris Poll on behalf of CNBC, nearly half respondents said they wish they had chosen a different path when they launched their careers.

"Most of us have imagined every now and then that our current situation could be better if we had taken a different direction," said Ricardo Rodrigues, a senior lecturer in human resource management at King's College, London, who has studied career regret. He added that, "the pandemic has heightened all of our sense of uncertainty and wondering."

Indeed, three years into the pandemic, which has compelled millions of workers to quit their jobs in record numbers, many people's sense of malaise has only intensified. For some, quitting was the answer. For others, it was a source of disappointment. A survey published in Janaury of 825 employees conducted by Paychex, an HR and payroll services provider, found that 80% of those who quit regretted their decision, including 89% of Gen Z respondents.

At a time when the American workforce is burned out, employers must look out for their workers, and workers must look out for themselves. Career regret is linked to anxiety as well as employee dissatisfaction, disengagement, and turnover.

"People need to regularly reflect on what they want — their key values and goals," Rodrigues said. "And employers need to support people with mentoring and engaging in conversations about careers goals and ambitions that go beyond the organization."

'You need to forgive yourself'

The difference between career regret and run-of-the-mill career disappointment is that the root of regret stems from a decision you made, as opposed to one that was made for you. A career disappointment is the job you didn't get; a career regret is the job you walked away from and can't get off your mind.

Money and family are often at the core of these decisions. They were for Alan Lemire, 59, who still thinks about the "dream job" he turned down six years ago.

A photographer and avid cyclist, Lemire applied to be the first on-staff photographer at Specialized Bicycles. The job entailed in-studio shoots as well as travel to events like the Tour de France. The hiring manager told Lemire his experience and knowledge put him at the top of their list.

But the pay wasn't enough for Lemire's wife to stop working as a retail executive if they were to move to Morgan Hill, California, for the job. "I couldn't be selfish and say, 'This is something I've got to do,'" Lemire said.

Today he works as a freelance photographer, and sometimes he gets envious watching photographers at cycling events on TV. But he said he won't let his nostalgia take away from the "meaningful advancements" in his wife's career that balance out his regret.

"It's not that I think, 'Life sucks,'" he said. "I just wish I had a crystal ball to see what could have happened."

Scott F., who asked that his last name be withheld but is known by Insider, also wonders what his life could've been like. He grew up with a single mother in a working-class family, so money was always tight. As a teenager, his passion was photographing punk-rock bands; he enrolled in community college to study photography. But he soon realized that he wouldn't make much money doing what he loved.

Today, he has a business buying and selling retail items online. Even though he found the financial security he's always wanted, Scott, 46, said he regrets that he was always focused on money and not on having a more fulfilling life.

"If I had gone and pursued photography, I would have most likely been in a much better place than I am now," he said. "I would make a lot less money, but I would've been around more people and had more friends."

Self-flagellation is a natural response to regret, but it's not healthy, said Anne Genduso, a career coach in the Washington, DC, area. "Regret implies that you did something wrong. But you need to remember that you made decisions based on what you thought would serve you well at the time," she said.

"You need to forgive yourself."

'In reality, there are plenty of do-overs'

It's important to grieve career regret, experts say. Write a letter to your past self. Cry if you need to.

"Try to let go of what you did not get to do but not catastrophize to the point where you start concluding, 'game over,'" said Ron Carucci, the cofounder of Navalent, a leadership and consulting firm and the author of nine books, including "To Be Honest."

"The narrative in your head is: 'You blew it,'" Carucci said. "But in reality, there are plenty of do-overs."

Gina Farran, 30, knows this well. As a university student in Lebanon, Farran planned to become an architect because that's what her father wanted. But after attending her first architecture lecture, Farran called her parents to tell them her heart wasn't in it.

After college, she moved to London and joined the investment bank Goldman Sachs, hoping once again to please her parents. But the punishing hours made her miserable. "This desire to break away started bubbling under the surface," Farran said.

In 2019, after five years at Goldman, she quit. She launched Glaize, a direct-to-consumer nail art brand, the following year. "I regret I didn't leave earlier," she said. "The regret is partly cultural because I knew that my parents wouldn't necessarily understand that I was leaving a very secure, well-paid job to do manicures."

But even if Glaize fails, Farran said she's happy that she left a career she didn't love to start a business that she believes in.

If career regret is gnawing away at you, some introspection is in order, Carucci said. The question you need to ask yourself is: How outsized is your regret relative to where you are in your life now?

Reflect on your values, goals, and what you want out of your career. Then think about how you might channel your regret into action. You don't necessarily need to take a cue from the tens of millions of Americans who are quitting their jobs — which could in some sense be seen as a massive, preemptive strike against career regret.

Instead, start small. Conduct informational interviews with people in jobs like the one you wish you had; explore possibilities of how you can devote more time to your side project. Don't squelch the regret, but don't be rash, Carucci said.

"Face forward," he said, "and decide what you can optimize for now."