Why Millennials Already Have Career Regrets

There was a little-known third cofounder of Apple named Ronald Wayne. Two weeks after Apple was incorporated in 1976, Wayne left and sold his 10% stake in the company for $800. Now 84, Wayne lives off his social security check outside Las Vegas. Today, his shares would be worth $63 billion.

This is a millennial nightmare.

In the age of online businesses, booming tech and an unpredictable economy, millennials live with prospective regret. We wonder if chose the right course, or if we should instead try one more of another million options.

Though 90% of adults report having at least one life regret, young adults may suffer particularly high rates of regret. According to Pew Research Center, millennials are more likely than other generations to regret not getting more work experience in college and not looking for post-grad jobs earlier. They’re also more likely than boomers to say they’d have benefited from a different major.

For all generations, careers nearly top the most regrettable charts. A meta-analysis ranking regret revealed that career choices are the most common source of regrets second to education — and surpassing romance.


Research shows that we regret more in the face of opportunity. The greater the perceived opportunity, the more intense the regret. “People’s biggest regrets are a reflection of where in life they see their largest opportunities,” sums one study.

For example, regrets of inaction are more prevalent, last longer and feel worse than action regrets in part because we associate them with greater (missed) opportunity. While regretting a specific action means just one alternative — not doing it — inaction signifies a whole field of possibility (“I could have done this, or this, or this”). Regrets of inaction are “more imaginatively boundless, meaning that there is always more one could have done and further riches one might have enjoyed,” notes one study.

Careers, then, may be fertile grounds for regret due to so many potential directions. The American dream taunts us.

Millennials especially see careers as endless opportunity. Unsurprisingly, educated young professionals constitute the highest percentage of workers looking for job opportunities.

So they may be more prone to regret than other generations. Indeed, even though older adults have lived longer, their regrets tend to be less frequent and less painful than younger people’s. As “opportunities fade with advancing years, so too do the most painful and self-recriminating regrets,” one study explains.

How do we capitalize on abundant choice without regretting our decisions?

Ronald Wayne’s solution was to rationalize his decision to sell his Apple stock. “I made the best choice I could with the information I had at the time,” he said in a CNN interview. He rationalized that “If I stayed at Apple I would have probably ended up the richest man in the cemetery”; and “If I just wanted the money, I could have been rich and miserable.”

Wayne’s rationalization might sound wishful, or even dishonest. Maybe it is. But it’s also an adaptive mechanism for coping with regret and preserving wellbeing and future performance.

Robert Frost’s “The Road Less Traveled” describes this psychological process. Frost wrote the poem for his friend, Edward Thomas, who always regretted the path he and Frost took on their walks together. Thomas would berate himself for not having gone another way, wondering if the other trails might have been better.

In the poem, both paths the speaker approaches in the woods are “just as fair,” laying “equally” and worn “really about the same.” The speaker, not truly knowing the difference between them and “sorry [he] could not travel both,” chooses the second path. He says he’ll look back on this decision and sigh, believing that his less traveled path “made all the difference” in his life. In truth, both paths might have been equally fated, but we need this kind of rationalization.


Related posts