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.