Make regrets a thing of the past

Woulda, Coulda, Shoulda.

So many people have regrets: If only I had taken (or not taken) that job. If only I invested (or didn’t invest) in that. If only I had gone (or not gone) to grad school. If only I married (or didn’t marry) that person.Yes, it’s usually good advice to stop beating yourself up and start moving forward. But what if you can’t stop yourself from wallowing in regret?  Perhaps one of these might help:

Might you still be able to do it?

A client with a bachelors and masters in creative writing, who’s still living with her parents regrets not majoring in marketing. Now she’s 40, still living with her parents and has averaged making just $20,000 a year, mainly temp work. When I asked her about going back for a degree in marketing, she said she’s scared that she’s forgotten how to be a student and that it could take her twice as long as does other students. I said, “You could be right but how about taking one marketing course and then reassess?” She got an A- in Intro to Marketing and has just enrolled in the second semester of that course.

Another client had decided to break up with a guy because he wasn’t making a reliable, middle-class income. It was 20 years later and she still had not found someone she cared as much about. She looked him up but alas, he was married. But he set her up with a friend of his who is similar to him. They’re now on their fourth date.

Another client keeps kicking himself for not having pulled the investment trigger. “15 years ago, I was saying Amazon couldn’t miss. The stock was 10. Now it’s 330!  I was thinking of buying a house in 2000 but I chickened out, thinking, ‘How can people afford a house that costs $200,000?! ‘ Now that house is worth $300,000! I could have made a hundred thousand dollars without lifting a finger!” I asked, “How optimistic are you now about Amazon’s future?”  He said, “I’m optimistic.” How about the price of housing?” Not so optimistic. Should you invest in Amazon now?” He just opened a Sharebuilder account and his goal is to buy one share of AMZN every month.

It might not actually have been a mistake.

A client quit a job as a medical researcher at a prestigious university. He regrets it, feeling he would have made a bigger contribution had he not left to become a social activist. But when I probed, he admitted that he quit not just because of “social consciousness” but because he was becoming aware that he wasn’t as smart or driven as the successful researchers. Deep down, he left mainly because he believed he’d more likely be successful in a less demanding arena.

Another example: Many people regret not starting their own business. A client said, “I had the idea of opening a pizza-by-the-slice place before there were any in town. Now there are three and two are very successful. If only I had had the guts.” On probing, the main reason he didn’t do it is because of its lack of status: “I’d have a hard time feeling good about myself, with a masters degree, and only running a pizza shop.”

A final example. A client had applied to law schools but was accepted only to a third-tier one and so decided to forgo law. Not thrilled with his current job as a banker, he was toying with going back to law school. But I showed him surveys finding that lawyers are among the most unhappy professionals. Indeed, one survey found law to be America’s #1 most unhappy profession. Also, I reminded him that people’s unhappiness is often intrinsic to them so his misery might–after all the cost and time of making a career change–travel with him to his new career. He decided to put away that dream that could turn out to be more of a nightmare. Instead, we’re working on his finding a better position within his current career.


After a brief exploration of whether it’s too late to undo your past mistakes, it’s usually wise to, instead of looking back yet again, forgive yourself and, yes, take the next step forward.

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Named the San Francisco Bay Area's "Best Career Coach," Marty Nemko has been career and personal coach to 4,500 clients and enjoys a 96% client-satisfaction rate. The author of seven books (250,000 copies sold) including How to Do Life: What They Didn’t Teach You in School plus over 2,000(!) published articles, including on where he also writes, Marty Nemko is in his 26th year as host of Work with Marty Nemko on KALW-FM (NPR-San Francisco.) He was the one man in a one-man PBS-TV Pledge Drive Special. Marty Nemko holds a Ph.D. in educational psychology from the University of California, Berkeley and subsequently taught there. He is married to Barbara Nemko, the Napa County Superintendent of Schools. They have one daughter and one doggie: Einstein, whose name is false advertising: He's dumb as dirt but sweet as they come. The archive of Marty Nemko's writings and radio show plus an active blog and Twitter stream are at