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Women share their biggest career regrets

Women have plenty of regrets when it comes to their careers.

The career I imagined when I graduated from college looks little like the jobs I have held. I have yet to travel the world covering important news, publishing novels in my spare time and appearing on talk shows as an expert source on pressing matters. OK, once I was on 20/20 to discuss The Real Housewives, but that wasn’t exactly what I had in mind as an ambitious, idealistic 20-something who wanted to change the world.

I’ve had some amazing opportunities along the way for sure, but I do have some regrets, passions I wish I had followed and roles I stayed in way too long out of comfort. There’s no going back, and ultimately, I’ve been happy working as an editor and writer from my couch in suburbia instead of from international hotels. But, as I look forward and think about giving my daughter and other young women career advice, it’s always helpful to look back and to learn from others’ experiences.

So I asked other women what their biggest regrets are, and they were plentiful.

Many made choices they wish they hadn’t based on men. Sasha said, “I wish I’d had more confidence in my 20s, and I wish I’d moved to NYC out of college instead of back to Boston for my boyfriend at the time. I spent my 20s focused on marriage and babies over career… now I feel way behind. Not sure if I ‘regret’ it per se, but it definitely affected me.”

Mary gave up a career testing airport security equipment to move across the country and get married. “Granted, I’m happy with my 2nd career now, but still,” she said. “I had a job where I pretty much got paid to travel and booze it up with my coworkers… and I gave it up for a man. Never again.”

Michelle, who left her career in academia for her now ex-husband, said, “I’m back but behind!”

Others regret leaving a passion behind for more practical work. “I don’t ‘regret’ anything per se because everything led me to the family I have now, but strictly career-wise, I wish I hadn’t dropped out of NYU (where I was majoring in drama at Tisch),” said Jacqueline. “I’ll always miss acting terribly, and it’s not exactly the kind of thing you can just pick up again at almost 40 with three kids!”

April said she also regrets not sticking to her lifelong dream of being an actress. “When I had my daughter, things were so uncertain, and I just couldn’t figure out how to focus on my current situation and the world of being in the theater. And then so much time passed… and it felt (feels) too late. I don’t regret at all focusing (on) being a mama (it’s my favorite, best thing in the world), and I don’t regret finding this new career of being a writer and editor… but it’s not what I had dreamed about and worked toward for so many years. I regret that I didn’t have the wherewithal to hold on to that part of me, while still allowing myself to figure out a new path. I guess I thought both worlds were all or nothing, and now I know that’s not necessarily true.”

Others look back on advice, circumstances and not trusting their gut, wishing they could have a do-over.

“I let people convince me that social worker was a bad career, and I was not going to make any money,” said Marilley. “So I choose another one instead and never worked one day of my life with the degree I got.”

“My biggest regret is not having enough confidence after college to take chances and make sacrifices for a master’s degree,” said Jennifer. “I settled for my career choices and just wanted to pay bills. Now, 20 years later, I have the confidence and continue to look at those options. I wish I would have done it then, so I can just enjoy where I am and not wish for what could have been.”

“I regret I didn’t move to NYC sooner and get a jump on my writing career,” Kiri said. “But I simply didn’t have any money/connections, and it took me four years to save up the cash. So I did it when I could. But I feel like that left me behind.”

“I definitely regret not keeping my CPA license,” said Jeanne. “I was recruited out of accounting into sales in my late 20s and thought I would never go back. Well, life happens… children, 9/11, layoffs, recession… they all happened. A few years ago my career came full circle, and I found myself doing accounting again. Sure wish I had that license now!”

For others, it’s more about how they let jobs affect them. “I regret all the times I got caught up in petty stuff that doesn’t matter and lost sight of the long game,” said Adriana. “This year I took stock of my limited number of f*cks to give and decided to deploy them more selectively.”

The biggest regret for Kate: “Letting male bosses intimidate me.”

What are your biggest career regrets?

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