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Mistakes I Made at Work: 6 Successful Women On the Art of Failing

8 minute read

Correction appended May 9, 11:35 p.m.

Nothing beats perfectionism like a whole bunch of successful women who are anything but perfect. In Mistakes I Made at Work, Jessica Bacal gathers humiliation and wisdom from women who have messed up and lived to tell the tale. Some of her contributors including writers, chefs, doctors and business consultants, assembled last week at the 92nd St Y in New York City to share their most embarrassing work stories and what they learned.

1) Anna Holmes (founder of Jezebel, editor of The Book of Jezebel)

How She Goofed: Holmes said she’s always found it difficult to ask for help, even back when she was an assistant at Entertainment Weekly. So when she built Jezebel, a popular women’s blog that mixes politics and high culture with pop culture and comedy, she became so obsessed with managing every aspect of the site that it almost destroyed her life. “My inability to delegate or ask for help made my life very unhealthy.” She described not allowing anybody to take any of the responsibility away from her because “it was easier to do it myself, I could do it the way I wanted it.” But the stress took a toll on her health and her marriage, and she and her husband ended up separating. She ultimately had to quit and hand the reins to somebody else.

What She Learned: Holmes said the experience taught her about the dangers of perfectionism, and allowed her to distinguish between “failure at a job vs. failure as a person.” She now thinks admitting mistakes and asking for help is a sign of strength. “Making mistakes is a sign of taking a risk, it’s a sign of fearlessness,” she said.

Does it ever affect her confidence? “The idea that women have less confidence than men– I don’t agree,” she said. “I think women express it differently. I think it’s powerful to admit you’re afraid. I think weakness is keeping it inside.” Besides, she says she gets reassurance from all the incompetent people out there who think they’re amazing. “In a way, people’s BS is really helpful,” she said. “I’ve met enough people who are full of it, that I think ‘if they can do it, I can do it.”


2) Dr. Daniele Ofri (Clinician at Bellevue Hospital and associate professor at NYU School of Medicine)

How She Goofed: Dr. Ofri tells a few different stories in the book about medical mistakes she’s made, but at the Mistakes book event she described a night shift at Bellevue where she mistakenly transferred an elderly senile patient to the “stable” wing without looking at his CAT scans. It was the height of the AIDS epidemic, she was overwhelmed with patients, and she assumed that this patient was just a little out of it. It turned out she had missed a massive brain bleed which could have killed the patient if he had been sent home.

What She Learned: “Mistakes aren’t this external thing, this adverse event,” Dr. Ofri said. “We make a mistake, but we are not the mistake.” She also drew a distinction between guilt and shame. Guilt, she says, is regret for a certain action. But shame is deeper and more painful; it’s the realization that you’re not the person you thought you were. The point was that it’s okay to feel guilty about making a mistake, but we shouldn’t be ashamed.


3) Gabrielle Hamilton (Chef and owner of Prune, one of NYC’s best restaurants, and author of Blood, Bones and Butter)

How She Goofed: “My greatest shames and failures have never been as an employee, they’ve always been as a manager,” Hamilton said. “It’s been in not sparing someone’s feelings when you’re letting them go. They leave and you know you’ve cost them 30 days of sleepless nights, and that’s a great shame.”

What She Learned: But Hamilton says that even as difficult as those conversations are, she’s learned to accept that they’re part of her job. “I’m bright and I’m psychologically astute and I’m a human who fails,” she said.


4) Laurel Touby (founder of Mediabistro.com, which sold for $23 million in 2007)

How She Goofed: “I usually rub people the wrong way, especially when I’m in a position of authority,” she said. When she started MediaBistro, she found herself managing a small staff of recent graduates. “I was driven to get the job done, and I just assumed my staff would figure it out.” She said that her tough management style eventually led her staff to nearly mutiny, and she had to adopt a gentler approach. “I didn’t know how to create a buffer, and I didn’t know how to behave in an office environment.”

What She Learned: She wrote in the her chapter of Mistakes I Made at Work that it’s always important to be gaining new work skills wherever you go, and to be aware of how your personality meshes with the office environment. But she also spoke about how even though she’s created a multimillion dollar media empire, she’s still vulnerable to criticism. “Even at my age, even at my job, I can be reduced to ‘this big’ by something somebody says,” she said. So that’s why she’s a fan of the “fake it ’til you make it” philosophy. “Bluff, pretend you’re on top of things, never publicly admit mistakes,” she said.


5) J. Courtney Sullivan (bestselling novelist, author of Commencement, Maine, and The Engagements)

How She Goofed: “I was a workplace Amelia Bedelia,” Sullivan said, referring to the popular children’s character who always seems to be messing up. She worked at various magazines and newspapers before becoming a full-time novelist, and once made a big mistake while she was an researcher for New York Times columnist Bob Herbert. “I got a phone call, and the person said, ‘does Bob want to meet with POTUS tomorrow?'” she said. She didn’t recognize the acronym at first, so she put him on hold. Then she went and said casually to her boss, “you don’t want to meet with POTUS tomorrow, do you?” It was only when he said yes that she realized that it was the President of the United States calling.

What She Learned: Sullivan said that as a writer there’s a constant pressure to always be performing because “we’re all one step away from being caught– and we’re only as good as our last book,” which is why perseverance is so important. “As a young writer, all you can do is keep writing, keep going,” she said. “When you’re a writer, all your mistakes are right there on the page.” She said it’s about accepting that every book will have an imperfection, and just moving past it.

6) Joanna Barsh (director emeritus of McKinsey & Company, author of Centered Leadership: A Breakthrough Program for Leading with Purpose, Clarity and Impact.)

How She Goofed: As a summer intern at a top consulting company, Barsh found herself in client’s basement at 1 a.m. going through pages of data about ad revenue. She was supposed to present the data in a way that yielded insight for the client, but none of the math was working out. So she fudged the numbers, and the clients loved it. But when her supervisor called her months later to ask how she’d come to that conclusion, she had to confess that she’d lied and made up the results. “But that wasn’t my mistake,” she said. “My mistake was that I carried the guilt of that for 30 years. Women carry things for a very long time and we’re always striving for perfection. In my case, one mistake was enough on the scale to obliterate 30 years of good work.”

And even though she was at the top of one of the world’s best consulting companies, she still had doubts about her own competence. One time a male colleague called her to ask for recommendations of accomplished women to serve on board and he said “what about you?” Barsh declined, saying she wasn’t qualified enough. Her husband said “are you crazy?” and then she had to go back to ask the colleague to reconsider her. She ended up serving on the board.

What She Learned: Barsh said she’s learned that letting that one bad decision stay with her for so long was her real mistake, because the most successful people in the business world are often the ones who have made the most mistakes. “Being a failed entrepreneur makes you more valuable in the marketplace,” she said.


The original version of this article misspelled Dr. Ofri’s last name.


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Write to Charlotte Alter at charlotte.alter@time.com