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6 Women on the Biggest Career Mistakes They’ve Made—and How They Survived

June 21, 2018 | Filed in: Your Career

What doesn’t kill us makes us stronger, right? That’s what our mothers and grandmothers and Kelly Clarkson said, and they know everything. But that doesn’t mean we can’t learn from our mistakes. Here, six formidable women share the story of their biggest career mistake to date, from unwittingly undermining a boss to failing to negotiate on salary. How they rebounded is both educational and inspiring.

Mistake #1: Saying ‘yes’ to too many things.

“My biggest career mistake was saying ‘yes’ to everything. I wanted to be successful so badly that I would commit to revamping the company’s PowerPoint template when I had zero experience in graphic design or PowerPoint. I would offer to train new employees when I knew I did not have the proper time to commit to them. I would sit on the board of outside industry organizations and offer to plan their events, while continuing to work the normal 40+ hours a week at my actual job. It all became overwhelming, and failure at some of these tasks was inevitable. None of the sales reps I trained succeeded, because I did not spend even half of the amount of time with them that would have fostered their success. Our PowerPoint template sucked: We had to have it professionally redone, which could have just been arranged upfront. While these might not sound like huge failures, if you rack up enough of them, it’s a recipe for disaster. Now that I have learned to say ‘no’ and choose which tasks play to my strengths, I’ve grown my skills in all sorts of areas. I wish I had said ‘no’ sooner.”

—Kristi Buckholz, VP of Global Accounts at WEST Forwarding in Westlake, OH

Mistake #2: Accepting the first offer.

“It was my first job in New York City. As a young person desperate to get off my brother’s couch, it felt cheeky even to consider negotiating; I would have taken any salary if it meant being employed full-time. But, as I learned right away—when my new boss joked insensitively in front of me about always making lowball offers to prospective employees, expecting that they will negotiate up—when you don’t negotiate, you shoot yourself in the foot. The $3,000 to $5,000 bump I could have gotten would not have made a huge difference to the company, but it would have to me, and it would have set me up for higher earning potential later on. I now make it my personal mission to empower every woman I talk to with knowledge about salaries, negotiations, raises, etc.; to help them walk into those meetings armed with the confidence to demand what they deserve; and to be ready to ask for more than what they want to end up with—since most employers expect you to do just that. If we don’t value ourselves highly, no one else will.”

—Maisie Wilhelm, Director of Partnerships at Goldbely in New York, NY

Mistake #3: Playing office politics.

“I was a young manager at the time, and a very experienced leader—we’ll call him Mark—looped me in on a plan to make a big staff change, which I happened to agree with. What I didn’t like was the espionage behind the plan to remove this person, who happened to be my boss (let’s call her Angela). At the time, I felt used and overworked, putting in 60+ hours a week. In a moment of feeling overwhelmed, I told another co-worker, Dean, whom I believed I could trust, what was happening to Angela. It was a big mistake that had major repercussions, and I was left having to face both the person who believed I had betrayed her (Angela), as well as the person who tried to do the betraying (Mark).

I tried to address the situation as best I could. I immediately went to Mark and told him that I had not told Angela directly—Mark was as icy and unforgiving as you’d imagine. Oddly, Angela came to me and we had a conversation about the situation; frankly, I was shocked she didn’t try to fire or threaten me, but she seemed to understand that I had been used. She made it clear she wasn’t going anywhere and things went back to normal, though I left shortly thereafter. I never truly felt at peace with what happened until I found out Mark, who had used me in his failed coup, landed a good job elsewhere. That’s when I let the guilt go. I never again actively engaged in the direct undermining of a boss, as that never ends well.”

—Stacey Rivera, Digital Content Director of Food, Travel & Luxury at Meredith in Birmingham, AL


biggest career mistake


Mistake #4: Not speaking up.

“I’ve served as a Department Chair at a private school for the last five years. While the job itself is tremendously rewarding and I genuinely feel blessed to work with such incredible colleagues, I’ve had challenging interactions with a handful of administrators. The challenges came in the form of minimal or no support when requested, negative feedback that was confusing to me but couldn’t be clarified or supported with evidence, and a general feeling that there was some kind of mute button on me when I was speaking in meetings. I spent years being frustrated and confused by these issues; when I asked about them, I was told that I was one of the most valued members of the team and they offered pay raises to match that sentiment. I just couldn’t figure out how to reconcile the two attitudes: Ignore me and fail to support me, but pay me more?

To add to the confusion, in my work environment the line between personal and professional is razor thin, making for a minefield of awkward encounters. Last summer, at a conference, I spoke with a number of other attendees at my administrative level, expecting to get the usual ‘me too’ and ‘it’s so frustrating’ affinity. Instead, I was met with confused looks. Several people told me that my work situation sounded unhealthy. After a lot of reflection, I told my supervisors that this year is my last at the school.

Looking back on it, I have to take responsibility for not clueing my bosses in. I never directly sat down with any supervisors and said that I was unhappy and that I was going to leave if substantial changes weren’t made. I have a hard time believing anything would be different if I had spoken up, but I never gave it a chance. My other mistake was in not reaching out earlier to other people in my position at other schools. The isolation normalized what was happening in my workplace and meant it took way too long to take action. Lesson learned: Stay communicative with supervisors, and stay in touch with colleagues outside your bubble.”

—Georgia W., Department Chair in Washington, D.C.

biggest career mistake

The one benefit of mistakes? They can become valuable career lessons.

Mistake #5: Abandoning a passion project.

“I started blogging back in 2007, before personal blogs were a thing. I mostly worked on beauty and knew a small crew of other girls doing it too—it was all indie back then. Around that time, I was also trying to find full-time jobs where I’d get paid to write every day. I fell into fashion copywriting and stayed because the money was good enough to pay my New York City rent. I landed a job at a major fashion retailer, and they expressed concern over their writers working in any other capacity (personal, non-paying blogs included). I was uncomfortable hitting pause on my side project, but, being a rule-follower, I stopped blogging.

I don’t have many regrets about my career because, as cheesy at it sounds, I do believe that every opportunity has made me a better writer, communicator, marketer, brand expert, and creative professional. But allowing an employer to take away the joy of having a creative side project and the momentum of developing my own brand was one of the biggest professional mistakes I’ve ever made. By the time I left that job two years later and tried to restart my blog, I had lost momentum. I tried to rebound, but I couldn’t keep up. It worked out in the end, because as the industry evolved, I realized I didn’t want to be a professional blogger. But moving forward, I wouldn’t allow anyone else to dictate my passion projects—if I feel strongly about working on something, nothing will stand in my way.”

—Deenie Hartzog-Mislock, essay writer and full-time freelance copy director in Hudson, NY

Mistake #6: Staying put for too long.

“I received my MBA when I was 28. I was working for Equinox at the time, but I knew I wanted to change industries. Equinox was fantastic in many ways: I was able to work out whenever I wanted, my colleagues were wonderful, and I worked for the most well-known health club chain in the United States. The money wasn’t bad, either. Right after I graduated, I thought about leaving, but after looking for a few months, I decided to stay put—and I didn’t leave for five more years. In the summer of 2017, I received an offer at Lyft that I couldn’t pass up, and I finally left after over nine years with Equinox. When I look back on it now, I realize that staying at Equinox for so long made it much harder to break into a new industry. When I finally left, I had to take a step down and accept a position that was lower than management. It was the only way to move forward in a new industry. I think nailing down the industry you want to work for, as opposed to the type of job you’d like to have, is more beneficial in the long run—and I wish I had done it earlier.”

—Kat Marion, Strategic Account Executive at Lyft in New York, NY