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6 Successful Women Share Their Biggest Career Mistakes

These women learned the hard way—so you don’t have to.

By Emma Steinbergs

Everyone makes mistakes. Learn from your mistakes. You have to fail to succeed. We’ve all heard these adages many times, whether in a personal or professional context.

And as someone who listens to an obscene amount of podcasts, I’ve noticed a recurring theme in interviews featuring accomplished women: they wish their younger selves knew that they would end up exactly where they are today because of their mistakes. But there’s another, smaller group of women whose stories stand out to me: those who acknowledge the fact that there is an element of luck or privilege involved in avoiding the truly negative repercussions of a career misstep. In other words, sometimes people make a miscalculation, are fortunate enough to come out on top, and still wish they’d done things differently.

When a successful person offers such a realistic, vulnerable perspective, it helps us relate to their experience and take pragmatic steps to prevent similar feelings of remorse. So on our readers’ behalf, I sought out a variety of high-powered women who, despite their successes, were willing to open up and turn their regrets into practical advice. Here’s what six female executives had to say about their biggest career mistakes.

Kimberly Paige, 54, New York

CMO at a major television network

I regret not recognizing the superpower in simplicity. Earlier in my career, teams that I worked on faced complex business issues, and oftentimes, the solutions that came to me seemed too simple, so I hesitated to share them. Over the course of my career, as I felt more empowered to use my voice, I recognized that my ability to decipher complexity was a unique skillset that added enormous business value. I was, in fact, not thinking too simply, but rather, I was cracking codes and developing straightforward solutions to business challenges that, to many, seemed too complex to solve.

I learned that my skillset for identifying convoluted concepts and boiling them down to clear, understandable pieces is a unique one; this differentiating factor was often my competitive advantage and an asset to the teams I worked on. Simplification has become a core skill of mine that I’m now well known for around the office, and I am often asked to help reorganize certain efforts and resources in order to improve efficiency, growth, and performance.

Wei-Shin Lai, 45, Pennsylvania

Doctor turned entrepreneur

I learned the hard way that it’s more important to follow your gut than to always trust the “experts.” For example, one advisor pushed for my business to enter large, mass-market stores with our niche product. We got rejection after rejection from buyers telling us the same thing, which was that our product was too niche. We knew that our products weren’t for everyone and that we may not be ready to service the biggest chain stores. However, the advisor repeatedly told us “not to give up.” When we finally got an opportunity to expand quickly, we looked at the financials and saw that it was really risky. Our advisor ignored our concerns. Rather than advising us through the negotiations to optimize the transaction, he told us not to worry and to go ahead. It took us 3 years for us to dig ourselves out of that hole that could have ended the company. I now make sure to seek out the perspectives of various industry experts, which has served me much better.

Rachel Blank, 32, New York

CEO at a reproductive healthcare startup

My biggest regret is not diving into entrepreneurship sooner. I think it’s common for people to feel some level of hesitation when they’re considering starting their own business. For me, embarking on this journey has unlocked an inner drive and passion I haven’t felt in some time. My advice to anyone in this position is to go for it! Like me, you could very well find that the rewards far outweigh the risks. If you know entrepreneurship is where you want to end up, start sooner rather than later—I wish I had.

Amanda Royle, 38, California

Co-founder of a technology business

One of the biggest career mistakes I’ve made is forgetting to focus on myself. It comes naturally to women to care for others before minding our own welfare. I was giving so much, but it always felt like it wasn’t enough—to the point of frustration. Then I remembered that famous quote: “We cannot give what we do not have.” I realized that I was burned out and didn’t have enough nutrition for myself physically, emotionally, or mentally. I started to value getting enough rest and the education and coaching I needed to help me with my business. Everything became so much better after learning from that mistake.

Tatsiana Kerimova, 30, California

CEO and Co-founder at a mobile app development company

Imposter syndrome is a serious mistake that affects high-achieving people, and it had a negative effect on me personally. Women are more likely than men to doubt their abilities and feel like frauds at work, especially when it comes to the IT sector. Many women in tech are working their fingers to the bones to become top-rated specialists, but they often get stuck in lower-level positions by underestimating their accomplishments, while their more confident male colleagues work their way up the career ladder, sometimes without the necessary skills and knowledge. 

It took me some time to overcome the consequences of imposter syndrome. First, I needed to admit that I was experiencing imposter syndrome, and then I worked on learning the facts about why I deserve my position, analyzing my strengths and weaknesses, and discussing my achievements with colleagues and business partners.

Alice Kim, 42, New York

CEO at a fashion company

The biggest mistake I made in my career was under-selling myself and not self-advocating. I thought I was being humble, but now I realize this humility held me back. Perception is reality, so it’s important to celebrate your wins and share your accomplishments and moments you are proud of. You have to remember that everyone is busy, so even if those around you have the best intentions, no one is looking out for you the same way you look out for yourself.

I did my job and did it well. There were times in my career that the department I led was the most profitable in the company; however, because I didn’t speak up for myself, other than the CFO, the teams didn’t know. The reality is that numbers are important, but politics matter. Think of it this way: You may have the best idea, but if it stays in your own head and you don’t share it, the idea doesn’t mean anything.

Written By

Emma Steinbergs

Emma is M.M.LaFleur's Senior Brand Associate. She previously worked as an M.M. stylist and Customer Communications Associate, and she still loves thinking through styling challenges and solutions for customers.

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