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Seven Women Share How Messing Up at Work Helped Their Careers

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.

Between listening to an obscene amount of podcasts and writing career-focused stories for the M Dash, 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 thanks, in part, to their mistakes. At the same time, they share these stories so that others don’t have to walk the same at-times-painful path.

Publicly discussing regrets and missteps is a vulnerable endeavor but one that’s incredibly valuable in helping us take pragmatic steps to prevent similar feelings of remorse. So on our readers’ behalf, I sought out a variety of high-powered women who were willing to open up and turn their past mistakes into practical advice. Here’s what seven female executives had to say about their biggest career mistakes.

Seven Women Share How Messing Up at Work Helped Their Careers

Miriam Airington-Fisher, Virginia

Owner of Airington Law and CEO of Mom’s A Lawyer

My biggest professional mistake was not blazing my own career path sooner. Before I had kids, I had a typical trial lawyer’s life: long days in court, late nights, and weekends at the office. When my daughter was born, I started my own law practice to give myself a better work-life balance. I didn’t have a clear vision for how I wanted to do things differently, so I initially just replicated the status quo. In law, there is a culture of workaholism, always being accessible, always taking the calls. I didn’t know any successful lawyers who picked their kids up from school everyday at 3pm. After my youngest son was born, I was burning the candle at both ends, trying to run a practice with young children, which was utterly unsustainable.

I wanted a business that could thrive while allowing me to have more time with my family. So, I started to develop my own vision for what a law firm could look like: a high-energy, profitable firm full of rockstars who valued a positive, family-friendly workplace culture. Once I committed to my vision, I learned everything I could about running a modern business efficiently—everything from automating systems to social media marketing to leveraging new technology. I focused on professional development and learned different aspects of business management from cutting-edge firms, as well as other industries, and then applied those to my practice. Today, I lead a multi-million law practice with a flexible culture for all team members, which allows me to be the kind of mom I want to be, too. I only wish I had started earlier and saved myself those exhausting years of trying to do it all the old way. Now, I consult with other women lawyers looking to create law firms that suit their lives.

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, thanks in part to a hot job market, 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 not burn bridges and to seek out the perspectives of various industry trends experts. It’s served me much better with my short-term and long-term goals. 

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

My biggest mistake—which is one of the most common career mistakes—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 Kirimava, 30, California

CEO and Co-founder at a mobile app development company

Imposter syndrome is a serious mistake that prevents many high-achieving people from realizing their career goals, and it certainly 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 other people I have professional relationships with. Recognizing it is the first step in allowing yourself to advance in your career.

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 Brand Manager. She previously worked as an M.M. stylist and still loves thinking through styling challenges and solutions for customers.

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