The Biggest Career Regret of 6 Wildly Successful Women

by Sacha Strebe

While we prefer to live by the “everything happens for a reason” philosophy, for many of us, there’s that lingering missed opportunity from our past where we failed to act or wish things turned out differently. Granted, mistakes are a part of life that often contribute to our later successes, but even when we’ve triumphed, kicking that niggling feeling of regret to the curb can be tough, no matter how happy or accomplished you are now. Remorse is okay, as long as you harness it for good not bad. Hindsight is 20/20, but instead of dwelling on the negatives and a barrage of what-ifs, think of them as vital life lessons and use them to activate exciting new opportunities in your personal and professional lives.

Whitnery Wolfe, Founder and CEO of Bumble

Whitney Wolfe, Founder and CEO of Bumble

Photography: Ellis Parrinder for Bumble

Whitney Wolfe has officially disrupted traditional courtship, as the founder and CEO of a feminist dating app that lets women make the first move. The app has taken off: Bumble saw 100,000 users swiping left and right within the first month. A Business Insider journalist went so far as to call it the best dating app, and our reviewer rated it quite highly as well. Before Bumble, Wolfe was the brains behind Tinder’s marketing division, helping the startup grow from a fledgeling idea to a $750 million business. Despite her phenomenal success, the 26-year-old founder has regrets just like the rest of us.

“I regret not pushing the envelope with some fun and creative marketing ideas I have had,” she told MyDomaine. “In fear of them being too grandiose or risky, I have sometimes taken a safer route. I think breaking the rules (not the law) can be healthy and help you grow into something you might not have known was possible.”

Key Takeaway: Don’t be afraid to take risks and break the rules sometimes.

Rachel Zoe; Designer, Editor in Chief, Author, Stylist

Courtesy of Laurel & Wolf via MyDomain

 

If you’re a fashion fan, you’ve most likely binge-watched several seasons of the hit TV show The Rachel Zoe Project like we have; it’s totally bananas. But beyond the camera, Zoe is a veritable fashion powerhouse with a slew of job titles in tow. When she’s not tending to celebrity clients with her styling prowess, she’s creating killer content as editor in chief of The Zoe Report (which reaches 13 million people worldwide), designing collections under her popular self-titled label, writing books, and being a mum to adorable her two boys, Skyler and Kaius. But even with all of her accolades, Zoe often looks back and wishes she had done some things differently. Which is why she told Who What Wear that her biggest regret is “being naive and trusting the wrong people.

Key Takeaway: Trust your instincts.

Anna Brockway, Co-Founder and President of Chairish

Courtesy of Chairish

If you’re a regular reader of MyDomaine, you’ll know we love scoring a steal and uncovering a rare vintage find at basement prices. Who wants to pay full price for furniture? Well, Anna Brockway has turned her thrifty nature and well-honed eye into a profitable profession with Chairish, and she recently schooled us in entrepreneurship. Thanks to Brockway, you don’t have to wait for the first Sunday of every month to visit this flea market; you can hunt for treasure online 24 hours a day. And we’re not the only ones who visit it on the regular: Brockway is a Today Show regular and has over 75,000 followers onChairish’s Instagram account.

But getting there has had its fair share of ups and downs. There have been many times when Brockway didn’t listen to her gut, and it definitely spelt trouble along the way. “I regret it every time I don’t follow my instincts,” she toldMyDomaine. “I’ve made this mistake in hiring, and it’s just a big disaster all around.”

Key Takeaway: Listen to your internal meter, and let your instincts be your guide.

Kathryn Minshew, CEO and Co-Founder of The Muse

Courtesy of Kathryn Minshew

Kathryn Minshew is proof that passion, perseverance, and “being scrappy” can lead to monumental business prosperity. With a mere $3000 USD in personal funding, Minshew has launched her simple idea for The Muse into a comprehensive career-development platform with five million new job seekers every month. She’s made the coveted Forbes 30 Under 30 list twice, as well as Inc.’s 15 Women to Watch in Tech.

For someone who dishes out career advice for a living, we were intrigued to discover her biggest regret was a common mistake we’ve all been guilty of at some point in our professional lives: “One of my big mistakes early on was not asking for a raise at the right point,” she told MyDomaine. “I’d just finished a massive project that had been a huge success for my employer, and the team I reported to couldn’t have been more thrilled. I knew that I wanted to ask for a raise at some point, but for various reasons (I didn’t want to look like I was capitalising too much on the recent success; I was nervous in general), I waited.

“Three months later, I gathered up my courage and made the request, my stomach in knots. I was so physically pained by asking for more that I threw up in the bathroom afterwards. And they said no. The organisation was stretched thin financially, it just wasn’t possible right now, etc. The crazy thing is, in retrospect, I’m almost positive that they would have had to say yes if I’d asked earlier. But hey—that’s how you learn. Getting the no made me stronger!”

Key Takeaway: Don’t wait. What have you got to lose?

Jenni Konner, Executive Producer of "Girls"

Photography: Austin Hargrave for The Hollywood Reporter

At MyDomaine HQ, we love highlighting inspirational women at the forefront of their fields, and Jenni Konner tops our list. There was a collective squeal of delight when she agreed to answer our Career Code questionnaire. If you’re fans of the hit HBO show Girls, you’ll feel us on this one too. Konner is the show’s executive producer and writer, and she runs her own production company and co-pens the feminist newsletter Lenny. Despite the glory of a hit TV show and an adoring global fan base, Konner looks back on her ascent and considers how she could have done things differently.

“There were times I felt so lucky just to be in the room that I forgot I had value,” she told MyDomaine. “It’s easy, as the only woman in a room full of male comedy writers, to be so excited to be at the table that you forget how important your voice really is.”

Key Takeaway: Speak up. There’s no such thing as a bad idea.

Michelle Lee, Editor in Chief of "Allure"

Photography: Amanda Villarosa

Michelle Lee has an impressive professional history. She’s had her creative hands on most of our beloved glossy titles, from Nylon, where she was editor in chief, and CMO to Us Weekly and CosmoGIRL, where she worked on strategy in both digital and print. Now Lee has been passed the editor-in-chief baton to reinvent a 25-year-old icon, Allure. While her career trajectory is nothing short of incredible, the sage scribe has had her fair share of regrets too.

“Staying in a job for too long because the money was great,” she told Byrdie. “I ultimately left and took a huge pay cut, but I wish I’d left earlier. We spend too much of our days working to not totally love what we do.”

Key Takeaway: Uncover your passion and love what you do; that way your job won’t feel like work.

 

 

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