5 successful women share their best advice from their most awkward moments

If you ask any entrepreneur, they’ll tell you how many times they had to fall down before getting back up. Of all those pitfalls, there’s probably one (or two or three) that felt more like faceplants than stumbles.

Part of growing as a professional — and as an entrepreneur, if that’s your career path — is figuring out how to learn from your mistakes. Not only does it make you a stronger leader, but it encourages you to listen to your instincts and to spend more time focusing on areas of improvement.

If you made a big mistake or you’re in the middle of a huge transition, let these face-plant stories inspire you to keep going. You’ve got this, after all. 

I caused a problem with our cash flow

Basic Outfitters, a men’s clothing company featured on Shark Tank, had some issues with cash flow in its early stages, said Laura Dweck, the creative director and co-founder.

“We over projected our inventory buys and invested too much money into product,” she said. “It became our biggest challenge as it tied up our cash flow.”

Though a tricky situation, it helped her to prepare for the future and become a stronger, smarter leader, she said.

It taught me the importance of planning inventory buys and the value of leveraging my network and contacts I’d made throughout my career,” she said. “In hindsight, it was a blessing that we had all this inventory on hand because when we aired on Shark Tank, we were able to capture the wave and fulfill all those orders due to the excess inventory we had. It taught me that the one thing that can seem like the biggest challenge can turn into the biggest blessing.”

I embarrassed myself in front of 100 clients

Though Claire Fountain, the founder and CEO of TrillYoga, has an unconventional, non-judgemental teaching style, there was still a moment where she felt uncomfortable. Or, rather, a piece of technology she often struggles with: microphones.

“More than once I have walked too close to the speakers during class and blasted my poor class — of more than 100 people in NYC one time — with this awful loud noise,” she said. “Like, grab your soul, loud noise. This might sound minor, but for me, having this horrid noise disrupt my class felt like it could be the kicker for if someone liked it or not, and decided to come back ever again, or tell others to never attend. People’s opinions of your class can be a huge thing and can make or break an instructor’s career in this industry.”

What have these face plants taught her? To let it go, she said.

“I have pretty bad social anxiety and am in front of lots of people often, sometimes even on camera, so instead of worrying or obsessing over mistakes or letting that anxiety and fear kick in, I turn on my confidence and self-assuredness,” she said. “I practice affirmations day-to-day while building a confidence that can roll with the punches, because we are all human. I remind myself that even the most intelligent, successful, and accomplished people make mistakes, yet their lives go on, so I accept myself as human and build my confidence from the inside out.”

I fell too in love with the idea, not with the work

A few years ago, Kimberly Walker created a site called Vinquiz, aiming to pair wine to customers’ personalities and have it delivered to their doors. But while she was obsessed with the idea, she didn’t plan for the next steps.

“I neglected the long game, which would have clearly shown me the margins were too thin to be worth all the effort,” she said.

And while she face-planted head-first on that company, her new company, The Vanity Projects, which provide wine wipes, in addition to other goods, is off to a smart start.

“I learned not to fall in love with ideas until I’ve thought them through to exit strategy,” she said. “I also always consult with mentors and colleagues who don’t mind telling me an idea stinks, and challenge my thoughts on why it will be successful.”

I didn’t stand up for myself

For Erin Motz, co-founder of Bad Yogi, a yoga and lifestyle brand, face planting was a common occurrence in her first years of business. How so? She didn’t develop the confidence she needed to demand to lead her success, she said.

“I used to be extremely hesitant to stand up for myself and defend my business,” she said. “For instance, instead of making sure we were paid on time from partners, I’d be worried about ruffling feathers. I was so afraid of coming off as ‘not nice’ or disagreeable that I repeatedly let people walk all over me, and that habit resulted in many, many epic faceplants that were very difficult to recover from.”

Through the trials of being an entrepreneur, she realized that sometimes, business isn’t pretty or easy, she said.

“If someone you’re working with is being difficult, it’s OK to match their energy sometimes,” she said. “I learned that I’m entitled to do what’s best for me and my business even if that makes someone else think of me as less than “nice” and gentle. I learned that I want to be the woman who gets sh*t done more than I want to be the woman who’s sweet and demure no matter what.”

I didn’t follow my gut

Your tummy might not have a seat at the table, but it’s probably speaking louder at board meetings than you realize. For Taylor Wilkinson, owner of Taylor Wilkinson Designs, a contemporary jewelry brand, ignoring that little inkling in the back of her head was a face-plant she said she felt over and over again.

“I’m still learning how to be in the business I’m in, but nine out of 10 times, I’ve doubted myself and instead taken outside direction, things haven’t turned out really any better,” she said. “I think women who are young in their process — no matter how old they are — and starting their own companies are innately hesitant, if not sometimes fearful, of questioning those who have been in business longer or know more about the subject matter. There is truth to a woman’s intuition. In business, in life, listening to my own voice, trusting my own instincts, believing in my product — that’s really when the good stuff starts happening.”