How To Master The Art Of Failure

It’s all about the comeback.

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For so many, the word failure is one that cannot or will not be spoken. It often is connected to shame and finality, especially in regards to one’s career. But, for the lucky ones who can see beyond the taboo, learning how to face failure is a gift, an opportunity to grow and become a better, stronger, wiser individual.

“No one likes to experience setbacks, but they keep us humble,” says makeup artist, entrepreneur, and beauty influencer Jaclyn Hill. “I am also infinitely more grateful for my ‘wins’ now than I used to be. It’s so important to realize that we are not superwomen. We try our best, but we make mistakes at the end of the day. The silver lining is that we grow from them. My fiancé says that my experiences give me ‘seasoning,’ which I love, so I like to think I have more flavor because of my setbacks.”

Indeed, Hill has had her share of highs and lows since launching her highly successful YouTube channel back in 2011. The meteoric rise of the Hill’s celebrity-inspired tutorials (which included the viral "Get Ready with Me & Kim Kardashian" featuring Kim K herself in 2017) led to countless brand collabs and eventually the launch of the artist’s own namesake line, Jaclyn Cosmetics, in 2019. However, the setbacks hit fast, when the highly anticipated launch was met with backlash as fans complained of flaws and defective products. After her public apology for not meeting her customer’s standards was met with more criticism, Hill went dark, taking a break from social media for a period of time. She eventually returned, relaunching the brand in 2021 and approaching the project with a renewed prospective.

“I’m much calmer in business now because I have accepted and understood that missteps are inevitable if you’re attempting to do anything worthwhile,” she says. “It’s just going to happen. But I have the choice to learn from it, follow my passion, and keep working at it.”

Indeed, failure and setbacks can be rife with valuable lessons for those wise enough to recognize them, receive them, and put them to good use. Ahead, Hill and three other female entrepreneurs across various industries share their experiences with failure and the vital takeaways that have shaped and molded them for the better.

Be Curious

“Failure sucks for the ego, but it’s great for curiosity,” says Srishti Dhawan, certified mindset and transformation coach and founder of career mentoring site The Mind Shyft Coach. As someone who’s had multiple careers over the course of her life — she owned a clothing brand, 1986, in the early 2000s followed by Haute Gali, a networking company for fashion designers — Dhawan has “experienced both the thrill of success and the disappointment of failure.”

After both of her fashion-focused ventures shuttered, the mentor joined the corporate world, where she worked as a consultant, but was eventually laid off. Despite the disappointments, Dhawan says she took the road less traveled — the road of introspection.

The Mind Shyft Coach

“I learned to balance the act of giving my ego a pity party, with the curious aspect of me, the need to learn and grow,” she explains. “[During this time] I journaled, I shared my feelings with my partner, I spoke to my therapist. I created spaces for my ego to feel sorry for itself. At the same time, I indulged in Ted Talks, read books, watched YouTube videos to feed my hunger for knowledge about my next steps. It was a balancing act between feeling sorry for myself, and letting myself move on.”

Lean Into The Discomfort

Just like a tough fitness session that makes your muscles ache while also toughening them up, working through the pain and discomfort of failure can lead to a stronger you. Just ask Lais Pontes Greene, founder of Florida-based public relations and branding agency The Pontes Group. “Failure makes you tough,” she says. “It gives you the clarity to understand that success is on the other side of discomfort, and you have to power through hard moments to reach your goals. Lessons from failures have taught me to become really comfortable with the uncomfortable.”

The PR veteran says her first big taste of failure was especially memorable in that, like Hill’s, it was very public. Greene (who was five months pregnant at the time) planned her first big food festival event some three years into founding her namesake company. While things started out smooth the day-of, they quickly went south as the party became overcrowded, vendors ran out of food, wait times to access food and drink samples were too long and slow moving. Adding insult to injury, the following day, media outlets reported negatively on the highly publicized event, and “an angry mob effect took over,” says Greene. “My home address was posted online and there were calls to find me and take me down. All for a $30 ticket, most of which were purchased at a heavy discount.”

The PR pro says we as people tend to view failure as a black-or-white situation, good or bad. “But that is not how things work in the real world,” she explains. “A successful project will always have room for improvement, and a failure will have some parts that worked well. For me, I had to shift my thought process on how to analyze failure so I could maximize the lessons learned when things didn’t work out.”


Sometimes failure isn’t so much, well, failure, as much as it’s a shift in the wind. “I’ve learned that failure is just God’s way of redirecting you,” says Dr. Angelique Johnson, CEO of medical technology startup MEMStim, and founder and CEO of Vissionaireum Business Coaching and Consulting. “That the worst thing you can do when you fail is stop because that’s when you’re closest to succeeding.”

The entrepreneur recalls her early day starting MEMStim, attempting to raise her first round of funding, and failing horribly. “I was told I was the wrong person with the wrong idea at the wrong time,” she says. “I took that to mean that I should just stop. Then I met someone who told me that I hadn’t failed, I had just been redirected.”

Johnson went back to the drawing board, reworking her offer and trying again, going on to get twice as much funding as she intended. “It’s a lesson I’ll never forget,” she says.

Recognize What Went Wrong

When the initial launch of Jaclyn Cosmetics went south, instead of wallowing, Hill took a beat and did some digging on where she went wrong. “Learning from your mistakes is crucial,” she says. “Otherwise, you’d just be going around in circles and never truly growing. With every potential misstep, there’s an opportunity to know better and be better, which I try to apply to my life and businesses. Recognize what went wrong, correct it, and move on. That last part is easier said than done, but it allows me to always move forward.”

Move forward indeed. To date, the new and improved brand has some 57K followers on Instagram, more than 15K followers on TikTok and is carried in Ulta and Morphe Brushes stores across the nation. “Working through professional and personal challenges has proven that I am capable of so much more than I ever gave myself credit,” says Hill. “I have learned every step of the way and came out stronger. It didn’t always happen right away, but I know now that there is nothing I can’t conquer as a woman in business.”

Reframe How You View Yourself

Dhawan says, through the course of her career roller coaster, she fought the urge to see herself in a negative light. “I reframed my thinking of myself,” she explains. “Instead of thinking of myself as someone who failed, I looked at myself as someone who tries. This kept the curious entrepreneur in me alive.” As it happens, it’s also what allowed her to start her third business as a mindset coach, where she helps female entrepreneurs build businesses.

Greene seconds this notion, going further to explain that failure is life’s greatest teacher, molding one to be a better version of themselves. In fact, one could see failure as a sign that they are on the path to success, she says. “Any successful person has a long track record filled with failure,” she reasons. “But success is not about how many times you fall down but how many times you get back up.”

Give It “2 Weeks”

They say time heals all wounds, and it seems like same can be said for failure. “My greatest piece of advice to anyone facing a setback is ‘just give it two weeks,’” says Johnson. “I grew up in a family that didn’t have much money and there always seemed to be some hurdle to get through: a lost job, a foreclosed house, or some other huge financial failure. My parents always said, ‘In two weeks this will all be over.’ To them, it was a metaphor for moving on and not getting stuck in the disappointment of the moment.”

The business woman goes on to explain that, obviously, not all problems can be settled in two weeks. Rather, failures and disappointments are simply temporary. “What they meant was, in ‘two weeks,’ the pain won’t be so fresh,” she adds. “In ‘two weeks,’ they will have redirected their mind and energy to something else. In ‘two weeks,’ these light and momentary troubles will have produced a glorious new direction.”

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