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Today's Trinny Woodall built a multi-billion dollar empire by facing her fears

Trinny Woodall, the Founder & CEO behind the successful beauty brand, Trinny London, shares her confidence and style tricks so you can be fearlessly happy too 

Today's Trinny Woodall built a multi-billion dollar empire by facing her fears
Donna Francis
Donna FrancisContributing Editor US
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When British beauty entrepreneur and The Today Show makeup expert, Trinny Woodall, was forced in her late 30s to close her first company, a lifestyle website, she thought that her entrepreneurial future was over. 

Yet Trinny, who turns 60 next February, has since become one of the most successful businesswomen in beauty, as Founder and CEO of her expanding makeup and skincare business, Trinny London, which is currently valued at around $250 million

The secret behind this turnaround? Being fearless. 

"Propelling yourself forward with something where you physically or mentally challenge yourself feels so great when you've done it. Especially when you think I can't do it, and then you let go, and you can. It's incredibly gratifying,” Trinny shares exclusively with HELLO!. 

Trinny on Today with Hoda and Jenna© Nathan Congleton/NBC via Getty Images)
Trinny on Today with Hoda and Jenna

Trinny has put this inspiringly brave approach to the test many times and it has helped her overcome many fearful experiences in both her professional and personal life. 

"[I was] fearful of being a single parent when my daughter Lyla's father died; [I was] fearful of jumping from having a paid job to become an entrepreneur; [I was] fearful to start an online business in 1999 and having to close it during the dot com bubble" she explains. 

Yet, facing these problems head on and recognizing that actually "fear of failure can motivate you to do anything," has given Trinny the inspiration to move forward every time she has faced a challenge. 

Her fearlessness has even inspired her to write a new how-to style guide, aptly named Fearless, and to launch a podcast where she interviews actresses like Debra Messing and beauty experts like Jo Malone all about the subject. 

"Fear of failure can motivate you to do anything you can do to succeed, that negative can be a positive to galvanize you to move forward," Trinny explains. 

Meditation helps Trinny hone in on her dreams and happiness. "When I had to wind down [my first] business and let everyone go, I went to Arizona to a retreat and really worked on letting out of my dream and being open to what was coming into my life next. This was my introduction to meditation and clearing my busy brain to let the important things rise to the top."

Trinny with her daughter Lyla at the V&A 2023 Summer Party in London © Photo by Jeff Spicer/Getty Images
Trinny with her daughter Lyla at the V&A 2023 Summer Party in London

She also surrounds herself with friends and family for support. Especially during difficult times like when her daughter’s father, Johnny Elichaoff, died from suicide eight years ago.  "When my daughter Lyla's father died, I overcame this by having supportive family and friends to get me through it as well as having a very close relationship with my daughter."

But it is Trinny's fearless style that she attributes to a lot of her success, which is the inspiration behind her new book. "Neon and silver are my go-to for confidence, they just feel present, fun, and engaging. They are my guaranteed savior when I'm feeling flat," she explains. 

Trinny encourages everyone to find their fearless outfit by wearing clothes that make us feel happy. "Once you get to a mindset of thinking what can I wear to bring joy? that gives you more confidence to be a bit more joyful and then things snowball positively from there. It may seem superficial, but having an exterior you feel joyful in, can help bring a bit more joy inside, to challenge yourself to do more."

The credo behind all of this? 

"I don't worry what people think," she says.: For example, a lot of people don't dress in a certain way as they're worried people will think they are overdressing, stand out too much, or they shouldn't be so ostentatious. When you can try to remove that worry about what other people think, you can start to dress thinking instead what will bring me joy."


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