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The American supermodel has marked her 56th birthday with a poignant letter to "little Cindy" and documented the things she would tell her if she could.
The mother-of-two - who has Presley, 22, and Kaia, 20, with husband Rande Gerber - admitted she could be hard on herself, and says she would advise young Cindy to not be "afraid to make a fool of herself" and "fake it until you make it."
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She wrote on Instagram: "On the eve of another birthday, looking back at little Cindy and thinking about what I would tell her. I would tell her to be kinder to herself, to treat herself the way she treats her friends. I would tell her everyone feels nervous in new situations, and sometimes you just have to fake it 'til you make it.
"I would tell her not to be afraid to make a fool of herself - dance, sing, etc. more - even if she isn't good at it. Laugh as much as possible. "Risk showing her true self to people she loves - the payoff is worth it. Practice gratitude. Keep growing and learning and becoming … life is a blessing!"
Cindy previously admitted she expected her modelling career to be over by the time she was 25.
The brunette beauty always knew life on the catwalk was typically short-lived, so she's astonished to still be in the spotlight, more than three decades after she first began working.
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She said: "Models used to be replaced every five years, so I assumed that at 25, I would have to go back to school. Here I am at 53! I'm representing different brands, which is appropriate, but every time I get my picture taken, to me, that's modelling."
Cindy joked that she and her fellow modelling icons, Christy Turlington, Linda Evangelista, Naomi Campbell, Claudia Schiffer, and Kate Moss, were like a "boy band" because of how they looked when put together.
She said: "Before Christy, Linda, Naomi, Claudia, Kate and I, models weren't well known.
"It was almost like we were a new boy band - we were all different, but we looked good together. Fashion was all about glamazonian shoulder pads, high heels, and strong women. We didn't look like victims, we looked empowered. I really think that we felt that way, too."
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While the catwalk veteran doesn't miss the runway, she does long for life backstage.
She said: "It was like a slumber party. We were all tired and a little bit punchy, but real friendships were formed."
Cindy's kids both followed in their mother's footsteps, and she joked she's more well known now for her association with her daughter in particular.
She laughed: "I feel I'm most known for giving birth to Kaia now."
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