When it comes to taking risks, Anna Wintour is a firm believer in provoking a conversation, having a strong point of view, trusting your own instincts, and learning from your mistakes. Here are five tips from Anna Wintour on making decisions and taking risks.Expect the unexpected.Anna Wintour’s first American Vogue cover was very different from those that preceded it: The photo crop was wider; the model was not looking directly at the camera; the clothing had a casual sensibility, mixing a Christian Lacroix couture top with Guess jeans. In other words, it made a statement and spoke to what Anna wanted to convey, which was that fashion can be accessible, spontaneous, and fun. Ironically, that particular photo was never intended to be a cover. But as soon as Anna saw the image, she realized its potential and pivoted accordingly. When you are in a new position, it’s important to find opportunities to communicate to others what your vision is and what type of leader you are going to be.Follow your instincts.For Anna’s first September issue cover, in 1989, she featured Naomi Campbell in a sequined pantsuit because Anna felt Campbell “represented everything that was happening in fashion at that time.” Some at Condé Nast questioned her decision, but Anna ignored them and followed her instincts.Be generative and reactive.In addition to creating new ideas and concepts that will set the cultural barometer, it is equally important to take stock of what is happening around you and react to it. Take, for instance, Anna’s choice in the early aughts to start featuring celebrities rather than models on Vogue’s covers. At that time, actresses were starting to engage with fashion more and more, which is why Anna and her team felt they made sense as cover subjects. It then became cyclical. As celebrities…
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