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At just 28, Cassidy O’Hagan lives a lifestyle that rivals Hollywood’s elite, winters in Aspen, summers in the Hamptons, and vacations in Puerto Rico, Maldives, India, and Dubai, all aboard her employer’s private jet. Every trip, meal, and wardrobe change is part of her job perks. Her “office” is a billionaire’s mansion, and her title? Nanny. 2 / 11
Her story, first reported by Business Insider, is a perfect reflection of how Gen Z is rewriting the rules of success. Gone are the days when corner offices defined prestige, today, it’s about flexibility, fulfillment, and freedom. 3 / 11
O’Hagan’s job comes with an enviable list of benefits: a 401(k) plan, full healthcare coverage, private chef-prepared meals, a dedicated “nanny wardrobe,” and paid vacations to some of the m

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