When Your Influence Reaches a Point Where Your Own Aesthetic No Longer Captivates You

Growing up in a quaint town on Long Island, Ms. Calderone found her perspective limited. She reminisces, “We were not exposed to much beyond our Italian American pasta-and-meatballs routine. Traveling was a luxury we couldn’t afford.” Raised by two hairdressers, her fascination with the beauty industry took root early on. “Visiting my father’s salon, I felt like daddy’s little princess,” she fondly recalls. Her mother was equally dedicated to her appearance, refusing to step out of the house without her lipstick.

Artistic ambition burned within her, but she struggled with consistency, attending and dropping out of two colleges. Eventually, she made her way to Manhattan where she boldly shaved her head and took up bartending at the renowned nightclub, the Tunnel. It was there that she met Mr. Calderone, who was living in his childhood home in Brooklyn at the time. They became inseparable, sharing a cozy Murphy bed together.

When Mr. Calderone’s career skyrocketed, Ms. Calderone initially took on the role of his manager and later became his loyal travel companion. She vividly recalls the whirlwind of excitement and novelty that enveloped her as she delved into the world of A-list parties and European fashion shows. In 1998, they made a significant investment as pre-construction buyers in the Clocktower Condominium in Brooklyn’s vibrant Dumbo neighborhood. “It was the epitome of a loft: grand columns, exposed beams, and breathtaking views of the skyline and waterfront,” she enthusiastically describes.

On September 11, 2001, the Calderones found themselves in their neighbors’ apartment, witnessing the horrifying collapse of the Twin Towers. While their neighbors chose to leave New York, the Calderones made a different decision – they resolved to start a family. Seizing the opportunity, they purchased the vacant apartment, settling in and joyfully welcoming their son, Jivan, into their lives.

Reflecting on their time in Dumbo, Ms. Calderone shares, “It often felt isolating.” Becoming a mother at a comparatively young age of 28 amidst her husband’s burgeoning career, she grappled with finding her own purpose.

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