The path to becoming a major designer or chief executive officer of an apparel firm, retail chain or publishing company is fraught with many hurdles. Some are surmountable, while others are more challenging and leave an indelible impression. WWD interviewed a variety of New York executives, from fashion companies and retail stores to ad agencies and publishing firms, about the toughest lesson they’ve learned in their businesses and why.

Tommy Hilfiger, honorary chairman, Tommy Hilfiger Corp.: "When I was first starting out in this business, I was young, impressionable and inexperienced, but there was one thing I was sure about: I was passionate about starting my own fashion company and eager to get started.Although I never went to design school, I knew I had what it took to begin to translate my artistic vision into a viable business. Everyone discouraged me from taking on this challenge without getting formal training first, including my friends and family. Their discouragement was very hard to accept, but it taught me I had to rely on myself and believe in myself in spite of the challenges before me."

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