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."

Terry Lundgren, president of Federated Department Stores: "I just started in Bullocks in 1975 as an assistant buyer in furniture, fresh out of college. They liked me and I liked them, but I didn’t like my boss. He was bossy, nasty and never said thank you. I wasn’t wed to retail. I had 13 job offers and could have been one of the suits at Xerox, in the management training program. I went to HR and told them I was thinking of leaving, but then Gene Ross showed me a sign: ‘Bloom where you are planted.’

"He told me, ‘The buyers are not there to teach you or motivate you. They are just professionals doing their job. Everything will work out.’ He totally turned me around and I went back to work the next day. Six months later, I got promoted and never looked back. The lesson for me is that you can’t always expect your situation to be completely positive at a young age, but if you work hard and have an aptitude, you’ll be fine."

Barry Schwartz, chairman of Calvin Klein Inc.: "When it comes to retailing, location is everything. You can get the greatest store for a great price, but if the location is bad, you’ll never do well. We did a store in Cleveland [in a mall near the train station] and it was a disaster."

Reed Krakoff, president and executive creative director, Coach Inc.: "When I think about the best lesson I learned it’s to take the time to step back and reevaluate your brand. Look at your brand image-wise and sales-wise, and really understand how it pertains to the world today. Whatever the success of the brand, leverage it into other categories."

Jack Kliger, chief executive officer of Hachette Filipacchi Media U.S.:"I'd say it would probably have to do with the John F. Kennedy Jr. plane crash, which happened just as I had started my term as president of Hachette. I guess I learned about exercising crisis management without making it a chance for personal publicity, which many people could have done, but tried to focus on the task at hand and doing the right thing for my company, for the employees, and for John’s family."

Kenneth Cole, chairman and chief executive officer of Kenneth Cole Productions: "After 20 years of business I have learned that regardless of your state of mind, it is easy to be successful by working only half a day — any 12 hours that you choose."

John D. Idol, chairman and chief executive officer of Kasper ASL: "In the process of creating, or re-creating, a profitable fashion house, my toughest lesson has been walking that fine line between building the image of the brand and not losing touch with the customer. When done correctly, it’s an incredible thing to watch the customer respond. But it’s a tightrope nonetheless to entice consumers, retailers and fashion editors."

Nicole Miller: "Not everything you love sells."

Ed Burstell, vice president and general manager at Henri Bendel: "My very first assistant buying job, at Bonwit Teller, was in the early Eighties. People made some adventurous clothing choices then, as did I. So my buyers and my divisionals used to always go out to appointments, and I wasn’t invited to them. I’m still thankful to this day to the person who pulled me aside and said, ‘Listen, we’re not taking you because you don’t look appropriate.’ And after that I started to temper it going forward. When you’re going to make a first impression, dress appropriately."

Furrier Dennis Basso: "When I first went into business, I had a trunk show at Martha on Park Avenue in 1984. The first day I was there I worked so hard to sell an $80,000 sable coat to this woman from out of town. I was so excited I went into the back room to tell Martha. There she was, all imposing head-to-toe in Galanos and dripping in David Webb, sitting on a little French chair. She said to me, ‘Dennis darling, that’s very good but the coat’s not sold until the check clears.’"

Diane Von Furstenberg: "There is no memory for pain. Tough lessons become less so over time. Usually, the tough lessons I have learned have been about making decisions too quickly and associating with the wrong people in business."

George Horowitz, president and chief executive officer of Everlast Worldwide: "Quality does not ensure success is something I learned in the mid-Seventies, when I was teaching history at Chelsea High School. I was also coaching sports, teaching at night at the Brooklyn House of Detention and taking courses because I wanted to become a principal. New York City was going through a financial crisis and teachers without tenure were going to be laid off, so as one of the younger teachers, I was nervous. At the end of the year, the principal wrote me a note telling me what a great job I was doing. But when I reported back to school the following year, I didn’t have a job. I learned a lot of valuable business lessons about trust and how doing the right thing doesn’t mean you’re going to be successful and how people in power don’t always have the power they think they have. I still have the principal’s letter."

Elie Tahari, owner and designer of Tahari Ltd.: "The most important lesson I learned is love every moment of the day, and if you don’t, then do something else. I used to work very hard in my business and do a lot of things I’m not good at, such as computer or finance — things I did not enjoy working on. I was miserable half of the day, and the other half of the day I was doing things I was happy about. A couple of years ago, I realized that nothing is more important than myself and the love I have to express in my work. I will not work in a situation where I’m not happy."

Denise Seegal, chief executive officer, Sweetface Fashion, the holding company of the JLo by Jennifer Lopez brand: "The toughest lesson I learned since I’ve been in the business is that an outstanding executive in one business may not succeed to the same level in another business."

Catherine Malandrino: "Anything can happen. That means that in life, you have to expect the unexpected. You really never know what is around the corner.It’s tough because we saw it through 9/11, and then after in things that you never even thought about."

Donny Deutsch, chairman and chief executive officer of Deutsch Inc.: "To me, in my business, people are everything. I like to draw a map when I hire someone, and on one axis I have smart, and another dumb, and on one mean, and another nice. I try to stay in the smart-nice quadrant."

Cynthia Rowley: "The old saying of hard work pays off. I’ve found out that’s true. You really do have to work hard. It gets a little more glamorous over time, but it’s still a lot of hard work."

Peter Som: "The toughest lesson I learned is not to doubt yourself. To do your own collection, you have to love it like there’s no tomorrow, because it’s a hell of a lot of work."

Richard Lambertson, co-designer of leather goods firm Lambertson Truex: "We have learned to just stay true to our own voice. What works best is when you ignore outside influences and just do what feels true to your heart and design integrity."

Jewelry designer Robert Lee Morris:"Whenever I have tried to move in a direction that is very new and very different, if I don’t maintain a strong anchor to my signature style, I lose my customer.

When I saw the movie ‘Basquiat,’ one of the key things I remember is the moment that Jean-Michel Basquiat’s friend said — when Basquiat was getting bored with his direction and wanted a change — that ‘if you do that, you can say goodbye to your career.’ I thought, bingo. In the school of hard knocks, that’s one of the lessons: Stick to who you are even though it’s tempting to try and be someone else."

Hal Upbin, chairman, president and chief executive officer of Kellwood Co.:"Over the years, I have learned not to take yourself so seriously that you think you are infallible. Never fall in love with a project or brand. In other words, don’t become emotionally involved when making business decisions. Be guided by financial principles. Manage risk."

Costume jewelry designer R.J. Graziano: "Hard knocks is about survival, and in order to survive in the fashion industry, it’s very important not to be pigeonholed for just one thing. If you’re not interested in every aspect of design, you may as well hang up your coat and go and find a job that requires a task."

Emme, model, designer and author:"The most important thing I’ve learned in this industry is being too trusting without having done your homework."

Stefani Greenfield, co-owner of specialty store chain Scoop: "Number one is to be a good listener. It’s not about what you think your customer is going to want, but about understanding and interpreting their needs and incorporating that with your vision. Also, if you make a mistake, you have to move on and get over it. You are going to pick out things that aren’t fabulous, but just make sure you have more successes than failures. And you’ve got to move on, don’t get too attached. Every day is a new day in retail."

David Yurman: "My biggest lesson was overcoming early concepts about separating the business from the personal. I now include in my work and personal my wife Sybil, son Evan and pooch Sushi, all sharing our life together. My work is my life and my life is my work."

Bradley Bayou, designer, Halston: "I’ve never told anybody this. I dressed Geena Davis for the Academy Awards in 1999 or 2000 when she hosted the pre-awards show. She wore a corset ballgown and looked great, but it rode up a little so she wanted the dress weighed down. I didn’t have any weights or chains, so minutes before she went on the air I ran around and found some knives and whipstitched them into the bottom of the dress. But as she went walking out on the red carpet, the knives all fell out and she was stepping on them. Her stylist was furious at me, so it was a moment where you feel like your career is over. But in retrospect, it was so funny. I guess what I learned is to carry chains or individual weights."

David Meister: "You have to be quick on your feet or you fall on your face."

Jim Gutman, president of Pressman-Gutman: "What we have learned is that our business changes every two years, and we have to be prepared to reinvent ourselves at that pace...."

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