How to Do the Impossible: Career Advice from Kenneth Cole
By The Editors
PlannedMan

To successfully launch his business, Kenneth Cole had to think fast, change the name of his company and tell the mayor of NYC just one, little, white lie. There’s a lot to be learned from Kenneth Cole’s story when it comes to your career.

How to Do the Impossible: Career Advice from Kenneth Cole
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Highlights


What are the roadblocks to getting what you want?

Kenneth used courage to change the name of his company, lie for that permit and to actually park his truck in front of the Hilton for two days.

Keep your feet in Kenneth Cole’s shoes—do what he would do.

When I was a mere 25-years-old, a major US magazine’s editor I didn’t know, called me and asked if I thought I could do the impossible. “What’s that?” I asked.

“I’ve heard you’re good at getting people to do things; and I really need to get the president of the United States to agree to do an interview with us and pose for a photo for our cover. And I need to get the queen of England and Mikhail Gorbachev to answer a few questions too. Can you do that?” He detailed.

I called the White House, the Kremlin and Buckingham Palace. I asked for interviews; every time someone put up a roadblock that might’ve stopped me from getting what I wanted, I figured out how to get around it.

It’s true; I was pretty good at getting best-selling authors, pro athletes, rock stars and TV stars to do interviews with me. But the president of the United States? The president of the Soviet Union? The Queen? They were all out of my league. I had no idea how to do that—any of it. I had no contacts at the White House, the Kremlin or Buckingham Palace.

“Sure, I can do that,” I said with my heart pounding so hard I hoped he couldn’t hear it over the phone—then I got it done.

How? The short answer is I asked.

I called the White House, the Kremlin and Buckingham Palace. I asked for interviews; every time someone put up a roadblock that might’ve stopped me from getting what I wanted, I figured out how to get around it.

I love hearing other people’s stories about doing the impossible too, as you can imagine. That’s why I was so thrilled when Fashion Designer Kenneth Cole told me one day about how he started his business. What he did to launch his company might have been ten-times harder than landing an interview with the respective president of the United States and Soviet Union and queen of England: he had to figure out how to get permission from the City of New York to park a 30-foot trailer on the street for two days—right in the middle of Midtown, Manhattan. If you’ve ever tried to park even a Prius on the streets in Midtown, you know it’s impossible to park for five minutes—let alone two, full days!

If you ever get a chance to hear Kenneth himself tell this story—you can hear him share it here—don’t miss it. But stick with me here, because I want to use Kenneth’s story to make a larger point about you and your career.

Kenneth wanted to start his own shoe company, as he explained to me, so he took a big risk with limited funds and had a factory in Italy produce 40,000 pairs of shoes based on his designs. He had the shoes at that point, but how was he going to sell them?

Kenneth sold all 40,000 pairs of shoes in those two days—you know the rest of the story.

He then had an idea: a big, New York City fashion show was then coming at the grand, New York Hilton at the corner of Sixth Avenue and 53rd Street. (Everyone would be there!) Except he couldn’t afford to actually rent an expensive booth inside the building…so he thought, “Why don’t I just drive a truck up to the outside of the building and show and sell my shoes from there?”

But how do you get permission from the City of New York to park a giant truck on the street outside the New York Hilton for 48 hours? (You ask, and when someone presents a roadblock that might stop you from getting what you want, you figure out how to get around it.)

Kenneth called the mayor’s office and asked if he could get a permit to park his truck outside the Hilton.

“Are you crazy?!” they asked. “The only way you can park a truck on the street in the middle of Midtown Manhattan is if you are shooting a movie.”

Now excuse the pun, but this is a good time to put yourself into Kenneth Cole’s shoes. Imagine all the money you have is tied up in a warehouse full of 40,000 Italian-made shoes. Tack on the need to park a 30-foot truck outside a New York City Hilton to sell those shoes, get some cash, so you can use that money to launch your business.

What do you do?

If you’re Kenneth Cole, you march down to city hall, change the name of your company from Kenneth Cole Inc. to Kenneth Cole Productions, lie through your teeth about making a movie and apply for a film permit. You then park your truck full of shoes right outside the New York Hilton.

Kenneth sold all 40,000 pairs of shoes in those two days—you know the rest of the story.

While you still have your feet in Kenneth Cole’s shoes, try thinking like Kenneth about the biggest problem you have at work—or at home. What are the roadblocks to getting what you want?

Even if those roadblocks are seemingly as difficult as trying to get the leaders of the United States, the Soviet Union and England to do a phone interview—or if you were trying to work around the impossible, parking rules in Midtown Manhattan—where’s the wiggle room you need to troubleshoot the roadblock?

It took balls for Kenneth to put all his money into those 40,000 shoes. Kenneth used courage to change the name of his company, lie while applying for that permit and to actually park his truck in front of the Hilton for two days.

It may take balls for you to tackle the roadblocks in front of you too. Keep your feet in Kenneth Cole’s shoes—do what he would do. Let us know how it all works out, so you can be one of our next stories about guys taking on the impossible.

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