Feature Story

Carolyn Kepcher

High-profile businesswoman, former judge on "The Apprentice"

Carolyn Kepcher is the founder of Work Her Way. A high-profile businesswoman, often recognized for her role as an Executive Vice President with the Trump Organization, Carolyn is known by millions for her role on NBC’s hit series, “The Apprentice.” Carolyn is the author of the best-selling business book “Carolyn 101,” which landed at No. 2 on the New York Times best-sellers list. She also writes the weekly “Your Career” column for The New York Daily News, which addresses business, career and balance.

Q: You have an interesting story about how you started in business and ultimately ended up starting your own successful media company and website. Can you tell our readers a little about your career trajectory and what sort of obstacles you faced along the way?

Carolyn: I worked for Donald Trump for 11 years, and in that time I learned that it is possible for a woman to survive and do well in a male-dominated culture. I held a senior management position at a very young age in a predominately male arena…the golf industry. While this was very difficult because I had a lot to prove, I learned many invaluable lessons about what it takes to be successful in business. My success was in not looking at it as a male-dominated culture, but as an opportunity to succeed and grow in a reputable company.

As for the celebrity aspects of appearing on “The Apprentice” for five seasons, I didn’t sign up for it and didn’t know it was going to happen. I never imagined it would turn out the way it did. It hit like a storm – a wonderful storm that led me to a new, very unexpected path.

Q: Work Her Way’s mission is, in a nutshell, to provide real-life, fluff-free resources for working women everywhere. What drove your desire to create this outlet?

Carolyn: Thank you for mentioning our “fluff-free” approach! My brand is that of a straight shooter, and that is not an advertising tag line – it’s who I am. With that in mind, I like to allow the experts who write for Work Her Way to tell it as they see it. Even (ok, especially!) when it results in differing viewpoints.

It appeared to me that too many people were putting a rosy, positive spin on some tough subjects, like the recession and what it means to people who were just beginning to look at different ways to fit work into their lives. The sunshine-y themes of most mainstream media seemed to imply that all you need is “a makeover and a positive attitude!” and success will come. It left people feeling even more discouraged to be facing layoffs and other troubles.

We should tell the success stories, but they have to portray the reality, which is that it takes an unbelievable amount of work to make things happen in your career these days. When you read about actual success stories, they almost always include some failures and missteps along the way. When that type of story has a happy ending, it’s inspiring.

Q: As someone who has taken on many different roles, what advice would you offer our readers that might help make a career transition go more smoothly?

Carolyn: Sometimes you have to know when to call in the troops. You have a support system out there, in the form of friends, family, and colleagues. Don’t hesitate to use it, and to pay that forward when you can.

Making a transition is all about the perfect combination of planning and leaping. You know who you are – do you need to restrain yourself from jumping too soon, or do you need someone to light a fire under you to get you out of thinking and into doing? Whatever it is you need, surround yourself with the right people who will actually make you a bit uncomfortable, in that they will care enough to guide you in the right directions. Even when it means telling you what you may not want to hear.

Carolyn Kepcher and Career Woman, Inc.'s Lisa Quast

Q: Career Woman, Inc. is a proponent of mentor relationships in the workplace. Did you have a mentor and what was the most valuable guidance they offered?

Carolyn: Yes…His name was John Murray and I worked under him before I worked for Donald. He taught me “the ropes” because he had a genuine interest in my success. I would not have the career I have had without him. It’s also what has made me a passionate advocate for mentorship. It’s a core focus of my company, and something I will always be involved in on the personal side. I’ve mentored groups, and in one-on-one sessions.

Q: We all know that you work hard, but what do you do personally to unwind and maintain your work/life balance?

Carolyn: I work hard, so when I am away from my work, it’s all about family life! Like many working women, I don’t have a lot of me-time, so when the opportunity comes along, I claim it! I love to spend time in the kitchen, either with the kids or by myself. People are often surprised by my culinary and entertaining skills! Gourmet food and wine is a great interest of mine. I also try not to pass up an opportunity to head to the golf course!