20 Questions

Shark Tank's Barbara Corcoran Explains Why You Must Make Time in Your Schedule For Fun

The real estate mogul says innovation doesn't happen while you're sitting at a desk -- you need to break free.
Shark Tank's Barbara Corcoran Explains Why You Must Make Time in Your Schedule For Fun
Image credit: Patrick Ecclesine | ABC | Getty Images
Entrepreneur Staff
Staff Writer. Covers leadership, media, technology and culture.
12 min read

Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

From real-estate mogul to angel investor on the hit series Shark Tank, Corcoran Group founder Barbara Corcoran has seen many a business rise and fall. Her own success story is one of scrappiness and eternal drive.

Corcoran learned a solid work ethic from an early age. Her mother was a homemaker that kept a household of 10 kids with almost military precision and her father worked two jobs. In her teens and 20s, even though her dyslexia made school difficult, she poured herself in a series of odd jobs that ultimately led her to her big break.

She famously borrowed $1,000 and quit her job as a waitress -- a gig which she says gave her a crash course in how to sell -- to start a small real-estate firm in New York City. Over the course of the next 25 years Corcoran took that loan and grew her company into a $5 billion real-estate business.

Since selling her eponymous business for $66 million back in 2001, the bestselling author and speaker has made helping other entrepreneurs achieve their dreams her mission, both as a Shark and with her own firm, Forefront Venture Partners. She also still has a foot in the world of real estate, connecting homeowners with the best agents.

We caught up with Corcoran to ask her 20 Questions and find out what makes her tick.

This article has been edited for brevity and clarity.

Related: Barbara Corcoran on the 5 Traits All Successful Entrepreneurs Share

1. How do you start your day?
I start my day focused on my daughter. Then I sit on my chair and make a quick cup of coffee. That's when I get my luxury 15 minutes. Then I go downstairs, meet [my trainer] Margaret and work out for an hour and then go to work

The coffee gives me a prize of sitting by myself for 15 minutes. I do not have my phone with me. I daydream. The workout is in lieu of a psychiatrist. I find that when I work out, I like my husband more, I appreciate my life more. What seems to be an inordinate amount of pressure doesn't seem so bad at the end of the hour.

2. How do you end your day and how does this help you wind down?
I end my day reading gardening books and catalogues and daydreaming about the garden. It just winds me down and puts me out.

I think the more important thing than the gardening book or the catalogues is I've eliminated my phone from my bedroom. That is key. I used to use my phone to wake up in the morning. Now I actually bought a battery-operated white clock and use that to wake up. What a difference that's made to get my phone out of my room.

What I used to do a year ago is spend the end of my day setting my alarm on my phone and then seeing a text and then another and then I went down the rabbit hole. Two hours later I'm going to sleep at midnight, even though I jumped into bed at 10:30. I don't do that anymore. The best thing I've done is to get my phone out of my room.

3. What’s a book that changed your mind and why?
Not a book but a quote from Nelson Mandela. He said "having resentment is like drinking poison and hoping your enemy dies." I thought if he's not resentful, why would I be resentful? I saw the stupidness of that and dropped my resentment toward the person I was [angry with].

4. What’s a book you always recommend and why?
How to Win Friends and Influence People by Dale Carnegie. It's a powerful book that especially gets young people's heads on straight. It keeps its eye on the ball as to what's important for succeeding in business, which is people and how you work with people.

There's so much written on the dollars and cents, the left brain analysis, making the business plan and such hogwash out there. It sounds cool when you're reading it, but I don't think it makes a big difference for anybody trying to figure out who they want to be in that life.

Related: Health and Beauty Mogul Bobbi Brown Shares The Biggest Time Sucker -- and What You Can Do About It

5. What’s a strategy to keep focused?
It's hard. I used to be the most focused person I've ever met. You couldn't sway me off what I was after.

Yet, I would describe myself in recent years as having a touch of ADD, which is not me or never used to be me. I think it's a result of all the technology. I've declared technology my enemy to a large degree. I have a need to answer everything properly and not to forget anybody. I don't have a computer on my desk; I just do everything on my phone. And what I did is I took my email off my phone. So rather than looking at God knows how many I got in a day -- all very important of course, until I realized none of it was important. I probably went from maybe 150 emails to none. I bought myself a lot of time. I feel so much better. I actually [have time to] reflect after I've had a meeting or conversation now.

6. When you were a kid what did you want to be when you grew up?
I had no idea what I was going to be. I just wanted to see what was outside the little town where I grew up. It was two miles long and two blocks wide -- not very big -- and everybody knew everybody.

7. What did you learn from the worst boss you ever had?
Milton Schweitzer. I worked for two and a half years in high school as a sales clerk in his little department store in a town away from my house. I learned not to be cheap and pay attention to people's ego or face.

I worked my buns off, and he was just a critical boss. One day, he asked me to go up to the attic, take all of the men's socks and label them based on the color. With a magic marker I labeled them black and grey. The next day he had me come in and brought me up to his office. I thought he was going to compliment me, because I had them in perfect order. I came into his office, and he said “look at this.”

He showed me a box that said "grey.” He said go up relabel those boxes you spelled grey wrong, [it's gray]. I was mortified. I hated him. I thought of quitting. Instead, I went up and relabelled all the boxes. That night I went home and my father was a meticulous speller. I said, “guess what Milton had me do?” I relayed the story, and he went and got the dictionary and looked up the word. He said you can spell it both ways. I went in and told him that and quit. I felt so good about that. I learned from him why be critical and not let somebody stand with pride?

8. Who has influenced you most when it comes to how you approach your work?
My mother without a doubt. She was a housewife with 10 kids. My mom's house was like bootcamp. Everything was in order. It was like an assembly line.

Everything I do I'm just like my mother -- from the way I organize myself to the way I create systems instantly in anything that's chaotic. The way I shortcut things the way she does, the way I see the positive things in people that my mother did with each of us. She never never told us what was wrong; she always told us what was right.

The way she kind of ran the neighborhood; she was the boss of the neighborhood. And the way she gave advice -- I give way too much without being asked.

9. What’s a trip that changed you?
Our childhood trips to Boston and Saratoga Springs. That was my introduction to a vacation and what it meant to get away. And so I love to get away. Even before I had any money I was going on vacations to Coney Island for day by subway. It was my mother's influence. She said everyone needs to get away from what they know.

Related: Use This Successful Entrepreneur's Scheduling Secret to Have Your Most Productive Day

10. What inspires you and why?
Seeing how far you could go is the challenge of life. I want to see how far I can go, how many things I can do, how many miles I can pile on before I drop dead. I'm so curious. I want to see what's out there and what's around the bend. That's why I wake up really excited in the morning. What's going to happen today? Even if it's bad stuff, I'm really excited to see what's what's right out there you know. I spend a lot of time planning fun, as much as I plan work, because I think it's very important.

11. What was your first business idea and what did you do with it?
Well, I failed with it. I was in my junior year of college, and I started a flower of the week club. For $8 you have a bouquet of flowers delivered right to your door. I had 42 customers. So by anyone' standard that's not a bad business start. But I didn't know how to ask for the money, so I would always stuff a little bill with the flowers. People didn't pay and I would keep delivering because I was too afraid to say “Can you pay your bill?” In the end, I went out of business.

12. What was an early job that taught you something important or useful?
I learned more from waitressing than anything else. I think it taught me sales. Somebody comes and sits at your counter, and you start schmoozing them up, making them laugh. I learned to make people like me and that's the beginning of all sales.

13. What’s the best advice you ever took?
I didn't listen to any advice. [But I find now when I invest in new businesses] the good ones listen; they're really excited. They ask questions [and for advice] and then they go out and don't do any of it. Because in the end, they listen to themselves. That's what all my good business entrepreneurs do. The ones who are taking careful notes, I know I'm going to lose money, because they don't have their own core. They don't listen to their own counsel. I listen to everybody, but I do what comes from my gut and feels right.

14. What's the worst piece of advice you ever got?
It was one of the worst and the best. It was from my first business partner who ran away and married my secretary. When I finally ended the business he said to me, which was the worst advice, you'll never succeed without me. He kicked me in the ass and gave me such ferocious drive to succeed. But another way of looking at it would be it was the best business advice. He insulted me. He really got me going.

Related: This Successful Entrepreneur Shares The Trick That Helps Her Tell The Difference Between Being Productive and Being Busy

15. What’s a productivity tip you swear by?
Master your phone. Use your email and texting in line with what you want to do. Don't fall for the reactive trap -- reacting to emails texts and hopping to it. Do it on your own terms.    

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I have endless to-do lists on my phone. Recently I learned how to put one of those little bubbles next to it which allows you to check it off. I use notes for everything.

17. What does work-life balance mean to you?
It doesn't exist. I think the best you can do is delegate your time exclusively to work and delegate your time exclusively to the rest of your life -- your kids, your family life, your friends, your joy.

18. How do you prevent burnout?
Take a vacation. And I plan for fun. I look at my evenings and think when can I have my best friends over for dinner. What kind of a theme party could we have? How about a psychic party? How about a learn to knit party? How about a make real pasta party? I always have a theme because then I get involved with planning that. Even though that's not a vacation, mentally it is for me, because [it allows for] total creativity.

19. When you’re faced with a creativity block, what’s your strategy to get innovating?
I go out. To a great store or a museum or ride my bike in Central Park. I do anything but sit. You will never have a creative idea at your desk.

20. What are you learning now?
What I'm learning now is how to dance. It's so delicious, this physical movement for the sake of not getting in shape or doing the right exercise but for the sheer joy of movement.

I'm also trying to be a better gardener, but I've been doing that my whole life. There is always so much to learn there.

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