“I couldn’t even cross the road” Dina Kaplan on the fear that lurks in the startup world, jumping headlong into the unknown and not meeting Sheryl Sandberg

bungee
bungee

You can almost touch Dina Kaplan’s energy. Despite her tiny frame, it feels like she could launch herself into the air and power off at any second. When she talks, her full attention is with you, when she smiles, it’s huge. She seems like a woman who has discovered a secret.

The co-founder of Blip, darling of the New York tech scene, organiser of The Founders Club and Calliope Group, and a woman that Sheryl Sandberg wanted to get to know better, from the outside Kaplan had everything going for her. But she was frightened to step across the road.

Here, after a refreshingly honest talk at DLD Women, she talks with us on the fears that many entrepreneurs can face, her own personal escape route from modern unhappiness and why facing your worst nightmares can lead to enlightenment…

width="225"The middle of success, the fear of failure

“Sheryl Sandberg emailed me one evening. She said ‘I want to get to know you better, I want to spend time with you’.” I got the email at night and literally nearly fell off my bed. But I didn’t schedule the meeting,” says Kaplan. “Fear was holding me back. I thought ‘She must not really mean this. I’m sure that if I respond that she’ll think that I am wasting her time…'”

Co-founder of Blip, a successful platform for original web series, Kaplan found herself wearing a variety of high-profile hats: “I was doing the books, the PR, the marketing, HR, business development, investor relations… all without even one full-time direct report. But I was afraid to ask for help, I was afraid I didn’t deserve staff and that I wouldn’t be a good manager…”

“I’m incredibly social, a connector as they say in the tech world, but I was also very hesitant to ask out anyone one-on-one who I perceived as ‘more important’ than myself.”

“My everything was the company, but my everything had to change”

Kaplan describes the situation that was her turning point: “After seven years of working there, and eventually running six departments, the Founders Club, Calliope Group I started to feel a sense of panic. I was afraid to walk down the street. I would feel dizzy, afraid, like I was about to pass out. I lived in fear of passing out in the middle of a busy New York city intersection. So I started to take cabs. Everywhere.

“If I actually had to cross the street I would try to make eye contact with someone crossing at the same time as me, in the hope that we would have enough of a connection that they would pick my body up of the ground if I fainted. It was a terrible way to live. My everything was the company, but I knew that my everything had to change.”

Tackling real-life fears

Kaplan gathered her family together and told them that she had to make a change. She booked a one-way ticket to Indonesia, beginning an odyssey that would change her outlook forever.

“A fellow traveller told me: ‘This time you have to travel is like a gift. Use it to conquer your fears…’ I realised that I was living in fear. I was afraid to speak up for myself, afraid to ask for help, afraid that my friends don’t really like me all that much. I was even afraid to walk down the street,” Kaplan admits.

So she set about confronting some very real and tangible fears – scuba diving (which she had vowed never to do again after someone died on her first scuba trip in her teens), zip-wiring, bungee jumping – in order to help her address day-to-day anxieties.

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“The bungee jump was in Queenstown, New Zealand,” says Kaplan. “I ended up in the bathroom, in a stall for an hour. I was staring at toilet paper, thinking ‘What a great invention that I have never realised before. I wonder if this is the last roll of toilet paper that I will ever see in my life…”

Eventually, she jumped. “I felt like I was flying into freedom. I felt like I was liberated from all the fear I had had my entire life. I felt like I was flying into a new me… When she had stopped crying (and completed a second jump) she wrote this: “I have decided to live a life where courage is more important than fear. With this jump I have conquered my last fear. In a few weeks I will return to the US a different person – more relaxed, compassionate and open and I will live without fear.”

Be authentic, watch the difference 

“Since then my life has changed dramatically. I used to live by responding to people, but now I live on my own terms. I ask for what I want, I am open and vulnerable. I live pro-actively rather than reactively.

Kaplan goes on to explain: “I had a meeting when I got back with a VC firm. Normally I go into these things all buttoned up and on-message. But I sat down for the meeting and the partner asked how I had changed during the year of travel. Before the trip I would have talked about how much I loved work or something else I thought they’d want to hear. But instead I talked about my meditation, how it changed me and why I think that every entrepreneur and VC should meditate. The old me would have walked out of the meeting terrified.

“I decided to write a funny, quirky email as a follow-up. I used to be queen of the boring business email, but the next night I got an email back and the VC said it was the best meeting he’d had in recent memory.

“In the past, I was so filled with fear that it permeated all of my interactions. I was afraid that people wouldn’t like me so I would talk too much and try to be entertaining all the time. People can sense when you don’t need their approval or their feedback and that normally draws people in like a magnet,” she says.

Kaplan beams: “So this is living without fear and I heartily recommend it. It makes you more relaxed, happier, better at your job and better with people – personally and professionally.

“But, no, I still haven’t set up that meeting with Sheryl…”

Read Dina’s top tips for conquering fear after the jump…

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Dina Kaplan’s tips to conquering fear

We can’t all take a year out of our lives to find enlightenment, but, says Kaplan, with a some self-awareness, we can all make a huge difference to the way we approach the world.

A healthy you is a healthy company

I was working so hard that it wasn’t healthy. It wasn’t good for me and it wasn’t even good for the business. I missed some strategic things because I was so knee-deep in the P&L and revenue numbers for each month. It’s important to be mindful of yourself and your company’s larger position within the market even when you’re focused on managing operations.

Be mindful

Be aware of yourself and your thoughts. And your drivers. A lot of us have instant reactions to incidents that happen to us throughout the day, but we don’t know why we’re reacting in a  certain way…and we don’t even know that we don’t have to react in this way.

Mindfulness gives you some distance between what happens to you and how you respond to it. If someone insults you, you can choose to insult them right back, start crying, hit them – but you can choose a response. It becomes a powerful way to make active decisions.

Meditate

As part of this mindfulness, I am a huge believer that entrepreneurs should meditate. Does it ruin the fire that powers everything? There’s a bit of a danger of that, because you get a lot happier when you meditate. But in the end it makes you much better at your job because it makes you much more strategic and lets you see things, whether that’s the market or how an employee is acting.

Do scary stuff

Doing tangible, frightening stuff does translate. In a way it’s less scary to be in a room full of spiders if you’re afraid of spiders than to face your fear of public speaking. It’s easier to conquer physical fears. So if I needed to write a scary email, I was able to do it because I could think: “But wait a minute, I just jumped off a bridge…”

Be authentic

When I did a Vipassana (a 10-day silent meditation retreat) I took a vow of truthfulness, which I have followed. It was difficult at first, but it’s made my life a lot more relaxed. We all have choices to make – am I going to lie or am I not? I know I am never going to lie, so it relieves some stress. It’d probably be harder if I was in sales.

Validate yourself

Get your validation from yourself. If you can learn to be happy with yourself and get everything you need from that then you become a lot less needy… and ultimately successful.

width="200"Embrace impermanence

Is it in your nature to simply not be good at public speaking, or networking? These things that we think are us – our likes and dislikes and thoughts that we think are permanent, Buddhism teaches us that everything is impermanent. Things change.

Image credits
Meditation: Flickr user IcronticPrime
Buddha: Flickr user archer10 (Dennis) 

For related posts, check out

The Zen Entrepreneur: how to attain spiritual and work-life bliss
The key to success in 2013? Focus not on your To-do List, but on your Already Done List
Heureka 2013: Angel Investor Peter Read on the perfect pitch and how mindfulness can help enlighten entrepreneurs