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I’ve never had a five or ten year plan. I pick things up, collide with people along the way, and that has a lot to do with how I shape things.

“Life makes much more sense in the rear-view mirror than it does through the windshield.” This is the first thing Sunny Bates says as she launches into her story. After I briefly mention the topic of choice, Sunny knows exactly what I want to hear. I don’t get a word in, and for once, I don’t want to. Perhaps this is what she offers everyone in conversation, perhaps she can sense my eagerness in wanting to absorb her insight, perhaps both. Sunny Bates specializes in connections between people, businesses and ideas. A serial entrepreneur, she is a mentor and advisor, author, Brain Trust member at TED, founding board member of Kickstarter, and has played leading roles in a number of globally prominent companies. As we sit on her terrace with a sparkling view of Manhattan, Sunny stands up mid-conversation and starts yanking weeds from her potted plants, saying, “I’m better when I’m moving.” I presume this has something to do with her physical self needing to keep up with her mind, which you can almost see in motion as she speaks. From decades of lacing patterns between people, there is a seamless flow to Sunny’s energy, coupled with a swift intuition that renders your carefully composed questions insignificant.

“I moved to New York City with my boyfriend after studying at Cornell. We had worked on a newspaper together during college and he thought I should get into ad sales, even though I didn’t really know what that was. After finishing a New York University publishing program, I called everyone I had met there as well as 200 people in the yellow pages looking for a job. In this case the method was the message: if you have the tenacity to cold call that many people, you’ll be just fine in sales. This launched me into my first career, which was publishing. I spent ten years going from magazine to magazine, with a bunch of different jobs. Along the way, I noticed I was really good at putting people together and having a sense of fit. That led to me thinking I could be a recruiter—again, not really knowing what that meant, but deciding I would be good at it. It turned out to be the right sort of thing for me to be thinking about, and we ended up selling the magazine I was working for. This was around the time I had my first baby, and I decided to start a business from home. I’ve never had a five or ten year plan. I pick things up, collide with people along the way, and that has a lot to do with how I shape things. It has almost always been people who have pulled me into different directions in life.

When I was younger, I was obsessed with finding my passion. I was so drawn to people who were completely passionate about things, and I always wanted to be one of them. I notice this a lot with the millennial generation too: passion has become such a buzzword. In reality, my passion came from bringing all of myself to everything that I did. People know that when they get me, they get everything: insights, wisdom, energy, relationships, someone who will follow through. And those are the characteristics of someone who’s passionate.

I was working with Girls Who Code recently, and I asked the girls there (who are juniors in high school): what’s something you want so badly you can’t even say it out loud? Because the only way you can get things is if you start saying them out loud. One of the girls said, I want to be part of the next big thing. I told her, of course you do. But that’s not going to help you get there. What will help you get there is studying what the big things are, looking at the forces behind them, and aligning yourself with that. There are people everywhere saying, I want to be part of a start-up. I want to be part of something big. And that is not an attainable goal. That is a fallacy. If you latch on to things for that reason you will never feel accomplished. It has to come from something more substantive than a successful trend. Balance can be hard as a passionate person. Personally, I’ve always struggled with reconciling the expectations that I have for myself with reality. But a home tethers you, children and family tether you. You need to have things outside of work to come back to. There’s such a heavy focus on career. I felt it very strongly in my generation, and it’s been mollified through the millennial—this idea that work is supposed to define you. To think that you’ll find total fulfillment through work is like saying you’re supposed to find complete fulfillment through one person. You’re bound to be disappointed.

I think there’s a great deal of wisdom out there, but not a whole lot of people who are following it… there are forces which interrupt the availability of it. There’s so much anxiety, particularly in the younger generation. There’s this idea of what you should be doing. Not only do we struggle with that all the time—there’s a sense that once we’ve done it, whatever it is, that it will get easier. But it’s a choice you must make every day. I don’t think it necessarily gets harder, however. It feels like it gets harder, but that’s because nothing shifts dramatically. The shifts are slow and subtle. You think, once I’ve done this ten or twenty times, it shouldn’t be an effort. Gradually, it does become less of an effort as you internalize it and it becomes who you are. You can liken it to healthy eating, where you think, one day I’m going to wake up and temptation will fall away. I won’t want to stop by City Bakery and eat that cookie that haunts me in my dreams. But the reality is it will always be attractive to me. I will always have to consciously say no.

I think we live in an era and culture that makes us feel like we don’t have to say no. That we can say yes to all kinds of things and that we shouldn’t have to think in terms of sacrifice. Sacrifice has become a dirty word, which I think has created a certain angst instead of just doing something and seeing how it feels. The discomfort associated with the thought of having to give something up manifests itself in all kinds of ways: from how paralyzing our choices become, to how we try and do so many things at once. Which means we never feel the satisfaction of hunkering down and getting really good at one thing, because we’re doing a lot of little things. That describes me very well too.

I don’t listen to what’s being said about me. Whatever I’m doing is just fine. It’s good enough.

You really should write a book, but you can’t because you have all of these commitments. If you’re someone who doesn’t want to tackle difficult choices, over-commitment is a perfect way of avoiding them—and it’s so easy to be over committed these days.

When you think about how you choose to live, there’s that exercise of writing your own obituary. That’s a valuable thing to do, because it pulls you forward in life instead of trying to see your way through it. After 9/11, the New York Times did a beautiful tribute by publishing an obituary for every singe person who died. For a long time it was this special section, and I would climb into the bath-tub every night and read it. It was incredible to see the descriptions of people’s lives—to see how they were looked at and how they were judged. They were judged by the quality of their relationships, their compassion towards others—not by the size of their bank account. There was a bunch of investment-banking, high-rolling types, who didn’t seem to have anything outside of that title, and it felt like such a hollow life. To see what people were remembered for had a profound effect on me. I’m at a point now where someone’s successes and failures mean much less to me, because I’ve seen the whole trajectory of that. Someone may have started something successful, and while it may be impressive, it’s not something that particularly wows me anymore. Whereas people who are vibrant and engaged and love what they do, whatever it is, are ageless. And that to me feels so wonderful.

It’s important to understand that you cannot live and die by what people say about you. It will kill you. A great example of this is a friend of mine who is a soprano. She received terrible press after becoming involved with a very successful opera singer. I asked her one day, how do you get through each day? She said, I never read my reviews. One day they love you and the next day they hate you. And I guess I do that too.

Most people don’t even get a chance to be here in the first place. We have these Olympian standards of perfection: everything that comes out of our mouth has to be perfect, we have to have perfect children who are reflections of us, we have to look like a supermodel while doing it. It’s exhausting. The media have done a great job at exploiting those expectations. For women in particular, it’s easy to become obsessed with our looks. We grow increasingly invisible with age, yet our best selves have nothing to do with our appearance. When you’ve spent time around a dead body—when you have literally seen the life force draining from someone—it’s astonishing to think about the amount of time and energy spent on making our bodies look a certain way. When the life force is gone, that physical vessel doesn’t matter. You need to try and see past things like that. If you live in a hall of mirrors, it’s very hard to have any sort of clarity, or to move beyond your immediate circumstance. For me, what sets people apart are those who can connect their struggles and successes to something greater than themselves. I don’t necessarily mean in a religious context—I mean that they recognize the meaning in what they’re going through. If you can connect your experiences to something bigger than yourself, it helps pull you through.

I think our emotional health can be compared to the health of our heart. The health of our heartbeat is measured by how quickly it gets back to normal: a fast recovery rate means a healthy heart. To be emotionally healthy is not based on however many times you go off the rails or get freaked out, or have a reaction to something that sets you off. It’s how quickly you return normal. When you’re trying to make a change, you’ll always have that natural response (like the cookie), but what’s important is how you respond to those voices. We all have those voices inside of our heads, judging everything we do—and to listen to them is a difficult way to walk through life. So often, life isn’t always what you imagine it will be.”