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How Jennifer Pastiloff Went From Being a Career Waitress to Building a Business Based on Being Herself

The Helm's Editorial Director chats with the author and teacher about why asking “Now What?” every day is the most important thing you can do for yourself this year.

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I’m usually allergic to words like “manifest”—as in “manifesting your truth”—or any other application of the word that reeks of New Age pabulum. Then I found myself at “The Manifestation Workshop: On Being Human” with Jennifer Pastiloff and my thinking shifted. Jennifer’s workshops, which last anywhere from a few hours to a full week, are hard to describe. When I attended a two-day gathering in Massachusetts last year, the group was made up of about 50 women of all ages, most of whom had never met before. And yet somehow Jennifer managed to create an environment where a guarded and jaded New Yorker (me) was able to reveal my deepest fears to a group of strangers–and a few hours later ecstatically dance with them. It was at that weekend that I was also introduced to Jennifer’s concept of “Now What?”–the idea that one must take baby steps every day in order to manifest one’s goals.

Jennifer herself is not New Age-y at all. Though she’s a multi-hyphenate teacher-yogi-social-media persona—she has built a brand and a business out of unabashedly being herself. Stuck until well into her 30s at a dead-end waitressing job in Hollywood, she eventually trained to be a yoga instructor,which in turn spurred a career leading workshops around the world to a growing cult following. (Her fans include bestselling author Cheryl Strayed and pop star Pink). At the same time, she built an army of followers on social media and has written a book, On Being Human: A Memoir of Waking up, Living Real, and Listening Hard, which will be published in June.

A near-pathological truth-teller, Jennifer opens her workshop with just two rules: “Listen and tell the truth.” But just because she doesn’t look or act the part of a traditional businessperson, she is a dogged entrepreneur just the same.

Jennifer, 44, lives in Los Angeles with her husband and two-year-old son. I caught up with her on the cusp of the new year to talk about “fearlessness-ish,” her ninja approach to book publicity, and why “Now What?” is the most important thing you can ask yourself in 2019.

LL: What exactly do you do?

JP: I say I’m a professional listener—which is ironic because I am deaf unless I wear hearing aids. Through my workshop and my writing, I was able to alchemize a lot of things I was good at. Most things I’m terrible at cleaning, cooking, you name it. But I’m really good at connecting people and at listening and at not taking myself too seriously.

LL: Before you started leading retreats all over the world, and writing a book, you had a very different career trajectory.

JP: I studied writing at NYU and spent years trying halfheartedly to be an actress. Then for almost 14 years, I waitressed at the same restaurant, The Newsroom, in Hollywood. When I was 33-years-old, I had what I think of as a nervous breakdown.

LL: What did that look like?

JP: I stopped being able to function. I didn’t care if I lived or died. I felt like it was too late for me to make any changes–which is absurd.

LL: How did you get out of that place?

JP: I started to do yoga to help myself. Then I went on antidepressants and everything changed. All of a sudden there was a glimmer of hope. After years of being in a dark hole, it was as if someone threw me a rope and I began to climb out. I signed up for yoga teacher training not because I was that excited to be a teacher but it was forward motion. It was a step. One year after doing the teacher training, I had enough money to leave the restaurant.

LL: And around that time you starting writing a blog, right?

JP: Yes, at first I used the blog to be clever and to try to get people to come to my yoga classes. Then I thought, forget this, I’m just going to be honest. I started talking about things like depression, my hearing loss, grief, and anorexia. As soon as I shared all the things I had always hidden about myself, people started coming to me in droves-both online and to my workshops. 

LL: So it sounds like you were validated right away—you knew your honesty, your message, was having an impact and your business sort of grew from there?

JP: Yes. But there’s a danger in that feeling of validation. It’s tricky, because you have to find a balance of not letting your self-worth be determined by people’s responses to you. You never want to feel like other people are giving you life.

"As soon as I shared all the things I had always hidden about myself, people started coming to me in droves—both online and to my workshops." Tweet

LL: Can you explain what happens at your workshops?

JP: They are really about listening—to yourself and to others. What I say at the beginning is, “You only need to do two things here: listen and tell the truth.” One of the goals of the workshop is for people to become not fearless, but fearless-ish–to let down their guard and start to share who they really are. The experience of being seen and heard is something so many of us are missing in our lives and it’s so profound and freeing.

LL: That’s easier said than done. How do you make it happen?

JP: At the beginning of a workshop I ask everyone to take a sticky note and write down what they want to manifest in their lives. We stick them all over the room so it’s basically a gallery of dreams. I specifically like using sticky notes because it’s a reminder that you’re not stuck to it, it’s movable. That was a big epiphany in my life: I get to change my mind. There’s something about the act of writing it down, and putting it out there, that is very powerful. But then I ask people to take someone else’s sticky note down off the wall and keep it, which is everything.

LL: Why?

JP:  The greatest words you can say to me are, “It’s going to be okay” or “I got you.”  But in order to be the recipient of that, you have to give it, too. People have written on their sticky notes, “I want to start my own business,” and then two years later they’re thriving. Speaking things out loud gives them power. And you’re doing it in an environment where people are holding you up. I love this quote from Freud: “How bold one gets when one is sure of being loved.” People feel like, “Yeah, I can do this.” It comes back to profound listening, bearing witness, not looking away.

LL: One of the things I like about your workshops is that they are transformative, but also fun and not all that New-Agey, the way these things can sometimes be. When I went to one, I belted out Journey’s “Don’t Stop Believin’” in front of an audience of strangers.

JP: Right, I definitely encourage people to “dork it out.” I say, “If you sing badly, sing louder!”  We dance a lot. I tell people to let the snot fly and laugh at themselves, to just be as childlike as they can be. Movement— yoga, dancing, whatever—is always part of the workshop so the body gets incorporated, so that the stories we have stored in our body, the stress, all the stuff that is stuck in there–starts to get released. I also believe we can be more vulnerable when we are less in our thinking minds and more connected to the body.

LL:  I learned the concept of “Now What?” at your workshop and it’s helped me a lot. Can you explain what it is?

JP:  I began to notice that some people would come to my workshops again and again and would still be talking about the same things in their lives that they wanted to change or let go of. If you’re not asking “Now What?” regularly in regard to your goals then all you are doing is making a list in a workshop that you’re going to forget about—and when you look at it again in six months, you will just beat yourself up about not making those changes.

LL: But it’s more than just setting a goal, right?

JP: “Now What?” is just putting one foot in front of the other. We have two options in life: keep going or shut down. I’m concerned with the keeping going. And asking myself “Now What?” has helped me with that. “Now What?” should feel like a gentle invitation, and I really encourage people to start small. That doesn’t necessarily mean the goal has to be small, but you need to take baby steps. For years I’d been saying I want to write a book. I did it by asking  “Now What?” every day for a few years, writing a little bit whenever I could, and guess what? That book is coming out in June.

“Now What?” is just putting one foot in front of the other. We have two options in life: keep going or shut down. I'm concerned with the keeping going." Tweet

LL: How does one keep herself accountable and make sure the “Now What?” amounts to real change?

JP: I’m a big, big believer in asking for help—that’s another part of “Now What?” When you’re not reaching your goal, or feel stuck, it’s important to call your “I don’t suck, right?” people who can remind you that you’re okay and hold you accountable. They are the people who don’t let you live in your bullshit story.

LL: Your “business” is not a straightforward one since you do a lot of different things, some of which, like the workshops, are a little hard to explain. I’m curious: Do you view yourself as an entrepreneur?

JP:Yes, even though I’m not a traditional business person. I teach yoga at Equinox for two hours a week—that’s my gas money. Other than that every cent I make is from my workshops, my writing, my online classes, lecturing. There are plenty of things about business I’m bad it—I’m not organized, for one. So my mom actually helps me with the business side of things. I try to stick to what I’m good at, like social media. 

LL:  Can you explain the unorthodox way you’re approaching the launch of your book?

JP: I didn’t have the $25,000 it would cost to hire an outside publicist. But after years of supporting others through my work, I figured people would want to lift me up, too. So I decided to just ask for help. I put a call out on social media and just said, “Who wants to be on my street team?” About 500 people volunteered. Those people are helping spread the word on social, they’re pre-ordering books–the day it came out on Amazon it was number one in self-help new releases, number two in the “movers and shakers” category. It was crazy. And now, the street team has turned into a community of its own. Every Friday I ask people to share anything they want to promote or sell so that we are all lifting each other up. I really believe there’s enough for everyone and we can all reach our goals if we help each other.

LL: Do you consider yourself an “Influencer”?

JP: I can’t stand the expression “Influencer.” I’m influenced and inspired by so many different people–my two-year- old, my special needs nephew, the woman who works in the parking lot where I teach yoga, different authors—and it constantly changes. And not one of them is because they have a big Instagram account. The term implies that you are an influencer if you have a lot of followers online. This is absurd to me. If you want to be influenced by me or inspired or feel like I have taught you something, great. I will never label myself an influencer, though. Quote me on that.

This interview has been edited and condensed for clarity.

You can pre-order Jennifer’s book here and learn more about her workshops on her website.

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