Sara Bliss, TAKE THE LEAP: Change Your Career, Change Your Life

Sara Bliss, TAKE THE LEAP: Change Your Career, Change Your Life

I’m excited to be here today with Sara Bliss. Sara is a New York Times bestselling author and a brand advisor. She’s the author of eleven books, which is amazing, including her upcoming nonfiction work, Take the Leap: Change Your Career, Change Your Life. She cowrote three books with makeup guru Bobbi Brown, who’s my favorite person ever. That’s all I wear. A former senior writer and editor for Yahoo!, she has written for The Wall Street Journal, Esquire, Town & Country, Oprah, and Travel & Leisure as well as for many other online publications. She speech writes. She ghostwrites for CEOs and other high-profile clients. She does branding work. She does everything. She currently lives in New York City with her two children and her husband, where she was born and raised.

Welcome, Sara.

Sara Bliss: Thank you. I’m so excited to be here.

Zibby: You are an amazingly prolific author. I’m totally impressed with how much you’ve done. What made you decide at this point in your career to write Take the Leap? Why now? Tell the listeners a little about what it’s about please.

Sara: I’ve written profiles my entire career. The one thing that I found that was really fascinating is a lot of the most successful people, it wasn’t a linear path. It ended up they had this whole other life beforehand. To me, that was fascinating and really inspiring, partly because I wasn’t really that happy with my own career. I’d gone into nonfiction as a little bit of placeholder with this idea that I was going to be a novelist. I had written a couple books. The one that was supposed to be my big breakout book just wasn’t. I became everybody’s ghostwriter. At the same time, I was doing all these profiles. There was a lot of takeaway from it. A lot of these stories, there’s a lot of takeaway. So many people want to do this themselves, so to hear stories of how people did it, that’s really the crux of it.

Zibby: You profiled sixty-plus people. Some profiles sometimes they wrote their own essays, like Jill Kargman for instance. How did you identify that group of people, those sixty people?

Sara: I wanted it to be that if someone is thinking of making this career leap — let’s be honest, everybody is thinking about this at one time or another — that they would find somebody whose story that they relate with. I picked the big types of careers that people tend to gravitate towards as second careers, going into wellness, becoming an entrepreneur, doing something creative, giving back. Then I found the most inspiring stories from each category. It was a lot, a lot of research, a lot of chasing people down. I’m really, really thrilled with the stories that we have. When I first put out in the universe that I was doing this book, I got a lot of people telling me that they had friends who left finance to become yoga instructors, and that’s fine —

Zibby: — I have a friend like that.

Sara: There’s a lot of people. I wanted the stories to really, really resonate and be really varied, so the reasons for switching, the hurdles they had to overcome. I wanted there to be a lot of takeaway for people.

Zibby: What would you say some of the big lessons that you got out of the book and all the research were?

Sara: The biggest is you have to prepare. I was going to start with the book with a sentence basically saying this isn’t a guide to blowing up your life. I think so many people hear this idea and they think, “I want to do that. I want to go into my boss’s office, and tell him to go to hell, and run off to Belize and open a beach bar, and never come back.” The people that are really successful in making these kinds of changes, even if it involves a move to the Caribbean, they’ve done their homework. They’ve prepared for it. The biggest thing is every single person was prepared in some way. They went back to school. They found a mentor. They worked for free on the side. They took online classes. They reached out to someone via LinkedIn who had already done it. Whatever it was that they did, they were ultimately prepared. They also didn’t go into an interview and say, “Just give me a chance. I can do it.” They were ready. They said, “This is why this would be the right thing for me.”

Zibby: Was it usually at the same age? Is it the forty-year-old breakdown, time to change it up?

Sara: There’s a lot of people in their forties who are doing this, definitely. There were definitely some younger people as well. A couple of the people who switch careers actually because they were having mental health issues with their previous careers, that happened a lot in their twenties. One guy was agoraphobic. Other people were having terrible panic attacks and depression. They found that being outdoors or working with their hands or whatever it was for them was ultimately healing. For a lot of people, being in an office nine to five, it just doesn’t work for them. That, to me, was one of the most interesting takeaways, that that was a reason that people change. For some reason, I thought everyone in the book was going to say, “I just wanted to be happier. I wanted to pursue my passion.” It wasn’t all because of that.

Zibby: Interesting. Were there people that you really wanted or you had in mind that were great examples of this but then they said, “No, I don’t want to be in the book,” for whatever reason?

Sara: Scott Harrison, I don’t know if he has a new book out called Thirst. I think it just came out. He’s a fascinating guy. He was a party promoter and was using a lot of drugs and drinking and living this very different kind of life. Then he had a spiritual awakening. Now, he started this charity called Charity Water.

Zibby: Oh, yes. I know that.

Sara: I really wanted him in the book, but he has his own book so the timing didn’t work out. I stalked Aaron Maybin. I really wanted him in. I sent him an email. Right away, he said yes. It was right at the time that he was getting a lot of press. For those that don’t know, he is a guy that was in the NFL. He left. He became an artist, which was something he actually had done since childhood. He was teaching art in the Baltimore public schools. He put out this video showing his classroom full of kids who did not have heat, were in coats and cold. He basically said how can kids be learning in these circumstances?

At the time that I was trying to get him in the book, he was getting all this national press attention. Amazon was shipping coats. All these people were offering to fix the heat. He was really busy. He said yes. Then I didn’t hear from him for a long time. I kept emailing him and didn’t hear from him. Then I was on the first pass of the book. Most of it had been written. I was like, “I’ll just try one more time.” He said yes. I was thrilled. His story is really inspiring. It’s also really insightful. This whole dream he had of the NFL and what that would be like, and when he got there, it just wasn’t what he thought. The reality of some careers versus the dream is something that also gets people to switch it up.

Zibby: Totally. You don’t really know until you do it a lot of the time. You can ask people and shadow people, but until you’re doing it, right?

Sara: I agree. Barbara Corcoran was one of the experts in the book. Her advice really resonated, which was don’t follow your passion. Sometimes your passion doesn’t make a good career. Sometimes it’s maybe not something that’s going to be financially viable. I also think there are a lot of people who don’t even know what their passion is. It’s so much pressure.

Zibby: Didn’t you say she used to deliver flowers every day or something like that?

Sara: Yeah. She was obsessed with flowers, and so she thought this would be the perfect career. She said she was by herself. She was by herself arranging flowers. She was by herself delivering flowers. She was lonely. Her skill is she’s really a people person. She realized that in all the careers that she had done well in, she had been with people. She was a waitress, which she says was the best preparation for being a salesperson. She ultimately went into real estate, which is where she made her money and found her biggest success. She had twenty-three jobs beforehand. Her advice to everyone is try as many jobs as possible. That’s really where you see what see your strengths are and go with what your strengths are. That’s how to find it.

Zibby: It helps also taking some of the pressure. You can have things you enjoy doing. You’re like, “Is this a passion? I don’t know. Would I call this a passion?” I worked in advertising. I’ve always loved writing, but I thought maybe psychology, maybe advertising, maybe branding. Then I had this whole thing where I was marketing Pepperidge Farm cookies. It was really fun. It was great. It was an account at one of these internships I had, but is this really my passion in life? This is my passion? Can I even tell people this is my passion, trying to sell more cookies? I don’t know, not that there’s anything wrong with that. I really enjoyed it. I think there are different things your career can do for you. It doesn’t have to fulfil necessarily, especially at the beginning stages — what you long for is your whole being. It can be something you enjoy or one part of your brain that you want to exercise. You learn skills and somehow, hopefully, they come together later.

Sara: I also think it puts this insane amount of pressure on your career. It’s a little bit like a relationship. If you have a healthy relationship, that person isn’t going to be giving you all your joy. You have to find happiness yourself. Then you come together as whole people. I really think that’s a similar analogy to what works best for a career. You have to be a happy person and an excited person about what you’re doing, willing to take all the bumps in the road, all the hurdles, all the setbacks — and there will be them, even when you find your “passion” or find what you’re meant to do.

This idea that your career has to make you happy all the time is ridiculous. I’m sure you love your career. I love what I do. I am obsessed with being a writer. I can’t imagine doing anything else. It’s the reason why I’ve hustled and done all these brand-new things, so many ghostwriting things, to stay in this world. There are times where it’s very humbling. There’s a lot of rejection. It can be frustrating. I have kids too. Sometimes I’m up until two in the morning trying to make a deadline when maybe I don’t love my career so much. At the same time, I would never do anything else. When you take out this idea that your career has to be this passion and make you happy, then you can be a little bit more realistic about what you’re good at, and what you like to do, and where you’re definitely going to be happiest, but it’s not perfect.

Zibby: Right. It’s still work. You still have to try really hard.

Sara: There’s actually a really interesting woman in my book. Her name is Caroline Waters. She’s now a librarian at the New York Society Library. She had been in finance forever and had been doing really, really well. She was a financial consultant. She kept getting promoted and promoted. She knew that she wanted to do something else, but she couldn’t figure out what it was. Her work was so intense and busy that she never could figure out what the next move was. All of a sudden she was like, “I’m twenty years into this. I know I want to do something different, but I don’t know what that is.” She took six months off. She quit her job. She didn’t tell anyone what she was doing. She did a bunch of volunteer work and internships. Then she volunteered at a library just because she loved to read and loved to be around books. When she was there, she was like, “Oh, my gosh. This is what I need to be doing.” She said she never would’ve figured it out while she was working. She also really, really hated that pressure, that whole passion pressure. It didn’t make sense for her.

Zibby: And it’s so public. It’s the first thing that people tend to ask. “What do you do?” Oh, gosh. Now I have to… “Well, I don’t know. You want the whole story? Do you want to know what I did before nine AM this morning?” It’s always so public. They write in your marriage announcement. “She does…” Why’s it so important? I don’t know.

Sara: Also, people really tie it to your identity. It’s easy to get wrapped up in the idea that it is your identity and tied to your self-worth. That’s ridiculous, but I think we’ve all been there because people place so much importance on it.

Zibby: If you’re miserable in what you’re doing, there might be other options. If people are like, “I go. I dread this every day.” There’s a tipping point where you’re like, “No.” It is the job, or it is the industry, or it is something about it. Life’s too short. It’s just figuring out where that line is.

Sara: Definitely. I think you should be a realist. Be realistic about your job, but I also do not think you should be unhappy and miserable in your job every day. That’s really soul-sucking. Then it transfers to other areas of your life. Maybe you’re grouchier with your kids or your spouse or whatever it is. It’s not worth it. The thing about all these stories and what was so inspiring is all of these people came out more fulfilled, happier, definitely living the lives that they always wanted to live. To me, what I realized after writing the book was it’s not so much about a career change. It is, but for most of these people it was really about changing their lives.

They wanted to live a different kind of life. They wanted to live a life where they were more adventurous. They wanted to live a life where they felt like they were helping people or doing good in the world. They wanted to live a life where they weren’t having anxiety attacks in their office or miserable with their coworkers. They were able to do it. I do think being unhappy is a big motivator for a lot of people. It is something to listen to as long as not you’re not pie-in-the-sky thinking your next career is going to be perfect. A lot of these people, they’re doing their dream job, but they’re working harder and longer. Some of them are making less money. There is a couple in Anguilla. They own a restaurant called . They are actually working less, making more money, and living in paradise, but it wasn’t the case for most people.

Zibby: Sounds good. Sign me up. Simon Doonan had this really funny quote in your book. “If writing makes you unhappy and you procrastinate or have to drink scotch in order to get going, then try something else. Writing should make you happy.”

Sara: I agree. That’s a good quote to apply to anything. If you’re feeling the need to use substances to get through the day, maybe that’s a sign. He’s interesting too. He didn’t write a word until he was forty-six.

Zibby: I saw this. I didn’t even realize that.

Sara: I didn’t either. I’ve interviewed him over the years. I know him. I ran into him. He asked what I was working on. I told him this book. He said, “You have to write about me.” I didn’t know what he was talking about. He said, “I didn’t write until I was forty-six.” I’m so jealous. He has the best voice. When you read his stuff, you know it’s him. That’s something that writers spend their careers chasing after, is having that kind of signature voice. He’s so witty and so clever. He makes it look so effortless. For him, it just happened. He was working on a book project that was supposed to be really visual. When he wrote the introduction, the editor was like, “You need to write more.” It became this thing where he gets up at five in the morning. He does all these books. He does it in tandem with his career he has at Barneys. He loves it. The whole dual career thing, it’s something that’s an option for some people too. You don’t have to give up one thing for another. A lot of people manage to do two.

Zibby: You said you’ve written three screenplays and a novel and that you’re disappointed those didn’t sell prior. What are they about, out of curiosity, even the abridged version, whatever you want to share?

Sara: The first one I wrote was about three sisters. I have a lot of sisters. I don’t even remember what it was about. It was not good. At the time, I took six months off to just write a novel. I was obsessed with it. It wasn’t any good. To be honest, I know for a fact, writing novels, that’s not my skill. I do think there’s something with the whole screenplay thing. I was working on a screenplay, which I need to revisit and this book has inspired me to revisit. It’s a similar topic. It’s basically about a woman who is everybody’s ghost-songwriter. She has three kids. She’s forty. She suddenly says, “I don’t want to be behind the scenes anymore. I want to be the one singing my songs.” That’s how she does that. Especially with this book and what I’m writing about, I need to go back to it. I will, actually. I will. It’s not something that I’m going to keep on the shelf. The novels, that’s not happening.

Zibby: I had the same thing. I took six months off after business school and wrote a novel. Well, first it was a memoir. Then I changed everything, rewrote it four times. It became this convoluted novel. That also didn’t sell. I was crushed. It was soul-sucking, crushed public failure, the biggest failure of my life. I didn’t think I’d ever pull myself back together.

Sara: I ran the marathon once. One of the pieces of advice I got was tell everyone you’re running the marathon because then you won’t back out. I did the same with my novel. I told everyone I was writing this novel. Then when it didn’t work out, it was definitely humbling.

Zibby: It’s like dieting. I already told you. I’m trying this keto thing. Let’s see how it works. No. Doesn’t always work to tell people.

Sara: It doesn’t. I do think it’s good to know what you’re good at and what you’re not good at, at the same time.

Zibby: Or at different times in life. I don’t know how long ago it was for you. I wrote that almost fifteen years ago. You change. Your skill set could change.

Sara: Ten years for me.

Zibby: Maybe if you wrote that book again today, it would be a totally different book, the one about the sisters. I’m getting off track.

Sara: I don’t think I can sit through it again. I don’t know how novelists do it actually.

Zibby: You also do a lot of travel writing. This book you did, Hotel Chic at Home, features cool hotels all over the world and how you can make your home feel like more of a hotel and get that vibe and everything, which is such a good idea. Every time I leave a hotel, I’m like, “Why is this so great?” It’s one room and I don’t want to leave. Is it the sheets? Is it the coffee table? What is it? What can you do for your home to make it have that same…?

Sara: The whole idea behind the book is basically I was writing travel articles and I realized that hotel owners, especially boutique hotel owners, have realized in the past twenty years that that’s a way to distinguish themselves from the competition, is with design and creating these magical universes where you walk in and you feel really hip or really glamourous or really sophisticated, whatever it is. To me, find that hotel where you have that feeling, or just a picture of it evokes that feeling that you want to create in your home. Then cramp some of the ideas.

For me, in my bedroom, there’s this hotel in Paris. They have these inky, dark blue/green/grey walls. I did that in my own bedroom. I was always really afraid to paint a room a dark color. I did it. I’ve never slept better. It’s like a cave. It’s amazing. That’s a super easy idea. I did another paint color-blocking thing in my son’s room when he turned twelve to make it more teenager-y and cooler. It took me an hour. It totally changed the whole space. Because all these hotels have all these super bold moves that you aren’t finding with residential designers, they’re full of inspiration. There’s so many ideas and so many things that you can take away, whether it’s color or fabric or really cool lighting or what soundtrack or some cocktail that you had when you were travelling. We all want to bring feeling of being on vacation back home. We’re all better when we’re in a hotel, to be honest.

Zibby: So true. As you mentioned earlier, you do a lot of profile writing. I loved even reading your one about Bobbi Brown at home and her home design. That was so cool. I never thought about how her home would look. It would probably reflect her overall aesthetic. What do you think are some of the tips in writing a great profile about somebody? What do you think makes a really good profile piece?

Sara: To me, when people really open up is when you ask them what the challenges have been, what the hurdles are, what the challenges have been, what the reality was of getting to the place that they’re at. Often, unless they’re too media-trained, they’ll really open up. Especially with this book or probably anytime when I’m writing a profile, I always say, “I’m so excited to talk about your story. I also really want people to get some sort of nugget that’s going to make them think differently or do things differently. Maybe they can follow a similar path.” Then when people see that telling their story can actually be helpful to other people, they’re often more inclined to be open. I’m not a bullshitter. I try and convey that to people. There’s something to be said about being honest, but I’m not a gotcha-journalist. Even with my celebrity profiles, every once in a while celebrities have told me things where I knew it was going to make page six, but I also sometimes didn’t include it because I knew that they just weren’t thinking when they said it.

Zibby: That’s nice of you.

Sara: I probably would be a more successful celebrity interviewer if I wasn’t so nice.

Zibby: You’re being so down on yourself. I feel like you’re this model of production. You’ve had so many books written, and really good. This book I just finished was amazing.

Sara: I’ve never been more proud of anything than this book, honestly. I had the idea ten years ago. I’ve had it for so long. My agent at the time told me it was a magazine article. I never gave up on it. I was at Yahoo! writing about wellness and beauty and doing a ton of profiles. I kept seeing this theme over and over again. I found a new agent. I told her about it. She really got it. We ended up having a bidding war over this book. The night that I sold it, I sat at a restaurant. Half an hour into it, my former agent who I hadn’t seen in ten years was literally sitting diagonal across from me. It was crazy bit of, I don’t know what it was. It was not an accident.

Zibby: Karma. Did you have to go over and tell her what happened?

Sara: Yeah. I was like, “I’m celebrating. I just sold my eleventh book.” I’d only sold one book with her. I really enjoyed the moment.

Zibby: What’s coming up next for you? What are you going to work on next?

Sara: I’m all in, in promoting this book. Part of the reasons why I was a behind-the-scenes person for a long time is I was never that comfortable promoting myself. I thought it seemed so terrifying. The idea of telling my story or being on a camera was so scary to me. That doesn’t help you when you’re writing a book. It was almost like it had to be hammered home for me. I realized unless you’re really good at promoting your own stuff and really get out there and feel comfortable calling every editor, every person you ever met that could possibly help with the book, then you kind of shouldn’t be writing books.

Zibby: Or publishing them, maybe.

Sara: Right, publishing them. Exactly, putting them out in the world. That’s my main focus. I do want to get back to that screenplay. I have an idea for a follow-up to this book that I really want to write. There’s a lot more stories to be told. I definitely don’t want this to be the end of the series. I’m also starting to write a lot of career-pivot pieces. I feel like that’s going to be my niche for a little bit, that and travel. I just can’t give up the travel writing.

Zibby: That’s great. I bet you get to go to great places.

Sara: You do. That’s how I travel. We get to go to places that maybe we wouldn’t go to otherwise.

Zibby: Do you get to bring your kids?

Sara: I get to bring my kids. Now, I’m a contributor at Family Traveller. That’s been great. One of my editors who was at Travel + Leisure and she worked with me at Yahoo!, Laura Begley Bloom, she is now heading up that magazine. I’m writing for her as often as I can, which is great.

Zibby: Do you have any parting advice to aspiring writers out there?

Sara: Yes. The key is to get your work out there. Now, you have the ability to do it with the web. So many of these content shops, they just want content. They’re not paying people a lot for the online stuff, but that gives you an opportunity. They’re hungry. They need people. That’s part of it. Also, you can launch your own website and have people see what kind of writing you do. A lot of great book deals have come out of blogs. You have the ability to get your work out there, showcase what you want to do.

Before, we had to wait. We had to wait for an editor to take our pitch or give us an assignment that would showcase the kind of stuff we wanted to do. I started out in design writing, which isn’t really what I wanted to do. I really wanted to write humor. I wanted to write about women’s issues. I kept waiting for someone to give me that opportunity. It didn’t really come. I had to make it for myself. That took a lot of time to do. Now, the whole landscape is different. Just do it, really. That’s really the bottom line. Whatever it is you want to do, you need to prepare. You have to research. You need to connect with other people who’ve done it. You need to buy my book.

Zibby: Take the Leap: Change your Career, Change your Life by Sara Bliss. When’s it coming out? December something?

Sara: December 4th.

Zibby: December 4th, 2018. Pre-order now, holiday gift giving.

Sara: Yes. I timed it for that. I did have one thing to say because I know your blog is called “Moms Don’t Have Time to Read Books.” This is actually the perfect book for a mom because every essay takes about five minutes to read. Sometimes that’s all we have.

Zibby: I agree. I’m a huge fan of short chapters of anything. This is great. You have images, and very visual, not just text. It’s really great. You can pick and choose. You don’t even have to go in order. Very easy, fun read with a lot of helpful life advice. There you go.

Sara: Thank you.

Zibby: Thanks, Sara. Thanks for coming on “Moms Don’t Have Time to Read Books.”

Sara: It was so fun.

Sara Bliss, TAKE THE LEAP: Change Your Career, Change Your Life

At the “Moms Don’t Have Time to Read Books” Holiday Book Fair.

Sara Bliss, TAKE THE LEAP: Change Your Career, Change Your Life

Sara Bliss, TAKE THE LEAP: Change Your Career, Change Your Life