They Took the Leap and Uncovered Dream Jobs! (You Can Too!), with Sara Bliss

They Took the Leap and Uncovered Dream Jobs! (You Can Too!), with Sara Bliss

They Took the Leap and Uncovered Dream Jobs! (You Can Too!), with Sara Bliss

My guest is New York Times bestselling author, Sara Bliss.

Sara has written 11 books.  Everything from Hotel Chic at Home, to The Thoroughly Modern Married Girl. She’s also co-authored books like Pretty Powerful and Beauty from the Inside Out  with wellness and beauty guru, Bobbi Brown,

Sara has some great ideas flowing. Her most recent book is where we’re going to focus today. It’s called Take the Leap, and it comes out in a few weeks, but it’s currently available for pre-order wherever you grab your books.

In Take the Leap, Sara actually interviewed people who transformed their lives for the better. These are people who went from a “normal” career, to find or create something they loved.

Listen To The Podcast:




Sara, welcome to DREAM THINK DO.

Thank you. I’m super fired up to be here.

I love it. It’s one of those where I love the title. What started you on the path to writing Take the Leap?

I have written about so many different things, I mean everything from beauty, to travel, to health. But profiles have been the one consistent thing that I’ve done for almost 20 years. I noticed really early on that a lot of successful people had had these entirely different lives before they found their greatest success. I thought it was really fascinating because it basically tears through this myth that so many of us have, that all successful people somehow follow this linear path that they know what their passion is, or they start really young.

Yeah, they were clear on it when they were five years old, right?

Exactly. I think for those of us who don’t feel that way or aren’t on the path that they want to be on, it’s super inspiring. I was a little bit lost in my own career, and kind of all over the place. I found these stories really comforting. I started collecting them. I would tell them to other people and everyone always had the same response, “Wait, I didn’t know that. I didn’t know that Carolina Herrera, the designer, didn’t start her business until she was 40.”

You know there are so many cool stories like that, and that’s really where the idea came from.

I love it. I couldn’t agree more. I think as a purveyor of strategy, and I know you provide a lot of strategy in the book too, strategies are great, but I think people need more stories in strategy.


Like if we have this story, then we’ll figure out the strategy. I think that’s what there needs to be more of in the world. That’s why I was so excited about what you’re doing with the book. Now, I see a title like Take the Leap, and I know the subject is all about getting that clarity and going for it. But one of the things I had to ask you is do you write this from the vantage point of always being a risk taker? Or, do you write this from the vantage point of maybe being risk-averse and having to learn how to take a leap like that?

I am probably a little bit more of the latter. I’m a little bit of a homebody. I literally live on the same block that I grew up on.

No kidding. That’s amazing. That’s awesome.

At the same time, I ended up taking leaps in my career literally every week. That’s how I’ve managed to stay afloat as a writer. I mean anyone who is a professional writer will tell you. The whole landscape of the job has shifted. When I started, it was not that hard to get a publishing deal if you were a well-regarded, not necessarily even famous, just you know, if you were a working writer.

Now they really want you to have a huge platform behind you. What I used to get paid for a magazine article versus what I get paid now, those are like two very different numbers. So I had to really hustle and I developed this whole kind of branding side of my business where I did ghostwriting, or I’d consult with brands on everything from PR, I’ve launched websites for them, I help them with content. I wrote this books on hotels and have been covering travels for years, so I also do hotel consulting.

I help connect them with cool initiatives for their guests or even consult them in design. And sometimes I’m doing all those things, plus articles in the same week. It’s not necessarily a natural thing for me, but it’s what I’ve had to do. I’m so happy. I love having this kind of crazy career where I’m doing so many different things. It’s exciting and it keeps me in business. It also really keeps me engaged and excited about what I’m doing.

I love that. You can hear it in your voice. I love reading a book like this written from somebody whose maybe naturally or more naturally risk-averse.

It’s a little bit like I don’t want to learn how to get in shape, or I don’t want to buy a diet book from somebody who’s always been 2% body fat, right? You’ve heard me say that before, but it’s so true. I want the guy who’s been fluffy and now is 7% body fat. I want to learn from that guy as opposed to the guy who has always been skinny.

So it’s that for a book called Take the Leap, to have it be from somebody who’s always been, “Oh, just throw caution to the wind,” is an entirely different thing than somebody who has had to learn it, cultivate it. You obviously have. That’s become a part of who you are, but again, I think most of the world is not just going to make these choices on a whim. I wanted to get your vantage point on that a little bit first before we start talking about the strategies.

Now, 65+ interviews with all sorts of different people, what would you say when you think back to all those conversations, what was one of the more surprising either stories or strategies that came from that story, that stands out to you?

I think I want to start by saying a little bit to the point you just made. I want this book to be for someone who knows they want to make a change, but maybe is feeling terrified of the process. They have no idea how to get started, because like what you were saying I think there is no better person to learn from than people who have done it. So the first step that I would advise for anyone who wants to make a leap is to talk to someone who has already done it, and that’s really the crux of the book.

It is advice from people who have already done it, who have stood where you are, who have been totally terrified, not knowing what to do, and they figured it out. So they are telling you, “These are the hurdles to watch out for. This is how you need to prepare. This is what you need to think about in terms of your financials. This is actually the reality of the job versus what you what might imagine it be.”

I think that once you are armed with that information and you read about all of these people who have successfully done it, even though maybe it was really, really tough, or they had so many obstacles, then you feel that much more confident.

Yeah, I love it. This is definitely a show where we talk about dreaming with your eyes wide open.

I love major steps of faith over blind leaps of faith. I mean those, “Build it and they will come,” kind of messages sometimes, I mean it’s great for a movie, I love Field of Dreams, don’t get me wrong. But I’m a big fan of saying, “All right. Yeah, talk to some people. Learn some strategies. Get a plan. Experiment, experiment, experiment.”

I mean the main strategy that comes out in this book, I think, is that you need to be prepared. So a lot of people get these fantasy ideas about leaving their job and telling their boss to shove it.

And you know, there are lots of people, they go on vacation and they say, “Gosh, why am I going back to my old life? I want to live here.” But there are people who actually do that. They do go live in the Caribbean, or on a boat, or in Europe or wherever it is. But, whatever it is, whatever move that they make, they plan. So they talk to people who have done it, they are going to school, they are getting mentors, they are working for free, they’re taking online classes.

There are so many different steps that people are taking to be prepared. That’s the key. You have to do the work. You have to do the work before you’re ready to leave, and every person in the book has done something before they did it.

Isn’t it interesting, I mean to do this kind of research in this day and age. It’s so different than our grandparents’ era. Right? We just did an interview with somebody who launched a coffee roasting company a few years ago. Fascinating, become one of the premier coffee roasters, kind of micro coffee roasters, in the country. And literally, he’s like, “Yeah, my biggest influence is YouTube.”

He learned so many of his initial skills just from watching YouTube videos. So I love that with a wide variety of the stories that you’ve got with people from so many different backgrounds. So what would you say is one of your favorite stories?

Oh gosh, there are so many. I love this woman, Tess Finnegan. She was a corporate lawyer in DC, and had this crazy life. She read this book called The Desire Map by Danielle LaPorte. In it, she talks about the way to figure out what you want to do with your life is to figure out how you want to feel. So this woman Tess thought, “Well what am I feeling in my current job? I have stress, illnesses, I’m a paid fighter. I’m angry all the time. This is not how I want to feel.”

So she came up with a whole bunch of ideas for things that she might want to do, and things that made her feel good. One of them was flower arranging. It was something that she always did on the side, and she just loved it. She loved working with flowers, she loved arranging them, she loved the art of it.

After she had, I think, her third child, she walked into her local florist and said, “Hey, do you need any help?” And she ended up working there and learning the business from the ground up before she launched on her own. I love that approach. It just felt like kind of a different way of going about it, which is great. I also love Nicole Latera.

She was a hairdresser. She has her own business, and she’s always loved the beauty world. But at the same time, she was always the person who would be helping someone in a crisis. So she went and trained to be an EMT. I think she is a mom of two kids. She trained when one of her kids was an infant, and then she saw the firefighters, and she was like, “You know what? I want to do that. I want to be the one running into the building when everyone is running out.”

She has this totally badass career on the side. They are so different, and she has kept both of them. She feels like they play off of each other. There are so many people like that where they’re in these dream jobs, and they’re so excited about it. They’re so lit up when they talk about it as well.

Yeah, and isn’t that awesome? I’m guessing a lot of them didn’t necessarily get an upgrade in pay, but more they got an upgrade in their life, what they were feeling and what they were enjoying.

You know, it’s interesting. So I really expected that everybody in the book was going to tell me they were happier, but they made less money.

I just thought that was going to be kind of a universal thing. For some people, that’s the case. There’s this woman, Marina who was a reality TV producer, and really successful and had a great apartment, and the great clothes in New York, but she hated who she was becoming. She hated the whole world that she was in, and she was like, “I’m not a good person. I don’t have any relationships.”

Not that she’s not a good person. She wasn’t happy with the person that she was. She ended up doing yoga and suddenly feeling at peace, and loving it. Someone said to her, “Hey, would you want to get your yoga teacher training?” She had never even thought of it, and she did it. She ended up a few years later meeting this guy who was doing these trips that involved philanthropy and also he wanted to have a yoga component to the trip. He hired her.

Now she lives this incredible life, and she lives three months out of the year in different, beautiful, amazing locations around the world. So she’s in Peru, she’s in Thailand, she’s in Bali. She says she really does not make a lot of money, but she’s starting to make more. They’re starting to figure it out. But she’s just so much happier.

Of course, because she’s traveling the world, right? She’s one of those people. That’s great.

Yeah, so surprisingly, a lot of the people I would say … I’ve got to look at and really figure out what the percentage is, but I would say that the majority of people in my book are either making the same or more than they were making before. The people that are making less are actually in the minority. Again, I didn’t expect that.

You know, that’s really interesting. I love that. I mean that’s definitely my story. I was in the pharmaceutical world and had worked myself into a bad fit job. It wasn’t a bad job, it was just a bad fit job, and it was just killing my soul. But man, there was a part of me that was like, “How am I ever going to do better than this financially?” And they provided everything: my car, my office, my computer, all those things.

I did a side hustle for a while and it took off. Now, what I make totally eclipses what I was making before.

How amazing is that?

Yeah, it’s an incredible blessing. I’m wildly, wildly blessed by it. And definitely, I got to that point where I was like, “I would do it even if I made less,” because my soul’s dying. I’m guessing that that to be a part of maybe everybody’s story and maybe everybody takes, or some, take a dip in their pay, at least for a little while, that kind of thing.

I think that is really common that they do. There is the initial financial hurdle to get over. But there’s this one guy, Jamie, who was on Wall Street. He went and slept on a mattress in a studio apartment in California, so he could shadow a winemaker. He was really happy, and now he has his own winery.

He actually even caps how much wine he produces, and he hates the idea of ever selling out to anybody else because he says, “I don’t even know what I would do for happiness if I wasn’t doing this.”

Right. Wow, that’s amazing. I want it. I always love asking this question, but of the strategies that you came across buried in the stories that you’re telling, what would you say is a strategy that you came across that you personally needed? I mean, I know that you’re in a career that you love, that it’s constantly evolving, constantly changing, but what was the strategy that you needed to hear?

There is in this incredible woman in the book. Her name is Talley Smith. She grew up in Bermuda, she always wanted to go to South Africa. She takes a trip there and decides she wants to move there and become a game ranger.

Wow. That’s amazing. Okay.

Yeah. She had no experience with wild animals, she had no experience with firearms. She had no experience at surviving in the wild. And now she works at Londolozi Game Reserve, which is this amazing hotel and reserve in South Africa. She manages 25 men, and she’s the only woman on the team.

So her advice is basically to go for it even if you are afraid. She tells this story, “In the wild you learn not to run away when you’re facing something terrifying.” That, “The only way you’re really going to see what you’re made of, the only way you’re going to grow, the only way you’re stronger and better and bigger, is to stay still, run towards it, don’t run away.”


At the end of her story, she says, “You have to step out of the box at your end and take risks, even if they may seem a little bit crazy at the time.” I am kind of naturally, definitely, like I’m a more inward person. It’s definitely why I’ve been everybody’s ghostwriter for a while. It’s why I was very comfortable being behind the scenes. I got to a point in my career, and really with this book, where I said, “You know what? I need to get comfortable with promoting myself, with promoting my own stuff.”

It’s just not a natural thing for me. So I’ve been taking all these steps to do it. When she and I were talking, and she was talking about that way to look at fear, it just really resonated with me. I’m really taking it to heart, and it’s something that I think about a lot, in this process. Right now, I’m beginning the whole promotion process which used to be something I really, really almost ran away from.

Right, but now you’re walking toward it, and doing a fantastic job with it.

I love it. It’s one thing to hear a quote, like “Step into fear.” But it’s an entirely different thing when you know the context, and you know the person who said it, and you know the stories behind it. You see, probably again, the smile on her face as she’s doing what she’s doing. It’s like, “All right. I want some of that.”

If that’s how she got it, then all right. That helps a person to step into it. I love that story, and that awareness too. That’s huge.

I’ve got one last question. I love the stories you’re throwing out, so DREAM THINK DO-ers, get ready to grab the book itself. But as you talk with folks about the book, whether it’s while you’re doing kind of the media blitz, but more just that person on the street, the family member who asks you what you’re up to when you tell them about the book, what would you say is one of the standout epiphanies or strategies as you throw that out there, that just resonates with people? What would you say is one of those either stories or strategies that you think is one that absolutely everybody needs to hear?

I say in the intro, and it’s the thing that I took away after reading all these stories, is the dreamers … And this is also why I love the title of your podcast, are the dreams really get separated from the do-ers pretty quickly. I mean I think we all have these ideas. We all have these ideas that come up at random times, and you think, “Gosh, what if I did that?” But you’re never going to know if it’s going to work or not work or be the right thing for you unless you actually do it.

For a lot of people, that’s doing a side hustle, which is how you got into it. And for other people, it’s diving in. There are so many people who talk about things endlessly, and year after year, and they’re not any closer to it because they just haven’t taken any steps. I think especially with dream jobs, it’s never the right time, there’s always going to be someone to talk you out of it, there’s always going to be someone who says, “maybe you really should wait on that,” Or, “Do you really have enough money to do that? You have no experience in that. How could you even do that?” Or, “You’re never going to have the money for that.”

Sometimes those voices are actually other people, right?

A lot of these people actually told me there were people really close to them that thought they were completely crazy. Talley’s one of them. She came home from vacation and told her parents she was moving to South Africa, a place that they had never been, and they really thought she was crazy. But she said they had to trust her. The same with Scott Neeson. He left this really glamorous, amazing job at 20th Century Fox International, he was the President, to go start a children’s charity in Cambodia. He worried that he was having a midlife crisis and other people told him he was.

I gotta agree, yeah.

You know, they’re like, “You have a beautiful girlfriend. You have a yacht. What are you doing?”


And so you have to turn off those voices and actually just do it. Barbara Corcoran actually, she says something in the book too, which is “You’re not going to know what you’re good at until you’re doing it.” Actually, I had breakfast today with this really interesting person who had just launched this really, really cool startup called Hoppin, H-O-P-P-I-N. It’s now based in New York, it’s just starting here. She basically gives people the opportunity to shadow people who are doing dream jobs.

So I think you can pay between $50.00-$200.00, and you get to spend the day with someone who’s doing the job that you might dream about and see what it’s really like. That’s obviously one way of diving in, and that’s like a safer way of stick your big toe in, but the key is just to get out there and try it. If it doesn’t work, then you’ve got to then be on to the next thing, and maybe it’s the next thing actually that’s going to be where you find your success.

Absolutely. It’s so true because you can dream by yourself. We talk about Dream, Think, and Do are three separate steps in a process.

You’ve got to dream first, and then think, you’ve got to plan, but then you’ve got to do because you’ll never know for sure unless you’re experimenting and trying things out. That’s what I love that it sounds like it’s just at the core of all these different stories. They had to take some training. They had to go shadow someone. They had to have coffee. They had to take the class. They had to take some risks. I’m sure in some cases it meant making major changes immediately and in other cases, it was probably in doing those small steps over time. But man, I love the examples, loving the strategies. So how do people get the book?

It’s on Amazon, Barnes & Noble, also pre-order for right now. And then it will be at your bookstore on December 4th. I also really like to support Indie Bound. I don’t know if you know that website, but it connects to your local Indie booksellers around the globe

Actually, there is an amazing bookseller in the book. Her name is Noelle Santos. She just launched The Lit Bar in the Bronx. It’s the only bookstore in the Bronx. She was an accountant. She was in human resources and accounting. She started this business because she was mad that Barnes & Noble closed, and maybe in the Bronx with no bookstore. She didn’t even plan on this.

That’s the other thing, is that for a lot of people it’s not necessarily that they have this dream since childhood, sometimes something happens in their life and they think, “Wait, this is something I need to be doing. If I’m not doing it, no one else will.”

Yep, it’s so true. We just spent the week in Arizona and we interviewed the Founder of something called Treasures for Teachers. It was a woman who happened to be in a classroom, a third grade classroom, and the teacher said to the students, “Everybody take out a pencil and paper,” and she watched this little girl walk from the back of the room to the front of the room, and she handed the teacher her shoe and then the teacher handed her a pencil. She went back to her desk and went to work.

After the class was over, Barb Blalock, was her name. She walked up to the teacher and said, “Can I ask what just happened? What was the thing with the shoe?” The teacher said, “Well, this little girl doesn’t have enough money to have school supplies. I provide a lot of school supplies, but I don’t have an unlimited budget so I need to get them back, so I have them turn in something so that they’ll be sure to bring it back. Shoes are just the easiest thing.”

Barb thought to herself, “Oh my gosh, that’s horrible.”


Of course, the teacher was actually tearing up as she’s saying that. It was obvious that the teacher did not want to have to do that, but she did. Barb was like, “That’s outrageous. That’s crazy.” And she didn’t want to make the teacher feel bad or anything, but she’s like, “I will bring supplies. I will bring supplies.” So she went out and got a bunch of supplies. It started to fill her garage, and then it took over her whole garage.

Then she went and got a warehouse and she kept getting more people to donate. Now they’ve got this 20,000 square foot warehouse in Tempe, Arizona where teachers can either come and buy either at low cost or no cost and walk out of there with school supplies for their classrooms. It’s one of the coolest things. But that was not her dream. She just saw there was a problem, and she’s, “I’m going to fix this problem.”

Initially, it was just one little girl in a third-grade classroom, and it turned into that whole class, and then in that whole school, and then that whole school district and it just went from there. She was one of the happiest people. We literally were interviewing her for our video series, and one of our crew, the editor, said, “What do you do on those days where you don’t really want to go to work? You seem really happy today, and that’s great, but what do you do on those days when you’re facing challenges, you’re tired, your grumpy or whatever?”

And literally looked up at the ceilings like, “I don’t have those days.”

Right. Right.

I’m sure as you talked with these folks that dream jobs don’t always mean there are not problems. Barb had plenty of challenges with her organization, and so many people do. But they love it. They love the work. And I love that you’re wanting to get more and more people into that kind of position as well.

Yeah, no absolutely. Absolutely. I mean it’s so inspiring to talk to people who feel that way about their jobs. When you do, you kind of want everyone to feel that way.

And to let people know what’s possible, right? It’s not always easy and it sometimes involves some risks, but it’s possible. That’s why I love you sharing so many great stories because I do think people need to hear more of that. Like, real world, authentic, not necessarily household names … I know you’ve got some household names on the list, but a lot of these folks we’ve never heard of before, but their stories need to be told. I’m glad you’re telling them.

Thank you.

Absolutely. All right gang, it is called Take the Leap. This has been Sara Bliss. Thank you, Sara, so much for talking with us today.

Thank you so much. This has been such a treat.

All right, DREAM THINK DO-er, what’d you think?  

Leave a comment and let me know what stood out to you.  

What do you think stands in the way of people taking “the leap” to something they feel called to… or want more of in their life?  I’d love to hear from YOU! let me know.


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