160: Take the Leap – Why and How to Transform Your Career with Bestselling Author Sara Bliss

Ep160 take the leap why and how to transform your career Sara Bliss TalentGrow Show with Halelly Azulay

Is a career path a straight line or more like a winding road full of forks and detours? On each episode of The TalentGrow Show, guests briefly describe their professional journeys. It’s inspiring to hear about the challenges that successful individuals have faced to get to where they are today and to draw lessons from their experiences. On this episode, freelance writer and bestselling author Sara Bliss and I talk about what it takes to transform your career and achieve what you want most from your life and your work. Taking the leap into a new career can be terrifying so it’s helpful to hear from others who have done it already. Sara shares her own professional journey and the journeys of others that inspired her to write her book, Take The Leap, and offers valuable advice on how to pivot in your career even when circumstances seem to be against you. Listen and be sure to share this episode with others in your network!


Sara Bliss is a freelance writer and New York Times bestselling author who writes profiles on the topics of business, health, beauty, design, and travel. Sara is coauthor and author of ten books including Hotel Chic at Home, Pretty Powerful, and Beauty from the Inside Out. A former senior writer for Yahoo, Sara’s articles have appeared in The Wall Street Journal, Town & Country, and Refinery29.


  • What inspired Sara to write her book, Take the Leap? (4:53)

  • Sara and Halelly discuss the dangerous mindset of feeling stuck in your career and how Millennials are breaking this mold (7:17)

  • Three inspiring examples of individuals who successfully pivoted in their careers to achieve what they wanted in life (8:55)

  • Sara shares her favorite mentoring advice from her book (13:54)

  • Don’t focus too much on where you are in the moment; focus instead on where you are going (17:02)

  • One woman’s story of overcoming the challenges she faced while pursuing her goals (17:42)

  • Halelly summarizes Sara’s advice and expands on what she calls the progress principle (19:41)

  • The importance of being comfortable cultivating risk (20:44)

  • Sara talks about perhaps the biggest reason she wrote her book (22:47)

  • What’s new and exciting on Sara’s horizon? (24:16)

  • One specific action you can take to upgrade your career satisfaction or success (24:54)



Episode 160 Sara Bliss

TEASER CLIP: Sara: A career leap is not an easy thing to do.

Halelly: No, it’s scary!

Sara: Yeah, and sometimes it involves taking a step back before you leap forward. Financially there are a lot of risks. It involves a lot more work or schooling or preparation or whatever it is. The thing is, they all kind of expected that there would be hurdles and that they took the hurdles not as a sign that this wasn’t going to work, but as just part of the journey. They knew that it wasn’t going to be a straight path to instant success.

[MUSIC] Announcer: Welcome to the TalentGrow Show, where you can get actionable results-oriented insight and advice on how to take your leadership, communication and people skills to the next level and become the kind of leader people want to follow. And now, your host and leadership development strategist, Halelly Azulay.

Halelly: Hey there TalentGrowers. Welcome back to another episode of the TalentGrow Show. I’m Halelly Azulay, your leadership development strategist here at TalentGrow and this episode is here to inspire you to think big and to evaluate or maybe re-evaluate where you are in your career journey. Most of the time this show focuses on leading others, but leading self is just as important and it’s the first job of a leader actually. In fact, in that way you are also responsible for making sure that you’re on the right track in your career. This is a theme that’s come up so much as it is in recent episodes, so it makes perfect sense that in this particular episode we focus on how you could create a transformation in your career and the guest on this episode, Sara Bliss, wrote a book that details multiple stories of such transformations. She shares some of them with us on this show and also what are some of the themes that have emerged from all of those interviews she did with people who created major transformations in their careers? I hope that you find this inspiring and educational and of course let me know afterwards what you thought. Without further ado, let’s dig in.

TalentGrowers, you know how I love to ask people about their professional journeys? Well, this week’s episode is actually all about that. We have Sara Bliss. She’s a freelance writer and New York Times best-selling author who writes profiles on the topics of business, health, beauty, design and travel. Sara is co-author and author of 10 books including Hotel Sheik at Home, Pretty Powerful and Beauty From the Inside Out. A former senior writer for Yahoo, Sara’s articles have appeared in the Wall Street Journal, Town and Country and Refinery, and her latest book, Take the Leap, is going to be the topic of our conversation today. Sara, welcome to the TalentGrow Show.

Sara: I’m so psyched to be here. Thank you so much.

Halelly: I’m excited that you’re here as well. I really look forward to our conversation, but I always ask my guests to describe their professional journey first. Very briefly, where did you start and how did you end up where you are today?

Sara: I have done a ton of leaps both within my industry and then I actually started in the art world, right after college, and pretty quickly I saw that I didn’t have what it takes to succeed there. You have to be obsessed with either selling art or uber passionate about the intricacies of the business and the artists and I felt like I wasn’t passionate about it. Every second of my free time I was writing. So I took a class at night at NYU, writing for magazines, and I switched into the world of magazines, where I thought I would stay forever. And then the industry really, really, really has shrunk dramatically since I started. It’s just a totally different business. After 2008, I had to really reinvent myself in order to stay afloat so I started a lot of branding work in addition to my editorial work. Working for brands and marketing and PR and branded editorial and ghostwriting for high profile people, so I really had two jobs. Then within that, I’ve leapt a ton of times in terms of the topics I cover on the editorial side. I worked at Yahoo as the Senior Beauty writer and I started at House Beautiful and Design, and I’ve really been all over the map. I’ve written celebrity profiles, I’ve kind of done it all. I really just hustled to stay a working writer.

Halelly: It’s pretty cool that you are a working writer. I think a lot of people just think that writing is some kind of a dream job that they maybe could do one day, but don’t think it’ll pay the bills. You’re an example of being creative and figuring out a way. In your book, which I really enjoyed reading through – it’s called Take the Leap – and it’s a lot of short profiles of people, over 65 people, that you describe a variety of career transformation stories. Each one of them takes a leap. You were calling it being a leaper or leaping, so they move from one career to another. A hairdresser to firefighter, an attorney to surf instructor. You say that your goal of the book is to inspire readers to go for the career that they’ve always wanted. I was wondering, what inspired you to write this book?

Sara: You know, so many people are unhappy in their jobs, and I really wrote this book for them. I think especially as you kind of get toward, or in mid-life, and you suddenly have this feeling that time is running out and maybe you’re not happy where you are, or you want something else, you want to make more money, you want to have more independence, you want more power, you want to create something, you want ownership, whatever it is that’s driving you, this is really the time and what was happening for me is, I have been interviewing some of the most fascinating people for over 20 years and I realized early on that so many of the people that are really, really successful, they didn’t necessarily have the dream from a young age, which I think is the idea we have about success. That it’s this linear path. But so many of them had wildly different careers and lots of failures and many leaps and detours before they got to where they wanted to be. I just thought that was really inspiring, and I found myself listening to friends telling me how unhappy they were in their careers and telling me stories and saying, “You know what? I know someone who went from stay-at-home-mom to CEO or start-up queen,” or, “I know someone who left their miserable corporate job and now is running a winery out in Napa.” And I just started making a running list of these stories for my friends and also for myself, because I wasn’t thrilled about what was happening with my job. Sometimes with these leaps, a lot of people, they have to leap. Their industry is shifting, as mine did with magazines. It was inspiration for myself and for other people and I knew that the stories needed to be told.

Halelly: I agree that there are so many people that allow themselves to stay stuck, to feel miserable and almost just deal with it, this is what being an adult is all about. Like this is what life is, so let go of those dreams about being happy in your work, which is really sad.

Sara: Right. And I think a lot of people feel that way, and also, for a lot of us, our parents just had one career and that was it. This idea that you switch in your 40s or even in your 50s, it would seem to their generation to be kind of a ridiculous thing. It’s really kind of changing that mindset, but meanwhile, the Millennials are switching jobs all the time. They’re switching jobs, they’re switching careers, they don’t always stay in things for a year – which is what we used to be told you had to stay at least a year in the beginning – they are much more comfortable with this idea of pivoting, and if you look at that whole start-up world, all of those people who are starting businesses, the majority of them have come from different industries and they’ve used the expertise from their previous lives to start something new. So, in that world, pivoting and the experience that comes from being in a totally different space is really, really valued. I think when we look at things through that lens of opportunity, change being a good thing, that's when there are lots of possibilities that can happen.

Halelly: Totally. I’m so glad you’re on this mission. It’s part of what I try to do is just, oh my gosh, you get one life and it’s relatively short but it certainly is long enough for you to make course corrections if you feel like it’s not working in the way you had imagined. I’m curious if when you were looking at all of these stories, each story obviously is unique and different, but did you see any kind of common themes, either about the inciting incident – the impetus for the change – or about the path or the things they did to change or about the lessons that they learned? Were there any themes that emerged?

Sara: One of the really interesting things for me was that I realized for every single one of these people, it wasn’t so much about changing their jobs at the end of the day, it was about wanting some sort of transformation. Something wasn’t working. One example that is a woman I wrote about, she was in a long-term relationship, she ran a gourmet food store and then she worked at a clothing store and she was in a long-term relationship with a doctor and she thought she was going to get married and have this life where she could kind of do whatever she wanted career wise and she would be taken care of. The relationship didn’t work out, and so suddenly she had this idea, “Maybe it won’t happen for me, but I want the kind of life that I would have had, had I been married to this guy.” So she ended up becoming a Wall Street financial services director, a wealth management advisor, and she realized that it was a career she could get into without an MBA. She went through a training program and now she is one of the top wealth advisors on Wall Street at Morgan Stanley and I love that she did it. It was about so much more than the job for her. It was about this whole life that she wanted and having that real independence as a woman.

Again, so many of the stories are about transformation and about wanting something deeper. The stories were not superficial at all. I got really, really into why people were making these changes and how their lives really changed as a result.

Halelly: So transformation beyond just the job, like it changes your whole life, I would imagine too. A lot of these kinds of shifts that you describe. A person who became a farmer, what were they doing before?

Sara: Oh, he is a really interesting guy. He was an Arabic teacher, one of the few non-Arabic teachers at the university level and he had done training in the Army and he just had this talent for languages. He was getting his PhD and decided to raise chickens with his wife, like kind of on the side as just something fun, a hobby to do, before he started his PhD program, and he just loved that life. He loved working with his hands, he loved the connection with the community. They have found a way to make that work and now they have a farm where they raise chickens and pigs and they have some fruits and vegetables and it’s called Nami Moon Farm and they’ve done really, really well. They’re really happy. He said, “I got to a level that people just didn’t understand what I was doing, and in a way I didn’t understand what I was doing immediately,” but he just loves that community connection and feeling like he was doing something bigger than himself. I think that’s really, really moving.

Halelly: That is really moving, and so cool. Really, I would just have you tell us each of the stories. What’s one more? Either your favorites or one of the most surprising ones?

Sara: One of my favorites is this woman who was in London and 65 and she had had a career in corporate management, corporate training, for many, many years. She ended up taking a year off to help her granddaughter who was sick, and everyone just thought she was going to go into retirement. Once her granddaughter got a little better and didn’t need her as much, she was getting really bored and said, “I can’t spend the next 30 years watching TV.” So she realized there was a gap in the market for makeup for older women, that all the makeup brands were marketing – their ads, even for wrinkle creams or whatever – is always with young, young models. So she started a business on You Tube, using her friends as models, using herself as a model, and now she has this international beauty brand. I love it. I love that she did that instead of retiring.

Halelly: That is such a creative idea and it is really very different from either of the things you were describing she was doing before.

Sara: And I love that she took advantage of this whole new medium, which is social media and You Tube. It was so ballsy of her, and she just realized she tapped into it. She realized it was an untapped market and she really succeeded.

Halelly: Fabulous. One other thing I liked about your book is, in addition to all of these little transformation stories, there is also advice from, you’re calling them, mentors. You take really successful people like Shark Tank’s Barbara Corcoran and beauty guru Bobbi Brown and you share mentoring advice from them on a variety of topics. Again, since we can’t share your whole book and we’re going to link to it so people can read it on their own, what is one of your favorite mentor advice from the book?

Sara: Everything that Barbara Corcoran says is brilliant. I could have listened to her all day long. She is a fascinating person, especially when she talks about negotiating. She sold her real estate business for $66 million, not because it was valued at that by anyone, but because she thought six was too low and six was her lucky number, so she did this arbitrary figure and stuck to it and got people to pay her that money, which I think is genius. She’s an incredible negotiator.

But she talked about surrounding yourself with the right people, which I think is such great advice. Especially if you really have a big goal for yourself and a big goal for your career is to be surrounding yourself with people who are also equally motivated, who have big dreams, who aren’t the ones who were giving you all the reasons why your dream or your idea or your career move is not going to work. It’s one thing to be realistic and see what the hurdles are, but it’s another thing, there are a lot of people who constantly find a reason why things won’t work. If you surround yourself with those people, then you can kind of start not believing in yourself. And so I thought that was a great piece of advice, to surround yourself with the right people, surround yourself with people that have huge, huge goals and big dreams.

Halelly: You’re right, the people around you have such a big impact. I think it was like Jim Rhon or somebody that said you become the average of the five people you spend the most time with, or one of those self-help gurus like that.

Sara: That’s fascinating. I think that’s really, really true. And I think people can really bring you down. The thing is, they don’t mean to – it’s often people that really love it. They just don’t have the vision and I think for a lot of things, the people that become CEOs or run their own businesses or become really senior management, a lot of them did this because they had this major vision and they put in the work behind it. It’s not always that simple, but sometimes you can’t look at where you are at the moment. If you focus too much on where you are in the moment, and trying to figure out, “I don’t know if I can ever do that,” but instead figuring out a path as crazy as it might seem, that’s the way to do it, to think big.

Halelly: Think big. Did you notice in the stories, whether at all if people seemed to be more on the optimistic side or more on the realistic side? I mean, did they seem to have in common this ability to dream big and see the positive?

Sara: Yeah. I have to say, I think that was really, when you talked about the common theme with everybody, these changes are hard. A career leap is not an easy thing to do.

Halelly: No, it’s scary.

Sara: Yeah, and sometimes it involves taking a step back before you leap forward. Financially there are a lot of risks. It involves a lot more work or schooling or preparation or whatever it is. The thing is, they all kind of expected that there would be hurdles and that they took the hurdles not as a sign that this wasn’t going to work, but as just part of the journey. They knew that it wasn’t going to be a straight path to instant success. Having that unshakable belief in what their vision was, was the key. There was one woman who actually started out as a housekeeper and saved her money. She always wanted to run her own business and now she has her own restaurant, but she’s in a summer community up in the northeast on Shelter Island. Her first summer she did really, really well, and she started to invest back into the business, and then in the winter, she started to lose money and she freaked out and said, “I don’t know if I can do this.” She just hadn’t planned for that. She ended up moving back in with her ex-husband for a year and I laugh about it and I said to her, “That’s such an example of not giving up.” She was like, “You know what? Even if I have to do this, even if it’s not the greatest year, I’m going to do it because that’s how I’m going to get to where I want to go.” Again, just having that unshakable belief like this, that this is going to happen. It’s just going to take a little time.

Halelly: I can’t remember who I heard it from, but somebody was saying that a true test of someone who can succeed as an entrepreneur from a startup is if you’re willing to sleep in your car while you’re building your business. There’s going to be a time.

Sara: There’s some truth to that! The interesting thing is that 70 percent of the people in the book are actually making more money now than they were at jobs that they hated, and I love that statistic. I thought it was really fascinating. However, when I tell a statistic, I also say, most of them, it took a few years to get there. That wasn’t like their first year that they were making the same or more. In a lot of cases, they did have to downsize and take steps back and sleep on mattresses on the floor or more somewhere where the rent wasn’t as high or whatever it was. Whatever sacrifice they had to make. I think that is probably a good barometer. If you’re willing to make those changes, if those changes don’t seem like a big deal to you in order to get to where you want to go, then you definitely I think have what it takes.

Halelly: This is great. This is kind of all connect-the-dot. You have this vision and it’s unshakable and you believe you can do it, you surround yourself with people who also support you rather than bring you down, and you’re willing to do what it takes in the interim, recognizing that it’s like the progress principle. It’s not like you’re seeking to sleep in your car forever or to eat mac and cheese from the dollar store, but if that’s what you have to do to get there and then you do! I think a lot of people are too scared of “what if it doesn’t work?” and I think a lot of people have maybe been lulled into a complacency, the path that they’re on is not satisfying, but it takes care of their basic needs and they kind of get comfortable being comfortable.

Sara: It is. It’s so much easier to kind of stay with what you know than the unknown. It’s just very scary for people. It’s interesting to me how much misery people will accept before they change. We’re not necessarily wired for risk, and that’s actually one of the things that Barbara Corcoran said – she talked about how she’s constantly seeing all these young people that have great ideas, but they’re not going to go anywhere because they’re not comfortable with the risk side of it. In a way she said you just have to be comfortable cultivating risks that once you understand that, sure, you can lose it all – lose it all is extreme – but sure, it cannot work, but what if it does work? That’s really the way that I think about it. What if it does work? Think about it that way. We spend so much time thinking about what if it doesn’t work? Well, what if it does? Think about how different your life will be. Think about how different your life will be on a daily basis. If you’re in a job that you like that you’re passionate about, that you’re invested in, when you think about it that way, then that’s more motivating I think and less scary.

Halelly: And the world will be full of people who are on fire and happier. It sounds like a pie in the sky kind of dream, but I believe that it’s possible. It’s funny, one of my earliest podcast guests, Caroline Adams, likes to say instead of saying, “Why me?” she says, “Why not me?”

Sara: Oh, I love that!

Halelly: That’s one way to think about it. We just recently had a podcast episode with Professor Rajshree Agarwal who was also, we were talking about this idea of risk and mitigating against risk, and she was saying entrepreneurs don’t necessarily take more risks, they just have calculated risks and they are thinking about how to address the different kinds of things that could happen and then knowing that ultimately, you take action even when you don’t have all the ducks in a row and you just work hard and believe it’s possible to go past it.

Sara: I agree with you, and I agree with that idea. I think that idea about risk is so key. And the thing is, you just said, it all seems pie in the sky – you know what? That’s exactly why I wrote the book. I wanted there to be proof of people that are exactly like you, have had the same fears, the same financial hurdles, the same dreams, and they made it happen. Because it always seems more possible when you talk to someone who has already done what you want to do. If you don’t know of anyone who has been able to dream that dream and make it work, then often you can talk yourself out of it. You might think, “Gosh, I’ll never make that work.” But if you talk to someone who says, “Yeah, I actually was where you are and I did make it happen and this is what to look out for and this is how I did it,” and each of the stories is really that person, sharing that kind of story with you.

Halelly: Very cool. Well, if I were in the advising business, I would suggest to you – in case you didn’t already do this – but you could totally start a movement. You could have a Facebook group where people share how they were motivated by your book and what they did and how that worked and keep collecting the stories. Wouldn’t that be cool?

Sara: Yes, I need to be doing that and I was just talking to someone about that.

Halelly: I think that would be this weird, awesome compound effect of the whole thing. This is fascinating. Thank you so much for stopping by. It’s been interesting and I know people are going to want to connect with you. Before you give us one specific action as we always end the show with that, what’s new and exciting on your horizon? What kind of discoveries have got your attention these days?

Sara: I am very focused on getting my paperback out in the world, and what’s really exciting is this book has actually launched me into a new Forbes column, all about people making career pivots. It’s been a way of continuing the conversation, which I love and I’m starting to kind of delve a lot into the whole startup, entrepreneurial world in that column. I love it. I love continuing this work and writing about these kinds of stories.

Halelly: That’s really cool. We’ll link to that in the show notes so people can follow you there. What’s one specific action that our listeners can take today, tomorrow, this week, that can help them upgrade their own career satisfaction or success?

Sara: I think the key thing is that we all keep learning and we all keep learning new skills, whether it’s taking online classes or reading books and teaching ourselves, or getting into a new group. I think learning new skills that are either directly relevant to your new job or just help you kind of enter a different space are really, really key. So many people right now are learning to code – and I have a whole section in the book on how to break into tech, even if you don’t code, actually – I think continuing to teach yourself and realize that we never know everything and when we stop learning is kind of when we stop growing, so every year, teach ourselves something new that’s big.

Halelly: Awesome. In your own career story, you did that when you took that how to write for magazines class, right?

Sara: Yes, absolutely. I still do it. I’ve taken screenplay classes, I took a class on building a website. I take little classes, big classes, I think it’s really, really important to keep educating yourself.

Halelly: I 100 percent agree. In fact, TalentGrowers, you may have listened to the recently episode where I did a solo show that is all about how to grow your skills for your next job or your dream job while you’re still in your current job. That might be a really nice compliment to Sara’s suggested action. I love it!

Sara: Aligned!

Halelly: Very aligned. We’re going to link to your book and to your Forbes column in the show notes and I know people are going to want to hear more from you, learn more from you, stay in touch. What else should they do? Where should they follow you?

Sara: On Twitter and Instagram I’m @SaraBlissNYC. And I have a website, SaraBliss.com, where I will update on fall events and panels and things happening around the book.

Halelly: Okay, very good. We’ll link to that as well. Sara, thank you so much for stopping by the TalentGrow Show and spending some of your time and sharing your insights with us.

Sara: Thank you so much. I was thrilled to talk to you and it was exciting and fun and I love how you connected everything. You have such a vision for how to give advice to people.

Halelly: Thank you, I appreciate that. You’re welcome, and you’re welcome back when you have more stories! Let’s bring them back on.

Sara: Absolutely.

Halelly: I really loved how Sara’s actionable advice at the end was completely aligned with what I have been sharing with you for all this time and especially recently on how you are ultimately responsible for your own development and you need to keep motivating and growing and inspiring yourself if you want to grow and inspire and motivate others. So be a role model and also be actualizing yourself to grow and be your best self. That’s what I want for you – be your best self and help other people be their best selves and the whole world will be best and awesome and lovely. Thanks for listening. I really appreciate you and I am glad that you stopped by, that you’ve listened all the way until the back of the podcast club, as David Burkus once named it, and I would love to hear your feedback and your ideas for future episodes, as you know. That’s it for this show. I’m Halelly Azulay, your leadership development strategist here at TalentGrow, and this is the TalentGrow Show. Thanks for listening and until the next time, make today great.

Announcer: Thanks for listening to the TalentGrow Show, where we help you develop your talent to become the kind of leader that people want to follow. For more information, visit TalentGrow.com.

Get my free guide, "10 Mistakes Leaders Make and How to Avoid Them" and receive my weekly newsletter full of actionable tips, links and ideas for taking your leadership and communication skills to the next level!

Don't forget to LEAVE A RATING/REVIEW ON APPLE PODCASTS/iTUNES! It’s easy to do (here’s how to do it in 4 easy steps). Thank you!!

Like the Facebook page of The TalentGrow Show!
Join the Facebook group – The TalentGrowers Community!
Intro/outro music: "Why-Y" by Esta

You Might Also Like These Posts:

140: How to Live and Lead Limitlessly with Laura Gassner Otting

Ep050 [The FLIPPED episode!]: Halelly Azulay is interviewed about her career, developing leaders, and going from light-bulbs to impact by guest host Margarita Rozenfeld

Ep12: Developing resilience and positivity with Doug Hensch