Ep063: Entrepreneurial You—secrets of the side hustle with personal branding expert Dorie Clark

ep063 Entrepreneurial You secrets of the side hustle with personal branding expert Dorie Clark TalentGrow Show with Halelly Azulay
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In today’s episode of The TalentGrow Show with Halelly Azulay, Dorie Clark, best-selling author of Reinventing You, Stand Out, and the brand new Entrepreneurial You: Monetize Your Expertise, Create Multiple Income Streams, and Thrive, shares some of her best insights on personal entrepreneurship and the ‘side-hustle’. She warns us against a common personal branding mistake, says what she thinks is the easiest and most low-risk point of entry into side-hustling, and shares an actionable tip that can make the early days of building your brand (when the finish line seems far, far away) much easier. She also shares several cool real-life stories and distills the entrepreneurial lesson from each of them. This is an episode that anyone interested in expanding their career success and broadening their value-proposition definitely won’t want to miss. Check it out (and don’t forget to subscribe and share)!


Halelly Azulay and Dorie Clark at the Los Angeles book launch of Entrepreneurial You on October 17, 2017

  • Dorie’s career trajectory was full of what she calls “misfires and missteps”. Listen to how she went from an aspiring academic (who was rejected by all the graduate programs she applied for), to a journalist (that got laid off after the first year), to a spokesperson for a presidential candidate (that lost) and finally to a successful marketing strategy consultant (3:11)
  • What was the common thread she saw throughout all those experiences? (4:05)
  • Why building your brand is important, not just for you and your career, but for the world (5:20)
  • How and why professionals should think about creating new income streams on the side (6:56)
  • Dorie goes into an impactful experience she had at 22 years old and how it taught her that the “safe option” isn’t always so safe (8:53)
  • The inspiring story of Lenny, the guy who went from nurse to head of communications (10:50)
  • Scott Oldford and why you need to really “listen to what people are asking for (15:53)
  • Halelly mentions some of the previous TalentGrow episodes that featured a guest with a side-hustle (19:25)
  • What does Dorie say is the easiest and most low-risk point of entry into the world of the side-hustle? (20:45)
  • How Michael Bungay Stanier (he was featured in episode 31 of The TalentGrow Show) evolved his business overtime (21:41)
  • What’s a common mistake that people make when it comes to personal branding? What should we do instead? (25:58)
  • What does Dorie mean by “living your brand”? (27:58)
  • Dorie shares a cool piece of personal news (29:18)
  • What’s the lesson Halelly wants the audience to take away from Dorie’s life? (32:00)
  • Dorie shares her final tip (it’s related to the early days of building your brand, when the “finish line” seems very far away) (32:58)
  • Halelly points out another cool way for leaders to make use of Dorie’s tip (35:39)
  • How listeners can access more than 400 free articles Dorie’s written (for places like Forbes and Harvard Business Review) as well as a free workbook that has 88 questions that walk you step-by-step through how you can become more entrepreneurial in your own life (35:55)


Halelly Azulay (that's me) excited to read Entrepreneurial You by Dorie Clark ahead of the release of the podcast episode!

Halelly Azulay (that's me) excited to read Entrepreneurial You by Dorie Clark ahead of the release of the podcast episode!


Dorie Clark is a marketing strategy consultant, professional speaker, and frequent contributor to the Harvard Business Review. Recognized as a “branding expert” by the Associated Press, Fortune, and Inc. magazine, she is the author of Entrepreneurial You (Harvard Business Review Press, forthcoming on October 3, 2017), Reinventing You, and Stand Out, which was named the #1 Leadership Book of 2015 by Inc.magazine and one of the Top 10 Business Books of the Year by Forbes. It was also a Washington Post bestseller. She consults and speaks for clients including Google, Microsoft, and the World Bank.


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. Welcome back Talent Growers. I’m Halelly Azulay, your leadership development strategist here at TalentGrow and I’m looking forward to sharing today’s episode with you. Bestselling author, speaker, consultant and coach Dorie Clark is here, and I’m so eager because she’s been showing people how to become a recognized expert and build their personal brand. It’s a crowded and noisy marketplace, and every one of us has to differentiate ourselves from our competition if we want to succeed, whether we are on the inside of an organization or outside in an entrepreneurial hustle. But Dorie has written a new book, it just came out last week, and in it she shows us how we can build a great career, and a lucrative one, by trying to expand our reach and monetizing our expertise with multiple income streams and thriving at that. I think this is really an interesting perspective for a lot of us who have been in one track. She’s interviewed 50 top entrepreneurs and has laid out a roadmap for exactly how regular professionals can use the same strategies to build a thriving and lucrative career in today’s crowded marketplace. Strategies and stories and examples on personal entrepreneurship and the so-called side hustle. She wants us against the common personal branding mistake, what she thinks is the easiest and most low-risk point of entry into side hustling, and she shares actionable tips that can make those early days of building your brand be much easier. So, I hope that you enjoy this episode and don’t forget to subscribe and to share it with others. Here we go.

Hey there Talent Growers. Welcome back. This is Halelly Azulay. I am here with Dorie Clark, a marketing strategy consultant and professional speaker who teaches at Duke University’s Fuqua School of Business. She is the author of Reinventing You and Stand Out, which are both some of my favorite books. I’ve used them with clients. They were named the number one leadership book of 2015 by Inc. Magazine, one of the top 10 business books of the year by Forbes and a Washington Post’s bestseller. She consults and speaks for clients including Google, Microsoft, Yale University and the World Bank, and today I’m really excited to talk about her brand new book called Entrepreneurial You: Monetize your Expertise, Create Multiple Income Streams and Thrive. Dorie, welcome to the TalentGrow Show.

Dorie: Thank you so much for having me.

Halelly: It is my pleasure and I am so glad you have agreed to spend some time with us, here on the TalentGrow Show. Before we get into some of the nuggets of wisdom in your new book, I would love for people to learn a little more about your professional journey. Where did you start and how did you get to where you are today?

Dorie: Well, thank you. I started with a lot of missteps and misfires along the way, which I think that probably a lot of your listeners can relate to. I originally thought I was going to be an academic, and after I got my Master’s degree, I applied for Doctoral programs in literature and I didn’t get into any of the graduate programs that I tried to break into. So, I had to go to my plan B, which was being a journalist, which was actually really wonderful. But, about a year into starting my career, I got laid off – as journalists so often do these days – and then I went into politics. I had been a political journalist, so I became a spokesperson, first on a gubernatorial campaign and then on a Presidential campaign, and both of my candidates lost! So, I think that sometimes for all of us, it takes a little while to find your fit and find what you’re doing.

For me, through all of those experiences there was really a trough line, about how to communicate your message, how to make sure that what you’re trying to say actually gets heard in an increasingly noisy, crowded marketplace. And so it’s now been about 11 years since I started my own business, doing marketing strategy consulting, and now I write and teach business school and speak and things like that. But what I’ve remained committed to is making sure that talented professionals are able to really get noticed and have their skills appreciated because I think so often we hear the loudest voices winning, and we hear about people who were sort of rising to the top, because they’re sort of screaming and rattling the cages. A lot of really talented people get left behind, and so I want to try to share strategies that talented folks can use to make sure that they’re able to really be appreciated and that they can leverage their full talents at work.

Halelly: Yes, and I have used some of your writing in workshops about personal branding and career development, because that is part of my mission as well, helping people be successful in their career and maybe become more, seen more as a thought leader. Because so many people are like a best-kept secret. It’s a shame! The thing is, it’s not like you’re trying to hawk something that’s not valuable or that you’re trying to pull the cloth over people’s eyes, which I think a lot of times is where people are afraid, or what holds them back from marketing themselves and branding themselves. Whereas you’re basically, the world is not receiving your gifts and you’re not receiving the full value of the return on that, if you’re quiet.

Dorie: That’s exactly right. It’s really important, not just for you, not just for your career – although it’s very important for those things – it’s really important honestly for the world, because if the best ideas are not winning, if the voices that should be heard are not being heard, that is doing a disservice to everyone.

Halelly: Yeah. Definitely. So, I know that with your new book, and congratulations. I read it, got an advance copy. It’s launching I think October 3, right?

Dorie: That is correct.

Halelly: I can’t wait for people to read it and to share it with some folks in my network, because it’s perfect. It’s definitely perfect for people like me, who are entrepreneurs and who are seeking to find a voice and an audience that really meshes well with it. I would say some of the listeners – because my listeners are not necessarily entrepreneurs. Most of them are inside of organizations. Most of them are leading careers that are within a structure, an organization, a system, might be like, “I’m not an entrepreneur, so this book is not for me. Monetizing and all of this stuff is not for me.” But I know that you recently said – and I totally agree with this – is that professionals can, and should, think about creating a new income stream on the side, because it can add benefits to them in a couple of different ways. I’d love to talk about that some more. Why should professionals be thinking about this what I sometimes call the side hustle?

Dorie: Such an important question, and just to start with your initial point, I think it’s really true. There’s kind of an old exercise that Brian Tracy, the business speaker and writer, used to do, where he would speak in front of a group and he’d say, “Okay, so raise your hand if you’re in sales,” and a group of people, maybe however many, 10 percent, would raise their hand. They were the VP of sales in their organization, something like that. He would pause and say, “Wrong! You’re all in sales!” And of course, it’s true, that we have to appreciate that whatever we do, whatever our title is, you need to be good at persuasion. You need to be good at selling your ideas and convincing people, “Hey, I’m the one you should promote,” or, “Hey, this idea has real merit. We should be exploring it.” I think similarly, many people might say to themselves, “I’m not an entrepreneur. I don’t have a startup. I don’t have a business of my own, so no, I’m not an entrepreneur.“ But the case that I would like to make is that no, actually, even if you are not technically not an entrepreneur, we all need to be entrepreneurial in our thinking. That that is the recipe for real success, whether it’s inside or outside of an established organization. There are things that can really be learned from the world of entrepreneurship.

I think if we’re just thinking specifically about your own career security, one of the things that I think really is essential is the idea of creating multiple income streams. I mean, I came by this personally. I mentioned at the beginning of the episode that one of the things that was really an impactful experience for me, I was 22 years old. It was my first job out of graduate school as a newspaper reporter, and I was laid off after a year on the job, totally unexpectedly. They called me into the office on a Monday afternoon and I had to go immediately and pack up and get all my things. They gave me a week’s severance pay – a week! – and I had already worked Monday. So technically it was four days of severance pay and it was like, “Okay, kid, go figure something else out,” and it was incredibly traumatizing. For all of us, it really drove home for me that sometimes the “safe option” isn’t so safe. We all know that it’s a bad idea to take the money we’ve earned, and if we invest it to only invest it in one stock. Everybody would say, “Oh, of course. That’s ridiculous. You need to diversify. You need an index fund or a mutual fund,” or something like that. But with our careers, we often times are not diversified. So having some kind of side project that you’re just doing on your own time can be enormously valuable for you. Number one, as a source of outside income – which is a useful thing for any of us to have – but number two, because it can help you build skills that you can apply and bring back to your day job that can actually sometimes help you leapfrog forward above the competition.

Halelly: Absolutely. I think that’s something that a lot of people completely don’t recognize. That there are ways that you build skills on the outside, when you’re doing something else, that bring value back to your employer. I think a lot of people are like, “I’m scared, I’ll hide it. What if they find out?” And it’s like, they’re going to benefit from this actually.

Dorie: That’s exactly right. One of the stories that I well in the book Entrepreneurial You actually comes from a Harvard Business Review article that I wrote a couple of years ago. I had been consulting for this organization, for the Mt. Sinai Hospital in New York, and the whole time I was doing this consulting project, I kept hearing about this guy Lenny who was the head of communications. Everybody was just sort of mentioning him, like, “You’ve got to meet Lenny. Lenny is really something.” The interesting thing about him, he had started his career at the hospital as a nurse, and he had somehow managed to work his way up to being the head of communications, which is not at all an intuitive career path. So finally, after a couple of months on this consulting project, I found myself in a meeting with him. Afterwards, I grabbed him and said, “Lenny, I’ve been hearing a lot about him. Can you tell me a little bit more about how you got to where you are? Like what’s your story?”

And it turns out, he told me, that he had decided, as basically just an interest of his, a self-improvement project, like something he thought was cool, he decided to develop a couple of apps on the side. Just it was his hobby, he thought that social media and apps were pretty cool and he wanted to learn about it. So he developed these apps, put them up for sale in the iTunes store and it was just a little thing he was pursing on the side. One day his boss calls him into his office and Lenny doesn’t know what he wants to talk about. The boss says, “Lenny, I hear you’ve developed some apps.” The world stops, right? He thinks, oh no, oh no. Was there a policy that I didn’t know about that I shouldn’t have done this? Does he think that I was using company time or company resources? What is the problem? He felt sure he was going to get into trouble. And the boss paused a beat and said, “I think that’s really interesting. Would you like to run social media for the hospital?” Boom. And so Lenny moved into this new position, not at all because of his professional training. I mean, he was a nurse, but he had shown that he was capable of that. When he did a good job running social media, eventually the position opened up and they gave him control of all the hospital communications.

Halelly: That’s a great story. What I think is really amazing, we live in such an amazing time where there are so many things that are possible now that are so much more accessible and so much easier to do than they had been before the world of the internet and social media and apps and all this. You can connect with influencers, you can connect with a purchasing audience. You can bypass the gatekeepers. You can publish without a publisher. There are so many ways in which people can do this now with almost no resources and almost no specialized knowledge.

Dorie: That’s exactly right. It really is more possible than ever.

Halelly: Your book, I love it. It’s got lots and lots and lots of examples and stories, and pretty much every single one that you mentioned I’m like, “Hey, I listen to that guy’s podcast, or I know that person.” So I loved it. You talk about monetizing through becoming a coach or consultant, building a speaking business or podcasting. Hello! Or blogging or vlogging. Hello, hello, I do that. Or putting on mastermind groups or putting on live events or creating an online course or creating a digital following with an email. I have to say, even as someone who tries to do all this stuff and I geek out on this stuff, I get overwhelmed reading about all of these different methods but I’m pretty sure that lots of the people that are listening, that maybe didn’t even think about this at all, when they look at this and say, “Okay, Dorie, I hear you. I think this is a good idea. Where should I start?” They might feel really overwhelmed. I’d love to break it down a little bit for the uninitiated side hustler. You know, what are some ways in which we can make this a little more chewable for them? What are some baby steps that you think are a good place to start?

Dorie: I really want to emphasize that this is very possible for almost anybody. Literally just a couple of days ago, I got an email from a gentleman that I’ve worked with. He’s a vice president of human resources at a very prominent organization and I had gotten to know him and even done some work for him, and he sent me a note and said, “By the way, on my own time – sort of my hustle – I’m pursuing coaching certification.” He had been taking classes and studying and practicing and he was just about getting ready to complete it and he just wanted to make me aware that he was launching his business and he told me a little bit about the kinds of clients he was specializing in, in case I knew of anyone who would be a likely prospect. But, I think for a lot of talented professionals, over the years, they have built up a deep well of expertise and they might not think of it this way, but it is the kind of thing that people often times, they want that knowledge. They would be willing to pay for that knowledge. I think that it’s very doable.

I think that one of the best starting points is to really just think about what the people around you are asking for. If you sit down and think about it, if people come to you sometimes – and I’m sure we all have examples of this – where they say, “Hey, I’d really like some advice. I’d like to pick your brain. I want to hear about blah, blah, blah,” what is the thing they want to hear about? It could be different for all of us. It could be a hobby that you pursue really seriously. It could be some aspect of your professional life. But that often is the place. That’s basically the market telling you what they find valuable in your skillset. And so just as one example, somebody that I profile in Entrepreneurial You, there is a guy named Scott Oldford. He’s mostly an online entrepreneur and he had dabbled with a lot of different business models and things like that, but there was a guy that came to him once, and the guy was actually the son of one of Scott’s clients. He was a young guy in his early 20s and he said, “Scott, you seem really knowledgeable. Would you just teach me everything you know about online marketing and online consulting?” Scott was a little bit dubious about this. He had never done anything like that. He hadn’t even gone to college and he was like, “Really? I don’t think I could do this coaching process with you. That seems a little just not something I’m comfortable with or familiar with.” The young man was really persistent and was like, “No, no, I want to learn from you,” so he actually floated a suggestion. He said, “What if it wasn’t just me? What if we found a way to make it really worth your while? I bet a lot of other people would be interested in this too. Maybe you could offer some kind of a course or a program.”

Scott was still pretty dubious. He wasn’t sure that other people would be interested in this at all, but he said, “We can test it,” and so he sent out an email to his list and just said, “Hey, I’m thinking about doing this thing. I’m thinking about offering this online program to just teach people everything that I know about online marketing. Would you be interested?” He named a good price, it was going to be $1,200. He said, “If you’re interested, here’s a link where you can sign up and raise your hand for it. We’ll see if there’s enough interest to do it.” Boom. Within a few days, it was sold out. He had his answer. And it all started from one person saying, “This is what I want to learn from you,” and just asking and seeing if other people agree. I think sometimes we get hung up on thinking, “I have to devise this perfect product or this perfect service,” and of course, if we’re trying to guess what people want, often times we’re going to guess wrong because even multi-billion dollar companies often guess wrong. But if you listen to the market, listen to what people are asking you for, you already have a pretty good sense of what they value.

Halelly: And what’s really cool about this is, if you’re doing this on the side, and you have a paying job, you actually have a lot more flexibility to make those mistakes or to try something that then proves to not work well, because you’re in a place where you’re not reliant on it for feeding your family or something. You have, I think, more freedom, to try different things out and see what works. I loved your story in the book also about this guy, Bozi Dar, who is a successful leader in his company, but also built this really successful side business, and by the way, listeners to the show, we have several episodes where I featured people who had – at least at one point – had a side hustle. Most recently episode 54 with Eric Barker. Episode 53 with Jessica Kriegel. Episode with 49 with Dan Potefract. Episode 42 with Alexander Levit, who actually has multiple streams of income and is one of the feature stories in your book, Dorie, and even episode 4, Larry Gioia, who is there with PricewaterhouseCoopers, but on the side built this business of teaching people leadership through kayaking and teaching kayaking to people with physical disabilities. He has all of these side hustles. And then episode 29, who is Hassan Osman, who wrote a book on Amazon and then wrote a book about how to write a book on Amazon. He’s doing this thing on the side too, so there are so many examples that we can learn from.

Dorie: That’s wonderful. What a great resource for people who might be interested in beginning to explore this.

Halelly: Okay, so the suggestion you had was listen to the market and what are people asking you a lot about, and you were saying that maybe you can create some kind of a course. That would be one option. Any other things you think are kind of really low-risk points of entry into this world?

Dorie: Yeah, absolutely. Of course coaching and consulting on the side is the easiest, because there’s no start-up cost whatsoever. If someone is interested, great. You meet with them once a week over coffee, or you do a Skype session with them. I’m a big fan of going as lean as possible. I think that sometimes when people are beginning some kind of entrepreneurial side venture, there’s a tendency to want to look bigger than you are because maybe you’re nervous, like, “Oh, gosh, it’s just me and I don’t know if people will take me seriously.” I know I felt that when I first started my business. And so people just get so hung up on things like, “I have to have the perfect business cards, and I have to have the perfect logo.” No, you don’t. That’s not necessary. What you need is a client. You need a human being that’s willing to pay you a little bit of money for something. It doesn’t have to be a big deal.

For instance, one of the people I interviewed in Entrepreneurial You is someone, Halelly, that I know you know, Michael Bungay Stanier, and Michael was talking about how he evolved his business over time. Now, his business is actually focused on training leaders within companies how to be better coaches to their employees. Kind of an interesting concept. The original place he started was coaching people directly, himself, and so as he was exploring this and building up his business, he was doing just about anything he could to sort of scrap by. He said that his first few months in business, he was doing coaching for about $200 a month, and he would do weekly phone calls. $50 an hour, basically, and it was just to get practice. It was just to get some money coming in. I think that’s something that is really crucial too. Because of course, if it’s your only source of income, having a client at $200 a month is not going to go too far, but if you have a day job that you’re happy with and comfortable with, that gives you this amazing runway.

Your earliest clients that you’re working with, you may decide that you just want to have a little side income stream, and honestly, sometimes it’s about having a little extra money, but often times it’s just about creating a new experience for yourself, something that’s fun, that's interesting, that’s meaningful, that you can learn from. Who cares if they’re paying you $50 a session? That’s fine in the beginning, because you’re doing it to get experience. You’re doing it to get testimonials. You’re doing it to become better and learn. Sometimes it can honestly be a passion project. I have a good friend who was, until very recently, she had a full-time day job doing marketing for a natural foods company, and that was great, that was her day job. But she had a passion project based on her own personal experience, where she was coaching women who were emerging from fundamentalist religions. That’s something that may not ever necessarily be a mass market, and it may not ever be incredibly lucrative, but it was work that was very personally meaningful for her. She did that and it really enriched her life dramatically.

Halelly: We could get into this. We don’t have time, but this is a perfect example of what’s possible nowadays with the long tail, if you’ve ever read about it. Who was it that initially came up with this? I can’t remember who came up with this concept of the long tail.

Dorie: Chris Anderson.

Halelly: Yes. From Wired, right? So you can just reach an infinitely narrower and narrower niche because of the internet, so reaching such a specialized group of people makes her perfect, because there’s probably very few people that are doing that and she can find them. By the way, folks, Michael Bungay Stanier’s episode is episode 31, if you’re curious to hear more about what he does, because he’s a great guy. This is such good, very valuable insight and advice. What do you think is a common mistake that a lot of professionals make when it comes to personal branding and certainly being seen as a thought leader and now venturing into this idea of monetizing your thought leadership?

Dorie: This is a topic that I’ve certainly thought about a lot, because the books that I’ve written over the years, in many ways I view them as a trilogy for professionals. My first book, Reinventing You, was really about taking control of your personal brand and reinventing yourself into the job or the career that you most want to be in. My most recent book, Stand Out, was about how once you are in a job or a company that you care about, how do you then become viewed as being one of the best? One of the best at your company or one of the best in your field? How do you really achieve that level of recognition for your skills? And then finally, Entrepreneurial You is about how to make that sustainable, financially, over the long-term and build the kind of life and career that you want. I would say when it comes to personal branding, one of the mistakes that is most common that people make is just assuming that other people will pick up on what you are good at, and what you are trying to do. In our culture, there is a strong strain, even though I think most people understand conceptually, “Personal branding, that’s important. Yeah, I should be doing that.” I think that there also simultaneously a very strong strain of, “Well, I don’t want to brag about myself, and really if I just work hard, people will pick up on that.”

And that’s great, and I think that certainly if we were going back maybe 20 years ago, that would not be bad advice. People’s tenures at companies were longer. You were working with smaller groups of people, and you’re right, over time, given enough time, people will notice. The problem is that these days, people are changing jobs more frequently, and we’re working with wider and wider groups of people. I’m willing to bet that almost all of your listeners have either some clients or even some colleagues and team members that are in different cities or even in different countries that they deal with on a regular basis, and that’s very different in terms of people having the level of exposure to you such that they actually know, really, who you are and what you’re capable of and what you’re good at. We have to understand that for a lot of folks, their understanding of us is very cursory. They are not spending a lot of time really thinking, “Oh, what would be the next leadership position that would be right for her?” That’s the last thing they’re thinking about. So what we need to do, we can’t just leave it to chance and like, “Oh, whatever they think is whatever they think.” We need to find a way to guide that far more strategically, and that doesn’t mean bragging about yourselves or saying, “Let me tell you about how great I am.” That doesn’t work. That’s a stereotype of what people should be doing. It’s not effective at all.

What we do need to do, however, is be strategic, and understand that with every action we take, we are sending a message to people. Really ask, are we sending the right message? Are we getting across what we want? That means doing what I call living your brand. Understanding that personal branding, it’s not a one-time thing. It’s not like, “Oh, I did that in 2015, so thank God I don’t need to do that again.” Every minute you’re sending a message. Really thinking through, “What leadership activities am I involved in? What do people find about me when they search for me on Google? What projects have I really taken a lead on? Who do I hang out with? What kinds of things do I talk to people about?” All of those things contribute to your personal brand, your professional reputation, and its’ worth really being conscience on an ongoing basis of how you are living out your brand.

Halelly: Great advice. Love it. Well, we’re going to leave everybody with one really specific action that they can take today to ratchet up their own effectiveness in this realm, but before that, what’s new and exciting for you? I mean, I know you’re in book launch mode, but is there anything else that is really holding your attention these days on your horizon?

Dorie: Well, on the professional front, certainly the launch of Entrepreneurial You is a big deal and something that I’m focused on. On the personal front, something that I will mention and as probably by the time this episode airs we will know the answer – although as I am stating it I do not know the answer – so we’ll just have to see, wait with baited breath, but one of the things that I really try to do is to focus on cultivating interesting outside hobbies. Just things that are fun, that I feel like I can learn and grow from, and so for me, something that I’ve been emphasizing this past year is actually all things musical theater. I live in New York and there’s a ton of resources here for that. Obviously it’s kind of the musical theater capital, and so there is a program that you can apply to that is a fellowship program that actually trains people to be musical theater writers. I thought that would be a really cool thing to do, so I have applied to it. This is actually my second year applying. You’ve got to be persistent. I didn’t get it the first time, but I have applied again and so I’m hoping – fingers crossed – that I will get accepted or at least get an audition and we’ll see how that goes.

Halelly: Oh wow. Well, I think that we’ll definitely have to have you get back to me and let me know what you find out so we can share it at least on the show notes page if it’s after the episode already drops. That’s cool, I love it!

Dorie: Thank you.

Halelly: And will you do this, let’s say if you get accepted, do you think this is something that you would then just do on the side or is that something you’re thinking about maybe as the next step in your career?

Dorie: You know, much as I encourage all professionals – even those working inside companies – to develop entrepreneurial side streams for themselves, I would consider this to be my version of that. I really love the work that I do, the speaking and coaching and consulting, but I think that it is useful for all of us to have kind of little side bets that we work on and nurture and we’ll see where they go. If I end up writing the next Hamilton, then maybe I’ll make that a more full-time enterprise, but certainly it is something that cultivating on the side is doable.

Halelly: Very cool. I recently came to know Elliott Masie, I don’t know if you’ve heard of him? He’s like one of the gurus in the e-learning world. He’s the grandfather of e-learning. He probably wouldn’t like that name, I just made it up for him. But he also produces Broadway shows and musicals. So, he produced Anastasia and he produced, I think, what’s the one with boots?

Dorie: Kinky Boots?

Halelly: I think he produced that. And then on the side, he has a racehorse. So, there are so many examples of it, and I want folks to notice, because I’ve heard you give several examples of this, Dorie, is that one of your strengths and an example that everyone can take from you – aside from what you’ve been explicitly teaching – is that you had many examples of where you got rejected and you didn’t let that hold you back. You didn’t let that cause you to not try anymore. So, I love that about your story, that you just, someone told you no and you kept going. Changed directions and you went forward or you applied, applied again. So, thank you for that example. That’s important.

Dorie: Yes, thank you so much.

Halelly: So, before we wrap up, what’s one specific action that listeners can take today, this week, that can help them ratchet up their own better use of the tools that you’ve been teaching or their own ability to diversify how they come at their skills and their gifts?

Dorie: One of the lessons that I found most helpful in Entrepreneurial You that I think your listeners might be able to benefit from actually comes from a woman named Stefanie O’Connell, who I interviewed for the book. Stefanie is a personal finance expert and as with all things, in the early days of really trying to establish yourself in your career, whether working for yourself or working inside a company, sometimes it’s slow going, because you can see the finish line, but it just seems a million miles away and if all your focusing on is the distance between where you are now – starting at zero, basically – and where you want to be, it’s really easy to get discouraged. Often, for many people to the point where they give up. And of course, that means you will never reach that place. But one of the things I really learned from Stefanie that I thought was most valuable is that she really consciously cultivated a strategy of celebrating little wins on the path to success. And so it takes a lot of effort to become a well-known personal finance expert, but for her, the way she was able to keep herself motivated as to really chart and track the ways that she was making progress. So for instance, she started out blogging for free, like just about everybody does. But over time, people would actually start to come to her and say, “Hey, will you blog for us? I’ll pay you $25.” Now, getting paid $25 is not earth shattering. It’s not going to change your life. But for her, she realized that’s a milestone, Someone thinks my work is worth paying for.

And that kept her motivated and kept her in the game to the next milestone. Maybe it was that a thought leader she respected re-tweeted her work and was taking notice of what she was doing. Maybe it was getting asked to be on somebody’s podcast for the first time. Even if it was a tiny little podcast. But I think that’s the thing, and it actually ties into research that’s been done by a professor at Harvard Business School named Teresa Amabile. She wrote a book called The Progress Principle and it showed that really the most important thing, when it comes to people feeling positive about their work, feeling like they are making a difference and getting somewhere is that everyday, having a feeling that you are at least moving a little bit closer to the finish line, that you are making progress. For all of us, we can and we should do that with our own jobs. Really looking at it and saying, “What is the small win here, and how can I make sure to celebrate that?” That gives you the energy and the momentum to keep going toward the ultimate goal.

Halelly: Beautiful, and as leaders, this is something we can do for others as well. We have like a double win here, because we can do it for ourselves and we can help point out the small wins for our team members. Dorie, thank you. How can people stay in touch with you, learn more about you and learn more from you?

Dorie: Well, thank you. One of the best ways that I’ll suggest for folks is to go to my website, DorieClark.com. I have more than 400 free articles available there that I’ve written for places like Forbes and Harvard Business Review, and I actually have a special free workbook that folks can download if they’re interested. It’s called the Entrepreneurial You Self Assessment Workbook, and it’s 88 questions that actually walk you step by step through how you can become more entrepreneurial in your own life and begin to think about multiple income streams and ways that you can move toward applying these principles to become even more successful in your day job as well. Folks can get that for free at DorieClark.com/entrepreneur.

Halelly: Great, that sounds like a great resource, so I definitely think people should go and grab a copy of that. It’s been a pleasure speaking with you and learning from you and thank you for all the work that you do and for sharing it with us, with the TalentGrowers community, Dorie. I appreciate you.

Dorie: Thanks so much.

Halelly: I really hope you enjoyed this episode, TalentGrowers. And guess what? I got in touch with Dorie to ask her how it went with that fellowship program and she got in! I’m so excited for her. She said she’s going to put it on hold for a year because she’s super in the throws of book launch mode and that’s a very big task, so she’s going to hold off for a year, but she’s so exited she got in and I wanted to make sure I let you know. So the book came out last week and this episode just went out one week after, if you’re getting it when it launched. I hope that you go and grab a copy. The link to her new book, Entrepreneurial You, and all the other resources we mentioned during the show, are on the show notes page over on my website. It’s TalentGrow.com/podcast/episode63. While you’re there, make sure to sign up for my free 10 Mistakes that Leaders Make tool, and that way you’ll be able to stay in touch with me via my short, fun, actionable weekly newsletter. I hope you go and do that.

We’re super proud that the TalentGrow Show podcast has been selected to be part of the C-Suite Radio Network of high-quality business podcast, so check it out over there C-SuiteRadio.com, and get lots of useful leadership advice and insights. Take a couple of minutes and go over to iTunes and help us get noticed, get found, by leaving us a review. It’s really easy to do. It doesn’t take a long time, but it makes such a big difference for the ability to reach more people with the work that I’m doing. I’m super grateful to you if you take a moment and do that. That’s it for this episode. I’m Halelly Azulay, your leadership development strategist here at TalentGrow and I thank you for listening. I appreciate you so much 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.

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