ICR282: Dorie Clark, Entrepreneurial You

Here’s my conversation with Dorie Clark, author of Entrepreneurial You, in episode 282 of Informed Choice Radio.

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Useful links

–Entrepreneurial You on Amazon

–Follow Dorie on Twitter

–DorieClark.com

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Interview transcript

Martin: Welcome back to Informed Choice Radio. I’m delighted today to welcome Dorie Clark, author of “Entrepreneurial You.” Dorie, welcome to the show. Can you start by telling our listeners a bit about your background and about what it is you do?

Dorie: Thank you, Martin. Absolutely and thanks for having me. I write books and speak and teach about them and consult. Really the goal of what I do is to help talented professionals in an increasingly crowded and noisy marketplace get their true talents heard. That’s really been the through line of the work that I do. From my first book, “Reinventing You,” which is about to reinvent yourself into the job or career that you want, to my next book “Stand Out,” which is about how to really get your talent noticed and how to become a recognised expert in your field, to my latest book, which just came out, “Entrepreneurial You,” and that is about how to actually monetize your expertise and make a great living with your skills.

Martin: What did your career path look like? How did you get to where you are today?

Dorie: It was all over the map, Martin. That’s actually really what inspired “Reinventing You” in a lot of ways because I felt like I was kind of reinventing myself in a little bit of a haphazard and ad hoc fashion. I wished that I could have more guidance. I ended up later going back and writing the book that I wished that I had by interviewing dozens of professionals who had reinvented themselves successfully. Very briefly, after college I went to Divinity School and I got a master’s degree in theological studies from Harvard. I then became a newspaper reporter, a political reporter, and did that for a while. I then transitioned into politics and became a spokesperson in the US on a governor’s race and a presidential race.

Of course, my candidates kept losing. I ran a nonprofit for a couple of years, which taught me a tonne about how to be a good business owner and then finally 11 years ago, I started my own business where I now have a mix of different income streams and do a lot of different things. In many ways, that’s the context of “Entrepreneurial You” is the importance of creating multiple revenue streams in your business and how to do it. I currently have eight of them and have really worked to diversify what I do.

Martin: I see you described in The New York Times as an expert in self-reinvention and also helping others make changes in their lives. Why do you think that’s become so value, so important these days, self-reinvention and change in general?

Dorie: Well, I think there’s a couple of reasons for it. One, of course, is that more and more as the economy is changing, we are sometimes forced into reinventions that we may or may not welcome. For me for instance, I thought I was probably going to be a newspaper reporter forever. I mean that was my intention when I entered the profession, but that was not what the economy seemed to want. In fact, I got laid off. Over the past 15 years, close to 40% at least in the US of newsroom journalists have lost their jobs. There’s been just huge changes and disruptions. In many cases and in many industries, people have been forced into reinventions and you have to get creative at that point. Of course, there’s also people who are reinventing for voluntary reasons.

That they have discovered a passion that they care about. They like to try something different. They want to stretch themselves. I think those are all really important and worthy goals if we want to keep developing as humans. The ability to choose to reinvent yourself is also really critical.

Martin: We’ve talked about your new book “Entrepreneurial You.” What prompted the book and who’s it designed for? Who is it going to appeal to?

Dorie: I wrote “Entrepreneurial You” in a lot of ways because I wanted to answer some questions for myself. I think anyone who follows the entrepreneurial space has probably heard stories of big success especially in the online realm. You hear about these people making millions of dollars. At first when I would hear about that, I thought, “Oh man. This is just a crack of you know what. These are people who are probably either exaggerating what they’re doing or they’re using shady methods to do it.” I just wrote it off in a lot of ways.

As I came to know more people and develop more colleagues in the field, I actually started to see people who are friends of mine who were having these massively successful launches and things like that where they were making literally millions of dollars. I thought wait a minute, what am I missing here? Maybe I should look into this a little bit more because I had built a good business, a very good solid business, but I was not necessarily making millions of dollars at every left and right turn. I wanted to understand that a little bit better about what was going on and how people were actually pulling this off.

I set out to interview about 50 top very high six, seven and eight figure entrepreneurs to understand in detail what were their business models, what were their income streams, how were they doing this, and to learn that for myself and to then write a book that could hopefully serve as a bit of a roadmap for other professionals for how they could achieve similar things in their own business. For me I would say that the target audience that I sought to reach was twofold. One is people who are already entrepreneurs that are looking for ways to become even more successful. Maybe they’re pushing themselves really hard over working like a lot of entrepreneurs do and they want to get more leverage in their business.

They want to maybe build out more passive income streams and so they want to incorporate new income streams. I really provided a lot of possibilities and options there. The other audience is people who maybe they’re not entrepreneurs. Maybe they have a day job that they love. They don’t want to leave it. For those people I encourage them strongly, this is one of the contentions in the book, that one of the best things that you can do for your career is to buy yourself your own form of career insurance by creating a side income stream for yourself. I provide possibilities and options that can work for them as well.

Martin: Thinking back to those interviews you carried out, I think you said 50 different entrepreneurs, were there any common themes which occurred from those? Things that entrepreneurs are doing which seems to make them successful?

Dorie: Well, I think that probably the most important underpinning to successful entrepreneurs and to people who think entrepreneurially is understanding the importance of small bets because what makes many people shy away from entrepreneurship is what I think is the mistake and belief that entrepreneurs are these risk hungry, risk loving people that just … They gamble it all on their idea. Of course, if that is what you imagine to be the case, a lot of sensible people are going to say, “Well, I just can’t afford to do that,” and so they stay away. The truth is that for entrepreneurs is the path … It could be the path to big success if you happen to get lucky and get it right, but luck is a terrible thing to rely on as your business plan.

A lot of times that goes wildly wrong. What you really need to do instead of just having this big bet and going for it is that you need to have a systematic fashion of testing a variety of small bets. If you do that, then the real trick is never betting more than you can afford to lose. If you do enough of that and just understand, “You know what? It’s not failure. It’s data,” and you are learning from it and it is not a destructive force because you’re never betting so much that it’s like, “Oh my god. Well, that was the rent,” then you can learn from it. You can incubate your ideas and then you can double down on what’s working.

Martin: For somebody listening to our conversation who wants to become an entrepreneur, who wants to start some sort of side income to create this career insurance you talked about, what tips do you have for getting started, for taking those first steps to entrepreneurship?

Dorie: One of the things that I talk in “Entrepreneurial You” is really the idea of starting with the smallest possible step that you can take. I think it’s important to start asap, start today, but start in a very small way. Again these myths about entrepreneurship is that it requires a lot of money or startup capital or oh, I need my angel investors or something like that. No. No. No. Ultimately what you want to do is validate a premise. For instance, if you want to start a side business, let’s say coaching, really all you need to do is just reach out among your friends and acquaintances and say, “Hey. I’m thinking of starting a side business coaching around whatever topic. If anyone would be interested in a session, let me know.”

I think that one of the most important things that you can do early on, if you are just getting started and kind of learning a craft, like let’s say coaching, do some for free. It’s not like you have to get people to pay you $10,000 right out of the gate, right? Do some for free in exchange for testimonials and referrals if they like what you have done. That’s great because it gives you confidence. It gives you validation. It gives you something to talk about with other potential customers and you’ve got forward momentum. Once you’ve done a few of those for free, then you can start building up a base of people and again early on this is a side project. You don’t have to be charging high rates.

You could get people to pay you 25 bucks, 50 bucks, whatever it is, but you get it going and then the fly wheel is spinning and it enables you to grow from there. I think the most important thing is starting and that propels you forward.

Martin: Do you think everyone has got what it takes to become an entrepreneur or do you think some people might be best suited to a 9:00 to 5:00 being an employee somewhere?

Dorie: I think anyone that wants to absolutely can. It’s not so much a question of skills, which can be learned. It’s a question of disposition. I think this is very much you can’t make the horse drink kind of thing. If you have people that are really motivated and they say, “You know what? I want to do this. I want to have my own business. I want to be an entrepreneur,” and they’re excited about it and they’re willing to learn and put in the time, then of course they can do it. I mean borrowing some huge deficit that whatever. I think the vast majority of people who have grown up in an economy where they have access to a reasonable amount of education and like a laptop and an internet connection, I think yes, they can absolutely do it.

It really is a question of motivation because there are folks who say, “You know what? I just don’t want to work that hard. You know what? That really just doesn’t sound appealing to me. I’ll do my thing at work, but then I really want to invest all my spare time in this hobby or in my friends or in my family.” That’s totally okay. That’s an okay choice, but for people who want entrepreneurship, I think that 100% it’s accessible.

Martin: Now you mentioned your varied career history and I’d like to talk in a moment about the work you did on presidential campaign, which of course is very topical at the moment given everything that’s happening in the United States with various FBI investigations and things. Not to do with the ones you worked on, but other ones.

Dorie: Yes, indeed.

Martin: First of all, I was intrigued to learn that you’re a Grammy Award Winner, but I understand you’re not a musician. How did that happen?

Dorie: Yes. Thank you. That is for me a real testament to the power of networking in a lot of ways because it is true. I do have a producer credit on an album, the Ted Nash Big Band’s Presidential Suites, which won two Grammies this year. I feel very fortunate to have been able to be a part of that. It really came about strictly through a connection that I had with a friend of mine, a guy named Kabir Sehgal, who is both a business author, that’s how I got to know him, and also a jazz musician and connoisseur and producer. Essentially as a favour for a connection that I had made for Kabir, he brought me in on the project, on the Ted Nash project. He said to me, “You know, I think this is a really good project.

I think this could go somewhere.” Sure enough, it got nominated for two Grammies and it won two Grammies. It was really incredible to be able to be a part of that to get to go to the Grammies, to get up on stage at the Grammies. That was extremely cool. I think the hope for business people and entrepreneurs everywhere out there is that you don’t even necessarily have to be this incredibly talented musician or whatever to be involved in some capacity in a project like that. If you are able to hone your other skills like networking or marketing, I provide some marketing assistance with the album, then those things can sometimes be valuable enough that you can cross over and become involved with really, really cool projects.

Martin: You’re definitely an advocate then of the power of networking and I guess being open-minded to opportunities.

Dorie: Yeah, for sure. You never know where it’s going to take you literally.

Martin: Yeah, absolutely. Now the presidential campaign. This was Howard Dean’s presidential campaign back in 2004. Our British listeners may not be familiar with Howard Dean, but they have heard of the movie its inspired, which was “The Ides of March,” which starred George Clooney. Again how did you get involved in the presidential campaign and what did you learn from that experience?

Dorie: The way that I had gotten involved in the presidential campaign. When we talk about reinvention, one of the things that I really like to stress for people is that while it is hard to reinvent yourself from one thing to a completely different opposite thing, something that’s actually not that hard to do is to make small steady pivots. If you can kind of envision a Venn Diagram, the two overlapping circles, it’s really a question of just kind of steadily pivoting yourself so that you’re moving from the part of the circle that overlaps with the other part of the circle until eventually you get to your destination. In my case, I was a political reporter, as I mentioned, and I got laid off from that.

I looked for other journalism jobs, but they just were not there because the economy for journalism was collapsing. I ended shifting and accepting a job working in politics as a press secretary on a governor’s race. I did that. Unfortunately, that candidate did not win, but it was a Massachusetts’s governor’s race. This is a little bit of inside baseball for the British listeners, but Massachusetts shares a media market with New Hampshire in the United States. New Hampshire is a very important state when it comes to the presidential primaries in selecting who is going to be the nominee.

I knew that that was going to be a little bit of an inherent advantage because since I knew the Massachusetts media landscape and all the players, all the reporters very well, I could use that as my argument for why they should hire me to do press on this presidential campaign. It took a long time. I had to be very, very persistent in how I approached it because working on a presidential campaign of course it’s kind of a coveted position. I was working all of my angles.

I was just networking feverishly to do it. It took about six or more months of kind of banging at the door and being very persistent, but eventually as a result of that and as a result of the case that I was able to make for myself by having this specialised knowledge in the Massachusetts media market, I was able to get on and ultimately become the New Hampshire communications director for Howard Dean’s presidential race.

Martin: It was an unsuccessful presidential race in the sense that Howard Dean did not become president, but what did you learn from the experience? How did that shape your career moving forwards?

Dorie: Well, it was actually a very formative campaign in a lot of ways because while of course he did not win, it was considered at the time to be a very revolutionary campaign when people look back on it because Dean was widely lauded as the first candidate who had fully harnessed the power of the internet in his campaign. He was really an internet fueled candidate. Whether it was for fundraising purposes or for organising purposes, he did actually an amazing job at that. The campaign was pretty celebrated at the time. The principles that he laid down and in fact, some of the same staffers, some of my colleagues, went on to work in 2008 for Barack Obama’s campaign, which of course was ultimately successful.

That was pretty cool. What I learned from it personally, I think that working on a presidential campaign is an amazing exercise in understanding how to break through in the media landscape, which I think today is something that everyday it gets a little harder to do because the noise level goes up. It’s something that nowadays not just presidential campaigns need to worry about. It’s what regular professionals need to worry about. Why should they hire you as the marketing consultant? Why should they hire you as the web designer? Why should they hire you as the leadership coach? Whatever it is, we have to answer that question. Understanding how to craft a message, how to be disciplined about conveying that message, and how to …

I think the great thing about campaigns too is you get practised breaking through not just when things are crowded, but also breaking through under very adverse conditions when you even have opponents that are trying to swat you down and to distract from your message. Those are skills that I still use everyday.

Martin: As a result with this very varied career and all the things you’ve gone through and the self-reinvention that’s taking place, today you’re a lady of many talents, writing, coaching, speaking. Which element of your work do you think is most enjoyable and do you see reinvention as an ongoing thing? Do you expect yourself to reinvent again and to become something else in the future or would you even consider going back to revisiting something that’s already taken place?

Dorie: Great questions. I would say if I’m thinking about the pieces of my work that are probably the most fun on a really pure basis if we’re isolating them, probably the most fun is speaking. I do a lot of keynote speaking. It’s just nice because for much of the work that I do, I do get feedback, which is great. If I write a book, there is feedback, or a blog post or something like that, but it is delayed feedback. For books even, it could be a couple of years between writing it and actually getting it out to the audience so that they hear about it. I mean I signed the contract for “Entrepreneurial You” in late 2015 and here we are 2017 it’s finally launching.

It’s great and people are receiving it well, but it’s hard to compete with the high that comes from the immediate feedback of speaking and seeing people in the audience really liking it and getting it and learning from it. That’s something that’s pretty fun. In terms of my own reinventions, I will say a concept that I developed in the course of writing my first book, “Reinventing You,” is the difference between what I call capital R Reinvention and lower case R reinvention. The capital R Reinvention is these sort of big inflexion points. The kind of things that people talk about and stress out about like, “Oh, I got laid off. I have to reinvention.

Oh, I’m finally deciding after 20 years that I’m going to become photographer like I always wanted to,” or whatever it is. Those are great and fun and important, but they’re also a little traumatic sometimes because they’re big changes. Something that I have become an advocate of is lower case R reinvention, which is making reinvention a habit and a discipline so that you’re constantly pushing yourself in small ways so that when you do in fact decide that you want to reinvent, it’s not quite such a big deal. It’s not quite such a break with the past and you’re able to transition a little bit more seamlessly.

One of the things that I am doing to try to facilitate that in my own life is for instance, I actually got accepted into a programme this year and I deferred it a year because I was going to be busy this fall launching “Entrepreneurial You,” but I’m going to be doing it and taking part of it starting in the fall of 2018. I got accepted into programme that BMI, the music publishing house runs, for musical theatre. It’s a wonderful, wonderful programme that they run and it’s a two year programme that you do part-time, so I mean I’ll be keeping up my regular business, but it trains you to be a musical theatre writer and exposes you to these meetings and interviews with the top minds in Broadway today.

That’s something that I think is really cool and exciting and a new direction that I’ll be pursuing.

Martin: Dorie, thank you so much for joining us on the podcast today. I really appreciate your time. Best of luck with the book and best of luck with this programme, which sounds fascinating. Before you go, how can we connect with you online and find out more about you on the internet and how can we get a hold of a copy of “Entrepreneurial You?”

Dorie: Yeah. Martin, thank you so much. It’s great speaking with you. For folks who’d like to get a copy of “Entrepreneurial You,” it’s available at Amazon, Barnes & Noble, many other smart and savvy booksellers. I’ll also mention as well that for people who are interested in learning more about thinking more entrepreneurially and ways to develop multiple income streams in their own business, I do have a free resource that they can download. It’s the 88 question Entrepreneurial You self-assessment that actually walks you through how to think about your own business and ways to make more money and develop new income streams. Folks can get that for free at my website, dorieclark.com, which is D-O-R-I-E-C-L-A-R-K.com.

Martin: We’ll make sure we put links to the book and to the self-assessment in the show notes for this episode as well, so our listeners can find that. Dorie, thanks for your time.

Dorie: Wonderful. Thanks so much.