66: Create Multiple Streams of Income with Dorie Clark

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What's next? This is a question we're all having to ask and answer more frequently. I'm Jenny Blake, your host of the Pivot Podcast and author of Pivot. The only move that matters is your next one.

For show notes from this episode, visit pivotmethod.com podcast if Change is the only constant, then let's get better at it. Here we go.

Hello everybody. Welcome back to the Pivot Podcast. I am super extra excited today to have one of my best friend tours and friends from New York City back on the podcast. Dorie Clark Dori, welcome to the show.

Jenny Blake, I am so happy to be talking with you. Thanks for having me on to chat about my new book.

Of course. We're completing our podcast trilogy for the Pivot Podcast. Dori and I have done two interviews together so far for my show and even a few for hers, which we'll throw into the show notes. So for those of you who haven't yet listened to a conversation with the amazing Dori Clark, she is a marketing consultant, professional speaker and frequent contributor to the Harvard Business Review. Her first book, which is we joke, it's like Pivot's older Brother, Sister, Cousin is Reinventing you, followed by Standout, which was named the number one leadership book of 2015 by Inc. Magazine. And now we we are celebrating and shepherding into the world Dori's third book, Entrepreneurial Monetize your expertise, create multiple income streams and thrive. Dori has been in business. Dori, has it been 11 years now that you've been self employed?

That is correct, yes.

Way to go. I know you said in your book that you were laid off from your job as a journalist, right when you decided to make that your career and that you vowed never to work for someone else again. Can you take us back to that moment?

Well, I actually did have a few more regular quote unquote jobs after being a journalist, but it began the process. Sometimes it is an iterative process beginning to work for yourself or figure out multiple income streams in your life. And so, yeah, I was a newspaper reporter in Boston and had been doing it for about year, and I got laid off unexpectedly. And it really was unexpected. I mean, now you hear about newspaper reporters getting laid off and it's like, well, duh, what did you expect? But it was 2001, and the newspaper industry was really strong then. People were not getting laid off. The Internet was really just starting to take hold. And so I was completely caught unawares. They gave me, Jenny Blake, four days severance pay. It was technically a week's. It was a week salary they gave me, but I'd already worked one day out of that week. So I got four days pay to go figure out how to support myself. And it really showed me exactly how alarming and sudden these shifts can be. And so it has solidified now, it's been a process of years, but it has solidified my commitment to having a business that has multiple income streams so that no matter what happens, no matter what the market conditions are, no matter if a client leaves or there's some disruption, you have other options and you are going to be okay.

One of the things that I think you do better than just about anyone else I know is positioning yourself as an expert. And I know that that was very intentional on your part that you wrote Reinventing youg partially as a strategy to reinvent yourself from your career as a journalist. And I even took, earlier this year, I took your rapid content creation class. And you say in the book that you've written 120 pieces for HBR and that you wrote 250 articles for Forbes in a span of three and a half years. So I actually, I want to jump kind of straight into tactics for this show because we don't have a ton of time together. Tell us, Dori, what is your secret? How on earth are you writing so many damn articles? It is amazing.

Well, thank you. Partly it's just practice. Since I started as a journalist, we would have a week.

To be writing our articles. But technically, you don't really have a week as a journalist. You have maybe four days out of the work week to gather your information and come up with story ideas, and then you have a day to write your articles. This, of course, is the cycle of a weekly journalist.

And so I became really accustomed to writing three to four thousand words in a day. And fortunately, in writing books and blog posts and things that served me well. But to understand, and this is part of what I teach in the course is that it absolutely is a skill that can be learned by other people. I think so much of the cultural conversation around writing and content creation, there's just way too much preciousness around it. People just work so hard around the edges to make things perfect. And, you know, I'm certainly not saying, oh, put bad things out there, but I think that there's only so much tweaking and fine tuning that you can do. And for most people who are listening to this, for most people who are educated professionals, you can do a perfectly good job quickly. And so I, especially for my Forbes post, for instance, what I would typically do, I tried to kill multiple birds with one stone. And this is kind of the cornerstone of my philosophy that I developed in writing Standout and creating my Recognized expert course about how you become a recognized expert. There's three things, creation, social proof, and network. And when you are writing and creating content, well, it actually hits all of those things simultaneously. Because what I would do for my Forbes pieces, first of all, I would interview someone that would usually take about an hour, let's say half an hour, an hour for me to interview them. The actual to doing that was a form of networking because it gave me access to new people that I could meet. And then I would write up the piece, which of course is content creation. That would be about an hour. Typically, as you are listening to the interview, you just need to be thinking, okay, what are the themes here? What are the key points they're making? If I had to turn this into five bullet points about the most important things that they've said, what are they? If you listen to that conversation, you can actually do the outline in your head in a lot of ways and then be able to just grab. Grab the quotes that you need to do it. And so you can write this piece pretty fast. And then if you are able to work your way up to publishing it in larger and larger publications, that becomes a form of social proof or credibility. So you're really able to build your platform as a recognized expert through doing that.

Yeah, I love the approach of thinking about that line in advance. And I know I can speak for myself that coming up with the concept for the article, or just what I want to say, what the salient points are, if I can do that in advance of sitting down to write it, then writing it is way less of a big deal.

That's exactly right. Yes.

Early on in Entrepreneurial you, you have a chapter called the Courage to Monetize. And it made me smile because for so many entrepreneurs or side hustlers, it is courageous to monetize and to charge for one's services. And you even quote one of our mutual friends, Michael Bungay Stanier, who's on the Pivot podcast, that someone told him your going rate should be fear plus 10%. And I know there are two schools of thought on monetization and starting to charge for one services, or even in an ongoing business, which is start slow and build incrementally, or start low and build incrementally. And then you also interviewed people who say, no, that's actually not the best way to go. Throw out premium prices and then fill in lower tier services later on. So I'm curious, after conducting over 50 interviews for this book and your own personal experience, where do you stand on that? And how do you find the courage to monetize and raise your rates over time?

Yeah, really important question. So I think that the way to answer this is that you have to charge rates commensurate with what your brand dictates. And let me explain what I mean by that. If you were just starting, oftentimes the situation that people find themselves in is that they don't have a lot of experience, they don't have a lot of connections, and so consequently their brand is not that robust. And if you don't have a robust brand, you need to start low because otherwise people are just not going to. They're obviously not going to pay some really high price for someone that they've never heard of or that they've never worked with and doesn't have a lot of credibility in the marketplace. There's not really an alternative. And so the challenge, of course, is that it is hard to raise your rates over time and you almost have to reinvent your customer base because the people who might have hired you at 50 bucks an hour may not be the same ones that are willing to pay 75 bucks an hour or $100 an hour or $500 an hour. So you have to find new clients that are willing to do that. And that can be a challenge, but it's sort of a common and sometimes inevitable part of growing your business. But there is a life hack which some people have used to good effect. And so, for instance, one of the people that I profiled in Entrepreneurial youl is a woman we also know named Selena Su. And she started with premium positioning in the marketplace and was charging pretty high rates early on. But the way that she was able to justify doing that, and this is the key part is that she went nuts. She went overboard on social proof. Early on she had built up credibility by having affiliations and endorsements from recognized experts and celebrities in her field. And because of her connection to them and, and their endorsements of her, she was able to justify high rates in the marketplace. So if you're able to do that, that's a really good workaround. But most people initially are not.

Yeah, she's a great example of someone who had been piloting her services as a side hustle for many years and had gotten results for those high profile people. So it wasn't even just that they wrote her a testimonial out of nowhere saying, oh, Selena is a great person, hire her. They actually had gotten results from years of working with her. And it sounds like she was really strategic early on about working with and offering her services, possibly in the beginning for free to very high profile people.

Exactly. Yes.

Another thing that I found really interesting as a, as a theme in the book is, well, first of all, we've all heard the term passive income, which I think is a myth. I'm curious what you think. I think some income is more passive than others. All of it ties back to a core business engine that's, that's. I don't know, I mean, unless you reach a certain point, you're always going to be feeding this engine somehow. But there's a really interesting conversation throughout the book of passive income versus service based income versus scale, things that can scale. I'm curious, you know, when you made that shift. And actually maybe we can start with you describe a really interesting shift where you for a time you had to start saying no to service based business like speaking at lower rates or even coaching in order to create some of your more scalable products. And it seems like that's this inevitable point or stage in a lot of people's businesses where you have to be willing to sit with that dip of saying no or raising rates in order to buy some time to change and shift the business model. So I would love to hear you talk about and take us to that moment when you decided that trading time for money was not really going to work for you moving forward in the same way.

Yeah, thank you for raising that, Jenny. I think that it is one of the big progressions that we have to make. I mean, literally just this afternoon, just before we got on the call, I got an email message and it was from a woman who ran a career services office at a college and she wanted me to come speak. And there was a particular date, and they had a $2,000 budget. And, you know, she was very sweet. She said, you know, we're not sure if we can afford you, but we wanted to at least ask, you know, could you do this? And, you know, the college is about four or five hours away from where I live. So for me, at this point in my career, the. The answer is a pretty clear no. You know, I'm not going to travel 10 hours round trip for a $2,000 speaking engagement. But, you know, at different stages in your business, you have different answers. And when I was starting out, I couldn't even imagine, oh, my gosh, getting paid $2,000 for a speaking engagement. I mean, I remember well when my monthly salary for an entire month of work was $3,000 before taxes. And so the idea of making that in, you know, an hour, a lunchtime would be astonishing. And so I think in a lot of ways, just the mental transition comes when you feel okay saying no is when you're not sad about the consequences of saying no. People ask like, well, when should I hold firm and when should I bend? And I think the real answer is if it would make you really sad to miss out on this opportunity for some reason, if you held firm on your price.

And you just knew that you would regret it because, oh, my gosh, I would get to speak at this company or I'd get to do such and such, then, okay, then.

You don't have to turn that work down. You can edge your way there. But at a certain point, it really does become clear, and for me, it's very, very clear that $2,000 for a full more than a workday's travel is not a good investment of my time based on the other things that I can do. And so, yeah, in those early days, though, it really is hard. And this is why I am such an advocate of making sure that the first thing that people do is make sure in their business that they are bringing in enough money so that they are not panicked about money. And. And they don't feel this constant press of, oh, my gosh, oh, my gosh, where is this going to come from? Because you need to have the latitude to be able to make smart and strategic decisions. Dollars, if you can't pay your rent is something you could never turn down. But $2,000, if you have margin in your life, then you can actually make a rational analysis about what you could be doing with your time. That's better. And so in entrepreneurial, you. I actually spend a lot of time talking about this process where first you build trust with your audience, which often comes with free content creation like blogging or this podcast, for instance. Then it's going deep. And that often means developing a steady income through a service based business, whether that's coaching or consulting or speaking. You know, things that really do require a lot of your time, a lot of your effort. And then finally it is transitioning to leveraging yourself, leveraging your ideas and scaling them and doing the kind of glamorous, passive income, Internet enabled things that many of us hear about and that I think intrigue a lot of people.

Yeah. On the speaking front, I found it so interesting, this dance that you described that I experience as well, between organizers and speakers where organizers will say, sorry, we just don't have any budget, or we're a nonprofit, we're totally strapped. And then you tell the story of starting from zero and eventually ending up at $5,000 for a keynote that you did simply by asking for it. And it's interesting because there's a lot of common advice that consultants will give to each other, which is ask for their budget first. But I think there's a very interesting budget dance that happens because I have to say I don't usually have success. If I say, what's your budget? Though, that can be a way to tease it out. And so I'm curious for you, do you try to suss out a budget in advance or do you just set your rate? It is what it is and they can decide and negotiate.

If I don't have any information from them, if they've just said, hey, are you available on blah blah blah date? Then I will often write back and say, yes, so far I am available on this date. Can you tell? And I'll ask a whole raft of questions. So what exactly is the event? Who are the attendees? Is there a focus to it? How many people will be there? What is your speaker budget? So I'll ask that as part of it. Now, sometimes they'll just answer you. They want to be sort of straight up and transparent. And if so, that's great because then you can very easily evaluate whether it's going to be workable or not. Other times they will give a sort of dodgy answer, oh, you know, we're still figuring it out. Or you know, blah blah blah, and it's. And that's fine if they. But the reason it's fine is that I have been speaking enough that I have a very good sense, I think, of market rates. And I do feel in stating my rate that it doesn't vary wildly from one client to another. It is a standard rate. And so if they are able to pay, great. If not, I actually don't want the conversation to drag out, because if I'm looking for 15 or $20,000 or whatever it is and they're paying 2,000.

You'Re not going to really be able to. Able to bridge that. And so it's better for me very quickly to pivot to saying, oh, well, maybe there's some other people that I could recommend for you, and at least in that way, you're able to be helpful to them and to perhaps continue the connection in some other way.

Yeah, I do the same thing. And then that speaks to the concept of drafting that I talk about in Pivot, where then it's great if you can help speakers who are at maybe earning a lesser tier, and this goes for any kind of services. But if you can get on each other's radar, there can be a whole network of people that passes the word along so that the organization gets someone that they're looking for, and we can recommend speakers at that level. One thing I found interesting is saying no and choosing what not to do in your business. So you also started a podcast at one point and kind of told the story of what happened. I'm curious to hear about your mindset for choosing what not to do in your business, even if it's something that it's seems like, quote, everyone else is doing, like a podcast. I know you have a ton of friends who have podcasts and probably even many readers who are asking you to do something like that. So how do you decide what makes the cut in your business portfolio?

Yeah, that's a great question. And yes, I did in kind of the early Vanguard in like 2008, 2009 experiment with starting a podcast. But I didn't keep it up. I was not persistent like you were, Jenny Blake. And so I treated it as just kind of something to play with, but I didn't really focus on growing it. And so as podcasting got to be more of a thing in the last couple of years, you're right. I have tons of friends that have podcasts. I have been encouraged by many people to start a podcast, and I love podcasts. I listen to them all the time. I think they're great. But I do not have one of my own, and I'm not planning to create one, certainly at least for the next year and possibly beyond. And part of the reason for that is that I do try to be very focused on what my goals are, because.

I actually do an online course about this as well, called Be More Productive. And one of the central tenets that I talk about in there and I've written about for the Harvard Business Review is the fact that I believe that you really can't pursue more than two large scale goals at a time. I think anything more than that.

You just end up confusing yourself and you falter. For any given six month period, I will only have two areas of focus, and frankly, sometimes not even that. For this six month period that we're in right now, my entire professional focus is around launching my book. That doesn't mean that I'm not doing other things. I mean, yes, I'm answering email because one needs to as an ongoing administrative responsibility, but in terms of where all of my effort is driving in the things that are focused, it's about the book. And the reason is that the book is a central organizing principle that I believe download will make more opportunities possible for me. And so if I am trying to get the book into as many people's hands as possible, sell as many copies as possible, it is better for me in this moment to be on a lot of other people's podcasts than it is to invest the time and space and the startup of trying to gain traction for my own podcast. So it was really just a focus prioritization.

Yeah, it makes a lot of sense. And those things all add up, all these different streams of income. I'm curious, after interviewing over 50 people, including at least a handful, if not more, who are earning six figures a month with their businesses, what surprised you most or what was the most interesting lesson that you learned from those interviews that you might not have known previously about running your own entrepreneurial, you type business?

Well, one of the biggest learnings for me, I mean, I actually came into writing this book with a very specific goal, which is that I had been thinking for a while, kind of incubating the concept of wanting to create an online course. This was something that was intriguing to me. I started experiencing, experimenting with it in 2014 when I did a Creative Live course and stuck my toe in the water. In 2015, I did another online course, the Economist. I got to see different models for how people did it and I thought, you know what, I want to do this myself. And so I realized that writing the book, I mean, again, it's thinking about upstream and downstream activities. And I realized that prior to developing the online course, I needed to research it, I needed to, to understand how the process could work well, and so I thought, well, if I'm going to be doing a bunch of informational interviews and trying to get really interesting open discussion about literally how people make money, how this works, what is a good way to do that? And I thought, okay, I can organize that under the rubric of book research.

My plan. In the first few months of 2016, I did more than 50 interviews with top entrepreneurs, entrepreneurs about their money making strategies for entrepreneurial you. And online course creation was of course a big focus of that. Although I talked about maybe, I don't know, close to 10 different income streams. Taking the knowledge from that. In later 2016, I launched my own online course and was able, over the course of the year, over the course of, you know, literally just applying the things that I had learned from researching this book, I was able in 2016 to earn an additional nearly $200,000 that year as a result of applying it. Yeah, so it was really fantastic for me. I wanted to prove for myself that these techniques really could work. I wanted to make my own business the laboratory for it and then share that with other people because I think that oftentimes you, lots of people leave it as sort of the lofty or the inspirational. Oh, you can do it too. But I wanted a nitty gritty book about really, literally what is the roadmap. And so I had very detailed conversations to provide people with plans about how to do it. And so for instance, in entrepreneurial you, I actually have resources that I make available to readers where they can do things. Like if they are interested in an exact script that I used for the pilot version of my online course, people can get it. They go to doryclark.com pilot email, they can download that and see the script themselves. Because I wanted to make everything really transparent. For me, that was the biggest learning, was just literally breaking down the process.

I love it. It just makes my tactical heart sing that you've had such a focus. And it's true, you put throughout the book very specific examples that people can check. So as we start to wrap up, I'm curious to know, on the subject of really tactical advice, if you could tell people to, quote, put down the podcast or you know, kind of whenever they stop listening and go do three things, let's say, whether they're side hustler or solopreneur, what would those three things be?

All right, so people are looking for specific plans, things that they can can do. Now when it comes to the entrepreneurial journey, the first thing that I'll mention, actually I created Another free resource that I think that folks might enjoy. It's called the entrepreneurial you self assessment. And it is 88 questions that people can go through to systematically think about how they can start to create multiple income streams in their own life. And so if they'd like to download that for free, they can get it@doryclark.com entrepreneur. So that would be number one. The second thing that I would mention as an idea that I actually thought was really pretty cool. One of the folks that I interviewed for the book, this is somebody that we also know in common is a guy named Michael Parrish. Dudel. And Michael had an interesting philosophy that I think in his case, he was pretty extreme. But I think that the principle behind it is a smart one. When he was thinking about launching an entrepreneurial venture, he knew that he was good at his craft. He knew that he was good at.

Marketing and creating things, but he had never sold anything before. He realized that if you're going to be an entrepreneur, you need to know how to sell. He gave himself a deadline. He said, you know what? If I can't close a client in a month, then I'm just not going to do this. I'm going to go get a job because an entrepreneur has to sell, and I need to force myself to do it.

I loved that one.

Yeah, thank you. And I thought it was great, too, because it's not that you have to close $100,000 account, but if you are interested in starting, the answer is to start, give yourself a deadline. Maybe it's just, can I get one person to pay me 50 bucks for a strategy session? You know, it doesn't have to be huge amounts of money, but if you can get proof of concept, if you can actually get someone to pay you for something that you do, then that is really valuable information. So that would be the second thing that I would suggest. And if I was giving a third one, then I would actually turn to an example of a woman that I profiled in Entrepreneurial U. Named Stephanie o'. Connell. And this from that, for me, was really one of the most inspiring stories. Because a question I get all the time is, in entrepreneurship, there's so many ups and downs. How do you keep yourself motivated when you're having a tough time, when you're not feeling like you're getting traction, what do you do? Stephanie was such a great example. She is a millennial personal finance expert. And starting out, she was not getting a lot of traction early on, but she became really smart about using what I call intermediate metrics to track her progress. And so for a lot of people, they start at zero, but then if they don't get the big hit like oh, I have to be on the Today show or I have to have a best selling book, then they feel like they're failing. But the truth is it's going to take years to get to that. So focus on the right intermediate metrics. And so for Stephanie, it was things like, okay, she started out blogging for free. So the first time someone offered to pay her to write a blog post, she was ecstatic because even though it was only $25, it showed people value her work enough to pay her. We have to notice and celebrate those things. When an influencer that you respect retweets your post, you have to celebrate that when for the first time someone comes to you and says, hey, can I hire you? Hey, will you speak at this? Hey, will you write for us? As opposed to you always having to knock on their door, that is something to celebrate. And if we can see those moments, milestones and celebrate them, it becomes extremely powerful.

I love it. So well said. And you say in the book, the world needs your ideas and you need to be paid for them. And that is truly the way to have a sustainable business. That courage to monetize, the courage to celebrate incremental metrics along the way. Dorie, thank you so so much for being here again to wrap up our podcast trilogy. Who knows, maybe we'll become like Game of Thrones and just go on for like six, seven, eight, eight rounds or seasons.

That is perfect.

I'll be your step podcast. Maybe you won't have your own, but you'll come on Pivot Podcast regularly as our business book doppelganger show.

Amazing. Anytime.

Anytime. Well, we'll put all those great resources in the show notes and for everyone, make sure to check out Entrepreneurial youl Dory's latest book. It is awesome. I zoo through it and you can get more of Dorie's great resources and keep in touch with her@doryclark.com thanks again DC. You're the best.

Thanks Jenny Blake, back at ya.

Thanks so much for listening to this episode of the Pivot Podcast. Make sure you don't miss an episode or my insider tips and templates by signing up for Pivot List, a curated twice monthly newsletter where I share the inside scoop on what I'm reading, watching, listening to and the latest tools I'm geeking out on. Sign up@pivotmethod.com pivotlist get show notes from this episode@pivotmethod.com podcast and connect with me on Twitter ennyblake.

Remember, build first, then your courage will follow. Hasn't it always.