Solopreneur vs Entrepreneur: Which Path Fits Your Life?

We're live. This is super exciting. We get to be here with Scott Perry again. Thank you so much, everyone who's already hopping in. So good to be back with Scott. Today we are super stoked to be talking about his new book, Intrepid, which just launched March 20th. So everyone can buy a copy now. There it is. That's awesome. So, yeah, Intrepid asks one question 27 different ways. Do You Care Enough to Commit? It's a short, pointed handbook for purpose-driven people who know they're capable of more and keep getting in their own way. And I'm just super excited to kind of pick your brain, Scott Perry. It was already an incredible read. I got to read it while I listened to it. It was only an hour, but it totally changed my mindset and encouraged me that it's actually feasible to make the difference that we want to make. So thank you so much for sharing that. And do you want to like kind of give a quick overview of where this book came from?

Oh, sure. Well, first of all, Jilan, it's always great to hang out with you and always pick up a lot of insights and inspiration from our chats. I love what you are doing over at, I guess you call it OBA. I've been saying OBA, but OBA is so much easier. And I love Just One Brilliant Arc is such a great name, such a great brand, because I think of arc always in terms of, um, like the, the Martin Luther King quote about justice, but the arc of history bending towards justice, and the arc of the hero's journey. Like, it's such a great— 3, 3, 3 letters that are so evocative. Um, thank you. Intrepid. Is, uh, so the origin story of Intrepid is that I have written several very short hand— what I call handbooks, about 100 pages more or less. Some of them much shorter, a few of them just a little bit longer. But there's two, uh, the first is called Endeavor and the second is called Onward. And I always imagined that Endeavor and Onward were part of a trilogy. I just never figured out exactly what the third book was going to be. And during the winter months, my wife and I are full-time daycare for our two grandsons. They are 8 months and 4 years old. Uh, and so fun times. Yeah, 9 days a— not 9, I'm sorry, 9 hours a day, 5 days a week. We are totally on duty. So I've engineered my business to fit around that lifestyle. But we had, uh, 2 weeks of no school because of snow days. My daughter-in-law is a schoolteacher, so she had the boys for 2 weeks. And after the second day, I was like, what am I going to do with all this time on my hands? And I literally wrote the book in about 14 days. Uh, I came— I, you know, intrepid is a word that I've always kind of been infatuated with. It's a word that people, like, know, but they don't always know exactly what it means. And I was just through a convergence of conversations I had with the Circle community at Creative On Purpose, you know, where we explore the art, where the art of living and work that matters kind of collide. I just, it came to me, like, do you care enough to commit? That was a coaching question that was coming up over and over and over again. And so, like I always do, I came up with a title. I knew what the title was going to be. I didn't— and then pretty soon the subtitle came, and then the tagline, "Do you care enough to commit?" came. And then all I had to do was come up with 27 questions that provoked people to answer for themselves whether or not they cared enough to commit to the difference they can make. And so I wrote it in 14 days, and people always say, oh, how can you write a book in 14 days? To which I say, I've never written a book in under or in over 90 days. I've written a couple in under 30 days. Every single book I've written is not— I always tell people, I don't write a book in 30, 60, 90 days. I write a book for 62 years, and then I sit down and type it for 30 days.

Yes, that's what I was going to say. It sounds like all of this comes from a depth of experience that you've lived. You've lived all of this information and learned everything the hard way. So it's in you, it's under your skin. You just have to, like you said, type it. That's so neat. Here at One Brilliant Arc, we often talk about how creatives have to use their voices to tell their stories because storytelling can change the world. We talked about that in our last live. And we help them specifically at the craft stage. So like when they are trying to find their voice and type their story into a product that is resonant and powerful. But you kind of speak to the next step that is just as essential, but you know, as creatives, kind of, it's a lot less fun for us, but that's marketing and building a business that, you know, telling your story is one thing, but it can't do the good that it is, you know, capable of doing unless it's actually being shared, getting out there. And so you're speaking to that with Intrepid. Um, and you know, speaking of what's in the name, I'd love to hear, uh, what Intrepid does mean to you and why you chose this word for this book besides just being intrigued by it.

Yeah, well, it's, um, there's, there's, uh, an old ancient saying from, uh, the Greeks. I can't remember the exact source, but it The saying is fortune favors the bold, and sometimes it's phrased as fortune favors the brave. And people often talk to me about how they perceive me as someone that is brave or courageous. And I've— while I love that I'm fooling everybody and that I come across that way, Everything I do, I do very strategically. And, you know, what, what people end up seeing is the last step in a long series of microsteps. Intrepid often is, is thought of as being courageous, almost more like reckless, like people you know, just running, you know, charging into the, the lines, or, you know, charging toward the machine gun nest in World War II or whatever. And, um, and intrepid actually means something closer to resolute, meaning not, not that you are fearless, but that you acknowledge and accept fear and you persevere whatever is in— whatever matters to you, regardless of the fear, like in spite of the fear or with the fear. So that's kind of the way that I think about, you know, because like anybody, like I'm sure everybody that's tuning in to a broadcast that you're hosting is either an advancing creative person or aspiring to become a more creative person. And one of the conversations we have to have with ourselves at the beginning is with fear. Like, that's one of the fundamental things that we're always trying to navigate. And it's not so much fear, like, it's all triggered by the amygdala and our kind of prehistoric brain and our fight, flight, or freeze response. But since we are now the dominant species on the planet that's pretty much able to do whatever we want with without much fear of reprisal other than Mother Earth letting us know that she's very happy with us, uh, and, and, you know, probably the quote-unquote lesser creatures will have their way with the world again soon. Um, we don't, you know, we don't have to beware of saber-toothed tigers in the underbrush anymore. Um, and so fear takes this more insidious, nuanced, unconscious, subconscious form around writer's block, or what Steven Pressfield calls resistance, or anxiety, or fear of failure, or what have you. And so, uh, what I have found is really effective is taking very small steps into possibility every single day. The steps that require no real risk. Like, I'm not— if I commit to, like, committing to writing a book, if you have never written a book, is going to be a scary endeavor. If you are committed to writing a blog post or a couple of blog posts, that's less scary, uh, but it can still be intimidating. If you commit to a writing practice where you're going to sit down for 3 hours a day You'll talk yourself out of that over time. Resistance will rear its head. But you know what? What if you just committed to sitting down and writing for a minute every morning before you did anything else? Like, you will establish a practice of sitting down to write. The hardest thing about sitting down to write is sitting down. So what if you just sit down for a minute and write regardless of whether inspiration or motivation has come? Because the chances that you'll continue to write for more than a minute is much higher than if you never sit down at all. And then, you know, that's for me the kind of thing that I was solving for myself, is I want to help other people, uh, and the best way I know how— like, the ways that I know how to help people are the ways that I've helped myself. So I'm just going to go through and clarify these fundamental issues that have to be navigated around clarity and around continuance and so forth. And then I'm going to share them in the most easily embraced and digestible ways possible so that people can take intentional action and start to step into possibility and their potential as creative people. I'm not sure I answered your question, but that was a lot of words.

That's so beautiful though. I love that mission that you have. And you're right, it's it's those small steps. Um, talking about like something that resonated with me when I read Intrepid was that picture of, and that validation that it is a commitment for the long haul if you want to build something that matters. Um, you know, being a creative myself first and then now as a job helping other creatives to build their things, whether they're books or movies or you know, documentaries or brands like author businesses, um, there's— and then also building a business that's helping those people, that entrepreneurship, you know, there's that really difficult commitment. Like, Intrepid does speak to— you have to be resolute in the difference that you are trying to make. And I really appreciated how in this handbook you talked us through the questions that help us to make that commitment, to stick to it for the long haul. Because if you give up, then think of the difference that you could have made, but now you're not. I am curious for everyone listening, if you want to put in the comments what medium of creativity you are working with. I'm really curious what the demographic is for people tuning in, whether you're— a lot of creatives are multifaceted, but whether you're working on writing a book or whether you're working on writing a film or whether you're building a business. Um, but that kind of, you know, building something that is, uh, you know, bigger than just you. Uh, what happens when creatives start with a vision and good intentions but they don't spend time on what we would call the technical boring stuff? Like building a business strategy, planning for a long-term gameplay, and being realistic about what it takes to build a business or a movement.

Well, I love that you use the word movement. I think that all of the best brands actually, whether they're solopreneur brands like a lot of the folks that I see in the chat here, Jeff Smith, who has a wonderful Substack around teaching, and Claire Machado, who has a great kind of health hacking, uh, Substack. You know, as, as independent creators, it is important that we establish a vision, of course, like, and I would suggest that the vision should be more around lifestyle than the work itself. Because work, whether that work is a business, a solopreneur business, an entrepreneurial business, or a business that you work for, you know, somebody else's business that you work for, work is just a way that we build identity and forge meaning. You know, we do, for better or worse, often attach some of our identity to what we do for a living. For solopreneurs, I think the really important thing is if you're going to go through the effort and the heartbreak of creating your own business, it should— the goal should be to fund and fit the life that you want to be living. And it's easy to get caught up in the excitement of, I'm just, you know, I want to do my thing. And then at some point you hit what Seth Godin calls the dip, and we address this in the book. Um, you know, it's going to get hard, and then it comes down to, are you going to persevere or are you going to quit? Well, if you quit after 2 years of trying just because it's not as easy as you thought it would be. That's— you just wasted 2 years of your life. Uh, you may have learned a lot of lessons, you may have got some clarity, you may have pivoted or what have you, but if you are clear about where— what you're aiming for in terms of lifestyle, if you're clear about the person that you want to become, and if you are clear about who you are what you do or want to do and where you belong. It doesn't have to be absolute clarity about who you are, what you do, and where you belong. It just has to be clear enough for now. It's much easier to, again, take those microsteps and run some experiments. Like, before I wrote Intrepid, even though I've got a great audience, I've had people, you know, Onward and Endeavor were both Amazon bestsellers. They continue to sell copies every single month. I always joke that, you know, my book sales allow me to take my wife out to dinner every month. Sometimes it's McDonald's, sometimes it's a white table, you know, white tablecloth restaurant. But, you know, that's kind of, you know, I'm not going to retire on my book income, but, you know, I do have a small, what Seth Godin calls, I have the smallest viable audience. They do want to hear from me. But even still, before I wrote Intrepid, I wrote, I shared a title, a subtitle, and a promise. And I went to the people that already know, like, and trust me and said, I'm thinking about writing this. It will, it will help people like you achieve this transformation, this outcome, get this result. Are you interested? And after 10+ people raised their hand, I actually had 15 people that signed on to be the first to receive the book with a promise to not just write a blurb for the book, which I put in the foreword, but to also promote the book. Like, now I validated my idea, I validated my audience. Now all I have to do is write the book. And again, if you're speaking from your experience and you have some clarity about who you are, what you do, and where you belong, it's easier to do that in a shorter time frame. Uh, and so that's, you know, that's how that all happened for me. And I, I think it's the same approach I talk to anybody who's thinking about writing a book. Like, when— so I get a lot of clients that say, I have to write a book. It's like, okay, why? Well, because a guru told me I had to write a book. I have to have IP. I have to create content. I have, I have to be able to say that it's a New York Times bestseller and a Washington Post bestseller. And there's this company that will let me buy a bestseller, you know, and it's like, okay, well, that's, you know, that is a way that you can build some authority with strangers, maybe. I mean, I think most people understand that the New York Times bestseller list is a joke and that it's all bought and paid for. You know, what if before you wrote a book, you thought you wrote a blog post and see if 10 people are interested in what you want to talk about? What if you, before you even wrote a blog post, you talked to 10 friends and said, I've got this idea that I want to start to unpack. If I, you know, I thought of you when I was thinking about this, would you be interested in reading seeing my outline or seeing my thesis or my premise or whatever. Like, that's— those are all things that are doable. My very first book, basically, I took— I wrote 100 blog posts over the course of a year. 30 of them went into chapters that became a book called The Stoic Creative. My first book was literally written blog to book, and most of the blog posts I used text or voice-to-text to write them. So very low impact on my time and attention, very low resistance, you know, because you might have writer's block, but nobody has speaker's block. I've never met anybody that can't open their mouth and have words tumble out. So it was all very, you know, became easier. It happened faster and it just gave me something that I could put out into the world when it was good enough and iterate and edit and refine and improve over time. And it can— now I have an asset, um, that I can share for the rest of time, uh, and, and repurpose and, and, and so forth. So, uh, that's my take on, on all that.

Yeah, it's so much more powerful. Like, you know, having a guru tell you that you have to write a book for authority, like kind of to buy authority, it's not going to work if you're not writing a story that connects with real humans. If you're just with polished prose and saying things that everyone else has said before, just because you think that product, the book itself, will buy authority, but you're not actually saying something that resonates with real humans, then you're not doing anything for yourself and you're not doing anything for anyone else either. I do want to take a quick detour because Jeff Smith wanted to ask your opinion about solopreneurs acting as entrepreneurs. And I do want to prioritize, he did say if you have time, but I do want to prioritize the questions that the audience who are tuning in has. And I think that this is a really interesting thing because they're almost the same, but they're different. What's your take on that?

Yeah, they are very different. When we talk about solopreneurship, and thank you, Jeff, for the question. So Jeff, just to be transparent, is a client and a member of the Circle community, which is why he's familiar with my rant about this. Most people that I would put in a solopreneur category like to think of themselves as entrepreneurs because it's a sexy aspiration. It's, you know, entrepreneurs are bold, entrepreneurs are creative, entrepreneurs have lots of energy, lots of entrepreneurs create things that are bigger than themselves. Like, it all sounds good. Um, most of the people that I talk to and work with that call themselves entrepreneurs do not have, do not have angel funding. Like, they don't. They are playing with their own bank account, which is usually not very big in terms of the amount of discretionary income they have to start a business. They have the same 24 hours in a day that we all have, and most of them have a day job and other obligations. So they can't leverage the collective momentum of having a big staff of specialists with, you know, who are writers or content creators or social media ad strategists or fulfillment strategists or customer service, you know, representatives or what have you. And most of the people that I talk to that call themselves solopreneurs entrepreneurs but are in fact solopreneurs look at the entrepreneurs on social media and on Substack and say, oh, I have to be everywhere all the time, all at once, in order to get reach, in order to grow my list, in order to growth hack. And your end— and, and so what ends up happening is solopreneurs end up spending 80 to 90% of their time doing things that they never really wanted to do, creating content for platforms that don't care a lick about them, trying to perform for an algorithm that nobody really truly understands and does not love you because you're not doing what it wants you to do, uh, spending time just cranking out offers and cranking out products because they think that's what entrepreneurs do. And I would say no. Like, if you are an entrepreneur, you're tapped into the municipal water system of resources. You have a huge reservoir of time, attention, money, and effort because you're leveraging venture capital and you're leveraging the power of collective momentum through partnerships and employees. If you're a solopreneur, you're tapped into a rain barrel. That isn't always full to begin with, and your— the hose that you're starting with is old and knotted and holey and kinky, and it doesn't really flow very well to water the garden of your aspirations. Like, entrepreneurs can just keep dumping resources on the, on the garden. They water the weeds most, and they still bear enough fruit to make it profitable or worthwhile. A solopreneur, when they're watering the weeds, they are choking the very thing that they want to grow. So I think it's important to— like, I'm not big on— like, I think there's also an identity trap that comes with, like, I'm a solopreneur, or I'm an entrepreneur, I'm an artist, or whatever. It's like, yeah, That's part of, like, you're not just what you do, you're actually how you show up in everything that you do. Like, I'm a husband, I'm a father, I'm a grandfather, I am a music teacher, I am a writer, I am a corner man to other aspiring creatives and solopreneurs. I am all these things, and I do all of those things that in a single day. But fundamentally, I'm just showing up as the best Scott Perry I can be, with the goal of engaging with the, the work and the relationships right in front of me to become a better version of Scott Perry, so I can even— so I can help you get what— closer to what you want, while I pursue becoming who I want to become through the work that I do. And so If you are a solopreneur, I think if you start with, who am I really? What am I good at? What are my core beliefs and guiding principles? What are my talents and skills? And where are the people who share my values and need my skills in order to enhance their lives? Then you can just show up and do your thing within, for the people that are around, you know, share what you have when you can. And you're going to be fine because what you're ultimately doing is improving in the areas that matter to you. And you are earning a reputation with other people. Like, you know, the other fundamental flaw in entrepreneurial versus solopreneur thinking is people think that they are their brand. And that they can create a brand and make everybody believe that this is, you know, this is my brand. This is who I am. And your brand is not your logo. And your brand is not even who you think you are or what you think you do. Your brand is what other people think you are and what other people think you do. And so it's not necessarily two separate things. They can intersect and align. But it really helps if you start with the clarity. And we talked about this at the beginning, like, if you are clear about who you really are, what you're really good at, and where you really belong, and you show up with what you have and do what you can for the people who already are listening, you'll be fine because your people will find you and they will tell the others. If you're going to go the entrepreneurial route, you're going to spend a lot of time doing a lot of things that you don't want to do, and it still doesn't matter because everybody is making their own decisions about who you are and what you do. And it probably does not line up with who you really think you are and what you're actually trying to accomplish because you're not doing enough of that work. You're doing too much promotion, content generation, algorithm dancing, you know, posturing and posing on social media and so forth. Yeah, I hope that answers your question, Jeff.

I'm so grateful that we got to hear this rant as well because that really resonated with me that, you know, I always just thought of it as entrepreneurs are people who don't have to go through this, you know, the scary thing of building a business on their own because they have a team. But you're right, there's a fast difference in resources and outcome that, you know, for me, even though we have a team of people at One Brilliant Arc, it's, it's very much in the solopreneur camp with what we're working with and how it's going. Um, and just having that validation of like, you know, even though you feel like you have less leverage, you're still doing better work. And so the work that is, you know, fruit that is growing is more effective at connecting with people more genuinely because you're telling your real story, you're being authentic, and you're not, like you said, posing and performing for an algorithm that doesn't love you back. And that doesn't have— you know, it's an algorithm, it's not a real human. You're connecting with a computer program, you're not connecting with a real human. Um, so yeah, I really appreciate that. And, you know, Lynette also mentioned, you know, another version of creativity is cooking. Uh, she does cooking and writing, and I also agree with her, much better than the other Scott Perry here, dude.

So, uh, I, I will comment on that really quickly because I think the other Scott Perry she's talking about is the congressperson from Pennsylvania. I have family in Dillsburg, Pennsylvania. We go there every year for the— they're in October for their harvest festival and, and the, the parade, and at the end of the parade is always the politicians, followed by Santa Claus, which is really disturbing.

Yeah.

And, uh, the— when he first came, uh, became a congressperson, uh, I owned the name Scott Perry on Google. If you Google Scott Perry, I showed up. And then he came on the scene and we would compete. And the first year that he was a congressperson and walk, or maybe it was even as he was trying to become, get elected, he was walking at the back of this parade and I literally ran up to him and I said, Scott Perry, I'm Scott Perry. And he said, you.

Oh, that's what we love to do when we become solopreneurs. That's when you know you've made it.

Well, I will say that. That the other Scott Perry is definitely winning the Google war these days, doing things that I hope he, you know, is proud of. I certainly wouldn't be. But yeah, again, don't get stuck in the identity trap. I'm not pretty— I'm not too hung up on, on what the other Scott Perrys in the world are doing. I think there's also the coach for the New York Knicks was Scott Perry, or maybe still is Scott Perry. So that, that, that I don't mind getting confused with, although I can't play basketball.

Well, I appreciate so much your time here. I know that we said we were only going to do 20 minutes, but every time we get together, I feel like there's just so much good stuff to talk about. So I appreciate you giving so much of your time here and everyone who's tuning in. I do want to wrap up with, if someone finishes this conversation and wants to take one honest next step forward, even if it's a small step, what would you suggest?

Uh, well, I mean, the, the book is available. If you purchase the paperback, uh, you'll get the ebook and the audiobook. Uh, there's a link in the book that will get you those things instantly. You can consume it in whatever way is easiest for you. But, you know, the fundamental question that it's asking 27 different ways is, do you care enough to commit? And I would just, if you want to take one small step into possibility and also make sure that you don't waste a lot of time and invest a lot of sunk cost into something that prevent you from the opportunity to do other things, check in with yourself. You know, is, is this difference that I want to make or this difference that I want to explore something that I'm willing to commit to and, you know, create a, a small, measurable, achievable, relevant, time-bound goal to validate that idea or to determine what's the difference that only I can make in the world. And, you know, do that first because you'll not only get clearer about closer to what you actually want in life, but you'll also find yourself at a much better starting point. You'll know who you are. You know what you're good at. You know where you belong. And then it's just a matter of strategic steps into possibility every single day. And they compound very quickly over time.

That's awesome. And we will put the link to the book that you can buy in the description of this recording once it posts. So definitely go check it out. Again, it was only an hour of my time. And it changed my mindset. And I really think that this handbook should be required reading for every purpose-driven creative because it really gives you the tools to realistically make the difference that you want to make, um, and not just be spinning your wheels in the mud, even though it feels like that often. And this book was also very instrumental in making me feel validated and encouraged when, you know, that's, that's your reality that you're looking at.

Thank you so much.

Thank you. And thank you everyone who tuned in. It was so great to have this conversation with all of you and to share this time, share this movement. And we're looking forward to all the creativity that comes next and hearing what you all are building with your purpose. So thank you again, Scott Perry, and we will talk again soon.

All right. Thank you, Jelam.

Bye, everyone.