Personal Productivity & The Future of Digital Publishing with Chris Guillebeau

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Tara:  How do you balance the pursuit of art and ideas with the pursuit of profit?  That’s the fundamental question we tackle on Profit. Power. Pursuit.  I’m Tara Gentile, your host, and together with CreativeLive, we explore the unique strategies that creative entrepreneurs use to take control of their lives, profit from their passion, and pursue greatness.

Today, I sit down with Chris Guillebeau, the New York Times bestselling author of the $100 startup.  An accomplished travel hacker, he has visited every country in the world 193 in total, before his 35th birthday.  Every summer in Portland, Oregon, he hosts the World Domination Summit, a gathering of remarkable, creative people.  Chris and I talk about how he still manages to do a lot of the work in his business, what systems he has in place to make sure everything gets done, and the key way he sees online publishing changing.

Chris Guillebeau, welcome to Profit. Power. Pursuit. Thank you so much for joining me.

Chris:  Awesome. Thank you so much for having me, Tara.

Tara:  Absolutely.  So let’s just get started by kind of talking about what all the different moving pieces to your business are.  You’ve got … You’ve always got a lot going on, so I’d love for you to just kind of explain to everyone what are all the different ways that your business or businesses are generating revenue right now.

Chris:  I do always have a lot going on for better or for worse.  I don’t know if that’s a good thing.  I can’t always keep track of it myself, but I would say maybe first and foremost, I’m an author, I write books, and I actually like the process of writing books.  I like everything associated with the publishing process and going on tour, seeing the books translated around the world, so that’s probably my main business.  It’s not something that I do to accomplish, you know, something else, but then maybe for the past 10 years or so, I’ve also produced a number of products.  I’ve done digital products, I’ve done eBooks and courses.  I have a business called unconventional guides that I operated for a while.  It’s still around, although I’m kind of phasing out of it.  I have a membership site called Travel Hacking Cartel, and I also do a lot of different events.  And there’s probably some other stuff in there, too.

Tara:  Yeah.  How about speaking?

Chris:  I do speak.  It’s not really a revenue model for me.  It’s more something that I do to kind of connect with readers, and you know, just to be out and about around the world.  But once in a while.

Tara:  Got ya.  Nice.  So you’re in Jakarta right now, and I think a lot of people know that you do a lot of traveling, and one of our listeners asked me specifically, you know, she just really wanted to know how people like you manage their time, and so I was trying to think about, like, how do I ask Chris Guillebeau how he manages his time when there is probably not a typical day in your life.  So instead, I’d love to know what are some of the systems that you have in place to make sure that everything gets done?

Chris:  You know, the greatest system that I have is that I love my work.  Like, I absolutely love what I do, and I feel very fortunate that I have the ability to write books and to publish the blog and connect with people, and so I’m very motivated by that.  Like it’s what I want to do.  If I won the Powerball, I’m pretty sure that tomorrow, I’d be doing exactly the same thing, and so that helps a lot.  I mean, when I say that’s the greatest system, it really helps a lot, because I get up in the morning, and I’m like let’s get to work.  Let’s do fun stuff, and yeah, I’m on the road all the time.  I’m traveling.  So I like to take time to see the cities and, you know, go on walking tours and have different experiences and discoveries, but then I’m also eager to kind of get back and do my stuff.  So you know, I always have my laptop with me.  I’m always kind of working on the next thing.  I’m a big list person.  You know, I love kind of writing things down and checking them off, and I always carry a notebook with me where I’m outlining stuff and planning ideas.  And so I get behind on things, it’s because I have too much going on, but I’m really motivated to keep going.  So that’s really the greatest system.

Tara:  Nice.  Is there any software systems that you use to kind of manage your day or manage your to-do list?

Chris:  Sure, sure.  Yeah.  I mean, I use Omnifocus.  That’s my number one, like, task, you know, program.  I don’t think it really matters which one you use as long as you have something that works for you, but that’s what I do, and then I have a lot of stuff in Evernote as well, which is great, because as most of the listeners probably know, you can access data from all kinds of different locations and devices, and it becomes more helpful the more you use it, so there’s that, and there’s some other stuff, but it’s all kind of cobbled together.  There’s no, like, one master system.

Tara:  Perfect.  So I’m sure, I know, actually, that another system you have is a team around you in your various ventures, and I’m privileged to be friends with a couple of people that are on your team.  So can you tell us a little bit more about what that team looks like and how they’re organized?

Chris:  Yes.  I should say, I am kind of a classic solopreneur.  You know, I was always doing my own stuff for a while, and I like working independently, so I don’t have like a huge team.  I have one employee, one full-time assistant, and she’s wonderful.  She’s been with me for a year now, but you know, for all the time before that, I was kind of doing a lot of stuff myself.  For the events that we do, we definitely have a team.  That’s not something I can do on my own, so I’m really grateful for them, but a lot of them are volunteers, some of them get a stipend, but maybe there’s 10 of those people.  We all work virtually, and then when I’m home in Portland, Oregon, most of them are based in Portland as well, and so we do have regular meetings either every other week, or once an event is approaching, every week, but everybody kind of does their own stuff, and everybody manages themselves for the most part, which is great, because I’m not a good manager.

Tara:  Yeah, that’s excellent.  I love the sense of independence that they each have, and I think it brings kind of a sense of creativity to your team as well.  I can see that, you know, in the different events that you do and just the way they talk about the ownership that they have over the work that they do with you.

Chris:  That’s good.  No, I’m glad to hear you say that.  I think it can be frustrating for some people.  That kind of work style doesn’t work for everyone, so it’s really important to get the right people, you know, in place for that, but for me, I think it’s a tremendously valuable skill whether you want to be an entrepreneur, whether you want to think entrepreneurially in another career working for someone else or working for a company.  It’s an extremely valuable skill to be able to kind of figure stuff out, basically, and to have a project or to have a responsibility, but not necessarily be given, like, here are the steps, you know, one through eight that you have to follow.  And so if you can find people like that, there’s just so much value there. 

Tara:  Yeah.  I think that’s a great point for everyone, because team-building is also a huge thing that our listeners are really interested in figuring out and finding out what’s working for people, and so I hear you saying essentially that you need to put together the team that’s going to work for you, and that that doesn’t mean that it has to look like a conventional job, or that it has to look like a conventional employee relationship, or that it even has to look like a conventional, like, management relationship.  That it can be something that works for you and works for a very specific type of person, and it doesn’t have to be a great fit for everyone.

Chris:  Right, exactly.  I mean … so it has to work for you as the business owner or the entrepreneur or whatever, but then it also has to work for that person, you know, as well.  So it’s not necessarily the easiest thing to find, but I think it’s something that’s kind of worth … worth investing in, you know, because anybody can follow a list of tasks, but it takes creativity, as you said.  It does take some entrepreneurial thinking to kind of figure stuff out and decipher it, and that I think is a skill that everyone can improve on regardless of your field, your industry, it doesn’t matter what you went to college for.  This is something that kind of sets people apart in life in general.

Tara:  Got you.  So you mentioned that you’re still doing a lot in your business or at least with the writing side of the business now.  What are some of the tasks that we might be surprised to learn you still actually do?

Chris:  Huh.  I mean, pretty much any sort of administrative task I still do it from time to time.  I mean, just putting together newsletters, I do all of my own social media.  I don’t know.  I guess … I guess there’s not much that I don’t do, but I also don’t want to take anything away from the people who, you know, work on stuff with me.  Like I’m very grateful for them.  I just don’t have much of a separation between like here are like these top level task and here are like these low-level administrative tasks, and maybe that’s something I need to work on, but at the same time, it’s also kind of helped me not get too distant from things.  It’s helped me kind of, you know, have direct contact with people and understand, like, where they’re going, what’s going on with them, and how I can hopefully be helpful or be of service in some way to them.

Tara:  Mm.  Do you have any kind of automation in place in your business, or are you pretty hands on with the day-to-day, you know, this needs to get done, that needs to get tweeted out, etc.?

Chris:  Very little.  I mean, I don’t have a problem with scheduled tweets or something.  Like that’s fine.  Like, we might like put up some posts or something that go out at different times, but I … I think, like, it’s important to not be disingenuous with it, you know?  If you’re sharing some content that you’ve written at some point, you know, nobody cares whether you’re like live-tweeting that or something, but otherwise, I try to be pretty, pretty hands on.

Tara:  Got you.  And you said you’re not a great manager, but I’m curious how you manage your team, if at all.

Chris:  Correct.

Tara:  You know, what … how do you set expectations?  How do you communicate with them on a regular basis?

Chris:  Well, we talk pretty much every day.  I mean, we talk by email, usually, or by chat or something.  The WDS team, we use Slack, which is a great network for keeping in touch with people in different time zones and things.  But I don’t like I said, I really don’t think I’m a great manager, so I try to focus on … I try to focus on the goal.  Like, okay, what are we actually trying to achieve here?  What are we hoping to do?  And then there’s lots of moving parts, and you know, as we said, the right people kind of pick up those parts and run with it, because you know, to go back to where we started, if you’re motivated by what you do, if you enjoy what you do, then you’re probably going to do it a lot better than if you’re just doing something because you have to do it.  So wherever you can find that magic fix, you know, between your own skills and the people that you’re working on, that’s where you’re going to see far greater success.  So that’s what I try to do.

Tara:  So the next question is one that I’ve asked just about every one of our guests, and the answers have been very different, and I’m really interested to see how you’re going to answer it.  So how do you balance the roles of writer and executive in your business?

Chris:  I think there’s a big tension there, and I think it’s a natural tension, it’s a healthy tension because I do enjoy, like, doing more than one thing.  I’m not good, you know, just working on one project at a time, but then, of course, there’s a cost to that.  So I think, you know, every year, I kind of evaluate, like, am I happy with the balance?  Am I, you know, am I creating art?  Am I actually writing?  That’s how I got started in this.  Or am I focused too much on business stuff?  And I think maybe a year or so ago, I went away and felt like I had, I wasn’t writing enough, and so I tried to focus more on that, but then I miss the other thing.  So I don’t know, I just go back and forth.  I guess every day I try to make progress on the things that I believe in.  I have these, it’s like kind of values-driven.  It’s like I’m not happy if I’m not writing on a regular basis, and so I know if I get away from that, I have to go back.  So I don’t know if it’s 50/50, I don’t know if it’s a precise balance, it’s more of like on a general basis, am I making progress on these things that I’ve identified are important to me?  If yes, I’ll be happy.  If no, I won’t be.

Tara:  Yeah.  I’m really intrigued that you mentioned kind of it being values-driven.  What are some of the values that you put, that you prioritize in your business and the way you work?

Chris:  I would say the, you know, the number two, the number one and number two values, and they’re interconnected, is these questions that I asked myself, like you know, what am I making, what am I creating, and whom am I helping?  Right?  And so it’s like every day, because most of us, like there’s all kinds of stuff that we could do, and the beautiful thing about this kind of creative work is there’s so many opportunities, but the tragedy of this, you know, creative work is that there’s so many opportunities, and how do we choose to focus, and so whenever I become overwhelmed, I try to go to these questions.  Like okay, am I making something, or am I just kind of spinning my wheels?  And if I’m spinning my wheels, I need to get out of that and focus on creating something, you know, that I can identify and point to and have some value for people, and then hopefully, I’m not just doing something that’s self-referential or, you know, self-glorifying, but it’s actually making a difference in people’s lives.  So am I making something?  Am I helping people?  If I’m doing that, that’s great.  If not, I need to adjust.

Tara:  Mm.  So continuing along that thought, every year, you post an annual review to your blog, and I know it’s a really popular post, and you know, it’s less about the kind of income reports that a lot of people put out at the end of the year every month and a lot more about the exact questions that you’re asking and the kinds of goals that you’re setting for yourself, and kind of a check-in on the goals that you did set for yourself and all of that good stuff, and as I was reading over this past year’s annual review to prep for the interview, I saw that you mentioned that you see a big change in online publishing coming, and I would really love to pick your brain on this, because I know what I think I see coming, but I know that you’re in a lot of different areas than I am.  So what is this change that you see coming, and how do you think you’re going to adapt your own approach to ride that wave or to take advantage of it?

Chris:  Well, don’t give me too much credit here.  I don’t think I’m a futurist.  I don’t think I’m like, “Hey, here’s what’s coming.”  I think I’m more of an observer that’s like, “Hey, here’s what’s already arrived.”

Tara:  Yeah.

Chris:  Like, you know what I mean?  Like this has actually happened, and I actually feel like I was kind of late to observe this, and I feel like everything that we have said for years, all of the great advice, you know, at least that I’ve dispensed, I don’t know if it’s as relevant as it once was.  I wrote a manifesto a few years ago called 279 days to overnight success.  It was one of the things I did when I was kind of first building my career, and it was like this case study model of how I, you know, built a sustainable business doing online writing, and so for years and years, like, that’s been out there, and you know, for years and years, I’ve said I think those lessons are still kind of relevant, and now I’m starting to think, like, well, the strategy of connecting with people and creating is still very much, you know, relevant.  That’s never going to change.  But I do think there have been so many changes in online publishing.  I think the thought leader space is incredibly crowded.  Everybody has a message; everybody has something to offer.  I think formats have changed.  I think platforms have changed a lot.  And it’s not just a matter of like, you know, this network is going down and this network is on the rise.  I think, you know, some of the traditional advice, which was, you know, well-meaning and accurate for a long time was all about this like hub and spoke model of like okay, so you got to, you know, built your hub, and like everything else is kind of a, you know, an anchor or something that drives people, you know, to your blog, but you really want to make sure everybody is on your site, and I think that’s still … that’s still great if you can make it work, right?  But you know, I think more and more people are choosing to be deliberate and engaging with platforms directly, and they actually want more of their stuff to be just on Facebook or on Instagram or Snapchat or whatever it is.  I don’t think the specific platform is as important as this overall trend.

Chris Guillebeau on Profit. Power. Pursuit. with Tara Gentile

I think, you know, maybe to kind of sum up what I see as either coming or has arrived, I would say the next big thing is small, and you know, the next big thing is far, far more focused on connecting with maybe not hyper-specific, but you know, much more intentional, smaller groups and going deeper than going broader.  And the thing is, people have said this for years, but I don’t know that they really believed it.  You know what I mean?  Like they were always like, “Oh, it’s far more important to have this small group of people and really focus on them than to like try to build a huge email list or a huge social media following or whatever it is, but in reality, I think most of us were like, oh, yeah, but it’d be really awesome, you know, to have the really big list or the really big social following.  And so you know, even though we said, okay, we’re going to focus small, but you know, our strategy is still kind of big.  I feel more and more and more that the people who are actually going to be successful on a scalable level, like, are intentionally and deliberately focused on that small group to the exclusion of anything else.  And that’s something I think you’ve done really well.  That’s something I see a few other people doing well, but I think a lot of people are still kind of behind.  A lot of people are using tactics that, you know, may have worked five years ago, but not necessarily going to work now, you know?

It’s like … I’ll tell you a quick story, and if this is going on too much, just tell me.

Tara:  No, it’s great.

Chris:  But when I first started, you know, online business, like so long ago, it’s like 17 years or something, you know, there was this new website called Ebay.com.  I went on Ebay.com, and I could like buy and sell, and it was a seller’s market at the time.  At the time, when EBay first got started, you could go to the store and buy things, and then put them on EBay, and people would pay more for it because it was like this new thing.  It was like, “Wow, I’m buying stuff on the internet.  Isn’t that cool?”  You know?  So that was fun, obviously, but it didn’t last because it’s a gold rush, you know.  It’s like this arbitrage thing that happens when something is new.

So the same thing has been true in online publishing, internet marketing, whatever you want to call it.  A number of years ago, you could, like, I’ll write an eBook, and I’ll write an eBook on, you know, I don’t know, how to clean my house better or something, and everybody will, you know, spend $100 on it.  That doesn’t work anymore.  You know.  I think things have changed so much because everybody has an eBook, everybody has a course, blah, blah, blah.  So I have a lot more thoughts, but I just talked for like three minutes, so I’ll stop now.

Tara:  No, I loved it.  Well, okay, so that got me … Actually, let me back up.  I love what you said about how people are being intentional about spreading their content out in a lot of different, or maybe not a lot of different places, but several different places now where they’re not putting quite as much value on the hub, although I do think people are still putting a lot of value on email lists, it’s less about the particular place people are going as long as there’s some way for them to get back on their email list eventually, but they’re putting content on Medium or they’re putting content on Facebook, and that doesn’t seem to be letting up at any time soon.

Chris:  Sure.  Sure. 

Tara:  But I also really liked and appreciated the way you talked about going small and how that’s going to help people create stronger connections with the people that they’re looking to serve, but I also think, as you kind of alluded to, that this idea of passive income, or at the very least, leveraged income is so attractive that people keep getting off-track with this idea of going small.  So could you talk a little bit about what you might see the relationship being between a small, focused, highly-engaged audience and this desire for passive or leveraged income?


Chris:  I think, I mean, this just relates to a classic, you know, business idea of what problem are you trying to solve, and I think a lot of people who are starting out now really don’t have a clear answer for that, and it’s probably our fault, the people who have been around for a while, you know.  I would say it’s our fault because, like, we didn’t necessarily have to have great answers for that many years ago.  I mean, we could, obviously, like, we could still focus on solutions, and focus on being helpful and genuine.  I don’t think it was, you know, fraudulent or something, but you know, I do think it was much broader and much more scattered, and I think, you know, the people who are successful now, whether it’s smaller pockets or bigger pockets, they really do have a clear and specific answer for that, and they’re not trying to be like this big thought leader, you know this online celebrity or whatever.  I mean, some people with really small email lists or social media followings or whatever can do very, very well.  You know, as you know.  I mean, you know lots of folks with stories and examples like that, whereas, you know, there’s many people who have very large followings who are actually struggling a bit, or not nearly as successful as you might expect them to be, and I mean, just a quick point on the email list, it’s like I totally agree that an email list is super, super valuable.  It’s one of those things where, yeah, if you could do only one thing, sure that’s great, but I also think we have to be mindful of giving people what they want, and I think what people want is changing quite a bit, and not everybody wants to give you their email, you know, sadly.  It’s kind of like the way I think about Facebook, because for years, I didn’t really like Facebook very much, and I was just kind of like Facebook is not my platform, I’m just not going to go there.  What I kind of realized over time was it’s not really about me, you know?  Because if my community, if a lot of people in my audience or whatever, if they like Facebook, then that’s where I should be.  You know, I have to find, I have to like adjust because it’s not like, you know, going to my readers and saying, hey, readers, like stop, stop, you know, this behavior or this pattern that you like.  You know, come and join my email list, right?  And so what’s interesting is you can look at lots of people who’ve been very, very successful, you know, just building businesses on social, which I understand is completely the opposite of the advice, you know, that we’ve given to people over the years, and I have, too.

Think about something just briefly before we go on, like Humans of New York.  I would say probably everybody listening to this is familiar with Humans of New York.  If not, obviously, go and look it up.  This guy has, you know, millions and millions of followers.  Does he even have a website?  I don’t know.  I mean, I guess he probably does, but I would say 99, you know, percent plus people, you know, have become familiar with this project and become passionate fans of this project simply through the stories that he shared through social.  So it’s a totally tricky thing because I guess it relates to where we started, it’s a whole new world, and it’s not like everybody should like shut down their website and their email list, but I think people should pay attention, because, you know, change is coming, change has already arrived, and the people who went are the ones who are aware of that and can adjust going forward.

Tara:  Yeah.  I love your point about giving people what they want, being very mindful of what people want as well, and I’m sure you can make decisions that work for you in that paradigm as well, but really being intentional about understanding and delivering on what people want, and I’m really glad that you mentioned Facebook, too, because I had totally forgotten about that, but I’ve noticed recently, maybe within the last four or five months how much your Facebook strategy has completely changed.

Chris:  Yup.

Tara:  Can you give us a little bit more detail on that?

Chris:  Yeah, you’re so kind when you say it completely changed.  You mean, like, all of a sudden I started posting.

Tara:  Yes, that’s what I mean.

Chris:  That was the change of strategy, right?  Before, I had a Facebook page and people could like it, but I didn’t do anything there, and then I had this great idea of like actually posting, you know, to my page.  That was the big insight I had last year.  And you know, historically, I loved Twitter.  Twitter was like, that’s my network.  I’m so … I’m comfortable there.  I like that, you know, but what I noticed was, you know, people were engaging less and responding less, and so that’s when I was like, well, I have to figure out where the people are, and so just as an experiment, I started posting more on Facebook, started seeing much more, much greater responsiveness and engagement, so I just followed them there.  I don’t think the lesson for listeners, necessarily, is Facebook is better than Twitter.  That’s not the point because that’s going to change again in two or three months or six months or whatever.  Again, the lesson is where we started, like give people what they want.  Figure out where they are and go to them, as opposed to saying like here’s where I am, you should come to me.

Tara:  Yeah.  I have done the exact same thing over the last six months.  You know, my whole Twitter life has changed, and I can be sad about that personally, but businesswise, I know the best decision is to go to where my people are, and you know, since realizing that and being very intentional about that, I’ve seen my Facebook following really explode, and I’ve really enjoyed creating content for, specifically for Facebook, but I also really appreciate you saying that you need to give people what they want and go where they want to go, but you know, be intentional about it.  It’s not about following whatever the latest, greatest thing is, it’s about making real decisions for your business.

Chris:  Absolutely.

Tara:  Awesome.  So let’s talk a little bit about the live events that you have been hosting for the past five years.  I’ve told you before that I was at the very first World Domination Summit, and it literally changed my life.  I am so thankful for that experience and the people that I met there.  I am still just a such … I mean, they’re my best friends in the whole world.

Chris:  That’s awesome.

Tara:  Yeah.  So hosting live events has really become a big part of your brand.  It’s something that a lot of people know you for.  Perhaps as much or more so than travel hacking.  So what do live events help you accomplish in your business because I bet it’s not profit?

Chris:  Well, you just said it.  Your kind introduction there of talking about how you came to WDS and it, you know, connected you with greater people, and you know, it’s something that you remembered, and of course, you’ve been part of our stuff for years, which is great.  I think that’s why I do it.  That’s the motivation.  You know, and the motivation for everything I do is to have some sort of impact, and you know, hopefully to, you know, maybe not necessarily be a catalyst in people’s lives, because I think people come to my work when they’re already in a place of like being pro-change or wanting to do something different or wanting to follow a dream or just looking for greater support, but hopefully being like an amplifier to that, and being able to say like, oh, that’s awesome that you’re doing that.  You know, here’s some other people that are also doing awesome things, and you’re not alone and let’s support one another.  So I think that’s very powerful, and it’s not completely like a selfless thing.  It’s not sacrificial.  I benefit from it, too.  I really, really enjoy it.  You know this process of hearing stories like that, so that’s why I do it.

Tara:  Got you.  So I’m going to ask you a selfish question now.

Chris:  Okay.

Tara:  Which is I’m putting on my first event in April, and I would love to know if you had one piece of advice to give me about putting on a live event, what would that be?

Chris:  Hmm, well, one piece of advice, okay.  Yeah, it’s just the problem … the problem is being succinct.

Tara:  Well, I’ve already hired Isaac, so that part is covered.

Chris:  Okay.  That’s good.

Tara:  So something else.

Chris:  Okay, okay.  No, I mean, you’re in good hands with Isaac, of course.  I would say that one thing, maybe, like you kind of touched on is like to really be clear on what your intention and goal for it is, and I’m sure you’ve done that.  You know, you’ve been to many events.  I mean, you’ve spoken at many events, you’ve been on teams for events, so I think you understand, like, what you hope to get out of it, and you understand that it’s probably not profit, or at least that’s not the primary goal.  If you have some kind of, you know, mission-driven focus for it, then I think that’s great.  If you can challenge your attendees in some way, I think that’s also great, you know, leave them wanting more, but of course, you know, try to excel in everything you do.  I’m sure it’ll be great.

Tara:  Wonderful.  Thank you so much.  So let’s talk a little bit more about World Domination Summit for a minute because you’ve made the decision after five years to change up the format in a really big way.  Can you tell us a little bit more about that and why you made that decision?

Chris:  Yeah, so I announced this at last year’s event, and I don’t think I did a very good job, because ever since then, people have been asking about it, and what people are saying is like, oh, you’re making the event smaller, and that’s not necessarily what I was trying to accomplish.  What we’re doing is we are kind of scaling the mainstage component of the event back, which is the weekend focus of like a, you know, Friday to Sunday.  That is going to only 1000 people now instead of 3000 where it’s been the past three years, but then we’re also expanding everything else that happens throughout the week, and so we’re moving to more of like a week-long total experience where I actually hope that we can serve, I don’t know, 3000-5000 people this year probably, but then for the, you know, the immersive portion, we are focusing on a smaller audience.  So it’s kind of a two-prong strategy to better serve the people who are like yes, I want to be fully immersed, you know, I want this kind of special, you know, special high-touch experience, but then also serving people who aren’t able to come to that or who just want to kind of connect with other people but actually formalizing that process so that they have a way to do that.

Tara:  Again, you’re giving people what they want, right?

Chris:  We’ll see.  We’ll find out.

Tara:  All right.  So you’ve got a new book coming out that should be out I think right about when we’re going to be releasing this episode.

Chris:  Awesome.

Tara:  And the book is called Born for This, right?

Chris:  That is correct.  Yeah.  New book is to help people find the work they were meant to do, and this is the culmination of many years of research with all kinds of people who have forged or created unconventional careers, and I found a lot of people who use phrases like I feel like I won the career lottery, you know?  I love what I do, I can’t believe I get paid for this, you know, I would do it for free, but you know, I actually do get paid for it, so that’s even better.  So how did those people, you know, find that work, how did they create it, whether they’re entrepreneurs or whether they think entrepreneurially, but you know, find their best path within a corporate structure or some kind of organization.  Like my mom, for example, was a rocket scientist for NASA.

Tara:  I didn’t know that.

Chris:  Yeah.  Fun fact.  And if you want to be a rocket scientist, you’re not really freelance most of the time.  You know, most of them work for somebody, and I talked to the first female firefighter in Mississauga, Ontario.  She’s one of my case studies for the book, and so the same kind of story there is like okay, if you want to be a firefighter, like, you have to, you know, do that with other people.  So how do these people like find that work, what lessons do they have that they can offer, and how can readers, you know, find the work they were meant to do.  So I’m excited about that.

Tara:  Brilliant.  I’m excited about that, too.  So beyond the book, what’s next for you?

Chris:  Well, the book is a big thing right now, because just as it’s out, I’m going on the road.  I’m doing thirty cities.  Would love to have, would love to meet up with people.  If you go to BornForThisBook.com, you can get free tickets to any number of events.  That’s about a two to three-month process, then we go into the new WDS, then I hope to just keep doing what I’m doing.  I hope to keep traveling, I hope to keep writing, I hope to keep connecting with people and learning, changing it up as we go, because as we’ve discussed, change is the only constant, but again, I feel very fortunate, so I hope I can keep doing it.

Tara:  When, specifically, is the book coming out?

Chris:  April 5.

Tara:  Love it.  Chris Guillebeau, thank you so much for joining me.

Chris:  Thank you so much.

Tara:  Chris’s CreativeLive Bootcamp, Make Your Dream Trip a Reality can be found by going to CreativeLive.com/business. 

On the next episode, we’ll sit down with Natalie McNeal, author of She Takes on the World and the Conquer Kit.  We went behind the scenes on how she plans her year, grows her email list, and works with her team.  Don’t miss it. 

That’s a wrap for this week’s episode of Profit. Power. Pursuit. CreativeLive podcast.  Download more episodes of this podcast and subscribe on iTunes.  If you appreciate this kind of in-depth content, please leave us a review or share this podcast with a friend.  It means the world to us.

Our theme song was written by Daniel Peterson, who also edited this episode.  Our audio engineer was Kellen Shemezu.  This episode was produced by Elizabeth Madariaga.  You can catch up on older episodes in the iTunes store, where new episodes are added every week, and learn more by going to CreativeLive.com.

The 3 Kinds of Work (including 2 you should be doing less of)

There are three kinds of work you do a regular basis.

First, there’s work that gets immediate results. It might be actually delivering the service you provide or creating the product you sell. It could be writing on your blog or updating product descriptions. It could be ordering supplies or promoting your work.

Second, there’s work that should be done by someone else. This varies depending on your business and your strengths within that business. It could be fiddling with your website, sending out emails, or scheduling clients. It could be writing copy or creating advertisements. It could be shipping packages or bookkeeping.

Third, there’s the work that contributes to long-term growth. Often this is work that requires your expertise but that isn’t the hands-on work that you sell. It’s systems work. It’s process work. It’s relationship building. It’s working on the vision (and the byproducts of it).

You probably do a lot of the first and second kind of work. You are constantly after immediate results (they feel good, right?) because immediate results are better than no results. And you do a lot of work that you really have no business doing because you have chosen not to invest the time or money in having someone else do it.

That means that the work that contributes to long-term growth gets the short shrift. When you don’t work towards the future, you leave yourself in the hamster wheel of constant hustling. Sound familiar?

…while you’re doing it, doing it, doing it, there’s something much more important that isn’t getting done. And it’s the work you’re not doing, the strategic work, the entrepreneurial work, that will lead your business forward, that will give you the life you’ve not yet known.
— Michael E Gerber, The E-Myth Revisited

If you’re beginning to lose faith in the dream of having a business that takes care of you (instead of you taking care of it), then it’s probably because you find yourself doing so much of the first two categories of work. When that type of work is disproportionate to the results you see, frustration is the natural byproduct.

When you exercise your responsibility to long-term growth work, even if you’re not seeing immediate results, you can better weather the ups and downs of entrepreneurship. If a particular idea doesn’t work out, you have the systems or relationships in place to get you through. Or you have the comfort of knowing your next idea or opportunity is already in the works.

If you’re ready to do more long-term growth work and less of the rest, you need to schedule it. Put it on the calendar. Honor it like it was a client appointment or a project deadline. This is the work that will keep your business in business – respect it.

Once you’ve got that kind of work on the calendar, make sure that you’re creating systems that reduce the amount of other work you’re doing. Use your scheduled time to create a training or on-boarding process for an assistant or business manager. Also use that time to plan for new products or services that require less effort or active time from you. Plan to shift your business model to one that leverages your time & talents.

Bottom line: how would you spend your time if doing work that contributed to long-term business growth was your primary responsibility?

‘Cause it is.

— PS —

Kick Start Labs designed a brand-new Lab to help you get out of this rut and into strategic product development. It’s call Product Development 101. It’s available for a limited time on its own or as part of a Kick Start Labs membership. Click here for more info.

Busyness is the enemy of business.

The road from follow-your-passion to thriving business can be a bumpy one. Once you realize “if you build it, they will come” isn’t a business strategy, it’s tempting to spend every waking hour tweaking, writing, emailing, networking, and trying to push through.

“…while you’re doing it, doing it, doing it, there’s something much more important that isn’t getting done.”
— Michael E Gerber, The E-Myth Revisited

Busyness isn’t business.

Don’t confuse the two. You can work until you’re blue in the face and still not succeed. That’s not to say that hard work doesn’t or won’t pay off. But is what you’re spending your day doing really getting you one (or better, a few) steps ahead? Are your daily actions tuned to the goal you’ve set in front of you?

Check yourself.

Your goal can’t be to work yourself to the bone. The sense of accomplishment you’ve been missing won’t come from just checking tasks off a list.

What you’re missing is progress, the sense that what you’re doing matters in the larger scheme of things.

Being busy doesn’t level the learning curve. Being busy doesn’t create ease. Being busy doesn’t create satisfaction.

Know where you want to go and create a plan to get there. Remove any and all unnecessary tasks and busy work. Take time off, explore, enjoy.

Have faith that your plan will take time and that doesn’t mean that you have to fill it with work that is meaningless.

what’s your hypothesis? making the art business a science

You didn’t go to business school. You don’t have an MBA. You don’t run a tech startup. The only “C” in front of your title stands for “cook” or “cleaner.”

You’re an artist. You may not use paint or stone or metal. You may not sing or dance or write. But your work is an art and your passion changes people. And you, my friend, have taken this art and turned it into a business.

What could your business – one that’s based on soul stirring, passion inducing work – learn from the science of creating corporations? Turns out, a whole helluva lot.

Your business is here to prove something.

Maybe:

  • that great writing changes lives & leads to more sales.
  • that elegant jewelry boosts your self-confidence and takes the pain out of the morning routine.
  • that quality materials & craftsmanship really are worth the big bucks.
  • that creative expression saves lives.
  • that great design tells a story that words & pictures alone cannot.
  • that a well-decorated home keeps a marriage happy & healthy.
  • that a New Economy can be built around artist-business owners.

Yes, indeed. Your passion comes from your undying determination that part of your worldview is a Truth for many others. Your productivity comes from the resolve to share that with as many people as possible.

But, like any hypothesis, it’s not simply enough to state it. To deem it so.

Your business hypothesis must stand up to scrutiny, experimentation, analysis, and… dun dun dun… customer feedback.

Your hypothesis isn’t an excuse to put on your dreamer hat and sit in the corner while the MBAs play at profit. Your hypothesis is what gets you into the trenches and compels you to do business.

People don’t by WHAT you do, they buy WHY you do it.
— Simon Sinek, Start With Why

In starting businesses, we are most often concerned with what product we’re going to sell or what service we’re going to offer. It’s easier to understand the transaction when you know what’s changing hands. But it’s not the particular service or product that creates crowds of loyal fans. It’s not the product or service that spurs us to innovation & creative thinking.

It’s stepping outside the this-for-that exchange and stepping into something bigger & more powerful: our vision for the world.

Startups also have a true north, a destination in mind: creating a thriving and world-changing business. I call that a startup’s vision.
— Eric Ries, The Lean Startup

Business starts with a vision. The vision inspires a strategy. The strategy ends with the product or service being sold.

You can’t know what you’re selling until you know what you’re trying to prove.

To prove your hypothesis, you must experiment with a plan. Build, measure, learn.

Eric Ries, author of the brand-new book The Lean Startup, explains this process in depth. It’s a constant cycle of innovation & iteration that has at its goal creating a product/service that works to prove your hypothesis and achieve your vision while serving your customers.

This is true startup productivity: not just making more stuff, but systematically figuring out the right things to build.
— Eric Ries, The Lean Startup

How do you test the hypothesis? How do you figure out the right things to build?

Eric suggests the Build-Measure-Learn feedback loop. That’s a fancy (or not so!) way of saying: do it, discover what happens, and figure out what it means.

Build

Sadly, the first step is where so many get stuck. Without a clear hypothesis, it’s hard to know what to build. Of course, “knowing what to build” is truly overrated.

The first few times through this loop, it’s not your job to know what to build. It’s your job to learn what to build. So we start somewhere.

Back when I started growing my business in earnest, the first product I created was 52 Weeks of Blogging Your Passion. It’s an ebook with 52 blogging prompts. Not fancy. Not overly sophisticated. Just a response to what I perceived as a need.

I didn’t stress about making the most comprehensive product or making the snazziest design. I built a product it and I shipped it. That’s when the real work started.

While you’re “building” consider:

  • Am I wasting time on details that don’t enhance the benefits of the final product?
  • Am I wasting energy on making the product more comprehensive than is necessary to test my hypothesis?
  • Am I wasting attention on tangential pain points that are unrelated to the product I’m currently building?

Measure

In the tech startup world where The Lean Startup was first developed, there are loads of customized metrics and formal experiments that can be run with the data from the first (and subsequent) product builds.

I would argue these sophisticated methods of measure are a distraction to the microbusiness owner.

Forget the percentages, click thrus, and dollars, and focus on what your customers actually tell you about the product. Consider not only the specific feedback but the tone of their words, the setting of their usage, and the community of users.

After releasing my 52 Weeks of Blogging, I got customer feedback. It was good. But it’s not enough to just revel in good feedback. Ask WHY? I probed deeper to find out how people were actually using the book and what questions remained for them. That process then lead to several other books and a course.

Measure the effectiveness of your product by considering:

  • How is the customer using my product?
  • What results is she achieving?
  • Is she closer to believing in my greater hypothesis?
  • What themes are emerging about the product I’ve built?

Learn

Learning is all about figuring out what you’ll do differently next time. If you thought building your product was the end of the production phase and the beginning of the promotion & PR phase, boy, were you wrong!

Production is constant. Learning helps you know what to produce next. What tweak to focus on. What features to improve. What about-face to make.

Each time I build a new product, I learn so much about the people who purchase it. I learn things from the metrics, of course, but I also learn from their reviews. Their frustrations. And their questions. I build those questions & frustrations into subsequent products, blog posts, and emails.

I engage buyers via social media and create conversation around these areas. I build a bigger & bigger picture from my learning so that I can act & produce based on what I’ve learned.

Learn about your product or service by taking the feedback you’ve gathered & measured, comparing it to your initial hypothesis. Contrast your actual customers’ reaction with the way you thought they would react. Compare their concerns with what you feel to be true.

And then build again.

While in the learning phase, consider:

  • What assumptions did I make that proved false?
  • What surprised me about the customer feedback?
  • What could be eliminated from the initial product?
  • What needs to be added to the product?

Just as scientific experimentation is informed by theory, startup experimentation is guided by the startup’s vision. The goal of every startup experiment is to discover how to build a sustainable business around that vision.
— Eric Ries, The Lean Startup

Bottom line: to effectively change and grow, your business needs to be plugged in to your vision for the world and the hypotheses you hold true.

Forget discovering what to sell and who to sell it to until you’ve got those details ironed out.

Early Adopters: yep, you’ve got ’em. Now put them to use!

Social media has transformed our world into one great big small town, dominated, as all vibrant towns used to be, by the strength of relationship, the currency of caring, and the power of word of mouth.
— Gary Vaynerchuk, The Thank You Economy

This, you know. Social media gives you the best opportunity to talk to fellow business owners and loyal customers since, well, the last time you strolled down a thriving main street.

Best of all, social media doesn’t mind if you’re in your pajamas.

We also know that social media contributes to tipping points and even revolutions. It connects neighbor to neighbor and grandson to grandma.

Social media has reinvented word of mouth by creating word of type, swipe, and tap.

But before there can be sharing, there has to be something to share. And there has to be people who want to share it.

And this is where Early Adopters come in.

What is an Early Adopter?

They’re the people who wait in line for the latest iDevice. They’re the people try out new software before you’ve even heard of it.

According to The Entrepreneur’s Guide to Customer Development:
“Passionate, early users of new technology or products who understand its value before mainstream markets.”

Yes, they’re most often associated with tech.

But they’re also the people who try out the new restaurant in town before the reviews come out. Or the newest microwaveable meal at the grocery store. Or the salon that just opened. Or the doula that just started her practice. Or the artist that hung her first show.

Early Adopters rely on curiosity to fuel their purchasing decisions far more than brand names or customer reviews.

But Early Adopters do more than just buy your stuff.

Early Adopters want to help you and (here is the best bit) want you to be successful.
The Entrepreneur’s Guide to Customer Development

Whether your business is 30 days old or 30 years old, you can harness your own Early Adopter community. Your new widget or service may be a hard sell for those who are used to using something else but, harness your Early Adopters, and you’ll be able to make your initial offering much more palatable to the masses.

Game? Here’s how you do it:

Use Early Adopters to make in-progress products better.

Create an email list for people who are specifically interested in a new product. Email them regularly with content tangential to the development of your product. Ask for feedback, opinion, and personal experiences. Create a conversation that informs the development of the product you’re working on.

Use Early Adopters to get feedback on in-use products.

Since Early Adopters are those most likely to “get it,” utilize them to provide the feedback that gaps your designer experience with the user experience of those you’re selling to. Survey the first wave of buyers and seek to understand how they’re using the product and why they wouldn’t live without it anymore. Adjust sales copy, your positioning, and your product/service based on a careful analysis of this feedback.

Use Early Adopters to produce more.

We spend too much time in development and not nearly enough time in testing, deployment, and analysis. Create a first run product that is high in quality but lacking in bells & whistles. Sell these products (or services) to an invite-only list (see point 1) and solicit feedback so that you can create a second run product with the features, bells, & whistles your wider audience actually wants. Then you’ll be creating your next first run product instead of banging your head against your desk wondering why the first product didn’t sell.

Reward Early Adopters for giving you a hand.

Reward? On this budget?! A mention on Twitter, an email conversation, or sending them a preview copy of your next product are all great – and cheap – ways to reward your Early Adopters. Luckily, they don’t require much more than acknowledgment and the very first heads up on what you’ve got coming next.

I know, I’m an Early Adopter.

Start finding your Early Adopters today.

Run a sales report, create a Twitter list, thank them by name on your Facebook page, create your “Sneak Peek” email list… do something that helps you identify these key people in your business.

But first, leave me a response below and tell me what you’re going to do with them!