Episode 161

Side Hustle with Chris Guillebeau

January 30, 2018

Chris Guillebeau joins us to talk about what it means to have a side hustle and how that affects the job market today. We’re talking about funneling your drive to be a creative entrepreneur and how to create boundaries, containers, and rules to help you do the work.

Learn More about the Topics Discussed in this Episode
This Episode Brought to You By:
"Maybe if you get burnout, it's because you're doing the wrong things, not because you're doing too much."
- Chris Guillebeau

Discussed in this Episode

  • Chris's experiences traveling to every country in the world
  • The difficulty with relaxing as a creative entrepreneur
  • What do you do when you change your mind, but you're already deep in it
  • Having a side-hustle without quitting your job
  • What to do if you have a creative drive but you don't know how to funnel it
  • How much money do you need to start a business?
  • Creating boundaries, containers, and rules to help you do the work

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In this episode, the Make $100 Today worksheet was mentioned. Download your copy here!


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Chris Guillebeau 0:00
For me, I find a sense of being alive in doing this crazy stuff like that every country in the world, like I'm doing 100 City book tour right now. And like, I have a podcast I produce every single day, when I when I get these ideas, I can't stop thinking about them. And that's how you know, you have a crazy idea that's worth paying attention to, because lots of crazy ideas come and go. But the ones that stick with you, you know, I, the more I think about this stuff, the more I'm like, Yes, I want to do that. And I'm going to be excited when I do that. And so you have to find what works for you. Like, obviously, like, you know, people listening, if you, you know, gravitate toward those other messages, and that's great. Like you, you find what works for you, but it's not bad to do it the other way as well. You know, I would say and so if maybe you're thinking, hmm, is that really work for me? Like Actually, I want to like find the challenge I want to do what's, what's meaningful to me, then, then that's what you do. And maybe if you get burnt out, it's because you're doing the wrong things, not because you're doing it too much.

Kathleen Shannon 0:52
Hello, and welcome to being

Emily Thompson 0:54
boss, a podcast for creative entrepreneurs. I'm Emily Thompson.

Kathleen Shannon 0:59
And I'm Kathleen Shannon. I am Chris guillebeau. And I am being boss. Alright bosses. Today we are talking about side hustling, travel and just that entrepreneur lifestyle with Chris guillebeau. As always, you can find all the tools, books and links we reference on the show notes at WWW dot being boss club. bosses. I did not get into business just to get bogged down by well, business. I knew I wanted to be creative, and I knew I needed help on the business side of things. That's why fresh books cloud accounting was the first piece of software I signed up for to help. I love how visual intuitive and simple it is, while also robust enough to handle my growing accounting needs. It makes invoicing my clients easy and professional and it makes capturing my expenses painless. And it helps me see at a glance where the financial health of my business is. And I encourage all of you to try it. I personally use it and love it. Try fresh books cloud accounting for free by going to freshbooks comm slash being boss and enter being boss in the How did you hear about us section. Chris guillebeau is the New York Times bestselling author of side hustle, the $100 startup and some other books during a lifetime of self employment. He visited every country in the world which is 193 in total, before his 35th birthday. Every summer in Portland, Oregon. He also hosts the world domination summit, which is a gathering of creative and remarkable people. He also has a daily podcast side hustle school, and that is downloaded more than 2 million times a month. We love chatting with Chris, and we hope you enjoy it too. Chris, thanks for joining us on being boss.

Chris Guillebeau 2:52
Thank you so much for having me. It's a big honor.

Kathleen Shannon 2:54
We're stoked to have you. So I think that one of the things that fascinates us and probably our crew the most about you I mean, you've accomplished so much that traveling to every country in the world.

Chris Guillebeau 3:06
Yes, well, it was kind of a compulsion. So it's not something that I said from the very beginning. I'm going to travel every country in the world that developed as I went along, but but thank you for saying that.

Kathleen Shannon 3:17
Alright, so one of the things that I've found whenever I'm traveling to different places, is whenever I come home, everyone's like, oh, what was your favorite part of the trip? And I feel like it never really sinks in until weeks, months, if not years later, like some of my most meaningful trips. I'm still learning lessons from five years later. So I'm curious to hear from you, if there have been any standout lessons along the way, or as trips have had, as you've had space from certain travels, if any lessons have really stood out to you.

Chris Guillebeau 3:55
Yeah, I love how you frame that. I think that's I think that's really insightful. Because often when it comes to trips, I think the anticipation is really important. So like the planning, and then the looking forward to something. And then of course, the experience of that something but then just as you said, like the space and what comes later in the reflection and, and realizing that there was this moment in time, that may have even been life changing, or maybe it was just pleasant or interesting or different or something. So I think for me, you know, like this was an 11 year quest, you know, I it took a long time and I'm still traveling now like you know, constantly. I just love the process of it. For me, some of the things that were the most insightful were when some kind of change occurred or something like I thought something was gonna go one way but then it went a different way. I remember the first time I went to Australia, which is now one of my favorite countries actually didn't go till close to the end of my trip and I had been to like 150 countries at that point, which I was scheduled to go to Nehru this really small country like off the coast of Brisbane and I was denied boarding I couldn't go on the plane. Long story didn't have the right visa, I ended up staying in Australia for like four days. And it was very serendipitous. And I felt so like peaceful and relaxed, I don't really relax very well, I don't normally want to relax. But that was just a great, great experience. And like, I still think of it now. And whenever I go back to Australia, like I said, it's one of my favorite places that I look forward to. So there was that. And I also had several years that I spent in West Africa as an aid worker. So some of those countries are pretty special to me as well, even though they're not places that most people go for tourism, like I have a lot of good memories, and it was also kind of impactful. So I keep seeking out those moments. And then like you said, You don't realize, you know, you had them sometimes until later.

Kathleen Shannon 5:38
Can we talk a little bit about relaxing? Sure, you're gonna have to be the expert on that. But I'm not. And that's, you know, one of those things where I've been told lots of times, like, just relax, like, just chill out, just calm down. And I think that for us, and I mean, Emily and I have just decided that we vibe at a higher level, or we're working at a higher level we're producing at a higher level, and we can't stop. And I think that we're made to feel guilty about that. And I think that, you know, there's there's these different things happening in creative entrepreneur worlds where it's like, work hard, work harder, you know, go go go if you're, especially if you're listening to someone like Gary Vee, which is super inspiring. And then on the other end of the spectrum, you're hearing like, you need to take care of yourself, you need to chill out, you need to relax. So what's your experience with that? Like? Did you ever feel guilt over not being able to relax? Or do you just embrace it?

Chris Guillebeau 6:35
Yeah, I mean, this is such a great question and topic. I mean, I could not agree more, I feel like, you know, I think there's these competing values, essentially, of, I don't know if you know, simplicity and slowing down and minimalism, and then like, intensity and challenge, and I guess I always gravitate toward the challenge and the intensity. And that's where I feel comfortable. That's where I feel like I'm coming alive. And there's a great quote from Joseph Campbell, about, like, people are not looking for the meaning of meaning of life, they're looking for a sense of being alive. And for me, I find a sense of being alive in doing this crazy stuff like that every country in the world, like I'm doing 100 City book tour right now. And like, I have a podcast I produce every single day, when I when I get these ideas, I can't stop thinking about them. And that's how you know, you have a crazy idea that's worth paying attention to, because lots of crazy ideas come and go. But the ones that stick with you, you know, I, the more I think about this stuff, the more I'm like, Yes, I want to do that. And I'm going to be excited when I do that. And so you have to find what works for you. Like obviously, like, you know, people listening, if you, you know, gravitate toward those other messages, and that's great. Like you, you find what works for you. But it's not bad to do it the other way as well. You know, I would say and so if maybe you're thinking, hmm, is that really work for me? Like, actually, I want to, like find the challenge I want to do what's what's meaningful to me, then, then that's what you do. And maybe if you get burnt out, it's because you're doing the wrong things, not because you're doing it too much. Right? Because if you love what you do, why would you not? Why would you not want to do it more?

Kathleen Shannon 7:58
Totally, I was just about to ask you like, but how do you ever feel like your own ambition is going to kill you?

Chris Guillebeau 8:05
But But how do you want it? Like how do you want to like leave life? You know, like, hopefully none of us are going to die, you know, this year, but like, do you want to leave life feeling really relaxed and chilled out or you want to look back and be like, Man, look at all that stuff that we did, like, wasn't that so cool? Like I had a dream. And I've pursued my dream, or doing to look back and say I had a dream, but it was too hard. You know, I thought I should just go and kind of take it easy instead.

Emily Thompson 8:28
Yeah, I'm I'm loving this acceptance of just how it is that you work as opposed to sort of soaking in what everyone else or how everyone thinks you should be working based on their own, like views and values. And I feel like most of the creatives that we talked to are in that place where they're still too concerned about what everyone else is thinking instead of just doing the work they want to do in the way they want to do it. And you seem pretty at peace with with your own drive and will to keep keep moving, if not a little faster than most other people are a little more busy going out whatever it is that you want to accomplish. And I think I think they're just there almost comes a sense of restfulness from that acceptance. So that may be a little less anxiety accompanies your your will to move forward so quickly. Oh, I get

Chris Guillebeau 9:17
Yeah, well, thank you. That's a good observation. I think it's not so much about comparing, you know, myself or yourself or anybody else to someone else. Like I don't, you know, somebody else's pace or speed that's that's for them to figure out. You know, I just make comparisons to myself, I think it's important for each of us to like, think about what is our potential, like, you know, what have we been gifted in life? Like, what privilege Do we have, first of all, and like, because we have so much privilege and so much, you know, so much in the way of opportunity and possibility available to us, like certainly talk to the three of us and probably lots of people who are listening as well. You know, what is then our responsibility?

Emily Thompson 9:51
Yeah, I completely agree with that. I think that's super important to consider whenever you're thinking about how it is how it is that you work, and what it is that you're here to Doing what it is that you are responsible for. I feel like responsibility has been a topic that's been coming up for me a lot lately, especially in observing other people and wondering how it is that they we all, I don't know process what it is that we're responsible for. And that is not a conversation for today, I don't think, but it is something that I'm thinking about a ton these days. Oh, good.

Kathleen Shannon 10:22
Okay, I have another question along these lines. Have you ever changed your mind in the middle like, Okay, I'm going to record an a podcast episode a day. Are you ever like, Wow, now I have 100 episodes booked? And at Episode 25, I've changed my mind. Like, what happens then? Do you just see it through? Or what do you do?

Chris Guillebeau 10:39
Yeah, I think it I think it depends on on, like, what stage you are in the process. I think that that matters a lot. I'm actually a big fan of giving up on things, I actually encourage people to give up on projects all the time. I feel like it's, it's another another, you know, complete set of bad advice to just tell tell people to always persist, because you can keep doing something over and over expecting different results, probably not get them, maybe eventually, one day on your 27th, you know, try this thing or something have worked out. But meanwhile, there's all kinds of other things that you could have been doing this whole time, you know, so that was a big kind of thing that I learned in the research from from my last book, I'm actually encouraging people to give up on stuff, which is, you know, contrarian, but for me, I think so it depends on how far you are in the process. Like, if I was going to every country in the world, 193 countries, and I made it to like country seven, and I was like, I'm sick of this. Like, I don't think the best advice would be just keep going. But if I was like, I don't know, 190 of 193. And all of a sudden, I hated it, which I didn't, you know, I never hated it at all. I think I think I would tell myself to suck it up, Chris, because you're almost at the end, right? You don't want to be that person that like went to almost every country in the world. Like Imagine that. You almost got there, but he didn't. Let's talk to Chris guillebeau about something else, you know? How did it feel Chris to almost do that? You know, so, alright, let's

Kathleen Shannon 11:52
talk a little bit about side hustling and starting up. So people will email us and say, just give me permission to quit my job. And we're never that person, like, we are never giving someone we're never gonna tell someone to quit their day job, because it's just not our place to tell them. Right? And so here's a question like, why should someone not quit their day job? How do you believe or what are your general feelings on day jobs?

Chris Guillebeau 12:19
Yes, I think everyone should quit their day job tomorrow. Alright, so goodbye. The episode like right there, and then people get emails later. You know, I actually so my experience is like, I've always been self employed, like, I've always worked for myself, for better or worse. Like I learned like 20 years ago, I'm unemployable. Basically, like, as a teenager, I'm like, not good at that. That's my own bias. Like, that's my own perspective. Right. And, you know, over the past few years, in particular, I think there's, there's been a bit of a backlash against this, like, entrepreneurial message, you know, which I'm partly responsible for, along with other people that like, this is the only way you know, and lots of people out there actually, you know, really happy in their jobs, and they're actually part of a company or a mission that they believe in, and they like the social environments, they like the values, maybe they like the schedule, and there's something else that's good for them. Or, alternatively, maybe they do eventually want to do something different, but it's going to take some time, you know, like, it's there, they're not 20 years old, necessarily, they, they have a mortgage, they have a family, they have something else that it's not wise for them to quit their quit their job. So for all those reasons, I think like, you know, what I'm trying to help people with now is, don't quit your job. But while you're there do create another source of income, like you can think entrepreneurially, even if you've never want to be an entrepreneur, like there's something that you can do to create that second or third source of income. And that is very powerful. And that's very empowering. And maybe eventually, that will lead some people to quit their jobs. And I have a lot of stories of people doing that. But it can also lead to a place of being able to say like, you know, actually, I've got this like, really great second income. Now I have options, I have security, I have a backup plan if something goes wrong, or I just changed my mind. And that I think is ideal place to be so that you can decide for yourself what's best.

Emily Thompson 14:02
Sure. And I also imagined that that second third revenue stream also relieves any or not any but some, at least of the stress around having the day job of is not the dreamiest day job you could ever have. It's easier to handle, because you're not so dependent on it for your livelihood. And I agree with you. I remember several years ago, being one of those people that thought that entrepreneurship was the cure all of like, it was the thing that would solve everyone's problems if they didn't like their day job, but now that I'm so much deeper into it, I totally disagree with that. So whole heartedly and I love I love what has come out of that in terms of this, this push for the side hustle, this idea that you can have your day job, I'm gonna have your cake and eat it too. Basically, you can have your day job and have that you know sense of security, but you can also feed your entrepreneurial spirit by having some sort of side hustle that fulfills you in different ways either by giving you a really great second income, or maybe just creatively fulfilling you if that's what you're looking for.

Chris Guillebeau 15:04
Yeah. I mean, the whole funny thing about cake is like, what are you supposed to do with cake? Like, why would you not want to eat it? Right? It's like, you're gonna have you have your cake sitting there, like, of course, you're gonna eat it. Like, that's the point. So I think in some ways people have felt shamed, even like because of this entrepreneurial message of like, oh, if I'm not quitting my job, tomorrow, I'm not taking a risk. If I don't have a startup or you know, something, then something's wrong with me, I just don't have it figured out. And obviously, like, so many great people out there doing awesome things, I think about my mom, like, my mom worked for NASA, you know, career for like 35 years, if you want to support the astronauts, you can't do that freelance, like, you have to be part of an organization. Like, I talked to a woman who is the first female firefighter in Mississauga, Ontario, like 20 years ago, and she's had a 20 year career as a firefighter, again, like meaningful work, like saving lives, literally. But you have to be part of something, you know, bigger than yourself. At the same time. She's also like, started her side hustle, and she eventually is create this whole second career for ourselves. So I think that's, that's really the goal to get people to the point of more freedom so that they can, you know, make the choices that matter to them.

Emily Thompson 16:05
I do want to talk really quickly about how I love how corporations these days, especially new ones, are totally acceptant accepting, accepting of people pursuing side hustles along with their day jobs, we were talking with our friends at freshbooks, a couple of days ago, I have a couple of friends who are at newer style corporations that to completely support their employees having creative or not creative side hustles. And bringing it into that the office office culture of having that be an acceptable thing as opposed to people sort of hiding, or like sneaking away during lunch hour or whatever it is to go to go do their side hustle, sort of in the backroom, if you will. And that's not as entirely necessary as it once was. So I'm loving that this culture is developing.

Chris Guillebeau 16:55
Yep, totally agree. Yeah, I hear stories like that, too. I just think it's I think it's so good.

Kathleen Shannon 16:59
Yeah. I also like how more corporations or even just people with entrepreneurial spirits are bringing their side hustle talents to their day jobs, like, if I was employing someone, and they came to me and said, Hey, I'm really passionate about writing, can I start a blog for our company? I would be like, hell, yes, that would be a dream employee, and they're getting to practice their skills or something that they're interested in on the job. I also think it's interesting. Did you guys ever hear that stat that, you know, most people have seven different careers during their lifetime. And I think that that used to be more linear. And I think now this day and age, it's all in the pot together. Like we might have seven different careers at the same time. Side hustling,

Emily Thompson 17:40
right? Or maybe that's just us, but who knows?

Chris Guillebeau 17:44
Yeah, hybrid lifestyle, people kind of jumping back and forth as well and used to only hear the story going one way of like, this person had a job. And then they started a business. But now I actually hear stories of people that like I actually worked for myself for a couple years, it was good. But now actually, I've got a job and or I'm doing a little bit of both. And I think that's that's also just more normal as well.

Kathleen Shannon 18:02
Yeah, we're about to interview our friend, Becky Simpson right after you. And she's doing just that. And we're going to talk to her about it on the show, because this is a show for creative entrepreneurs, but we're finding that it's actually becoming so much more of a blend. And it's more just about having a creative spirit and making what you want to make, by coming back to this idea of freedom and having more freedom. And one of the things that I'm finding is that people with day jobs and side hustles, or even full blown, creative entrepreneur jobs, and then they're kind of following a passion project, that they feel anything but freedom, like they're freaking out over time. So do you have any time management strategies for side hustlers, or recommendations or ideas along those lines?

Chris Guillebeau 18:45
Yeah, I think the worst thing to tell those people would be, hey, you just have to get up two hours earlier every day, which is what, which is literally what I've heard people say before, like, if you believe in this, you got to get up two hours earlier and work on your project. That's not realistic. For most people who fit that description exactly, as you described, like, they are already very busy. They're already sleep deprived, like they have very little time to fit into their project. So I think what they need, what they what they're also lacking is what they're lacking is like a blueprint or a plan of like, here's what you do with your limited time. And that's exactly what I'm trying to provide with a side hustle. Because I think if you have 20 to 30 minutes a day, and you can actually do that with focused work. And you know, before you get started, what you're going to do next, I think you can actually, you know, create a project, you know, in a relatively brief period of time. So it's not so much about like, yeah, I'm going to give up half of my sleep every day, or I'm going to give up all my free time, or my family's going to sacrifice or whatever. It's like, no, there's, there's something that I can do like we all have a little bit of free time somewhere. So where can I? Where can I pull from that? And how can I identify from the outset what my goal is, like, what am I actually trying to achieve here with this little project? am I creating a product? am I creating a service? How am I going to get that out to the world just thinking really, analytically and logically about that from the beginning? I think which which still allows for a creative process, of course, just being intentional, I think I think goes a long way.

Kathleen Shannon 20:06
Let's talk a little bit about that blueprint. What are some other very first steps in taking an idea? and making it a side hustle reality? Like, where do you even get started.

Chris Guillebeau 20:16
So I've been doing a lot of research for a number of years. And in writing about this concept for probably eight years in different ways, I've noticed that people struggle with with one of two things, and it's like half and half like 5050, half of the group of people says, I don't have a good idea. Like, I don't know, actually what my side hustle idea would be like, I have these skills that I use for my day job, but I don't know how to like, transfer them or adapt them. And the other half of the people are like, maybe more like us, or like, we have plenty of ideas, ideas are not the problem. Our problem is in like making those ideas happen, or how do I choose which idea to work on next. And so like, what I try to do with that blueprint process is it's 27 steps to five weeks, the first week, you learn what makes for a good idea, like you learn to develop your your power of creativity or observation, which is not that hard to do. It's just most people haven't been taught that, like you didn't, you didn't learn that growing up unless you had an entrepreneurial household, you certainly don't learn that in higher education. So we're going to show people how to do that, then, you know, the second week is okay, once you've got a bunch of ideas, what's what do you choose, like what's best for you at this time, and this season in your life based on your goal, I think is critical. And then the whole second part of it is like, okay, let's bring it to life, like what do you need to have? What are the outcomes? What are the what are the deliverables? Let's get really specific about that. Do you need a website? How can you make a simple website? I mean, tools, resources, all this stuff that you guys know about very well. And then how do you you know, launch that project before you feel ready, basically, because that's how we're going to get real world feedback about it. It's not so much about validating the idea before it goes out. And then lastly, okay, once it's out, what next, you know, how do you regroup? How do you take the information you've gained from actually putting it out into the world? Instead of just asking your friend like, Hey, what do you think about this business idea, which is terrible advice as well?

Kathleen Shannon 21:59
Why is that terrible advice, because your friends are afraid for you?

Chris Guillebeau 22:03
Or your friend or your friends? Not your friends, you know, but like, let's say, listeners, friends, your friends may not necessarily be qualified to answer that question. Right? Like, is it a good business idea? Like, what do they know? You know, they're gonna give you their opinion, that's fine. They're also exactly like you said, they're not going to, they're just going to say it's good, most likely, because it's your idea. You don't wanna crush your idea. So I think, you know, you could ask somebody who's more qualified, or you could just kind of build it and see what happens.

Emily Thompson 22:26
Right? Friends are not the best idea. And I feel like families even worse, like whenever people tell me, they ran this by their mom, or their aunt, or whatever, I'm like, nope, no, no, that does not count.

Kathleen Shannon 22:36
It's like, your mom just wants you to have health insurance and someone else be paying your bills, like don't ask your mom.

Emily Thompson 22:44

Kathleen Shannon 22:45
Okay, can we go back to the idea that someone has a creative drive, and they don't know how to funnel that into a deliverable? Like, how do you get them to that point of, I don't really know what I want to do. But I want to be an entrepreneur to making the thing.

Chris Guillebeau 23:00
Yeah, I think there's a couple of different paths people can go down to answer that question. And maybe you guys have a process as well, I'd be curious to know, one thing I try to encourage people to do is, it's not so much about like focusing on your passion, like, instead of following your passion, what if you follow the problem? Right? What if you think about all the problems that you encounter in daily life, and things that frustrates you? things that annoy you and things that can be done better? Like once you start thinking about that, then you become more solutions oriented. And if you have this problem, obviously, lots of other people probably have the problem, too. So you're not just kind of going back to like, I like to play tennis. Therefore, what is my side hustle, you know, the second thing is, like, let's make a whole inventory of your skills, like all the stuff that you're actually good at. So the things that you learned in school, what you do for your job, but not just that, like also your life experience, and maybe something you were good at when you were younger, or something that comes naturally to you that other people struggle with. That's also a good sign of like, what are people asking you about? All the time, like, if people are asking you these repeated questions about certain topics, then that's a great thing to kind of, you know, go down and follow up. Like when I first started writing my blog, the art of nonconformity, I was I didn't actually didn't have any commercial, like, purpose or mission for it at all. I was just like, I'm going to write this little blog about like traveling every country in the world and how I do it. And I was much better about writing and like logistics and planning stuff. And I was about like, travel destination. And so I had a lot of people that questions like about how I do travel, hacking and use frequent flyer miles and all that stuff. So I ended up kind of developing a whole business around that. And I never would have noticed that or thought about it if it wasn't for like people asking me that question like over and over. So those are my two kind of general journal paths.

Emily Thompson 24:42
I love that. I feel like this creative problem solving piece is so important, and it's something that I definitely see missing, and like most standard education these days, and I homeschool my daughter and she's nine. So I feel like we're just starting to dive into this creative problem solving piece and it's something Like when she's hanging out with her friends, like I can see the ones who are getting it and the ones who aren't. And I absolutely believe that we should be teaching kids creative problem solving earlier. If it's something that you struggle with, now, start getting that really mindful place where you're seeing the problems and coming up with creative ways of solving it. Because as an entrepreneur, having the ability to do that relatively quickly and easily and try things out without being too attached to the outcome is how you do it. Basically,

Chris Guillebeau 25:33
I like that part about not being too attached to the outcome and not not thinking that this is your life course, necessarily, like you're not deciding like who you're going to marry or have a relationship with, like, you're picking something for now to try, and we'll see how it goes. And there's not going to be a lot of risks to it. Hopefully, that's also part of like, the side hustle model, I think is like don't spend a lot of money don't spend, you know, six months or a year working on something without having any real, you know, feedback about it.

Kathleen Shannon 25:57
Yeah, can we talk about that for a second, I even just with people asking us for advice on podcasting, I'm like, stick your Apple iPads, or like iPhone earbuds into the computer, I see I don't even know what it's called. But it doesn't have to be fancy, like stick it into your computer and hit record. Like it does not have to be fancy, or photographers, people who want to be photographers, but they think that they need the fanciest lens, just pull out your iPhone and take a photo. You know, one of the things that I think about whenever it comes to problem solving, that kind of overwhelms me a lot I look at or I listen to the podcast, how I built this quite a bit. And a lot of them are finding a hole in the market. And I kind of in my heart, don't believe I don't believe that there are any holes in the market. I think that everything is being solved and everything's being done. So for me, it's kind of this idea of resourcefulness, which I think is the cousin to problem solving. And so for me to spark, like my entrepreneurial spirit, or especially entrepreneurial spirit is how can I make $100 today, like, let's just tap into this idea of hustling, right. And that for me, gets me into the skills that I have to offer and quickly making a deliverable. And it's just $100. And that's to that idea, Chris, that you don't have to be married to it. And you can try a lot of different things, you can try making $100 in lots of different ways and start to see which one sticks.

Chris Guillebeau 27:23
That's great. I wrote that down. I love that question.

Kathleen Shannon 27:25
There we go, I might steal it from you. We have an entire worksheet around it. Um, I have I have a question. Speaking of $100. So I once read or you know, heard at one of the world domination summit that you were hosting, you gave everyone $100. And it was really just around this idea and coming from your book $100 startup, this idea that you don't need a lot of cash, you don't need the fanciest thing, you don't need the most expensive equipment to start doing what you're doing. And so I just wanted to ask you, why do we need less money than we think to start a side hustle? Or to start a startup? What does it really take?

Chris Guillebeau 28:06
Yeah, it's funny, you mention that story. Like that was probably like five years ago now. And it's still, like, it's a really good memory, cuz I remember like going to the bank to get something like $85,000 in cash, you know, and I was like, how do you do that? Like, do I need to make an appointment? You know, like, like, I slide

Emily Thompson 28:23
the briefcase or do you bring your own? Right,

Chris Guillebeau 28:25
good question. Good question. Yeah, no, I brought my own. And we took it back to the kitchen counter or like, put it all and I took it took lots of photos of it, obviously, like, I got a bottle of tequila. And I put it next to me. And then my cat also had my cat up on the kitchen counter. So it was like my cat but tequila at $5,000. It's like this is just this is worth it for the photo. Yeah. But

Kathleen Shannon 28:45
yeah, have you seen that show? Ozark? I have not. No. It's this guy who is like working as a he's cleaning dirty money. Right? So he has to figure out how to clean $8 million. Wow, okay, legit. I thought of you whenever I was watching

Chris Guillebeau 29:02
$90,000 is a little bit less than than 8 million, but I forgot

Kathleen Shannon 29:06
so hard to get 85,000 but it was still logistically complicated. Right. Okay. Was it all did the FBI come like?

Chris Guillebeau 29:13
No, no. I mean, apparently, it's not totally uncommon, you know, like, it doesn't happen, like every minute or whatever. But apparently like people do withdraw, you know, that amount of money. Let's say touchier more relevant question. But thanks for the memory throwback. I think people just have a perception that, you know, business takes money. And this perception is probably reinforced by shark tank and Dragon's Den and all those shows, which are very entertaining. Or this the startup world in general, the Silicon Valley model of entrepreneurship, which is, you know, has always been very different. And you know, what I've done and I wrote the $100 startup out of visiting every state, authentic states and every province in Canada for my first book, and just hearing all these stories from people that people in middle Middle America and elsewhere, who, you know, didn't relate to that model at all, but they were they had like Either found their passion or they found their skill or a problem or resourcefulness. And they had created this business that had changed their life. And so, you know, I kind of got come from that school of thinking. And so people, maybe people, maybe people might need examples, people might need stories, they might need to like, Okay, how do I? Like, what if I hear a story, like every day? Or what if I read this book, or on your show, or somewhere else of people who do this without spending money, then maybe I can relate to it a little bit more. And you know, also people ask me, maybe you guys have this too. Like, I have X amount of dollars? What kind of business should I start? Which is also like a misdirected question. I understand why people can think that. But you know, saying I have $5,000, what kind of business should I start? It's like, well, what are we trying to do here? Right? It doesn't matter. So much like what the capital, you have an idea, and then that relates to how much you need to spend for it.

Kathleen Shannon 30:48
It's so funny how $5,000 like thinking about starting up with $5,000, right now feels like a luxury because I was one of those people that started with nothing. And I was just talking to some entrepreneurial friends of mine the other day, who have this really amazing shop, they bought a house, they have a couple of kids. And it all started with basically $100 startup, they didn't have hardly any money and started a T shirt printing company. And now it's even whenever they're feeling down about progress, because we all do like we all have these hiccups, where we're like, Am I doing the right thing, they were able to look around and see everything that they had created out of nothing. And I think that's what I really love about the kinds of businesses that we've created out of nothing is that it's not like we're borrowing against somebody else's dollar or that it was given to us in some sort of way. And we're just trying to figure out how to like manage our money, we were actually creating something. And I think that that's a fun challenge whenever it comes to having not a lot of money. And I think that you're far more creative and innovative whenever it's not just something that you can throw money at.

Chris Guillebeau 31:56
Yeah, thank you. I think you said that more eloquently than me, I like that I like you spoke to that, that sense of ownership that comes from, you know, creating this new source of income that you haven't had before. And I hear over and over, like, I'm on this big tour. And every night people are telling stories of like, the first time I did this, like they got the Pay Pal notification. And they're like, Oh, my God, is this fake? You know, is this like, do I click the link? Is my computer gonna be hacked? If I click the link, you know, and sometimes it's a very small amount of money, but it means so much to them. And very often it does go on to be something, you know, really big and substantial. Sometimes it doesn't, that's okay. They still feel like the sense of ownership and empowerment that comes comes from that. So I think it's a beautiful thing.

Emily Thompson 32:34
I agree. And the thing I love about this as well is that it really does speak to the level of business that 99% of us are at maybe not 99 totally made that up. But this idea that we're not all starting with VC backing, and we're not we don't all have like really great trust funds that are you know, feeding our feeding our kids while we're you know, here hustling, hustling, doing the thing.

Chris Guillebeau 32:57
I mean, it may be it may be 99% it's the vast majority are not in a place,

Emily Thompson 33:01
for sure. So you know, we see the shows like Shark Tank or whatever. And so we see that like super upper crust. And we think that that's how it's done. But whenever you look at all the businesses around you pretty much they're all doing it this way. And I think whenever we put the spotlight on those select few who are doing it with lots of cash backing, again, it almost brings up like all those frosty feelings and things that come up around, around if you can do this with what you have. And you can just look at everyone else, not what's happening on the TV.

Kathleen Shannon 33:34
Great. I once had someone asked me they were like, if I wanted to invest in your business, what would that be like? And I couldn't even think of an answer because I've never even thought about just a windfall and what I would do with that money. I like growing from the ground up. It just feels more my style, I guess. All right. Are you still doing world domination summit?

Chris Guillebeau 33:57
I am Yes, we are going into year number eight. Now. Yeah, it's so fun. And it's something that myself in a small team we put a lot of work into. We all do. It is a labor of love, you know, for the most part, like our profits go to a nonprofit that we've founded. But it's it's so great. Like we have people from all over the world coming about 1500 people over the past couple of years. And people come together for a weekend in Portland, Oregon. And we have workshops, we have mainstage talks, we have lots of activities. It's essentially just about fostering community and bringing together like minded people, whether they want to be entrepreneurs or if they're artists or travelers or just just you know, they think differently of friends who I am or they grew up from a place that's not like a big city or you know, it's easy to find people with with interesting connection in common So, yep,

Emily Thompson 34:50
I love it. And what have you learned after hosting this for so long because the world domination summit has become has become a thing like before short where a lot of our listeners Go every year and like you said, they go and they meet with their group of people and all of these things. So, so it's definitely grown into grown into really quite a movement. What have you learned from putting it on? as the person who is putting it on?

Chris Guillebeau 35:15
Oh, great. Well, thank you for saying that. And yeah, I hope to see some more listeners there next year, that'd be great. What have I learned? It's, it's grown like far beyond my original vision. And unfortunately, it's like, it is a thing of its own now. And I like that, like, it's not just like Chris guillebeau is conference like, I wouldn't, I wouldn't want that. And so for me, maybe maybe some of my observation kind of steers toward that direction. Like, I'm really, really proud that people, a lot of other people have kind of taken ownership of it as well until like, this is my community, I'm going to keep coming back, I'm going to host, you know, activity or a workshop or a meetup or something. And we have a lot of good stories that kind of come out of that, which is for me, like probably the main motivation of doing it. And I think, you know, we didn't have any idea of how to like run an event when we started, for sure. And so there was lots of stuff that we had to learn. I think one thing that we got, right, lots of lots of mistakes we made. But one thing that we got right was, we found a good blend between, like, there is an actual agenda to this, like this is not an unconference like I actually believe in putting forward a mission and like, you know, actually having speakers that challenge the audience. But yet, we also allow, like a lot of opportunity for connection and for attendees to do their own thing. And I don't know where the right balance of that is, if it's 5050. But I think I think that was a, that was a good thing. So we keep kind of focusing on that on community, how can we, you know, other other conferences are going to do a much better job with other stuff, like, we're never going to compete with Ted in terms of online video, for example. And we don't have any corporate sponsors. So there's lots of other conferences that could have millions of dollars to invest in technology or something else, and we want to do a good job and all those things. That's not we're going to be best at. So I guess what we try to be best at is like fostering those in person community experiences.

Emily Thompson 36:57
For sure. I love it. It sounds like a good lesson to learn. Well, it took me eight years. But here we are.

Kathleen Shannon 37:04
I will tell us about the book that you're working on right now. So obviously, we've been talking about side hustling. But tell us about the book.

Chris Guillebeau 37:12
Sure. Because called side hustle from idea to income in 27 days. And this was my attempt to to provide that blueprint for people who are busy. People who love this idea, love this concept, but don't necessarily know what to do. And so I was trying to put forward the step by step plan. I like to teach through storytelling. So on my podcast, side hustle school, like every day, I have a different different true story of an employee who's done this and in some way, and I kind of look at, like, what were their challenges? And how did they get the idea in the first place? And, and what was the outcome? So I tried to be really specific in terms of here's how much money they made. And, like, here's how that affected their life or their family's life. So I like throughout the 27 day process, like there's a different story every day as well. But then it's also like, okay, here's what you do, right? So you go and do this. Now people can adapt it, of course, in their own way. Like, I've gotten a lot of emails from people that are like, do I have to do it in 27 days, like, what if I miss a day, like, you're gonna be okay, like, you can do it however you want to do it, right? I'm just trying to provide a framework, and

Kathleen Shannon 38:11
I can't help but laugh at those emails. I mean, it's probably like someone following a recipe like where they think they need to haul it to the tee. That's just a type

Emily Thompson 38:19
of person that I know people who will not go off a recipe to save their life. So I get it too. But I know I'm not that person either.

Chris Guillebeau 38:30
So I'm getting lots of emails from people who are actually who are doing this and following the process and launching their projects, which, which makes me really happy and, and then I wanted to go and talk to readers and listeners about it. So I am doing 100 city tour. And at the time of recording this, I'm just kind of like I'm kind of like stopped number 20. So I got some I got some time to go on it. But it's it's I'm having I'm having a great time.

Emily Thompson 38:51
Awesome. And where did the idea of this come from? This like blueprint book.

Chris Guillebeau 38:57
So last year, I had another book out and I did a tour. And I had like a 30 minute stump speech. And for like, one minute of my 30 minute speech, I talked about side hustles. And I was like, oh, by the way, it was like a little aside. Like, by the way, like even if you love your job, I think you should have more than one source of income. And here are a couple things you can do toward that toward that end. And people responded to that, like far more than anything else, like 50% of the questions I would get afterwards. Were about that. So I was like I should I should pay attention to that. And then over time, like over the rest of the year, as I worked on the book and prepared to start start the podcast, I got a little bit more specific about that targeting as well. Like, I'm actually not trying to make this for everyone, right I'm actually which everyone is always like terrible targeting but I think in a lot of my projects, I haven't been very clear on the targeting. And this time like I really am trying to focus on employees for the most part like I think entrepreneurs should have a side hustle as well. So obviously there's lots of entrepreneurs like in the community still, but my intent for the black quest to provide it like for those people who are kind of on the outside looking at They don't relate to other books about entrepreneurship. But they would like to have this like, they love the idea of having an having options for themselves or more security or creative outlet, just like you said. So I'm trying to provide a template for that. And that's, that's essentially where it where it came from.

Emily Thompson 40:13
I love this because I feel like it does fill a hole sorry, Kathleen, where where there's so much content in the world about taking the leap, like just jumping in both feet first and going for it. And I love the idea of, of giving people this way to ease into ease into anything with a day job, to move into a second income or whatever. I also think I also feel as an entrepreneur, I have side hustles that are more life hustles. And I like I don't need a 27 day blueprint to make income off of it. But I do think this is a really great, really great idea for getting people into this idea of living a multifaceted life, or you don't just have to get up every day and do the thing and go to bed. And then at the end of your life, you can call it done. You can really pull in any interest or hobbies or traveling to all the countries or whatever it may be while you do anything. And that's the that's the idea of side hustling. And your book is about day job to side hustle. But side hustle can be so many other things to really give your life so much more flavor. Oh, yeah. Oh my god.

Kathleen Shannon 41:23
Yeah. And I think that, you know, we're so excited to have you on the show. And one of the things that I've had my I've been reading your stuff for years and years. And I think that one of the things I've always admired about your work is just that you do create these containers around your creativity, creativity, or like boundaries, or challenges or rules that help you actually get it done. And so I don't know, thank you so much for coming on the show. It's been so great having you. We've got a couple more questions. So where can our listeners find more like where can they buy the book? Or where can they find you online?

Chris Guillebeau 41:56
Yeah, I was just thinking right before that, about the boundaries and containers thing is a great, great quote from a friend of mine, Elise blaha. Cripe. And you might know her she has this quote about how you how you should be cast Oh, great. That's, like one of her things is like, get in the box. Don't think outside the box, people are always being told, think outside the box, you know, it's like build yourself a box, like build your own box. So it's not somebody else's box and somebody else's rules, figure out what you want, but then actually, like put those boundaries around your life so that you can actually be successful in the thing that you've identified. You won't just get waylaid and distracted along the way. I've thought about that several times. Where can people find out more so the book is called side hustle. It should be at any bookstore. Always great to support your local bookstore. But of course it's also on Amazon or any other online retailer. The Daily podcast, his side hustle school. So you know, however you found this podcast, I'm probably in the same place. And I'm Chris guillebeau on social media, which no one can ever spell. But if you type something close to that it will kind of probably bring it to me.

Kathleen Shannon 42:56
Perfect. And then what makes you feel most boss lately?

Chris Guillebeau 43:00
Oh, it makes me feel more spice. I think you you actually really hit on it so well at the beginning of this conversation, which nobody ever talks about by the way it's super super great about this concept of intensity and just giving your all to something and finding something you believe in and and really jumping in so I like that I really don't feel satisfied unless I'm being challenged in some way and feeling I guess I feel boss when I when I'm like taking on this big challenge. I'm a little bit afraid. But I'm not terrified. I'm just a little bit afraid because I feel like if I if I got a couple of variables right I can probably figure it out. And that makes me feel good.

Emily Thompson 43:40
Awesome. Love it. Thank you so much for coming to hang out with IC o chatting with you guys are the best. Thank you. We have gotten so much amazing feedback over the years from listeners about how our podcast has helped them start to grow and uplevel their businesses. So we want to celebrate you. Here's the boss we're celebrating this week.

Kathleen Shannon 44:02
Hi, my name is Maggie Germano and I am being bought. I'm a financial coach for women at Maggie germano.com and this week I'm celebrating being a full time entrepreneur after two years of working a full time job and doing my coaching business on the side. I'm so excited if you're feeling boss and when to submit your own boss moment or when go to WWW dot being boss club slash I am being boss. This episode of being boss was brought to you by fresh books cloud accounting thank you to fresh books for sponsoring us and you guys can try it for free by going to freshbooks comm slash being boss. Thank you for listening to being boss. Find Articles show notes and downloads at WWW dot being boss club. Thank you so much to our team and sponsors who make being boss possible our sound engineer and web developer Corey winter. Our editorial director and content manager Caitlin brain, our community manager and social media director, Sharon lukey. And are being countered David Austin, with support from braid creative and indicia biography.

Emily Thompson 45:10
Do the work. Be boss, and we'll see you next week.