06: You Need a Side Hustle (Here’s How) | Chris Guillabeau

Chris Guillebeau (he/his) is New York Times best-selling author, lifetime entrepreneur, and the host of the Side Hustle School podcast. In his new book, 100 Side Hustles: Unexpected Ideas for Making Extra Money Without Quitting Your Day Job, Chris shares stories of regular people with jobs, responsibilities, and busy lives, who start moneymaking projects in their limited time. In today’s podcast, he’ll share why you (yes, you!) need a side hustle, tricks to help you target potential opportunities, some of his favorite side hustle stories, and how to make your side hustle both successful and fulfilling.


Chris Guillebeau (he/his) is New York Times best-selling author, lifetime entrepreneur, and the host of the Side Hustle School podcast. In his new book, 100 Side HustlesUnexpected Ideas for Making Extra Money Without Quitting Your Day JobChris shares stories of regular people with jobs, responsibilities, and busy lives, who start moneymaking projects in their limited time. In today’s podcast, he’ll share why you (yes, you!) need a side hustle, tricks to help you target potential opportunities, some of his favorite side hustle stories, and how to make your side hustle both successful and fulfilling.

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Chris Guillebeau

NYT Best Selling Author, Host Side Hustle School


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Website: chrisguillebeau.com & sidehustleschool.com
Podcast title and link: Side Hustle School (or Apple Podcasts)
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Episode Notes

100 Side Hustles book tour with Chris Guillebeau
World Domination Summit


100 Side Hustles, Chris Guillebeau
Side HustleChris Guillebeau
The $100 Startup, Chris Guillebeau

MU: 00:03
Hi, my name is Melissa Urban and you’re listening to Do the Thing, a podcast where we explore what’s been missing every time you’ve tried to make a change and make it. Today my guest is Chris Guillebeau, New York Times bestselling author, lifetime entrepreneur and fellow podsquad member Chris is the host of side hustle school, another member of Gretchen Rubin’s onward project podcast family and his new book, 100 side hustles; Unexpected ideas for making extra money without quitting your day job. Chris shares stories of regular people with jobs, responsibilities, and busy lives who start moneymaking projects in their limited time. In today’s podcast, we’ll discuss why everyone needs a side hustle, how to spot the right money making opportunity for you, key factors in making your side hustle fulfilling and profitable, and common factors he’s seen across the most successful and sustainable ventures. Chris Guillebeau is the New York Times bestselling author of the $100 startup, side ,hustle and other books. During a lifetime of self employment that included a four year commitment as a volunteer executive in west Africa. He visited every country in the world, 193 in total, before his 35th birthday. His daily podcast side hustle school is downloaded more than 2 million times a month. He’s also the founder of the world domination summit, an event for cultural creatives that attracts thousands of attendees to Portland, Oregon every summer. All right Chris, welcome to Do the Thing. I’m so excited to talk to you today all about the side hustle.

CG: 01:42
I am so honored to be here. Thank you so much Melissa. (MU) So the first question I ask all my guests is, what’s your thing? (CG) Well, my thing broadly speaking is I help people live unconventional lives. Um, and that can mean a lot of different stuff. For the past three years in particular, I’ve been focused on this project called Side Hustle School, which is essentially all about financial empowerment, helping people to create an additional source of income even if they love their job and have no desire to ever be a full time entrepreneur. (MU) I love it. Did you know that Whole30 started off as a side hustle? I ran it side by side with my full time, nine to five. I worked for an insurance company doing operations management and business analysis. And I ran it for probably three years side by side until I finally took the plunge to take it full time.

MU/CG: 02:25
So you mentioned that everyone needs a side hustle. Why is it something we all should be thinking about? (CG) Yeah, I think there’s a couple of reasons for that. This is kind of the obvious one. This is what people often, you know, think of. They’re like, well, in this day and age, you know, you just can’t depend on a corporation. you can’t depend on really any employer, you know, like you need to create your own security. we all have kind of seen that, that there’s a lot of uncertainty in the world. There’s a lot of anxiety and so on. And so I actually think that’s completely true. Like I think we have to be able to look out for ourselves. Nobody’s going to care about our career and our wellbeing as much as we are. I think it’s also true that, you know, these days there’s just so many opportunities and so many possibilities.

CG: 03:05
There’s so many things that you can do. , but there’s never been a better time to do it. And what I’ve seen over and over, like throughout this whole process of, of doing the podcast, which I’ve done for more than 800 days in a row now what I hear from people is that like the first time they do this, it just feels so good. It feels so empowering too, to have like a different source of income coming in apart from your paycheck. Even if it’s a relatively small amount of money, it feels different. It often in some cases leads to something like Whole30 or something, you know, really big and huge, but even when it doesn’t, it still feels really good to be able to say like, I’ve got something that I made for myself.

MU/CG: 03:38
(MU) To your first point, I was just listening to NPR and I heard a statistic, 60% of Americans couldn’t afford being hit with a bill of $1,000 unexpectedly. (CG) Yeah, I read that too. It’s crazy, super staggering. (MU) you know, that, that kind of unexpected expense, whether it’s a medical expense or kid expense or who knows what could throw you completely off your game. So I understand that’s one reason why a side hustle could be effective. You also talk about how there’s more opportunity now than ever. So you wrote the $100 startup in 2012. Side Hustle was about two years ago in 2017. What’s changed in the world of the side hustle in the last two years?

CG: 04:21
You know, more than ever, there’s this mainstream recognition of it. It used to be kind of a strange thing, but when I started, I didn’t know a lot of other people who had side hustles or we’re doing online business and this goes back like 20 years, whereas now it’s almost kind of expected, you know, like you walk into a coffee shop and like every single person there, it was like working on their project or whatever. So I think, you know, along with the mainstream acceptance, um, you know, more tools, more technological tools, more platforms, just more and more ability to, to get your work out to people, whatever kind of work that is. And more and more people like around the world as well, coming online and beginning to embrace e-commerce. You know, I, I hate to, I hate to use the word easy cause I never say like, oh this is easy. Right? But I think it’s never been simpler. Like the opportunities have never been as plentiful as they are now.

MU: 05:08
Does someone have to be on social media or have to be really familiar with ecommerce platforms to have a successful side hustle today?

CG: 05:15
I mean I’m not really good at social media. I kind of look to you for social media. You know, I’m like, what’s Melissa doing? Like I need to keep up with her and ecommerce. I’m not even selling that much ecommerce stuff myself now. There’s a lot of different things you can do and there’s so many different things. That’s why like with the side hustle school and now the new book, like I’m trying to just shine a spotlight on so many different categories and ideas and approaches because you know, it’s not a one size fits all thing, but there is something for everyone. So, so yes, I do believe there’s something for everyone. I think everybody can do it. , but there’s lots of different ways they can do it and that that to me is one of the beautiful things about it.

MU: 05:49
What I love so much about your book is that you’ve interviewed like hundreds, thousands of people about their side hustles. You’ve taken their stories, their successes, learnings, their experience, and you’ve categorized them and you’ve put some practical application in there so that when people are reading through the book, they’ll see their own situation, their own, their own scenario, their own opportunities in that. I think that approach is going to be really, really helpful for people. What I also love is that there’s a huge mix of people in your book. So you have some who have taken their side hustle and turned it into a really lucrative full time job and you have others who are just making you know, a little extra money on the side.

CG: 06:24
Sure. Well thank you for saying that. First of all, , my whole goal with this book is to show instead of tell basically, you know, my whole book, my whole goal is to say like, here are all these different stories. Let their stories kind of come through. It’s very much, that’s very much the goal is to just break down objections and for somebody to kind of flip through and be like, Oh, you know, I could do this. Or Oh, that thing is kind of crazy. That’s kind of weird. I wouldn’t want to do that myself. You know, as you said, like this range of different stories, different perspectives. And , some of them go on to be really big. Others, $500 a month, $1,000 a month, you know, $2,000 a month is a lot of money can make a huge difference in a lot of people’s lives.

CG: 07:00
So I get just as excited about some of those kinds of stories. You know, like if I go on a tour and I was asked the audience, like who here has a side hustle and do you remember the first time that you got paid for something and people’s eyes always light up and they’re, they’re just so excited. It’s just, it’s just so empowering as I said, as for the goal. Like is it your goal to, you know, have a, have a company, is it your goal to make extra money? That’s an individual question. You know, some people are in this situation of maybe even being, you know, desperate or like I need to make a change in my life. Like fundamentally right now or other people are like, I want to be entrepreneur, wants to have a business, but I can’t just like walk away from my job. I have a family, I have responsibilities, I have, you know, bills to pay and all that kind of stuff. I also think it’s okay to just start, you know, it’s okay to just like not have a huge business plan, not necessarily know where you’re going three years from now or five years from now. I mean, who knows that like most people will have no idea.

MU: 07:51
Yeah. I’ve never had a business plan a day in my life for better. And I do remember the first time I got paid for my work and I remember thinking to myself like, oh my gosh, this is a real thing. Right? It’s like a thing that I’m doing. I think when you talk about side hustles, because there’s such a big kind of entrepreneur culture, especially on social media, people immediately go to this idea of like, just follow your passion and turn your work into something you love and it won’t feel like work. But it’s not really practical for everyone. Right? Like we can’t all be living our dream and making our money that way.

CG: 08:23
Yeah. I mean it’s really problematic to, to tell people, you know, just go follow your passion and the money will follow because there’s all kinds of things that we can be personally excited about, you know, but are not necessarily bringing value to others. And that’s fine. Like there’s stuff you have to do for yourself, stuff that you believe in for art, for love, for whatever. But when it comes to making a side hustle or when it comes to turning something into some sort of money making project, it has to be something that you enjoy. So I guess I, I do believe in that. Like I think it’s important to do work that we enjoy because there’s all kinds of stuff we could do. Why not choose something we like, but at the same time have to have value for other people. So maybe a better question.

CG: 08:58
This is a good little like listener assignment. Perhaps a better thing than saying like, Hey, what are you passionate about? What do you like to do? Is to take more of an inventory of your skills and like, what are you good at? You know, what, what are you good at? What do other people notice that you’re good at? Because you might not always know that yourself. If you ask some of your friends, your colleagues, say what you know, what do you think I’m particularly gifted or talented at? If you think about all the different training you’ve had, whether it’s formal education or elsewhere, , all the different experiences you’ve had or just even like the hobbies that you’re kind of, you know, really knowledgeable. And I think starting with this list of, of skills, um, can often be more helpful than starting with your list of passions. Most of the time what we’re really good at something we tend to like that thing anyway. So following your skills rather than your passion can be a better start for a lot of people.

MU: 09:42
That’s so smart. I love the idea of asking someone else, what do you think I’m good at? Because it’s often really difficult to assess our own strengths and weaknesses. It actually reminds me of another tip that I read in your new book, which said, you know, as you read through the book, look at the stories that you identify with the most and then see if you can think of another way those people can make money. And I thought that was so smart because it’s always easier for us to like solve our friends’ problems or see our friends opportunities than it is our own. So you turning it around in this way and saying, look at this case study, can you see other ways that this person could succeed is a really smart way of getting them to kind of apply that information in their own life.

CG: 10:22
Yeah. Well thank you for saying that as well. First of all, I feel really fortunate to be able to tell these people’s stories. I think they’re all doing just really awesome stuff. And some of them, , to the point you were just making before, a lot of them are solving problems. They are solving problems that they may have had themselves, , that they may see in someone else’s life. , they’re, they’re saying, okay, here is this, this need that people have. Maybe I can meet that need. Maybe that will then lead to something else. And it just kind of following things organically. Um, I, I think is, I think has value. People often ask me like, did you have like this grand strategy, you know, to do everything that you’ve done? And I’m like, not at all. I had like one thing at a time. There was one thing I was interested in and I went and did that. Then I got excited about something else and then I did that. And then, you know, looking back, you can see like the building blocks, but you don’t always know that looking ahead and that’s, that’s okay.

MU: 11:09
That’s so true. I want to ask about some commonalities. You’ve seen, you’ve interviewed, I keep saying hundreds or thousands. It’s like tons of people about their side hustles. You’ve seen the ones that have done really well. You’ve talked to people who have failed and then maybe rebuilt. What are some big picture commonalities that you see across people who have a sustainable, successful side hustles?

CG: 11:30
Yeah, that’s great. Um, first point might be curiosity. First point is like an identifying a side hustle or identifying a business idea and just being curious about something, willing to then explore that curiosity. You know, recently did a story about this woman who’s done like DIY flowers, you know, for a wedding essentially. And she’s saving people like lots of money, you know, all across the country and she’s also doing really well herself. Um, there’s a guy who’s doing weighted blankets and he’s put together this whole campaign around it. , somebody recently who did, um, Instagram soap and she’s making tens of thousands of dollars a month, you know, on and on basically selling stuff through Instagram. So curiosity, willing to say, willingness to say like, I wonder what that that’s about. Could I do something with it? And then, um, perhaps, you know, just kind of starting quickly rather than getting bogged down into a lot of planning, um, starting without a lot of money.

CG: 12:20
Like I actually think starting without him, without a lot of money is a benefit, not a hindrance. Um, if you can kind of just be resourceful and bootstrap and get to that first sale as quickly as possible. You know, in the time to invest in your business is when your business is successful or when you really believe it really does have the potential to be more successful. Those are the first things that come to mind, like curiosity, willingness to take action, um, and then just willingness to follow. Okay, what’s the next step? How can I do one thing every day because I don’t have a lot of time. Let’s say most of it, most of the listeners probably don’t have a lot of time, but can I do one thing every day, maybe 15 or 20 minutes a day to get me a little bit closer to the goal that I believe in? You know, if you can do that, then I think you’ll be successful.

MU: 12:56
I like that. I did that kind of 10 to 15 minutes a day when I was starting off with whole 30 stuff at, you know, nights and weekends. Is there a role in this kind of getting your side hustle off the ground in giving stuff away for free. I gave a lot of stuff away for free in the beginning with Whole30 that I could build my material and get feedback and build community and trust and loyalty. Where do you draw that line between giving stuff away for free because you really want to like get your name out there and maybe you’ll work for trade or maybe you’ll do this like Instagram posts for free. How do you know when it’s time to start charging what you’re worth?

CG: 13:28
Yeah, I think that’s just going to depend on the kind of business or industry for an ecommerce business it could be one thing for a more content driven personality. You know, brands could be something different. I also kind of fell on that side of let me see how much I can give away. Um, and my business model now is pretty much 80 to 90% of my work is either free or you know, accessible at a very low cost, you know, through a book and you can go to the library and read the book, you know, that’s fine. Um, and so probably only 10 to 20% is for sale, but because of how things work, you know, with the Internet, the scalable model, et Cetera, um, I’m able to have a sustainable business with that. So I tend to lean more on that side. But philosophically speaking, I think, you know, giving stuff away for free, serving your audience, doing whatever you can to think, how can I help this person that’s only going to help you as well in the longterm, it’s only going to just build value and trust and empathy, you know, between you and that person.

MU: 14:17
I agree wholeheartedly. And even if you are selling a product and you can’t afford to give your, you know, weighted blankets away for free, you can still give your time and your energy exactly. Some research into why this, this is helpful. You can do a case study with, you know, a mom who uses it to help with her son. There are other things that you can do to, like you said, build connection and offer service and and build that loyalty so that when you do have something to sell, people are more willing to buy it.

CG: 14:40
Yeah. I think it’s always good to ask yourself if you’re trying to grow a business like and you’re not sure what to do because there’s so many different things we could do and people are often overwhelmed. If you’re looking at your 20 minutes a day or whatever time you have to spend on your business and you’re not sure what to do. I think if you do two things, number one, you do something that helps you make more money. Whether that’s developing a product or thinking about a promotion or sending an email about a sale and a second thing you do something that helps people. These two things can be connected of course. But the second thing is like is there someone that is looking for something that I can provide? Is there this need that I’ve noticed that I can address? Not necessarily in a way that’s going to, to have me get paid more, but in a way that’s going to be helpful. I feel like those are two good, good directions to go in as you try to grow your business.

Speaker 4: 15:21
That’s so great. You’re preempting a question I had, which is, if you’ve got a hot a side hustle and you don’t, it’s not taking you where you want to go. [inaudible] what should you do when you just get people to really brilliant action items. So I love it. I love it. Thanks. What might be some common mistakes that you see with people who are trying to launch or, or maintain their side hustle?

CG: 15:44
Yeah, sure. Well I think this actually kind of kind of relates to that question as well because , to the part about, you know, when something isn’t going super well, I’m a big fan of actually just stopping things too. Especially when it comes to a side hustle. Like, if you’re trying something for awhile and it’s not getting traction, then you know, maybe the answer is to do some, you know, analysis and, or to work harder or to try a different direction or something. But it’s also could be like, this is not the project for me. So maybe if you actually let go of that project and try something different, you’ll be more successful. And if I think about my own life as well, like, you know, I, I tend to do to do better when I let go of things that aren’t working and focus on what is working.

CG: 16:21
And it really depends on your own situation. If you’re really motivated for something and you believe this is the, the answer, then of course, you know, they would see what you can do to course correct. Um, but if you’re like, you know what, I thought this was a thing for a while, but now I realize that it’s not, or maybe it was for a time and now I have changed in some way, then it’s perfectly valid to say, what else could I do? You know? And I might, you might actually find yourself feeling reenergized, um, through that thought process.

MU: 16:44
That’s really good. You’ve got to get your ego out of it too though, don’t you? Like, yeah, of course. If you invest so much time and energy into something and you tell everybody you’re doing it and you think it’s going to be really successful and then it’s not like you have to be able to check yourself enough to say, okay, we’re gonna, we’re just gonna like pivot in a different direction and it’s not a failure. It’s an excellent learning experience.

CG: 17:03
Sure. Yeah. I mean, like you said, ego is, is a tough thing, but the alternative is, you know, you’re just going to keep kind of walking on that treadmill and not really getting anywhere. Ultimately, you’re going to be in a worse position than you are and saying, you know what? I’m going to try something different, which I think is actually a very brave and courageous, you know, for, to let go of something and to try something new.

MU: 17:21
It is, it is very brave and courageous and that just might be the thing that leads you to, you know, the perfect side hustle for you. You’ve mentioned a few times that your philosophy is about encouraging people to do side hustles around their jobs, around their responsibilities, around their kids, within their limited time because we all have these responsibilities. Yes. How do you prevent your side hustle from becoming a major burnout?

CG: 17:44
Yeah. This is something that that I hear about all the time. I mean we do have stories of people that are, that are like, actually it got to where it was taking all my time and it got to where it was this conflict, you know, between either my family life or my other personal life or with my day job or whatever. That’s why I think it’s important to have goals and to ask yourself, you know, and to repeatedly ask yourself because the answer could change. Why am I doing this? And usually the answer in one way or another connects to freedom. Whether it’s just the freedom of being able to pay off my debt. Like, I feel like I have this depth, it’s a burden in my life. I want to deal with it somehow or just to have some extra money, which is also totally fine and valid or I’m actually trying to create like an off ramp from my job to be able to go into this full time.

CG: 18:24
I think once you, once you understand what your goals are, then you know how to handle these situations of potential burnout or am I doing too much? You know, I’ve had a number of stories of people who are searching for that off ramp and so they do understand that there is a season in which if things start to take off of their side hustle, it is going to be really busy and they might have to make up, you know, a bit of a compromise and they know that they’re not doing that, you know, forever. Hopefully. Um, but then also if people are like in a different situation where they like their job, they’re just trying to do something different. It’s a creative outlet or they’re trying to build, you know, an additional income source without necessarily going full time. Then it’s also a perfectly valid answer it to say I’m going to scale back and say I’m only going to work with you know, certain number of people. I’m only going to have this product for sale for so long. I mean whatever you have to do to kind of constrict yourself and say this is my side hustle space and you know, I need to maintain that the other space in my life as well. Right. I think if you connect your short term actions to your longterm desired results, then that kind of makes it all worth it.

MU: 19:20
When I was working my insurance job, I was balancing this nine to five with pursuing this whole 30 and trying to make the program grow and at some point I realized I was doing both poorly, right? And I had to make a decision. Are there other triggers to help people know when the time might be right to like jump in with both feet?

CG: 19:38
I think there are, I mean, so the answer is it depends, but I think there actually are some really specific things you can look at to make that decision. And what you just said was one of them, like another one is ask yourself just financially with your situation, what is the minimum amount that you need each month to be okay, essentially. So not just to pay the minimum amount of bills but to be okay, , that may be less than your current full time salary. Now ultimately of course, you know you want to do better than that, but if you’re trying to make a transition and like can I actually go all in with this now? I think that’s, that’s like the number that you start with. And then also you ask yourself, if I invest more time in my side hustle, do I think I’m going to make more money? Right? Are there things that I identify that I know if I, if I only had five more hours a week to work on it, then I’d be able to make x more money. If you can kind of see a direct connection there, then it can give you a lot more confidence to say, okay, maybe now is the time to do it.

MU: 20:29
I like those tips for people who have a service based side hustle. It can be a little bit hard to figure out how much to charge for your services and how much you’re worth. You know, it’s easy if you’re making widgets, you look at how much it costs and what your you want, your margin to be. Service is harder and it’s very difficult to charge what you, your services are worth. And people generally undervalue what your services are worth, especially if you’ve been giving them away for free for a really long time. Any tips for helping people with a service based side hustle? No. What their worth is and charge what they’re worth.

CG: 21:02
So I think it’s also helpful to look at what is your floor. So it’s Kinda like the, the previous answer about your budget. You know, obviously you want to make more than your full time job. You want to do well that’s great, but, but maybe just identify like, like what is the minimum in an hourly rate or daily rate or whatever it is, you know, that I feel comfortable with. And then you kind of say, okay, I’m not going to do anything less than that. And then, you know, if I can go more than that, that’s great. Um, you can look and see what competitors are doing. You can maybe create a new service that doesn’t actually have an easy comp, which can work to your benefit I think because then you’re, you’re the kind of anchor, um, for what that price can be.

MU: 21:37
Do you think that if you have a service based side hustle, this is maybe getting into the weeds and do you also need a source of passive income? Because if you’re a service based, because I, so you are your own rate limiting factor in that like you can only give so many haircuts a day or knit so many beatings.

CG: 21:51
Right. Um, I think it certainly helps a lot of the side hustles in the book. Some of them don’t actually make a lot of sense using a traditional business plan analysis. And so I like to be mindful of that because you know, there, there’s a guy in that book who developed an APP and basically signed up for an affiliate program. There’s a whole long story, but the short version of it is he signed up for this program. He started getting these affiliate commissions of tens of thousands of dollars a month and he was in the army before. He didn’t have like a, a great income or anything. And over the course of the year he actually received hundreds of thousands of dollars in commission. Like a completely changed his life. Um, passive income is good and if you have a service based business, I think there’s still ways that you can achieve that. I mean, can you get people on retainer? Can you have clients make a commitment for a certain number of months? , because then essentially you have passive income or at least you have recurring income, let’s say. I mean you still have to do the work, I understand, but it’s recurring. You can at least count on it. There could be some kind of product they create in addition that could lend itself to that passive income kind of framework. Or they could, you know, partner with other people who do something like that.

MU: 22:50
I was thinking of the story in the book of the woman who created like a course to teach people how to bake bread, right. Instead of like baking bread for people or like doing one on one classes. She created this virtual experience to teach people how to bake bread, which I thought was so smart and interesting.

CG: 23:07
Yeah. And she’s doing really well. I may of course about sourdough bread in particular, I can really niche down, you know, and then she actually made like four or five more courses on Udemy. I’m all about sourdough bread, like advanced sourdough, intermediate side. Like it just goes on and on. And um, I, I like that story because it’s like you always think of like technology stuff and like somebody teaching about programming or about making apps again or whatever. But a very, very simple skill. Baking bread. And also, you know, there’s lots of ways to learn how to bake bread. I don’t have to go on Udemy and pay for her course learned to bake bread, but like so many people are doing so because they’re attracted to her personality and her message and our brand. So I think that’s, that’s another lesson to take from that whole thing.

MU: 23:45
You mentioned U-demi, everyone knows about Instagram, everyone knows about Facebook. Are there any other really interesting platforms that people are using for their side hustles?

CG: 23:54
Oh yeah. Um, I’m not always good at that because I like to encourage people sometimes to, to kind of do their own thing and not be reliant on any particular platform. But U-demi is good for, for online courses. Um, there’s a few others like skillshare, creative, live, linkedin learning, which is what used to be linda.com. Um, a few things like that. But, but in general, when I think platforms I think of those things is kind of started platforms like Etsy of course is a wonderful marketplace. A lot of the most successful people that I profiled who’ve gotten started on Etsy tend to eventually like go off into their, to their own website, but it’s a great way to like jump in because you don’t have to make a website, you can start selling something right away. They have a huge marketplace of people, , but then maybe your goal is to to actually have your own website in the long run so that people can buy from you directly.

MU: 26:50
I would love for you to share a story of one of your more inspiring side hustles, but also one that speaks to where you think side hustles are going in the next few years.

CG: 27:02
Wow. Okay. I gotta get my crystal ball out of the desk here. Okay, so here’s the one that’s really good and this is in the book. This is a guy who makes teddy bears and their their teddy bears that are actually licensed with the u s military. So he’s got like these marine bearers and army bears and navy bears and they’re all about helping kids sleep at night and he got it started. You got started with it by creating one called Sergeant Sleep Tight. His daughter was having a hard time sleeping and like he made this bear and put a little uniform on the bear and, and set all the, you know, the bear’s going to like, you know, watch out over you at night. Um, and it worked really well for her. And so he started figuring out, how do I actually do this?

CG: 27:41
Like, he wasn’t, you know, in the teddy bear business. He never made any kind of product like that before. Um, but he learned about manufacturing, he learned about licensing, he learned about distribution, like all these kinds of skills. You just, just as he went along and he didn’t have a lot of money either when it got started, but now that business is doing really well, they were in target for awhile. They’re in some other stores. I guess I just see over and over people doing something like that in the sense where they don’t know what they don’t know how to accomplish something, but they find a way to, to kind of decipher it or decode it or to go back and say, you know, how hard can it be to have a product based business where to start my business as a service provider, a coach or whatever it is. Um, there’s gotta be a pathway forward. I would say the main thing that I see like looking ahead is just more and more people becoming comfortable with that and understanding that it’s, it’s something that they have to do in some ways. Like we said, it’s important to have more than one source of income, but also that this is a, a really good thing to do. It’s a fundamentally positive, affirming, empowering thing to do for yourself. Um, and I hope that more and more people will be able to do that.

MU: 28:38
That was the perfect story to close on. Also, my heart is exploding at the idea of these military bears keeping kiddos comfortable and safe and secure at night. That’s really, really sweet. At the end of every episode I ask, what’s one piece of advice you can give to someone who is ready to do the side hustle thing?

CG: 28:58
Great. Um, I think we’ve talked about a couple of things already. Talked about making a list of your skills, like make a list all the things that you’re good at. Um, the next thing I would say is ask yourself if I had to make three to $500, you know, next week through it, through a source that I haven’t used before, how would I do it in my tip for that is like if you’re really not sure at all, um, think about buying and selling because reselling is probably one of the most simple, easiest things you can do for a side. Also, it’s how I got started 20 years ago. I had no idea about any of that, any of this stuff, and I just learned to buy some things and sell it on Ebay and that kind of changed my life. Um, and then like I’ve been doing all these different projects since then. All because I learned I could buy something for one price and then sell it for something else. And so ask yourself, if I had to make to $500 in the next week, you know, doing something that I haven’t done before, what would it be?

MU: 29:45
Wonderful. This has been so chockful of practical application, which I absolutely love. Tell people about your new book, which comes out today. By the way, congratulations on your book birthday, but tell people about the book and where they can find you and learn more about your work.

CG: 30:01
Awesome. Well thank you so much. I have really, really enjoyed this conversation. I prospected your work for a long time, so I’m so thrilled to be, um, to be in the next year. And the new book is called 100 side hustles, unexpected ways to make additional money, , without quitting your job. And so that book should be at any book store or amazon.com or wherever you like to shop for books. My name is Chris Guillebeau. You can listen to the podcast side hustle school, which is on the armored project, just like Do the Thing. And I’m also doing a 14 city tour, so you can learn about that at sidehustleschool.dot com/tour

MU/CG: 30:32
You’re going to come to salt lake so we can do something together, right? Absolutely. 100% Yay. Chris, thank you so much for talking to me today here and Do the Thing. I really loved our conversation. Thank you, Melissa. It’s a huge honor.

Thanks for listening!

Continue the conversation with me @melissa_hartwig on Instagram. If you have a question for Dear Melissa or a topic idea for the show, leave me a voicemail at (321) 209-1480.

Do the Thing is part of ‘The Onward Project,’ a family of podcasts brought together by Gretchen Rubin—all about how to make your life better.  Check out the other Onward Project podcasts– Happier with Gretchen RubinSide Hustle School, and Happier in Hollywood.

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