MGU 54 | Financial Uncertainty


Just because the world is put on hold due to the COVID-19 Pandemic doesn’t mean your life has to. Most especially in this time of financial uncertainty, it can be very difficult to keep still without thinking about our finances. In this episode, Jason Wrobel and Whitney Lauritsen talk to author and host of Side Hustle School, Chris Guillebeau, about maintaining to live a life in abundance even during times of uncertainty. They zone in on the issues people face with making money now, offering some great unconventional insights and strategies on how to keep yourself productive. With his upcoming book, The Money Tree, Chris provides some sneak peek into the very timely story of overcoming financial struggles in life. Touching on the stress these trying times brings out, Chris then talks about mental health and recommends some practices that help manage anxiety.

Listen to the podcast here


Staring Down Financial Uncertainty In The Midst Of The COVID-19 Pandemic With Chris Guillebeau

Making Money During Times Of Uncertainty

I feel like a good place to start, Chris, is to admit something that’s slightly embarrassing. In time, I’d have vivid dreams and one time, you’re in my dream and we’re at a grocery store shopping.

Am I helping you picking avocados or in the almond milk section?

What I want to know is was he clothed?

Yes, for sure.

I do live in Portland, Oregon, at least a lot of the time and in Portland, it’s not a thing to see somebody in any attire or non-attire.

Is, “Keep Portland weird,” the official slogan of the city?

Which interestingly they stole from Austin, so they can’t claim it to be their original slogan. It is accurate and reflective. That’s good because who wants to be normal? The alternative of weird is normal. Why would you want to be that?

That reminds me of a book that I finished reading. There are two books, Chris. One is Status Anxiety. Have you read that before?

I have.

I have never heard of it. It was quite eye-opening. They talked about many different things. That book is incredibly in-depth. Jason, I feel like you would love that book. They talk about the rebellion against society, the desire to fit in and the whole history of how humans have had this desire for status. The other book I was reading and I’m almost done with, which I’ve been loving, is called The Anatomy of a Calling. Chris, your name was mentioned in it. It was like this random moment. That’s something the two of you have in common. You both know the author. I was randomly reading along and all of a sudden, your name pops up. I forget what the context was. Have you read the book or do you know that you’re in it?

I did quite a while ago. I may have blurbed it, if not that one, a different one of Lissa’s. I’ve known her for maybe a decade.

Chris, I know we have some things that we want to have an expanded conversation. Things about abundance and facing financial fears and self-worth fears in a time of great stress and strife. I want to get back to cats. What is it about the feline energy that seems to appeal to you? Why are you attracted to cats?

Cats do what they want. Cats don’t care basically. I’ve always been like an independent thinker for better or worse. I was fortunate to have something like life-forming experiences, dropping out of high school and later going to college. Navigating this whole early adulthood thing in a different way than a lot of my peers did. I spent a number of years in West Africa as an aid worker. I always had this independent path. I respect that trait in cats. They’re fluffy and fun to be around. It’s nice when they sit on your lap. Even though they are independent, they do what they want. My cat at least is co-dependent. She likes to hang out with people.

What is your cat’s name?

Her name is Liberia or Libby.

That also reminds me of how I was reading the books I talked about, which is Libby. I’m anxiously waiting for your new book to be available on Libby. That’s how I get a lot of books is to go on there and get the Kindle or audiobook version. It’s neat because I’ve always loved libraries. It’s neat to be able to borrow books digitally. I do all my highlighting there, so I can return books without all the notes scribbled in them. It’s such a great resource. Do you use that as well, Chris?

I don’t use it actively. I do have it on my phone. It’s a wonderful thing. I’m a fan of libraries as well. I like to support them. It’s a great way to bring that into people’s households or wherever they are. I always want my books to be accessible to anybody in any form, whatever is best for them. That makes me happy.

It’s also nice from a minimalist perspective and for you as an avid traveler or somebody that has been bouncing around the world a lot. I’ve been reflecting a lot about book ownership. I’ve always loved having books and Jason too. Jason has many books. He doesn’t know what to do with them. Whenever I did the life-changing magic of tidying up and going through all my books, it gave me perspective on what it means to have a book. A lot of times, they sit on our shelves and we pick them up once in our life and they sit there the rest of the time. I started borrowing books through Libby and you can still highlight them. It saves all your highlights and you can get them again and again. It’s been a wonderful process because it’s kept the clutter down in my life.

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I read eBooks and I still like print books as well. I like all formats and sometimes audible.

That’s the one trick I know Jason’s passionate about having physical books. I enjoy it, but I feel conflicted because I don’t like them taking up all the unnecessary space. It feels like a waste when you’re done with a book and you’re no longer reading it.

You could pass it on to somebody else at that point. It goes back to what you’re talking about being intentional and does this spark joy? Does this have a place in my life? As long as it does, you keep it there and if it doesn’t, it can go perhaps to someone else.

Unless you’re like me and you highlight every book that you read and put notes in it. I always feel awkward passing that onto somebody else because I don’t feel I can comfortably read a book without putting notes, highlights, lines, all sorts of things in there.

Is it because you know that person or you’re worried about what they see or is this you don’t want you to go like a book that you feel has been defaced in some way?

It’s more the latter. It’s not that I’m don’t want people to see what I’m highlighting. It’s more that I don’t want to ruin their experience of reading the book. It could be helpful.

It shows them what to focus on.

Do you do that too with your books?

I do. I don’t highlight a lot, but I will sometimes make some notes in the margins and such.

It’s a little bit of an obsession. Do you know what’s neat is that highlight a book in the Kindle, which can be connected to that Libby app, you can go back and search through all your notes. I use that for a lot of my projects. I have all of my notes from books that I’m reading. Anytime I want to go back and reference something, I can go and search for a keyword in my highlights and have all of my notes from books in there. It’s a nerdy process.

To me, my relationship with books is something that is a massive carry over from childhood. Whereas instead of going to sleep with stuffed animals as a young child, I would go to sleep with books. I started reading at a very young age. I don’t know if abnormal was quite the word but unusually young age. For me, having a physical book, I do realize it probably contributes to clutter and I probably realized that it’s not exactly going in the direction of the minimalism that I would like. There’s something about the tactile smell, sensation and feel of having a physical book that for me having a Kindle or a tablet, it doesn’t quite replace that feeling for me.

The other thing, Chris, this visual of the money tree in your book. Another thing that I’m a little embarrassed to admit, but not quite because we’re at the time of quarantine and physical distancing. First of all, let me ask you a question. Do you use, watch or contribute to TikTok at all?

I do not actively use TikTok. Once in a while, usually when I can’t sleep or something and I’m up for an hour in the middle of the night, which happens a fair amount. I’m like, “Let me watch some TikTok videos.” I like to keep up with what the kids are doing.

There are some good cat videos on there. Jason found an amazing one he sent me.

I observe from a distance.

MGU 54 | Financial Uncertainty

Financial Uncertainty: There’s something that only you can do, and you should do everything you can to try to figure it out.


I feel like you could create some great content. There’s a lot of good travel content on there. Maybe you can upload old videos or something. Because of TikTok, that’s been fully integrated into my life. I got into this game called Animal Crossing. Have you heard of this or come across that?

I have spent a lot of time playing Animal Crossing.

That makes me happy, so I don’t feel alone. I’m brand new to Animal Crossing.

What did you name your island?

This is also embarrassing because I got the game, I decided to call it Corona.

That’s an island that a lot of people are living on. You can never change it.

These are the things I’m learning. Sometimes you’ve got to name it. It’s founded during a certain time and I’ll never forget the history of my island on Animal Crossing. The reason I bring it up is I learned through TikTok, which is where I’m learning a lot of Animal Crossing strategies is that you can plant money trees. There are different versions of Animal Crossing. I don’t know if this is like New Horizons, which is the new version of it or if that’s been around for a while. Do you have any experience with money trees in Animal Crossing?

It was a long time ago that I played the previous incarnation of it. It’s been a few years or something. I don’t remember if I had a money tree in that or not. I have seen it in the new one that they have them. I’m looking forward to discovering that.

Maybe you can create some TikTok content around the money tree and Animal Crossing. That’s what the kids are all about on TikTok. It’s a nice segue too because the reason that I decided to download Animal Crossing was that many people were talking about how it helped them feel calmer. Culturally as a society, not necessarily as individuals, but many people are experiencing anxiety and stress. They’re looking for outlets. They’re looking for an escape.

I was curious about what that experience was like through Animal Crossing. It’s interesting how people can be a bit opinionated when it comes to things like, “You’re wasting your time playing a game.” If that is making you feel less anxious, if that’s giving you a calming feeling or a temporary distraction, I feel like it can be helpful. It’s funny how I’ve been observing myself play this game from my personal level of an outlet. Also almost like from a professional standpoint of trying to understand why people enjoy games like this.

It goes to that old saying about how time you enjoy wasting is not wasted time.

That’s interesting to me because what I reflect on and I was discussing this with Whitney, Chris, that many of the coaches, thought leaders, a lot of people on social media who are in the motivational realm. I know that’s a large umbrella to classify people under, have been putting out a lot of messages about using this time to be incredibly productive, to build toward your dreams and to keep a high vibration, keep hustling and keep moving forward. It’s interesting to see that there seems to be this pressure coming from certain people of like, “Make the most of this time.” Some people are like, “I want to eat vegan pork rinds and play video games. That feels productive to me. That feels good.”

To me, I’m trying to be in a state of non-judgment. Not so much toward others, but toward how I feel I’m spending my time because I do feel there’s this subconscious pressure that I start to feel of I’m not doing enough, which is part of my whole lexicon of not-enoughness in general that I’m still fighting. Especially having all this time at home, I’m curious, what are your relationship with productivity, abundance and work that you’re indoors? What’s been your dance with that consciously?

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I’m on that side of use this time well. What that means is going to be different for different people. I understand if somebody needs to getaway. I understand that people need to withdraw. I totally accept that. I’ve had different mental health issues on my own in the past and had to deal with them in different ways. This is why it’s an individual answer. For a lot of us and certainly for myself, I do want to use this time to invest in myself, see what I can create and see what I can offer to the world. Try to see it as an opportunity because there’s not much I can do about it.

There’s not much that most people reading can do about this global situation. First of all, it’s like shout out to everybody who is working in the medical field, first responders, everybody in the hospitals, etc. They’re on the front lines. For all the rest of us, what can we do? The first thing we can do is we can be safe and we can try to keep other people safe. We know that. That is fairly passive. For me, it’s like, “What can I do actively?” The only thing I can do is create. I am motivated to create. For me, it’s not a burden. It’s more of an imperative. It’s more what do I do when I wake up in the morning?

I want to make something. Maybe that’s problematic in some ways to like base my self-worth on what I produce. For me, I’ve found the right balance. There’s that whole question about if you could do anything, time and money were no object, what would you do? I feel that for me the answer is like what I’m doing pretty much. I would be writing books. I would be trying to reach people with a positive message. I would be trying to provide practical tools. That’s what I like to do. There’s a place for the challenge. There’s a place for saying like, “Use this time well.” If you need to withdraw, that’s fine. If you find yourself watching Netflix or whatever all the time and you don’t feel great after that, maybe the answer is you should be doing something different.

It requires a lot of us to be self-aware and tuned in to how we’re feeling during all of these different daily experiences and what makes us feel our best. To piggyback off that conversation, one thing that comes up for me is this is such a great time for a book like yours to come out, Chris, about money because a lot of people are terrified about their finances. That’s part of the stress that people are feeling. It seems like part of the world is looking at this almost from a break standpoint. “I don’t have to go to work so I can relax a little bit more than usual.” “I don’t have to go to school, so I don’t feel like I need to get dressed in a certain way or have to rush on to campus.”

All these different things that we think about when it comes to work, our careers or education. Those have been removed and most of us are still doing something unless you were completely laid off or whatever happened with your job and you don’t have any work. A lot of people are having different responses to it. I feel like one of them is this fear that if you’re not productive right now, the time is wasted and that you won’t be making money as a result. This is another thing Jason and I talk a lot about is like the hustle culture. You have to keep going all the time. You have to keep hustling. Otherwise, you’re not going to get where you want to be career-wise, which is usually tied into some financial objective.

You’re talking to the person who wrote the book, Side Hustle. I produced the podcast, Side Hustle School. That is a belief I validate for myself, but I try not to put it on other people. It’s not about judgment. I know that there are a lot of people out there who do feel better when they are doing something. It’s like if the shoe fits. I’ve tried to be like building up to be like that for several years since I started the article nonconformity. I remember when I started that and I went on my first book tour. It was this crazy experience of going to all 50 states, every province in Canada and some places I’d have ten people that came out.

I tried to build relationships with those people. I had all these interesting conversations because I’m trying to put forward a bit of an agenda, trying to challenge people, present these unconventional strategies for life, work and travel is what I called it at the time. Sometimes, I would get emails from people because I always said my market is discontented people. Anybody who’s dissatisfied, anybody who’s discontented, which is not the same thing as being unhappy. It means like you’re looking for something more than what you have. Sometimes I would get emails from people and say like, “My life is good. I don’t want to change. What do you have against me?” I always thought that was funny because I was like, “I’m not against anybody. I’m a recruiter. I’m not an Evangelist.” I’m not happy with the way this is. I need to make some changes for myself. Nobody is coming along to rescue me. What can I do? Those are my people and that’s what I try to attract and to serve.

I’d love to know what your definition of hustle is?

MGU 54 | Financial Uncertainty

Financial Uncertainty: If you don’t have the big picture and know what your life mission is, then do what’s in front of you.


I never thought about the hustle. There’s a scrappy pioneering element to it of, “I am trying to start something. I am trying to make something happen.” It’s not necessarily, I’m like doing the same thing all the time, expecting different results. It’s not like I’m trying to do something because other people expect me to do it or I think I need to post all these social media posts because that’s how you hustle. You can think of it either like a high level or low level. They’re both appropriate. A high level is like there is something that you have to do. You have a calling. You have a mission. There’s something that only you can do and you should do everything you can to try to figure it out.

Low-level is life is short. How are we going to spend it? Mary Oliver says they’re like our one wild and precious life. “If you don’t know what your life mission is, do what’s in front of you.” Do the next right thing and there’s always the next right thing. What is it that you can do that either advance your own position, improves your life, which can be your finances? It could be something else or something that improves other people’s lives. That’s what I think about it. I’m always trying to ask what’s next. That would be my superpower. If I could have any superpower besides flying, everybody would choose flying and invisibility like those two. Let’s say I couldn’t have those two. My superpower would be always to know, “What do I need to do next?”

I love your definition of hustle too because it sounds different than mine. It’s important for us to define what words mean to us versus assuming that everybody has the same definition. Sometimes people use words in a way that we assume means what thinking of them. When we had these open conversations to define them, we realize that other people look at things completely differently. Your perspective is much more soothing and meaningful. It sounds nice. From my perspective, I’ve often put a little bit of a negative connotation on the word hustle. It evokes in me this feeling of rushing, pressure and not allowing us to fail. Even for me, I’m like, “What is my definition?” All these negative words are coming up for me and it’s nice to know yours. What about you, Jason?

Hustle is one of those things where it’s a double-edged sword for me because growing up in an extremely blue-collar family in Detroit, Michigan, we have a family motto. The family motto is, “We’ll make it fit. We’ll make it work.” There’s always been this grit your teeth, get your hands dirty, bleed from your eyeballs to do the thing you want to do. There are two sides to that coin though. There’s the coin of the resilience, the determination and the persistence that I feel like was a common ethos growing up in my family. I have at times as an entrepreneur taking that to the point where I’ve put my health in some precarious positions.

You mentioned, Chris, some struggles with mental health. That’s been something that I’ve been dancing with for the last few years. I was diagnosed with clinical depression. I had suicidal ideation. It’s something I still struggle with from time to time, nowhere near as acutely as I did a few years ago. Part of that, around that time was my TV series on the Cooking Channel was out. I was doing my first book and I was working so much that I was ignoring my own self-care and my own health. To me, hustle can be something where for me, I’ve had to learn where my edge is and not push myself over that edge. I know if I push myself over that edge, the consequences of that tend to not be pleasant for my health in particular.

It comes back to self-awareness essentially.

I wanted to touch on a note because I want to thank you for bringing up the mental health component. I had a conversation with my mom, Susan, about there are some challenging things happening with her career and other people in my family back in Detroit and friends of mine. With many people having the proverbial rug pulled out from under them, whether they had a full-time salaried position or perhaps the gig economy. Many people are having what is familiar and what is known completely removed from their reality. What would you recommend in terms of practices to have people manage their anxiety, their stress, their mental health? As a follow-up question, do you feel like this is a phenomenal time for people to having their jobs being evaporated and their rug pulled out from them to start careers as entrepreneurs and doing businesses for themselves?

Thank you for sharing that about your experience as well. I can probably speak more to the second question than the first. Since I don’t know that I’m the most qualified to tell people how to deal with their anxiety. Anxiety has lots of different factors and such. I can speak from my own experience, but that’s about it. Let’s focus on the second part about this the time, with all the change. What it made me think was this is a time of incredible disruption. If you think about disruption on this pendulum with progress. You think of disruption as negative. There are a lot of things happening that we wish were not happening.

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We could press a button or flip a switch, that wouldn’t happen at all. Since we can’t do that, the first thing we can do, and maybe this helps with anxiety as well, is to recognize reality. That’s exposure therapy has been good for me in terms of looking at things as they are, not the way I want them to be. You realize here’s the actual situation. I’ve been thinking of it this way. Maybe I didn’t want it to be this other way, but here it is, what can I do next? For example, to go to the other side. Whenever there’s progress, there are lots of advances in technology, healthcare or education. Whenever there’s progress, somebody else harms. Progress always harms somebody.

When the automobile industry came out, everybody in the horse and buggy industry went out of business is the classic example. In the case of disruption, it’s the opposite. A lot of people are harmed. A lot of the economy is being devastated in lots of different ways. Kids aren’t able to go to school. We could talk on and on about the negative effects. Conversely, what are the positive effects or what does this then allow people to do? I think of it as a reshuffling of the deck. All of a sudden, a lot of things that we have believed or we have put our security in, we understand are not secure.

I have always said that you shouldn’t put your trust, your security or wellbeing in a corporation, a government or an organization, any anything external. Not because every corporation is evil, not because the government shouldn’t provide services to people, but because nobody’s ever going to care about your wellbeing as much as you will. People understand that more. There is an opportunity in a time of uncertainty. It’s like a big theme that I’m starting to explore myself a lot more, write and share about. You always have to look and say, “What is the opportunity? What can I do with this time?” A lot of people in addition to taking care of themselves, which is the most important thing if that involves Animal Crossing, that’s totally cool.

In addition to that, a lot of people are “How can I again use this time to maybe get in a situation where I’m not dependent on my employer, either now or when I go back to work?” How can I create something that if not address this direct need of coronavirus, but some other need that it’s coming out of it, the need for connection and community? What you guys are doing, your work is going to be more and more relevant. That’s maybe an example of something that advances. Everybody is uncertain. Everybody’s afraid. They’re going to come to leaders and resources who are providing some reassurance and also hopefully some practical help as well. It’s good to think about all that stuff. To be self-aware like we said, but also like what is happening in the world and how do I interact with that? What is my place in that?

I am excited to read your book. One of the sections of it in the Amazon description was, “You are never at the mercy of fortune as long as you have an appetite for hard work and a willingness to step outside of your comfort zone.” I am fascinated to see what that means in this book for this character that you write about here and how he’s being evicted. It must be interesting for you, Chris, to have this book come out. A lot of people are experiencing things that your character in this book is experiencing. How long have you been working on this book? What does it like to release something that is like accidentally timely?

It’s interesting for sure. We are in interesting times like all around. For the book, in particular, I started working on it maybe 1.5 years ago. It’s different than all my other books. Most of my other books are how-to. In this case, I am telling a story. I’m still teaching it. It’s like a prescriptive fiction in a way. The goal is for people to read it and enjoy the story, but also go away, feeling challenged and empowered to a certain degree. The main character in this story is having a lot of financial trouble, partly related to these student loans that he had long ago like many people. That’s a major problem for lots of people.

The financial issue affects the rest of his life. He ends up getting evicted. He’s at risk of losing his job, even though he has a good job because a lot of people have good jobs and that’s not enough. It affects his relationship and all that. My hope is that it does connect with a lot of people out there who can see themselves in that situation and maybe identify with how he gets out of it or at least see some hope for themselves and see a little bit of a path for themselves. As for it coming out, that’s interesting. I’ve had to change my whole approach because I was supposed to be going on a 40-city tour. I was excited about it.

I tour for all my books, but I haven’t done a major tour like that in quite a while. I had everything planned. We had all the venues and stuff, the bookstores and other spaces. I had at least 26 plane tickets booked about halfway through the process and so on before we realized that’s not going to work. For me, I have to walk the walk. This is a little bit disappointing, but it also gives me an opportunity to think, “What’s another way to reach people?”

In that regard, I’m very grateful to people like you and your platform to be able to come on and talk about the book. My greatest challenge is can we get this book to people? I do believe if they read it, then it can be helpful to them. There are always many resources out there. There’s so much noise. Ninety-nine percent of the news now is about a single topic. That’s the challenge that I have to embrace and overcome.

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The timing of this specific book is amazing. It’s wonderful. When we work on something and it happens to hit at the right time. Reading a fictional book is very needed. One thing I’ve noticed so much during this time and in general, a lot of advice out there is nonfiction. It’s people giving you lists of things to do or giving you lectures and training. Those are all wonderful, but there’s much of that happening. There’s not enough storytelling. Here you are sharing this book. First of all, it reminded me of one book I loved by Brendon Burchard, who Jason and I reference a lot. He’s made a big impression on our lives. He wrote this book, Life’s Golden Ticket.

That was either his first book or one of the first that he wrote. It’s such a wonderful story similar to yours. He says it’s a story about second chances. The book has many lessons in it. You’re reading it and feeling like your transported into a different world, which is one of the magical things about reading fiction. That opportunity to be transported, as I was saying at the beginning, feeling like you can go on an escape. That’s one of the huge advantages of fiction. You get to go along with somebody whose journey and not constantly be thinking about implementing it in your own life. When you’re reading about somebody’s hero’s journey, which I imagine is probably part of the structure of yours is the obstacles that this person is going through and you get to step out of your own life.

It starts to come back and you reflect on, “I’ve seen this character go through that and that reminds me of what I’m going through.” It’s almost a cathartic experience where you get to play out in your head how this could work in your own life versus taking in somebody’s information and agonizing about how you’re going to apply it yourself. I love that. The same is true with The Alchemist. These wonderful stories that teach us all these great lessons. I’m looking forward to reading your book for that reason. A lot of people will find it helpful and end up beyond. We never know when we’re going to go through something like this again or even when people go through challenges as individuals, as we all do. It doesn’t have to be a global experience. It can be any time of hardship where we need something like this to turn to.

What comes up for me too in all of this situation, the timeliness of your book and the narrative behind it is the opportunity for people to flex their improvisational muscles and be making decisions on the fly. It was Mike Tyson who said, “Everyone’s got a plan until they get punched in the mouth.” As a society, one could perceive this as a great collective cultural punch in the mouth for humanity. The narrative regarding how we ought to live our lives are sometimes structured so much about planning, investing and making sure your portfolio is diversified.

With the stock market being what it was, a lot of people have temporarily taken a hit to a lot of their wealth that they’ve built. One thing that I don’t see as necessarily emphasized in our society and I love to know your thoughts on it is the ability to improvise. The ability to make things up on the fly, the ability to take a spark of inspiration that you’ve never felt before and just go with it. What are some ways that you see improvisation working in your life as a human and an entrepreneur? How do you suggest people cultivate that ability more in their lives?

That is the essential ability. You explained it well there with the Mike Tyson quote. The value that you always hear about is persistence. That’s everybody talks about. Keep going and you fall down twenty times, get up, try again. I did a lot of research for a previous book called Born for This, and looked at all these different companies and individuals. The lesson that emerged was that the most important predictor of success was an adaptation. It wasn’t persistence. It was the ability to improvise. It was the ability to say, “I was going to do this but now this happened, so I must do something else or I changed my mind somewhere along the way.”

Changing your mind is powerful because we were told all the time that changing your mind is this negative quality or your wishy-washy or whatever. If you get new information, the other quote is like, “When the facts change, I changed my mind. What do you do when the facts change?” Do you keep doing the same thing? How do you cultivate that skill? First of all, you give yourself permission to change your mind. You give yourself permission to not keep doing something that is not working anymore or not keep doing something that you no longer enjoy. Those are the two fundamental qualities of side hustling or entrepreneurial success or success in life in general.

It’s like you’re doing something that matters. It does have an effect and impact however you choose to measure that. It could be different metrics or whatever your own standard is. Is it something that you take pride and you take joy? If you get to that point, that’s the golden ticket. If you get to that point where you’re doing something that matters and you can tell it’s having an impact on at least some people and you’re excited to do it every day. That’s why I said to go back to when we were talking about being productive and such. I feel like for me I have found that golden ticket. I want to do everything I can to be able to keep doing it.

You cultivate it by expressing to yourself that it’s okay to change your mind. The more experiments the better. We also put too much pressure on young people, in particular, to know what they’re supposed to be doing for the rest of their lives when the reality is your brain doesn’t develop until you’re 25 or whatever. Most people don’t know their life purpose when they’re 22 or whatever the age is. The way that I found what I’m doing is by trying a lot of different stuff and having a lot of different ideas. Some of it works and some of it didn’t. If I didn’t do those things, I don’t think I’d be doing what I’m doing. I’m very grateful for that.

MGU 54 | Financial Uncertainty

The Money Tree: Finding the Fortune in Your Own Backyard

You have had many phenomenal resources on all these topics and I remember vividly listening to the audiobook version of The $100 Startup. Jason might’ve been with me for part of that. I have this memory of us being in the car. Is that right Jason? Do you remember that?

I believe we were on a road trip somewhere because I do recall listening to it in long chunks. It might have been the cross-country road trip for the Fiesta Movement maybe.

I feel like we were coming back from somewhere in Southern California. I tend to get vivid memories of when I was listening to parts of podcasts and audiobooks. My most vivid memory is cleaning out my closet and listening to that book. The way that I started to reframe all of these different possibilities. That’s been one of the greatest gifts that you’ve given Chris. It’s something that I want to touch upon here for anybody reading whose life has been turned upside down. A lot of the times when we’re shaken out of how we’ve been doing things and suddenly we have to almost like starting from scratch. It can feel incredibly scary because that it’s that uncertainty.

One thing that I’ve loved about your books and your messaging, Chris, is that you talk about all the different things that you can do. The $100 Startup is you can do this with no money or little amounts of money and create this whole business based on your passions and your skills. That’s incredibly important because I’ve been coaching people on things like this for years. I always come back to this idea that there are many different options out there for you, but you have to think outside of your box. Sometimes you do need to get outside of your comfort zone.

One message that has resonated with people is this set of words that we share on our Instagram, which is “If you can’t go outside, go inside.” To me, that means this is such a great opportunity for us to get more in touch with ourselves and figure out what is that we want to do. What is the most important? You talked about the calling and what are our skillsets? What are the things that we can offer the world that is valuable that other people would pay for?

To me, that is always the most helpful piece of advice when it comes to figuring out our finances. Many people are used to going to a, “Regular job,” that 9:00 to 5:00. I also love, Chris, that in your book such as The Side Hustle that you’ve done, you talk about how it doesn’t have to be your full-time job. You don’t have to pursue your passion full-time. You can do it on the side. That’s important to you. That’s how I got started. My whole career started on the side of my 9:00 to 5:00 job. Eventually, I had the confidence, the stability to quit my full-time job so I could pursue my side hustle full-time. A huge part of that was tapping into what I love to do and following that desire. I don’t think I would have known to do that had I not been more connected to myself. That’s the blessing that we have in my opinion.

All those years ago, you were listening to that book and then here we are going to the grocery store together in the middle of the night that we talked about before we began this episode.

I don’t think I’ve ever read your books about your travel. I feel like that’s been such a huge part of your career. I know that it’s impacted a lot of people that I know Jason and my mutual friends named Krista. She was influenced by you that she started traveling around the country in a van and travel for vegan food. That might’ve been the very first time I heard of your work because of your passion for visiting every country in the world. I love that it is still your Instagram handle, @193Countries.

I keep waiting for them to make a new country and then what do I do? It doesn’t happen often. It happens about once a decade.

Has that happened since you traveled?

Yes. It was originally 192 and South Sudan was recognized as the newest country in the world. It doesn’t often happen because there’s always little breakaway states and places that declare their independence. To be recognized as a country by the UN is difficult because Russia has to agree and China has to agree, everybody has to agree.

The most important predictor of success is adaptation. Share on X

Going back in time for you about several years ago when you released The Art of Non-Conformity, which was set your own rules, live the life you want and change the world. Sometimes we say things and we look back on them and we think, “It doesn’t feel good anymore.” For you, how does the word, non-conformity, play out in your life? I feel like that resonates with Jason. Little side note, I imagined close with Gretchen Rubin because she gave you a quote for your book. It’s her that did The Four Tendencies. What is your tendency? Jason is a rebel, which is why I bring it up.

I am as well. I am the archetypal rebel. I blurbed that book on the back as she got blurbs from people from all four of the archetypes and I was the rebel for it. Jason, you and I, you probably know this, but it’s the smallest group of the four and obviously the best as well.

He’s a rebel. He didn’t read the book. I’m the questioner.

I rebelled because I was told to read the book and I’m like, “No.”

It’s an outer expectation that you resist. I’ve had this conversation with Gretchen because when I first took the test and it said I was a rebel, I was like, “I don’t think this is quite right.” She said, “Yes, that’s what every rebel says.”

I love that book because it empowered me as a questioner and made me feel less self-conscious whenever I asked the question of why. I feel like I can back it up. It’d be great to talk about rebelliousness and non-conformity. That’s something I wanted to touch upon before we do is for both of you, you’re very passionate about nonconformity and setting your own rules. What does that like several years later for you, Chris? I’d love to learn from both of you how that’s playing out with the change of the world.

For me, if I go back to why I chose that in the beginning, partly it seemed like this is the value that I’ve embodied for most of my adult life and some of my childhood life too, for better or worse. Everything has a pro and a con, but I identify with it. Also, from a professional perspective of like, “I’m going to be writing about these topics.” What is broad enough that can evolve with me because I had started a lot of different projects and then stopped. I started stuff and did it for a while. I was excited. The ADD part of me, which is diagnosed ADD, not like I have a hard time paying attention.

The part of me that stops projects and loses my motivation and such. I needed something that could evolve, grow and change. The Art of Non-Conformity, the tagline, “Unconventional strategies for life, work and travel.” I was like, “You could not get broader than that.” That’s the opposite of a niche. People are always like, “Choose your niche.” I was like, “Life, work and travel, that’s everything.” I wanted to start with that as an umbrella. To combine a personal and professional life. Here we are several years later. If I look back on everything I’ve done in the past several years, the stuff that has gone well has always been when I have found some different approaches or different take. I don’t want to say pioneered something, but I have not done the same thing that everybody else was doing.

The stuff I tried because it’s not like it’s 100% of that. It’s probably 10%. The other stuff that I’ve tried 80% or 90% or whatever the percentages play out. “This is how people use social media. This is how people develop products. This is how people create an online course. I should do it that way.” The results are not usually that good. Whereas when what’s different, who is not doing this thing this way? When I started the podcast a few years ago, I was like, “I’m going to do a podcast every single day. There were no interviews.” Nobody was doing that at the time.

MGU 54 | Financial Uncertainty

Financial Uncertainty: Give yourself permission to not keep doing something that is not working anymore or that you no longer enjoy.


It helped quite a light on it. There are some other examples of what has worked well and a lot of examples of stuff that hasn’t worked well at all. That’s the buckets. I try to think about that when I make decisions. What am I doing that’s different and unique versus trying to do what everybody else is doing and maybe do it better? I’m probably not going to be the one that does it better. There are probably other people that are going to do all those other things much better than me.

That’s interesting too because I have that side of me wanting to do things differently. Maybe I have a little bit of rebel in me because when I see a lot of people doing the same thing, I feel repelled. I’m like, “I don’t want to do that. I want to do something completely,” or if I’m doing something that a ton of people is doing it too, I get annoyed. That’s for me tricky as an early adopter for things. I like to try things out early on. When other people do them, I get frustrated. I feel I need to move on to something else new. That can be exhausting. It’s like chasing after how do I do things differently?

It’s something that I’ve been reflecting a lot about because it suddenly feels like many people are talking about wellbeing, mental health, wellness and all of these topics that I talk about and Jason talk about we do collectively. I think, “Is this becoming oversaturated?” It’s an interesting balance because you can’t keep running away from something and doing something new all the time. Sometimes you have to stay steady in the course. I’ve found that it’s been a disservice to me the times when I’ve given up on something too early because other people were doing it. It became huge. I’ll regret it because if I stuck with it a little bit longer, maybe it would have worked out for me. Jason, how about you in terms of your rebelliousness and non-conformity?

It’s been a lifelong thing. My mother, my caretakers and my family can certainly verify this from as early as they recant and I can remember. I’ve had a healthy disrespect for authority. I’ve sat and try to get to the heart of why that has been a part of my personal cosmology in this lifetime. I haven’t come to a specific reason in my personality why that might be. For me, there’s been this part of my soul, we get spiritual for a moment. That’s like I need to experience the thing and figure it out for myself.

Oftentimes, Whitney knows this that one of the triggers that I have is people giving me unsolicited advice in life, “You should do it this way. You ought to do it that way. Guess what, I made seven figures doing it this way so use my roadmap and you’ll do it whatever it is.” Chris, if I may, you said something about a pioneering spirit. My entire life I’ve had this thing I want to experience for myself. I want to figure it out on my own. I want to have the visceral life that no one else has lived. It’s my choice. It’s my path and it always reminds me of one of my favorite Joseph Campbell quotes speaking of the Hero’s Journey about carving your own path.

If you go to the middle of the forest, the proverbial forest or the literal forest, and you’re walking on a path, it’s someone else’s path. Your path is found by going into the darkest point of the forest where no one has ever been. To me, that’s been something that’s always stuck with me as the curiosity, the sense of experimenting and wanting to figure it out for myself and not listen to too much advice from other people.

Is it possible to go where no one else has been? Anything is possible. That’s the other thing I’ve been grappling with. Chris, I’m curious about your perspective and all these different side hustles and paths that you can go on. You’ve traveled all throughout the world. You have an amazing perspective of how often is it that you come across a path less traveled by? Is it important to go down a path that few have gone down or is it equally valuable to continue down a path that somebody else is going down? Is it necessary to do things differently? What is your perspective on that?

It’s important to find the right path for yourself. That path can be something that is new and different or after evaluating lots of different options, you realize there’s a reason why a lot of people choose this path and this is the best choice for me. That’s you do. If you want to be a medical doctor, for example, there’s a prescribed course for that. It may not be a bad thing to go down that route. The bad thing is for everybody to assume. My peers did it. This is what my parents expect me to do or whatever. Therefore, that’s what I’m going to do. If you think for yourself, you don’t have to be a nonconformist and everything. Nonconformity is about questioning assumptions and expectations. That healthy mistrust of authority that Jason talked about. In the end, you make the choices that are best for you and ones that don’t harm other people. Hopefully, you end up helping other people as you help yourself.

If you think for yourself, you don't have to be a nonconformist. Share on X

The doctor’s example is a timely one because there are a lot of doctors in the world, but it almost feels like there aren’t enough. What a great point to make is that sometimes we feel everybody else is doing this, so maybe I won’t be seen or recognized. Maybe I’ll fall into the crowd, but sometimes we need a lot of people doing the same thing in order to make a difference. It’s certainly true environmentally speaking. Since I haven’t read The Money Tree yet, I’m curious for you, Chris, what do you feel like is people are predicting people are going to resonate with the book and some advice that is needed in this time that you speak on this book. Are you predicting that certain people are going to say, “This is the part of the book I most needed,” or maybe a favorite part of the book for you?

I don’t usually make predictions. I’m not good at making predictions. Before I started my podcast, it was two years before I was quoted in the Wall Street Journal of saying like, “Podcasts are going away. Podcasts are a thing of the past.” It’s not good for me to predict. I would say two things, not about the book, but broadly speaking, people are desperately looking for connection and community. That’s going to continue for some time. I would say probably even whenever somebody is reading this and people are still going to be looking for those ways to connect, to be seen, to be heard, to feel that they’re not alone and so on.

A lot of what I try to do with my work is to show people like, “If you have thought differently, if you’ve wanted something more for yourself, you’re not the only one.” The second thing is even though the book ultimately is about financial independence, financial freedom and helping people get rid of that burden of debt and being able to make more choices for themselves, the deeper part of that, is not having more money in your bank account or not having those debt payments every month. The deeper part of that is understanding one of the key themes of the book is that you can do more than you think. There’s a character that says that repeatedly and the other character like discovers it as they go along.

I want people to know that they can do more than they think and maybe they’ve had this vision to do one thing. The vision could be bigger or more than that. Bigger is not quantity necessarily. The bigger is more depth or a more expansive vision or they thought they were going to do one thing but that opened the door to something totally different. All they had to do is walk through that first door. I want to help people walk through that first door and see what lies beyond.

You have me already as a fan, Chris. Now that you’ve ruptured some Star Wars galaxy war into it, I’m going to dive into this as soon as possible. Chris, having you as a resource in these massively uncertain times is wonderful. The courage to stare down the uncertainty, in some ways that thing that I’ve been reflecting on is that things are uncertain all of the time. We can’t predict the future. You don’t like to make predictions. We don’t know what’s coming for us. We don’t know what ought to be. To go back quickly to one thing that you said that stuck with me is to see reality clearly and not what we think reality ought to be or try and bend reality to our will. A lot of the opportunity that we can see collectively through humanity is seeing life for what it is and using that as our jump-off point instead of wishful thinking or trying to manipulate reality for our own egoic desires. You as a resource and your wisdom, your experience, your journey can serve as a certainly guiding point through North, but as a soothing balm for people emotionally to see like, “This is the state of things. Where do we go from here?”

That’s the goal. Both of you are doing something similar. I’m grateful for this conversation.

MGU 54 | Financial Uncertainty

Financial Uncertainty: Nonconformity is about questioning assumptions and expectations. It is that healthy mistrust of authority.


We’re grateful for it too. Thank you so much for joining us. I’ve said multiple times, I am excited to read this book. We hope that you check out. We’ve referenced a number of different books and resources to support people through all these different topics. Chris is @193Countries. Is that your handle on all platforms or is that just Instagram?

That’s just Instagram. The rest is my name, Chris Guillebeau. It’s or you can also go to to learn about the book.

You’re a little rebellious with Instagram. Why is that? Was Chris Guillebeau taken?

There were a lot of other Chris Guillebeaus in the world. I was like, “I don’t want to be Chris Guillebeau number 724.”

Have you come across a number of Chris Guillebeaus?


There’s another Jason Wrobel and that Jason Wrobel took a username on Facebook and Gmail too.

Not just one, there are many Jason Wrobels. I’ve messaged them and been like, “Who are you?”

I remember the Gmail was taken and sometimes people accidentally emailed [email protected] and it does not go to this Jason Wrobel.

It’s annoying, but I’ve learned to live with it.

You’ve got to recognize reality.

I’m not unique. There are other Jason Wrobels.

Make the choices that are best for you, and that don't harm other people. Share on X

Thanks, Chris. We appreciate you and all that you’re doing for the world, in the past and the future and all of eternity. We are grateful for that and happy to have you part of this uncomfortable conversation. What would you say was the most uncomfortable part of this, the part about the grocery store or maybe something?

I felt comfortable throughout. We’ll have to come back sometime and do it again and try to get more uncomfortable. It was a wonderful conversation. Thank you, Whitney and Jason.

Maybe you’re used to going outside of your comfort zone that this feels like a breeze. What a great example is that for other people.

Thank you.


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About Chris Guillebeau

Financial UncertaintyChris Guillebeau is the New York Times bestselling author of The $100 Startup, Side Hustle, The Happiness of Pursuit, and other books that have been translated into more than thirty languages. 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 two million times a month. He is also the founder of the World Domination Summit, an event for cultural creatives that attracts thousands of attendees to Portland, Oregon every summer.

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