MGU 168 | Humans Navigating Life


Social media has literally changed the social landscape of being human in this day and age. From heralding individuality and authenticity, many have now been proclaiming themselves as social media experts trained to market every chance they get. As obvious as it may sound, finding humans “navigating life” has become a rarity. In this episode, Jason Wrobel and Whitney Lauritsen invite two amazing people who have been doing that amidst the noise of the world. They sit down with Jason Zook and Caroline Zook of Wandering Aimfully to talk about how they are carving their own path as entrepreneurs and creators versus following a formula that’s already been set out in front of them. They define what being “good enough” is, how to overcome the pressures put on you by the world, and how to reframe if you’re in that season of questioning. Join Jason and Caroline in today’s show to get authentic insights about struggling from the daily pressure and grind and how you can move your way past them.

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Humans Navigating Life: Defining “Good Enough” And Overcoming The World’s Pressures With Jason Zook And Caroline Zook

There’s so much to cover in this episode. It might be more tangential than we normally are on the show because we also have two other people that are similar to me and Jason Wrobel. We have Jason and Caroline here. I might not be acknowledging that we’re on a podcast at all. A good phrase to start this episode out with is it was on one of your Instagram posts for Wandering Aimfully said that you are humans navigating life. I read that and I was like, “That sounds cool. It’s refreshing to talk to humans that are navigating life.” I thought, “Aren’t all humans navigating life? Why do we have to state that? Are we at this point where we’re trying to differentiate ourselves by saying, ‘We’re not only human, but we’re humans that are navigating life?’”

We are in a weird time as someone who got in early to the influencer economy before it was a known thing. People are brands first online before they’re humans. It is a thing now. We say this all the time. We’re like, “Just be a person. Just be a human. Be nice and be kind. Think about people before you think about profit.” It does seem mind-blowing, but it is the existence that we live in, in a weird way, especially on social.

For us specifically too, sharing a lot about business content, the path that we’ve carved out for ourselves is trying to remind people that it’s a perfectly okay option to choose creating a business, creating an online business, staying small, staying human, and being connected to the person behind the brand. There is a path that a lot of people take where the more they grow, the bigger their team gets. Almost like the more vanilla corporatized they become. Part of sharing that message was to remind people that we’re separate from that. We want to let people know that it is possible to earn a living doing something that you love and being a human in the process.

The more that you can check in with your audience and remind them of your values and remind them of the way that you operate as you go along, then they go on that journey with you. The context of that post was probably something related to maybe why we hadn’t been posting much or a mental frame of mind that we were in. We always like to check it with our audience and tell them that stuff to remind them that we are human people and not just corporate people.

It’s fascinating to me that we feel the need to do that because Jason Wrobel and I are constantly examining ourselves as well because we started off fairly early in this world ten-plus years ago and seeing that the age of influence grows. I remember discovering Instagram for the first time and watching that develop. I never would have predicted that so much of my life would be on that platform. I definitely went through all these different phases of how I was presenting myself and now I’m like, “Why?” I don’t want to feel like I’m presenting anything. I would so much rather be authentic, but now, even authenticity is a trend on Instagram. You have to weed through posts to see like, “Is somebody authentic or are they just presenting themselves as authentic?”

It’s super interesting because we’ve even talked about the quality of video on YouTube. There’s almost this bell curve where it went from flipped cameras, which is trash quality, and then it’s up to 4k video and everyone’s videos are great. Now it’s almost like you want it to be a little bit less high of quality content because that feels like I’m seeing this person in real-time. Now it’s like this pose, seventeen cameras or red camera, a camera guy, a boom guy, and all this stuff. You’re like, “None of this is real anymore. You’re just a TV show at this point.”

What’s weird about that is it is a meta, but once you start having that conversation in your head, even making that choice to go almost back up, that’s a weird presentation of yourself. It’s exactly what we’re saying, which is not a forced authenticity but calculated authenticity. It’s interesting. I had this weird experience where I came across a photo of myself. I know 2020 is a bad year for a lot of people. 2019 was a bad year for me and for us personally because I was dealing with a lot of health challenges. I came across this photo in my camera roll of me in tears and it struck me in that moment of what a difference a year can make.

The moment I saw the photo, I was in so much better place. A year prior, I could never have imagined that I would feel better and get out of that dark place. I posted it and I was sharing like, “If you’re in a dark spot right now, I promise you it can get better.” They DM’d me and they said, “I’m not usually a big fan of crying selfies, but your post spoke to me.” I was like, “What’s a crying selfie?” They were like, “Where people post photos of themselves crying.” I’m like, “I just did a crying selfie, but I didn’t know that’s a thing.” I was like, “This is a thing now?” For engagement, I’m trying to almost share vulnerably. It’s interesting.

It’s such a good segue that I want to discuss with everyone where it seems like vulnerability, as a general topic, started to pop-up on social media with crying selfies or people talking about loss or heartbreak or disappointment. One thing I started to notice was that authenticity and vulnerability, hand-in-hand to a degree, started to get co-opted by certain entrepreneurs or content creators as a marketing tactic. It wasn’t just about, “I’m having a hard moment and I want to let you know you’re going to make it through this, even if it feels hopeless and even if you’re dealing with depression, anxiety, confusion, or whatever the case may be.”

I have my own mental health story, but I’m always trying to be super mindful whenever I share anything about mental health, not letting any framework of a marketing tactic seep in. I’ve been good about that, but I’ve noticed that people will do that. Sometimes, they’ll start videos like, “I’m going to get super vulnerable right now.” If you’re telegraphing the vulnerability and giving me a spoiler alert, then maybe it’s not that vulnerable if you’re telling me you’re going to get vulnerable.

I’ve been thinking about this a lot lately because this entire 2020 I would say is probably the year that we’ve been the least vocal on social for a number of reasons. It’s a hard year and you want to manage your screen time and all of that, but also, in examining it further, it’s a rebellion or a response to what you’re describing. I don’t know if you guys are into Enneagram, but my personality is in Enneagram four. Authenticity is in my DNA. It’s my thing. By seeing it be co-opted, it turns me off from it so much because I don’t want to be grouped in with that.

I found myself having such a year of personal transformation and going through a lot of different things as the world is going through these different things and trying to process them. I’ve been wondering to myself why I haven’t been sharing about that process because that is normally my process. It’s in response to what you’re describing, which is that I almost want to take a step back to reclaim my own authenticity by not sharing it, if that makes sense.

I don’t know if you remember, but I had done my first social media detox for 30 days in 2014, but in 2015, I was on my third one and I was like, “I don’t think I want to be on Facebook anymore. I don’t like it.” I remember having a conversation with you and saying the reason why I don’t want to be on there is not because your uncle can share all of his political views with you and you can’t have him do that, but it’s more the fact that I know what works. I know that if I post something vulnerable or whatever, the likes are through the roof and my dopamine response is through the roof.

I don’t want to be in that world. I don’t want to play that game, and then manipulate people to feel something about me because I can then know what will get the reaction. That was a moment where I was like, “I don’t want to be here anymore.” That’s trickled through. Many of us are now getting on all social platforms. It’s not just one or the other. It’s like, “I don’t want to use this as a tool to get followers, get people in my funnel for my business, or any of that stuff. That’s gross.” That goes back to the original thing of, we want to be humans first. We want to take care of people and be kind, helpful, entertaining, and whatever. Not just use the tactics that work and can get people’s attention because we’re just not about that in life. We don’t care.

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It’s fascinating too because I have that love-hate relationship with social media. I’m fascinated by it and I like playing around and testing and experimenting with things. Similar to you, Carol, I love the design side of things. We were talking about how I’ve been wanting to do more digital art because it stimulates me on a mental level to create something, put it out there, get feedback, and adjust it. There’s that side of me wondering how much of this is me trying to manipulate people and see what I can get from them or get that validation or that dopamine hit. That makes it a bit confusing. I don’t know too much about your history, Carol, with social media before you started working with Jason. It sounds like we each have been on social media significantly in a good amount of time.

To see this evolution happening with the different marketing tactics, everybody can proclaim themselves as a social media expert. We have all these twenty-year-olds being hired as a social media consultant after maybe only doing it for a few years. Everybody has been trained to market in a certain way, but then we’re being trained to be authentic in a certain way. There are a lot of conflicts there. I start to get overwhelmed. I don’t even know what to do. Should I be taking a detox? Should I be marketing this way? It’s culturally acceptable to manipulate people too, and that is also incredibly confusing.

Maybe some people even perceive your authenticity as not authentic and you can’t control how they perceive you. My brain sometimes gets to this point of like, “What do I even do anymore? Do I want to be on social media? Should I be on there, maybe trying to shift things?” Which is definitely the route that I’m going. When I step back from everything that I’ve done all these years and try to do things differently or get back to my roots, I start to wonder, “Do I even want to get back to those roots? Is that the right place for me?” I’m sure you guys go through this all the time because you’re like-minded with me and Jason Wrobel in that sense.

I have definitely experienced all the questions that you went through. For us, part of what helps is allowing ourselves and seeing it as a good thing to constantly be questioning and allowing space for our opinions or feelings to change on the subject as time goes on. Exactly what I was describing to you about how 2020 felt more aligned and more right for me to take a step back, be much more present, and not be documenting everything, be in the moment more, be processing things, and be consuming things. With all of the stuff I was learning about racial justice, I needed time to consume that, process it, and think through it. It felt good to take a step back from social media, but I can already feel a shift and being like, “Now I’m ready in a more conscious way to show up and share a little bit more.” I allow space for that to change as we evolve as people.

When you guys were starting, I’m curious about the origin stories of you with Wandering Aimfully and your experiences as entrepreneurs and creators. There’s almost like this mantra, and not necessarily at the beginning, but it seems to be more prevalent or maybe a little denser at the beginning of starting a new venture. We’re encouraged to find an avatar or find someone who’s further along on the path. We have a lot of examples in the entrepreneurial world. I don’t need to name off the names, but people who are in this business are like, “Make it huge, 10x everything. Make it big and take big swings. No fear.”

There’s a lot of the same means being parroted over and over. My question is, did you pick up the notion or this idea of, “We ought to observe other people’s methodologies or formulas,” and then either copies them or co-opt them or change them slightly? Has that been a part of your journey? Where are you in terms of carving your own path as entrepreneurs and creators versus following a formula that’s already been set out in front of you?

Caroline slowly turned and looked at me.

Because it’s perfectly teed up.

It also is the perfect question for my journey through entrepreneurship. Caroline coming along in that and seeing what’s possible, but then also not falling into a lot of the trappings that I did. When I first started in 2007, I had a design company, but that was less about like a startup and wanting to be seen. It was more like, “I want to make money and not work a 9:00 to 5:00 job.” In 2008, when I had this idea for this IWearYourShirt business where I wanted to wear a t-shirt every day, film a video, and do all this stuff, I was in the hustle culture that I didn’t even know I was in. I was like, “I’m going to work every day. If I work weekends, my competition isn’t working weekends. If I do all this extra stuff, I’m going to be the one who succeeds while everybody else who’s around me isn’t getting as much as I am. I’m going to have $1 million in the bank. I’m going to drive a Ferrari.” It’s all these stupid, ego-driven things.

Thank goodness I didn’t meet you until 2010 because that guy sounds like, “I do shirt.”

I’m grateful that I went down that path because it showed me what I didn’t want and how I was trying to chase after those things. It made me unhappy. It’s funny because I didn’t know who Gary Vee was in 2009, but we both ended up speaking at a conference together. I was doing a live video show every day. I’m setting up for my live show and this guy walks up and he’s like, “What are you doing?” I’m like, “I’m about to go live.” He’s like, “I’m an advisor of Ustream.” I’m like, “Cool.” He’s like, “Can I sit down with you?” I’m like, “Yeah, sure.” I started my live show and at the time, I was partnered with Ustream, so I was on the homepage of Ustream, and 20,000 people were watching.

This guy, Gary, I didn’t know who he was. He’s like, “You’re a big deal.” All the people in the chatter is like, “Is that Gary Vee?” I turned to him and I’m like, “You’re a big deal.” It was this super odd moment of those worlds colliding, but then they quickly veered apart because I was already doing all the things like the Gary Vee mantras and all that stuff without even knowing who he was. I bought into that because I thought that’s what I was supposed to do in startup life and running your own business. Only to realize that that led me to be super overweight, stressed, and unhappy chasing all these goals that had no bearing in my life.

Super in debt.

It was a stunning realization for me of not defining my own goals based on what is right for my life and for me and knowing what my values are. Before I met Caroline, I didn’t know what values were. I was just like, “Ferrari.” I started to tap into understanding what drives me every day? What do I care about every day? Money is not going to be something that if I have a ton in my bank account, it is going to make me happy every day. The chasing of trying to get to that is also not going to make me happy and working hard.

MGU 168 | Humans Navigating Life

Humans Navigating Life: In the influencer economy, people are brands first online before they’re humans.


For me, what’s happened over the years is I have tried to figure out, “Let me define what a perfect day, as perfect as it can get, looks like for me.” As far as like, “What am I doing? What am I creating? Who am I helping? Who am I surrounding myself with? What is all this stuff that relates to that?” that has been such a huge shift for us. We can definitely talk about how we’ve shifted our mindset around money, growth, marketing, and those things. That’s my backstory on how I got started.

To pick up where you left off, the reason why that story adds so much context to Jason’s question is that, to answer your question specifically, we are the opposite of a growth mindset that you see a lot out there. A lot of what you’re asking is a lot of people see a blueprint that works. They see someone that’s a little bit farther ahead than they are and they think, “I will follow that path because that’s where I want to be.” The reason that doesn’t work is because our idea of what we’re trying to achieve is not a quantifiable money/growth/increase in business.

It’s this intangible life that we want to live that feels good. It would be pointless to look at someone else who’s done it because they’re not living the life we want to live. It has to be created from within us because we’re unique people with a unique partnership with a unique vision for how our life is going to unfold. Over the past couple of years, the way we’ve shifted to what we call an experimenter’s mindset is a lot less about identifying someone else’s trajectory and trying to follow that. It’s a lot more about trying to envision your own, and then experimenting until you get there.

I thought of this. We have the three Es we focus on.

He’s never ever said this before, so I’m scared.

Let me guess. Is this going to be in an upcoming newsletter after this episode?

We’ll see. We’ve got Experimentation. What’s the second one?


No, Enough mindset, which we can talk more about, and then the third is Elephants because they never forget. It’s just the two Es that are the most important ones. Experimenter’s mindset is definitely something that I’ve used.

He has never said this before.

Never in my life.

This might become a new roadmap for Wandering Aimfully.

We might have to come up with an actual third E that makes sense. I was just being silly.

I love elephants.

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They are great.

This is an insider secret though. For the readers, we’ll circle back to Wandering Aimfully for sure because I definitely want to talk about that more. Let’s go back to the elephants.

Experimentation is the first E, which Caroline explained. That has been something for years where we want to test all the assumptions. It’s like, “Why can’t I wear t-shirts for a living?”

“Why can’t our business grow without social media?”

“Why can’t you make a good living doing hand lettering and having a digital course that’s $20?” It’s challenging and trying to do all these things, whether someone’s already done them and succeeded or whether you’ve never seen anybody do it, figuring it out and seeing what happens and learning from those experiences. The other thing for us is this idea of enough, and this comes up a lot, especially now because we continue to talk about it. The first thing is, how much is enough money? One thing that we rail hard against is these businesses where they’re like, “I want to help you be a seven-figure entrepreneur.” It is totally fine to make millions of dollars. We don’t care about that, but why?

I want to know why many of these people had this dream because I know what it takes to get close to running a $1 million business with my IWearYourShirt business. It sucked and it was miserable. It was not fun. I hated every single day. Sure, I wasn’t running the most sustainable business, but I know what it takes to get to those different levels and the things you have to sacrifice and do. We ask this question, how much money is enough for us? What does that look like? Let’s define it. Also, how much content is enough for us? Do we need to be on all these different social platforms?

Sure, we would love to be on TikTok making stupid videos, but we spend our time doing other things. To add that to the mix, it would stress us out. It would add a bunch of friction to our life that we don’t want. We do enough on social media by using Instagram, and that’s all we use. We constantly come back to this enough mindset of how much time are we spending on things? How much money are we investing in this? All of this is like, “How do we define what enough is for us?”

That’s just for us. It can be different for everybody else in different situations. We’re all about people defining what that means for them. Make sure that you check your ego at the door to know, am I making this decision because it’s ego-driven? Is this applicable to my life, not because I’ve seen some entrepreneur online who has an incredibly well-crafted feed of photos that they look like they live a perfect life, who’s telling me that I should have a life like theirs?

That’s part of the reason I love you guys. I feel a sense of relief when I go on to an Instagram account and don’t see a ton of followers and perfect photos all the time. I hope that you don’t ever grow a massively successful Instagram. Part of the problem that Jason Wrobel and I are working on is that we have spent so much of these last several years thinking that social media was the key to making money. It is exhausting for us. That’s the important element of this. One of the best things that you said, Jason, is that it is a for us factor. Some people love making tons of money and some people love spending every minute on social media.

I’ve had to step back and examine this a lot because I lost a lot of my joy in video editing. A little background for you and the readers is that I was on the path to being a filmmaker and that was my huge passion since I was a teenager. I thought that that’s all I was going to do, and then I pivoted my career and started doing all of this digital work and moved away from filmmaking as an industry. I still continued to do video editing for many years. I used to love it and I would stay up so late. I would go into my 9:00 to 5:00 job completely exhausted with little sleep because I could stay up all night editing YouTube videos. That’s how my career started.

It was great for that time, and then it hit me like this massive burnout or lack of desire for it that I felt bizarre about. This goes back to some of the emails that you’ve written. Another huge perk of the work that you do is your wonderful newsletters. Signing up for your newsletter is wonderful because you bring up this not-enoughness and talk about burnout and all these things. I can relate to that. One of the emails which I had up for reference was simply about this self-imposed pressure. It was written by Jason and you were talking about something that you addressed, which was being in debt. You were feeling like you were lacking a sense of purpose and you felt disconnected from your work.

This is something Jason Wrobel has expressed a lot too, so I’m sure he’s interested in learning more about this. All of this self-imposed pressure that you would maybe never make anything of value or substance again. We beat ourselves up when we think, “I don’t feel like editing videos. What if I never want to edit another video again?” We get into this mindset of complete fear that’s ruled by all of these ideas that if you’re not constantly creating and hustling, you’re going to lose out and nobody’s going to care about you anymore.

That’s incredibly toxic. It’s also something that not everybody experiences, but those of us who have, for one reason or another, based on much of our career and our self-worth on how many likes we get on Instagram or how many people view our YouTube videos or listen to our podcast. It can lead to a ton of burnout. Also, making us feel like we don’t even know who we are anymore.

There’s such an identity crisis in being a person online. There’s something that I learned over the years too, which is that it’s easy to think being on social or having a newsletter or having a website or having a YouTube account is a business. For most of us, it is not a business. While you can make money through sponsorships and other things, unless it’s consistent and sustainable, you don’t have a business. You have something that might generate some revenue. The big thing for me that helped out was when we figured out how to make online course platform and Wandering Aimfully, which is a membership coaching community, work as businesses, and it didn’t require a constant flow of us doing things like posting stuff on social.

MGU 168 | Humans Navigating Life

Humans Navigating Life: We beat ourselves up with all of this self-imposed pressure that you would maybe never make anything of value or substance again.


2020 has been the quietest we’ve ever been on social, on YouTube, and maybe our podcast has been the most consistent thing. Our email has always been consistent for years. We’ve made the most money that we’ve ever made this 2020. This is not a blip on the radar for us. I did the same thing in 2016. When I quit Facebook and reduced my time on Twitter, I made the most money I’ve ever made that year. The reason that happened, and I believe that it happened with all my heart is because it now freed me up to go, “The way that I’ve always been doing things is not the way that I need to keep doing things.” I can now take all that time and attention that I thought was worthwhile because I’m seeing these vanity metrics.

I’m seeing more likes and I’m seeing more comments. I’m seeing these little digital pats on the back. That’s not money. That’s not revenue. That’s not an exchange of goods for services. That doesn’t mean I have a business, and having a business is not everything. That’s not what I’m trying to say. What I’m trying to say is for many of us and yourself included, Whitney, in the story, you put all your time and energy into something and you’re not getting the return out of it. If you stay in that cycle, it’s going to lead you to burnout. It’s going to lead you to a feeling like, “What do I do now?” For us, that’s where that first E of our three Es that we completely made up.

That we now have as a core tenant of our business.

The core pillar of our business is to keep experimenting and to keep asking yourself these questions like, “I’ve been in this rut of doing this thing the same way. What if I shifted everything? What if I realized that if I’m being honest being on social right now, it’s not helping? I feel like it is because I can see some movement in some digital metrics, but it’s not helping in my bank account, so I need to do something else. I need to make a shift.”

That could also be, “My life feels out of balance. I don’t have enough time for my family, friends, health, and anything else. Maybe I need to change that up because I’m investing all that energy and time into something that’s not making me feel good. I need to look at that and I need to change that.” That’s definitely where I was. I’m speaking from my own personal experience. I’ve run into that now multiple times, but specifically in 2014 and again, in 2016. I had a reckoning for myself of where I was spending all my energy and making a huge shift with that. It has helped to make those shifts and changes.

If you’re in that position like you were describing, Whitney, where you’re having those fearful thoughts of, “If I’m not video editing anymore, what am I doing? Am I valuable? Is my work valuable?” everyone have those thoughts. If you’re experiencing that, it’s worth digging a little bit deeper on where that fear is coming from because if that fear is tied to, “If I’m not creating, what value am I bringing?” That’s a deeper question that each of us has on a journey. We all have to go on about our own self-worth and divesting our self-worth from our work output.

A way to reframe if you’re in that season where you’re questioning all of that and you’re like, “This thing used to bring me such self-esteem because I was putting it out.” For me, that’s my art. When I was putting art out every day, posting on Instagram, getting this instant feedback, and people were saying, “This resonates with me,” that was building up my self-esteem. The problem is that it’s then creating such a deeper connection between my self-worth and my work. When I didn’t feel like painting every day anymore because of burnout and health challenges I was going through, instead of going, “Now I’m not posting. Does it mean I’m irrelevant? Does it mean people don’t care?” and reframing that as, “This is my chance to step away from that work output and experiment with, what does it feel like when I’m not doing that every day? How can I use each day that I’m not putting that work output out there as a day to deepen my self-worth apart from that productivity?” 2020 has been about not sharing and realizing that I have a chance to build up my self-worth apart from what I’m sharing online. That makes me more resilient and more in control so that when I do share it’s not because I’m seeking validation, but because it’s pouring out.

You got to unhinge your jaw like an anaconda to take a bite. You got to dislocate it and dive right in. I find myself in this amorphous floating in the middle of the ocean. I’ve used this analogy before. To piggyback on what you guys are talking about, the things that I’ve been doing in many regards creatively or entrepreneurially aren’t bringing me joy anymore. It’s almost like a reckoning of knowing that I felt that way for a few years, but finally saying it out loud and speaking the truth to not only myself, but people close in my life and also to the 50 million followers.

There are almost a liberation and a terror. Here’s what I mean by this. There’s a certain amount of brand equity, I suppose, that gets built up when you’re known for something. On the one hand, life keeps giving you carrots. It’s like, “You’re doing a great job as a chef or a host or an entrepreneur or an author.” All these titles and labels that we, I suppose, craft for ourselves. These identities we create in the world. On the one hand, we keep getting sponsorships, book tours, and speaking appearances. The carrots come in the form of money, attention, significance, importance, or whatever that is.

The thing that I’m in the process of unraveling and detaching is that carrots are not the source of joy because, on some level, my soul is like, “We don’t want to do this anymore.” It’s almost like you can become a slave to your own success in the sense that you have a book, course, TV show, or whatever the case may be that does well. You get the emails and the dummies are like, “When are you going to do your next book? When are you going to do your next show? When’s the next YouTube video coming out?”

It’s this framework of, in some ways, constantly either comparing ourselves or falling into other people comparing us to the work we’ve put up previously. To me, that has felt crippling at times to almost try and measure up to a previous bar I’ve set for myself and feeling the expectations. Not only internal but the external expectations. I’m at a point where I don’t want to operate in that mechanism anymore.

I felt that so much in 2013 because I had to shut down this IWearYourShirt business that for five years was my entire identity. Every single day I poured my heart and soul and I got so many carats from that business. I was on every news network you could talk about. I had all these different offers to do these different things but on the back end of that, I was truly miserable. The business was not working, I was in debt, I was not happy, and I had these thoughts all the time like, “Am I going to be one of those one-hit-wonder internet memes?” It drove me almost nuts thinking about it all the time. I finally told Caroline, “It doesn’t matter. I want something easy now. I want to do something easy.”

That was when I made my first online course and was like, “I want something that can make money without me having to dance around a puppet for six hours a day and be heads-down to my email for the other six hours that I’m working a day.” It’s not sustainable. That was the first time that it showed me, “I can teach people something. With them learning how to do this skill and benefit their life in some way. That feels more fulfilling to me in the joy that they get and the money that they get than the purchase that they made of the thing that I sold.”

That was the first realization. I was like, “This is more fulfilling. Yes, I need the money because cash does help you run your life and you can’t pay your bills on happiness, love, and admiration, unfortunately, not yet,” but that was a helpful turn for me. What’s funny is when I made that turn, is when I started to have more creative ideas. The more that I stayed in this environment of, “I have to have a good idea,” I had no good ideas and as soon as I shifted out of that into experimenting, doing things, and trying more stuff, the ideas started to come. Also, a huge thing for me was removing myself from all of the physical attachments to social, email, and to my self-worth tied to those things that Caroline was talking about. It freed me up so much to have more mental clarity and whitespace that I hadn’t had, which then produced results and ideas for me.

Stepping back is getting ahead. Click To Tweet

We can both relate in different ways to the terror/liberation that you’re talking about of being on the precipice of knowing that you want to break free of this box that you’ve almost put yourself in, or people put you in. That is terrifying. When I’ve come up against that point because it’s happened multiple times, the thing I always think about at that moment, one way to prevent myself from having this fear, is by taking a left turn or doing something unexpected.

Early on in our business lives, I realized that the more we pivoted and told people why we were pivoting, why we were trying this new thing or breaking out of what they expected from us and took them along on that journey with us, the more people stopped seeing us for the one thing like the t-shirt business or the design business in my case. The more they started seeing us for the broader thing which was, “We like you guys. We like seeing how your business has changed as your life changes.” If I could go back and tell myself when I was in that terror liberation phase, early on, I would say, “The sooner you do this, the sooner you break free of this box that you’ve put yourself in, the sooner you’re going to prevent yourself from ever feeling this trapped ever again. Because now you’re going to broaden your possibilities and you’re going to give yourself the freedom to make decisions as you evolve.”

It goes back to what we said at the beginning of this, which is we’re humans navigating life. It’s silly to think that we’re going to be interested in only one thing for the entirety of our business lives or only care about a certain value or only be a certain version of ourselves. We early on have prioritized that evolution as a value and take people along on the journey with us. It’s made for some interesting twists and turns but now there’s so much freedom and knowing that whatever we choose to do, our audience is going to come along with us, most of them.

The last point too is, as all of us who have been through a lot of change, you’ve pivoted a lot and you’ve tried different things. You start to realize that’s a badge of honor. People look at you again as the experimenters. They’re like, “They try a lot of things.” You may think internally when you start to do that, “I’m flaky. I can’t stick with anything.” There is a difference between trying something and giving it the old college try and making it work for 3 to 6 months or a year, as opposed to being like, “I tried to create an online course and sell it for three days and no one bought it.”

There’s a big difference between those two things but then it’s also realizing it’s empowering to be someone who is willing to try new things and to put yourself out there. You have to do it for enough time that people see, “You’re not trying a new thing and doing a new thing every single day for 100 days.” That’s a whole different thing you could do but it’s more about being someone who’s intentional about those decisions that you’re making as you change and sharing with people what you learned, how you learned those things, what you’re going to not do next time and what they can avoid if they’re going to try that same thing.

Side note, that’s where the name Wandering Aimfully comes from because it’s this notion of allowing yourself to evolve and that wandering piece but always doing it with an aim in sight with an intention behind it.

I’m sold.

But not on the sales page.

Honestly, whatever you guys pitched me on was brilliant. It was vulnerable and real, and it worked. I’m signing up.

Spoiler alert, this is going to get really vulnerable.

We are authentic.

It’s a $25,000 mastermind. You paid $25,000 a day for seven days and you’ll get invited to our sound bath, which is $100,000 but you pay that ahead of time.

You will be at the Silver Platinum level of membership which means that you’ll get a tiny BMW cardboard cutout.

You’ll also get 200 extra growth of yourself and your hair.

MGU 168 | Humans Navigating Life

Humans Navigating Life: We get into this mindset of complete fear that’s ruled by all of these ideas that if you’re not constantly creating and hustling, you’re going to lose out, and nobody’s going to care about you anymore.


That’s our business pitch. Do you guys like it? Is it good?

I’m already in it for life.

We got Whitney to buy-in.

She got the BMW cardboard cutout.

Sometimes I sit back and think, “This is the best deal I’ve ever bought.” The fact that I purchased what used to be called Buy Our Future, which was one of the most brilliant and unique marketing tactics I’ve ever seen. At the time, I thought I was thinking more short term. I’m like, “Sure, it’s the future but I don’t know what the future is going to hold.” I’m looking at what I’m being given now. When was that? Was that 2017?

Yes, because it was the year we got married.

It’s been a few years with you guys.

This is the future, Whitney. You bought it.

It is. This is what I bought and it’s awesome. You don’t offer that like it was anymore. That was quite a steal.

This is an interesting road to go down in a way that I have tried to pressure Caroline into believing that it is a thing that can work in the business. I want, when people buy things from us, in almost every single thing they purchase to be like, “I can’t believe that’s all I paid. I can’t believe that that’s the deal I got.” With this Wandering Aimfully business model now what was originally called, Buy My Future so it was me, eight online courses, and two software products I had. I basically said, “If you pay me $1,000, anything I make in the future, because I’ve got a track record of making things, you’re going to get and you’re never going to pay for it again.” A bunch of people bought into that, which was great and we changed to Buy Our Future.

I convinced Caroline because we had been doing a little bit of crossover. Our email newsletters were mentioning each other a lot. We were talking about each other’s things we were working on. I finally convinced her to be like, “Let’s do Buy Our Future.” At that point, we had 30 online courses together and a bunch of other workshops and things. It’ll be fun. No one’s ever done something like this. My thought was always, “Let’s give someone the maximum lifetime value of us and we’ll probably get maximum customer lifetime value on average of a customer.”

Because it’s a $2,000 product, most times you’re never going to get someone to pay that amount over the term of all the customers you have. what that evolved into was Wandering Aimfully. We started it and wanted to do a $100 a month membership and we ran into this problem where the label of it being a membership became expensive in people’s minds. They’re like, “I’m used to paying $14 for Netflix, and now I’m paying $100 for this membership. I don’t even know what I’m getting. It seems a little bit nebulous.”

We shifted it back to the Buy Our Future model where it’s a $2,000 product called a program and you pay it at whatever payment plan you want. There’s no penalty for paying it faster or slower and once you get to $2,000, I love sending these emails, I send them to every person who pays it off. I tell them, “You will never pay us another dollar again.” It is a surprise and delight because even people who buy into it months ago, if they bought the $ 100-month plan they’re like, “I didn’t think that was necessarily real.” That’s amazing.

We’re waiting to answer your question. Yes, it’s still basically a Buy Our Future. Once you pay it off, you get anything that we create in the future and whatever form the business takes three years from now, you’ll still get that. People who buy now the membership will still get that. It’s our favorite thing.

Create from a place of joy, adapt from a place of business. Click To Tweet

It is brilliant and I am so excited to share this with you because I forgot about it. All the nostalgia’s coming back. This is so brilliant, also from grassroots but authentic marketing. It’s truly authentic. You guys are authentically authentic.

We need a new word.

You send out these Thank You boxes to people. I don’t know what you call them.

That’s exactly what it was.

It was called a Thank You Box. They’re these beautiful boxes and you ask each person what their favorite snacks were and you put one of their favorite snacks in the box along with a handwritten letter and a coin. I feel like there was something else.

Those little spinning tops.

An Infinity top.

I saved that. It is in my closet. I repurposed it Marie Kondo style and I put a bunch of thank you cards in there. I saved it because it felt so special to me and you put so much love into it. It did make such a deep impression and something that Jason Wrobel implied, “We’ve taken so many online courses, been to so many events, and we’ve enrolled in coaching programs.” Sadly, a lot of them are focused on getting you results that you may never get but that simple process of giving somebody something that comes from the heart, and truly from the heart, like you both have given me and so many other amazing people in this group.

That ripple effect is so huge, and you don’t have to have this massive online platform and make all this money. That defines what is enough for you from my perspective and that’s why I show up to your monthly calls, started participating in Slack, and having you on the podcast. It’s because of that impact that you’ve made in my life. It’s so inspiring and such a great reminder for me, and hopefully the reader as well. Making that impact on a few people is so satisfying.

Caroline and I’ve talked about this a lot. I’ve been trying to figure out why because social media was so important to me for so many years and now, I’m so okay with not being on it. It’s because I have our WAIM Slack channel, where I interact with this group of people who I resonate with and I truly love. I look forward to every day, opening up my laptop, opening up Slack, and seeing all these different messages from people around the world. It’s a small community. It’s 700 people, but we’re talking about 200 people who are active in Slack at any given time. It makes me so happy because these people are intentional and they are truly authentic, not in the buzzword form of it. They’re trying to experiment and trying to carve out their own path in life and not follow this blueprint that they’ve been fed by some startup person who has a fancy Instagram feed.

To me, that is the purpose of my day now and I look forward to it. I get to wake up and feeling like I’m impacting these people and getting back to the Buy Our Future thing and the original thought of that is, “You are the embodiment of what I hoped would happen,” which is someone buys and two years later, they’re like, “I still have access to these people.” You log in and you’re like, “They have a bunch of stuff I can use or I’m interested in at this time in my life and it resonates.” I hope that that is a thing for many years to come for all the members who joined. It’s that repeating thing because here’s the thing that so many people lose sight of and you were talking about these programs where they make your promises and they can’t fulfill them. They’re also focused on customer acquisition. They’re constantly in customer acquisition.

We want to be in customer happiness because what we know is, as soon as we open up enrollment, you’re excited to tell someone that it’s open and we don’t have to do any extra work for that because we’ve done the work for years in providing value to you. That’s the long-term strategy of business. It’s hard to teach people but it’s showing it to people in action that worked for us and saying, “If you believe in this, if you continue to do this, three years from now you are going to say, ‘Thank you so much for starting to do that because now I’m reaping the rewards.’” That’s a hard thing to think because you’ve got to pay your bills now and I totally get that but if you change that mindset now, it’s the Chinese proverb or whatever, “The best time to plant a tree was a year ago. The next best time is today.” That is the most important thing to do is start thinking about how to make those decisions for the future you.

Another big element of this is feeling cared for. Listening to you share this, I’ve always felt cared for by you guys. I feel this is one big testimonial but my point being is Jason Wrobel and I signed up for a coaching program in 2019. We won’t mention who ran it but one of the huge issues I had was I didn’t always feel cared for. I didn’t feel like I mattered, and the worst part was it was a yearlong program and we got a good amount of value, but we did not get the results they promised us, which was misleading. I ended up feeling a lot of shame. I felt like a failure because they were like, “If you follow our steps, you will get these results.” This is a reputable person that I’ve been following for many years. It’s similar to how I signed up for your coaching program.

I had been following this person for many years, trusted this person, and felt good about investing. I do think that we got our money’s worth, but we didn’t get those results. We learned a lot but we didn’t get the results so I ended up feeling like, “What am I doing wrong?” The other part that was so hard for me is that when the program ended, I felt like I was discarded because I didn’t sign up for another year with them. As soon as I was no longer interested in working with them further, I never heard from them again.

MGU 168 | Humans Navigating Life

Humans Navigating Life: We’re humans navigating life. It’s silly to think that we’re going to be interested in only one thing for the entirety of our business lives or only care about a certain value or version of ourselves.


One thing I wanted from them was like, “How did the program go for you? How could we do better?” I wanted to give them some feedback and feel my feedback mattered and it was nothing. Even thinking about it gives me this horrible feeling in my stomach so I can never trust that person the way that I used to because I didn’t feel cared for or supported by them. In fact, the opposite effect happened. I didn’t get the results that they promised me and I’m like, “Was that my fault? Did I screw up something? Am I the person that is not following the strategy, right?”

That’s what bugs me so much about that racket specifically. If you’re running your business that way, that type of marketer, the crazier or the shinier the result that you can promise people, the more money you can charge. They charge that and they get people, but then the key is, if a person doesn’t get those results, they feel like, “The person marketed this to me so confident that I could get these results that it must have been my fault.” It absolutely absolves the marketer from the responsibility of following through on that promise and it leaves them virtually not being held accountable for anything.

That’s what bugs me so much about it is that they can charge so much for it because of the result and have no consequences for not getting that result for people. That’s why we are so careful about the things that we promised people when we sell our program. We are careful about not prescribing one size fits all solutions. To be perfectly frank, it makes our job a lot harder and selling things because our promises are a little bit more nebulous and intangible, but we refuse to say, “We can guarantee X, Y, and Z will happen for you,” because we’re honest people.

I never want someone to come into our community and not get certain results and feel they did something wrong, that there’s something broken that they didn’t figure out or they’re not cut out to be an entrepreneur. That’s not what our community is about and it makes it so much harder to sell at times and you see these people doing these messaging things, or coaching programs for thousands and thousands of dollars. I’m not going to lie to you in certain months, before when money has been tighter, I’m like, “Should we go for it and be total snake oil salesmen?” I have those days where I’m like, “I’m doing it. I’m going off the deep end.” We always come back. This is a long game and I would so much rather be honest and not be responsible for somebody feeling like it’s their fault. Whitney, it’s not your fault. They didn’t follow through on their end of the bargain.

It’s so helpful to hear this, and hopefully, the reader feels refreshed by this too. This reminds me, and it is funny to share this, I wrote you guys an email that I never sent at the beginning of 2020. I didn’t send it because I was feeling so crappy about myself and I was reaching out to you guys because I knew you would understand and now, I’m like, “Why didn’t I send this email?” Because I bet you would have had such amazing advice for me. I pulled it back up because it was saved as a draft. My question to you back then was, “I feel I’m doing everything right. I finished this coaching program, but nothing’s working.” My big question was, “Why do I feel I’m trying everything I know how to do but I’m not getting the results that other people are getting?” That was part of the issue.

Back then I was part of this bundle sale, which Jason Wrobel and I have talked a lot about because we’ve been experimenting with these bundle sales. I did this one in January 2020 and I was seeing all of these other people that were my contemporaries or whatever that were getting these insane results. They were making so much money. They were getting all this great feedback. They’re constantly celebrating it and I was sitting there thinking, “I’ve been doing my work as long as they have. I’ve been creating the same type of posts. I’ve been using the exact same marketing strategies as them. Why am I not getting those results?” It led me to days of depression. I couldn’t get out of bed. I felt so horrible.

I wrote in this email to you, I’ve said, “Positive self-talk is important to me, but I have to be honest. Today, I feel like a loser and a failure. I feel lost and confused. I don’t know what to do because I feel like I’m trying a lot and barely getting results.” I know Jason Wrobel can relate to this too. Sometimes we feel almost angry and resentful and it’s such an important thing to discuss because we are in this time where so many people are saying things like, “Follow this and you’ll get that.” What people don’t talk about is what happens if you don’t get those results?

First of all, thank you so much for sharing that. Second of all, you should hit send because you know I reply to every email. You’re going to get a reply. That’s the difference for us and a lot of people. In getting back to what you said earlier, we care about how people feel when they contact us. We never wanted to feel, “Our assistant replied.” There’s nothing wrong with that. If that’s something that someone wants to do because they can’t handle that and it affects their mental health.

This is where the robot emoji comes in. You’re an email robot.

To specifically talk about your question and hopefully make you, fellow Jason, and other people reading this feel validated is we all have felt this feeling. We will continue to feel it, unfortunately, and it’s one of those things where the immediate practical problem solver in me is to go, first of all, you got to take inventory of your life and your business and go, “What is working now?” Remove all external things and go, “Are you able to provide for yourself? Are you able to put a roof over your head? Are you able to keep your family safe? Are all those things taken care of?” If they are then all the stuff that you’ve been trying to do, it doesn’t matter. You spent money on it, you invest time in it and all that, and that’s fine.

The second thing to do is to be like, “Who am I comparing myself to? Who am I surrounding myself with? Should I continue to do that?” I know for me, that’s where 2013 me was like, “I don’t want to be in the same sentence as Gary Vee, Lewis Howes, and all these other bro entrepreneurs,” because I was definitely living that life. I don’t want what they have. I don’t want the growth, the stress, and all that stuff. The thing that was important for me at that time was to literally mass unfollow everybody and go, “Let me get back to ground zero.”

Who do I want to surround myself with? Who do I want to be looking at and getting inspiration from? Maybe it’s from nobody, maybe I need to step out completely and go, “I’ve got Caroline, my wife who is amazingly creative and we have lots of awesome conversations.” That’s good enough and now let’s get back to, if I am trying to grow the business or do whatever, why am I trying to do those things? It goes back to enough mindset. We’ll get to elephants later. Understand it. I do want to two times my revenue every month. Why? I’m trying to save it for a house. I’m trying to whatever. I know what I’m trying to do. How am I trying to do that thing? I tried it this way and it didn’t work. That’s fine. It may work for other people. I have to ignore that. Let me try another version of something I can do that I can control and let’s see how that works.

This is one area where I tend to be the more emotional of the two of us.

A hundred percent.

There is no right answer for everybody, there's just the right answer for you right now. Click To Tweet

Readers, if you’re picking up on that but this is where your logical brain helped me because the last time that I felt this way, going back to what you said, Whitney, with your email, I have felt that. The resentment, the feeling like a loser, the seeing people celebrate their big launch or their big thing and going, “I know that they are not somehow more magically talented than I am. What am I missing?” This is where I realized that the more I focus on their results, the more I try to figure this out through the context of what someone else is doing. I’m trying to deconstruct what’s the missing piece that they have and I don’t. The more I feel crappy about myself, and the crappier I feel about myself, the less motivated I am to work, to experiment, and to try something new because the voices of self-doubt get louder. This is where my Jason, you’re a logical brain part helped me.

That was where the logical part helped me to go, “I know that it’s only a matter of time before going back to the first E, experiment before I experiment with something that does click, but I can’t get to that experiment if I feel crappy about myself and if I focus on these other people.” I did the same thing that you did, which was I’m not going to allow that into my exposure. I’m not going to focus on them. I’m going to fight the urge to go look them up on Instagram and see what they’re doing. I’m going to fight the urge to go to their website so I can nitpick it and feel better about myself because those are all things I’ve definitely done. I’m a human being. Once I trained myself to do that, I realized that it’s a matter of finding the motivation to get the next experiment going and believing that it’s only a matter of time and that’s how we approach it.

I will say one more point to that. Whitney, I wish that you would have sent this email because you see this when you hang around our Wandering Aimfully Slack community. When people are willing to share this and be vulnerable, it helps you get over that situation much faster so you’re not internalizing, not continuing to think about it so you’re not staying in your own head. This is for anybody reading, hit send on the email because that may in itself be the relief. You need to be like, “I finally got that out of my brain. I sent it off into the world to someone else. Regardless of what they respond with, if that’s helpful or not, I feel a little bit better.”

We know from experience the more that you can share those losses especially, the more that you can see other people say, “I’ve been there. I know exactly what that feels like. Even if I haven’t been in this exact situation, I’m here to support you if you need that.” That in itself is why we’re so happy to have a community as we have and I also think why it’s also worth hitting send on that email, DM, or whatever it is if you’re in a position that you want to reach out to someone and share. Most people, if they are good people, if you share that with them, I will definitely be like, “I’ve been here. You’re seen and it’s all okay.”

This is going back to the blueprint question of why we don’t subscribe to anyone else’s blueprint. Business is so nuanced. Everything is different, you change one thing and your outcome could be different. You change the name of your business, the branding, the product, your audience, and who you are. For all of these things, there is an infinite number of variables. When you think about comparing your journey to someone else’s, it does become irrelevant, because you’re like, “Their variables are so different from mine.” It’s a matter of working with the variables you have and experimenting to find something that does click.

To end this, it’s so wonderful to get your responses now after I wrote this and to think about where I’m at now versus where I was at the beginning of 2020. I don’t know why I didn’t send it. Maybe I felt shame or embarrassment. Maybe it was so intense because it was rough. I normally wouldn’t have even written an email like that because I’m such a person that tries to figure things out myself for better or for worse. It’s like, “I can do this. I’ll meditate, do some yoga, or journal about it and I’ll get the answers.” It’s that desire to want to do it on my own because I don’t always trust that other people are going to support me.

That’s one of my core challenges. I get triggered when I don’t feel supported and I remember in that time, you guys, were the only ones I could think of. I remember sitting down and thinking, “Who can help me through this? Who’s not going to give me some generic answer?” That’s why I wrote it to you and maybe in the process of writing it was all I needed. To your point, Jason, I didn’t need to press send or maybe I didn’t press that or maybe I didn’t press send because I was feeling so embarrassed and ashamed. It’s like the, I’m such a failure mentality. Jason Wrobel, I’m curious where you come in on this because I know you’ve struggled with this too.

First of all, without turning this episode into a therapy session with Jason and Caroline. Although the third E could be ecstasy if you guys, in your next care package, want to send out MDMA.

We’re down.

In those Thank You boxes are missed opportunities.

It’s a suggestion. One pill on MDMA, if people want it.

No label. Have fun and see how it feels.

In taking the virtual MDMA, to piggyback on what Whitney was saying, having been on my career track for a couple of years, doing online content and entrepreneurship for more than a decade now, I feel like burnt toast. I feel the crispy chunks of the crust that have fallen to the bottom of the toaster oven and two years later you’re like, “That’s why it smells everything’s burning all the time because there’s this crispy edge in the back of the toaster.” I feel like that now. I want to admit that I feel that way and part of it is the Einstein quote, “Doing the same thing over and over again and expecting different results is the definition of insanity.” I don’t have any desire to keep doing things the same way. I feel like a burnt crispy toast crust on the bottom of the oven, but I also don’t know what to do next.

It’s interesting because I’m vibing so hard on what you guys are talking about with experimentation, but I have no idea what experiment I even want to conduct next. It’s almost like this purgatory of wanting to detonate my old identity and the people that I hold in high regard are these chameleonic people. David Bowie is one of my favorite artists of all time because he was such a chameleon in reinventing himself all the time with his sound, look and vibe, but also at the core he’s very much David Bowie. It’s very much David.

MGU 168 | Humans Navigating Life

Humans Navigating Life: Business is so nuanced. Everything is different. You change one thing and your outcome could be different.


My question, my rant, and my mental vomit piggybacking on Whitney’s comment is, I’m done doing the old stuff and I want to proverbially detonate my old identity, but I have no idea what experiment or who I’m even becoming. It’s like, “What do we do,” but also taking a sabbatical is this weird thing because I don’t have seven figures in the bank so it’s not going to be this Eat, Pray Love movie of,
“I’m going to go to Bali for six months and screw it.” There’s nothing wrong with that but I don’t necessarily feel that that would be a great option for me financially.

We’re in COVID.

If we feel lost and burnt out, and I don’t know what’s next, how do we reinvent ourselves? I know that’s such a macro question but that’s where I’m at and I want to pull the plug on everything I’ve done before but also entering that part of the forest. Joseph Campbell talks about the dark path in the forest. It’s like, “I don’t know where this is all leading God Almighty,” and it gives me so much anxiety.

This is where I go with this question because this is a great question that a lot of people can relate to. I’m going to use a metaphor and if you listen to our podcast, you’ll know sometimes they land and sometimes they do not. I want everybody to walk on this journey with me. The visual that’s coming into my brain, as you’re describing this is I feel like you’ve constructed this Lego tower out of all these different pieces and you said your career has spanned for years and all these pieces have come together to build this thing. You’re ready to blow up the thing but in your mind, you’re like, “I know I want the tower to be different. I want it to be a different tower.”

I feel that some of the pressure is coming from thinking you’re going to assemble a new tower right away. The way that I approached this is going, “Let’s not focus on the new tower, let’s focus on the pieces.” Let’s blow up the old tower into its individual little teeny tiny pieces and let’s see what of those pieces is a spark of joy that you can pursue that can turn into an experiment. The simplest way that I would approach this is to write a list and be like, “What is everything I can think of the old Lego tower that I liked? Everything from talking to this person to this actual skill that I developed along the way or this thing that I always find myself reading articles about.” I call it your Light Up list, the things that light you up. Those are your Lego pieces and not putting pressure on yourself to construct a tower right away out of all those things but to go, “Which one of these sparks a little bit of curiosity in me? Can I go down a rabbit hole? Can I allow myself to pursue the tiniest step forward on a path using one of those things as the first step?”

Whitney can forward you the email that we sent out about burnout. That’s going to be a lot of what I’m about to repeat.

It’s a missed opportunity for us not to call ourselves burnt toast because I love that.

Full disclosure, I probably did forward it to Jason, but he does get overwhelmed and burnt out by reading emails. How do you overcome that when all the information is there for you, but you can’t even read it?

Our emails are long so it’s like, “Great. I’m buying into a tome here via my computer.” The interesting thing that you brought up, which a lot of people deal with is when you think about taking a sabbatical. It becomes this idea of like, “I’ve got to have six months to a year of not doing anything.” A 30-day sabbatical, which is something that most people can figure out in some way.

We don’t always tell people that you should do this but there are people, and we’ve been in this place before, where maybe you have to put all of your expenses on a credit card for a month. We’re not the people who want you to accrue debt. We are all about paying off debt and being super frugal with money. Sometimes you need to leverage that as an opportunity to create space for yourself where you can go, “I need 30 days to not do. I need 30 days to be with myself, my thoughts, my family, and write down the Light Up list and to examine all my little Lego pieces,” and to go, “What do I want to be doing?”

We don’t make any guarantees, except for 10X-ing your revenue if you pay us $25,000 a day for seven days. It’s not like you’re repeating the process every single day, you’re going through the thinking, the exploration, the, “What could I create? What could I make? What is exciting to me? What opportunities are around? Maybe I want to work for another business for a little while and take all the stress and pressure off of myself.” By the end of that 30 days, you will have something that is staring you in the face and it’s going, “I’m your next Lego tower to build.” You’re not going to build it in a day. You’re not going to build it in a week. You’re not going to build it probably in a month. I am showing you the opportunity where you can take the pieces from your existing tower and you can start to lay the foundation of that next tower.

The other important thing is acknowledging the fact that burnout is not something we have an understanding of how to deal with because it is new to us. Jason, you and I have been in business for about the same time and working for ourselves about the same time. When I got burnt out in 2013, I’m not trying to win an award saying I was early on burnout. Not a lot of people were burning out of working on the internet back then. I didn’t have anything to look to understand what I was going through, other than a supportive person next to me to be like, “We’re going to figure this out.” The key is to not try and force figuring it out because forcing is what got you into burnout by doing all these other things and as opposed to being like, “Let me loosen the reins on everything a little bit and try and chip away and allow things to happen.”

The sagacity that is flowing through this podcast is legendary.

Is that because of the MDMA?

Business is just a tool for me to be able to do life in the way I want to. Click To Tweet

It’s because I’m high.

Good. I wanted to be aware.

I have been high on the podcast before but it’s because of pain meds, but that’s a different conversation. It’s interesting to podcast when you’re high. The offshoot that I have is maybe scaling back to reinventing ourselves or inviting the new evolution. When you guys have shifted away from the t-shirt thing and all the different variations and versions of your business offerings, did you find value in communicating to the people on your mailing list or on social media? “We’re not doing the t-shirt thing anymore and here’s why. This is what we’re doing now.” I don’t want to use the word training them or conditioning them. People get used to you doing one thing and doing it well and then they’re like, “You’re the t-shirt people. You’re the chef. You’re the dog walker. You make hydroponic lasagna.” Did you find value? Did you guys do this where you’re like, “We’re going to publicly announce the fact that we’re pivoting and here’s why.”

This is our favorite thing to do.

I don’t know if I can say that this is how you should do it, but this is how we’ve always done it and it goes back to what I was saying before. Maybe a part of it is selfish because we want the freedom to be able to pivot in the future. If I want that freedom, I have to be making sure that every time that box starts to get solidified, you have to actively break the walls a little bit so that it doesn’t get unmovable if that makes sense. Along the way, we’re always checking with our audience and saying, “Here are the decisions we’re making. Here’s why that doesn’t work for us anymore. Here’s how we’ve changed as people and why we’re going to move towards this other thing.”

Luckily, we have built up enough credibility and trust with our audience. They’ve seen us move projects forward. They’ve seen us deliver on our word. There’s trust there. When we check in with them and say, “We’re not doing that anymore. We’re moving on to something else,” it doesn’t come across as, “These people are untrustworthy or can’t keep their word or can’t stick to anything.” They understand where that intention is coming from and it’s because we’ve been super transparent with them from the beginning. I find that checking in with people and saying that is a way to make sure that those walls and the box don’t ever get thick that it becomes like a prison. Instead, it keeps the walls flexible and it says, “Here’s the container we’re in for this year and maybe it’ll change in two years.” Our audience has come to expect that.

Another element of this that Jason Wrobel could speak to, and I want to begin with Carol’s input on this, is managing mental health when you’re going through a challenging time with your mental health like running a business during that time. You guys spoke openly about Carol’s experience with anxiety, which I felt was helpful because it reminds people like me like, “You struggle with your mental health too sometimes and this is how you handle it publicly.”

You guys are fortunate to have each other where Jason was able to take over the business for that time. It wasn’t like, “I need a week off to recover from my anxiety.” This was a long process for you, Carol. Another part of this equation for Jason Wrobel is he publicly talks about his struggles with mental health. It’s not easy when you’re feeling depressed, anxious, sad, stressed out, or burnt out. Burnout is another element of mental health that’s becoming more common. I’m curious, Carol, how long was it that you were taking the time off? How did you even know when you were ready to come back to do your work?

Luckily or unluckily, my mental health struggles, specifically anxiety, shows up in my body in ways that I can’t ignore. To answer the last part of your question, first, I know I’m ready when my body is not rebelling against me and I ease back into it carefully. I am attuned to my body signals. If I’m sitting at my laptop for an hour and I’m getting dizzy, I’m not ready to come back to work. My body is sending me those signals.

To answer your question, 2019 was such a hard year. I’ve dealt with anxiety in varying degrees my whole life. Looking back, but more acutely over the past years, at the beginning of 2019, it hit me to such a degree that I had never experienced before. It showed up in crazy, physical symptoms. Not that I had depersonalization and derealization. For anyone who doesn’t know what that is, you physically feel you’re not seeing the world from your perspective. It’s like you’re disconnected from your consciousness, which is a weird way to describe it. Also, I’m not a clinical psychologist in any way but this is my understanding of it and it’s a scary feeling because you feel like you’re going crazy. Jason had to walk me through that for, what lasted in a severe way, about six months but I was healing for the entire course of the year.

It’s hard to give people advice about walking through that because I am privileged to have a partner who was able to support me and a partner in my business who was able to keep the business afloat while I was dealing with that. The things that worked for me, I can’t necessarily prescribe to other people to say, “Devote 100% of your time to your mental health and your business won’t fall apart.” The only reason our business didn’t fall apart is because of Jason. I know that was a hard year for him as well because he was caring for me and keeping our business afloat and somehow managed to grow the business. I’m not sure how he did that.

An important thing that I’m passionate about and why it showed up on our Instagram feed, “We’re humans navigating life,” is because we have seen the detrimental effects of what happens when you don’t care for your mental health, mine specifically. We now know, as a family, that is our absolute number one priority. If our entire business had to fall apart for me to be okay, we would do that. Money cannot buy health. The darkest places that were going in my head, a business is not worth staying in that dark place. If push comes to shove and I have to get out of that dark place or I have to show up for my business, I’m going to do whatever I have to do to show up for my mental health first. What that year taught us is that this is the most important thing and that’s why we are more focused than ever on being intentional and deciding how much work is enough for us. I’m not going to push to my limits anymore because I know where that gets me and I can’t go back there.

For what? To make an extra $1,000 a month and then you’re derailed for six months? It’s not worth it. I have heard that anxiety feels a certain way so I can empathize slightly. Everybody knows what it feels like when you’re run down, you’re burnt toast. Something is not right. Until you go through that, it’s hard to realize how much that matters more than everything else. It’s easy to get stuck in the rabbit hole of, “I got to make more money. I got to optimize my funnels. I got to get my marketing going. I got to get my content. I got my podcast,” all these different things.

When something hits you and when it derails you, especially a mental health issue, you then realize all that stuff is trivial and it is not important, but we build it up to be important. We surround ourselves with people who are also building it up to be important. That was a big thing for us too. When all this started happening, I was only focusing on keeping our business afloat and your mental health. They’re my two things. I had to be like, “Everything else gets pushed to the wayside.”

MGU 168 | Humans Navigating Life

Humans Navigating Life: We need to stop giving people advice as though there is an objective right or wrong way to make choices in life.


I’m not worried about creating any content. I’m not worried about doing anything. I’m trying to figure out how do we continue to make our members happy? How do we get a couple more new members a month so we can make our bills? How do I make sure you’re taken care of? It strips away everything else you can do to show you, “We can still survive.” We can thrive but we have to get scrappy and we have to do things a little bit differently or come up with different experiments we can try. There are many things I tried in those first three months while you were down for the count. They didn’t work at all. They would fall flat on their face, but I did see a couple of things that worked, and I learned things and it’s because I was willing to keep trying stuff that wasn’t what we’ve been doing forever.

You go through a crisis and you realize what the most important things are, and you also realize how you can get by only focusing on the most important things and how much the other stuff falls away. That gives us this amazing context. That’s why it’s been a little bit easier for us to focus on the things that matter and then let everything else go because we have the context before. The mantra I say to myself is, “Stepping back is getting ahead.” I used to have this mentality of getting ahead is getting ahead but now it’s like, “I see what happens when I push to the edge and it could potentially end up with a year where I can’t work.” That’s what happened, a year of not working. If I feel myself getting to that, even way before that edge, I pull back way sooner because stepping back is getting ahead because it means I’m not going to have potentially a year where I can’t work.

This is valuable for many reasons for me to hear. I appreciate you guys sharing in such depth and being real. I’m decoding and deprogramming a lot for myself in the sense of taking a step back from the fear of disappointing people, of disappointing people on my mailing list, of disappointing people on social media, of disappointing Whitney as my business partner. I’m getting better at communicating with the people in my life, “I’m not going to do this right now because I need to go and take a nap. I’m not going to do this right now because if I sit down and answer one more email, I feel like that is going to be pushing me to my edge.” For some people, that’s not their edge. Some people can sit down and plow through 50 emails.

This idea of paying attention to our body signals is valuable and useful. There are some days I can sit down and bang out 25 emails in a row. There are some days where I sit down and I know that I need to reply to certain people but my body starts to react to the idea of emailing them back where I’m like, “The world will not end if I take a day or two.” Even though some people might go, “We got to get these emails.” It’s like, “I know that but I’m also going to try and either delegate or put a pause button on this thing and get to it in a day or two.” The somatic experience of listening to our bodies is critical and I love that you’re saying this.

It is wonderful to know people like you. One word that I wanted to make sure I share before we wrap this episode is that I feel like people like you are giving me permission. You showing up the way that you show up is like, “I can show up that way?” For better or for worse, I like to look at other people for examples. I do this with artwork, too. Carol, I’m curious about you as I’ve been inching my way towards doing more digital artwork. I’ve been looking at other accounts. I want to see what’s possible. What are people doing? It’s not necessarily what’s popular, but what makes me feel good.

Podcasts like yours were helpful for me and Jason when we were developing this podcast because it was like, “It’s okay to have long podcast episodes.” I know you guys did a three hour one yourself. A lot of people will see that and be like, “That’s such a bad practice as a podcast. They need to be short.” We were advised not to do long podcasts when we started this. People wanted us to make them 30 minutes, 20 minutes. It’s like, “Make them bite-size. Who’s going to listen to that long of a podcast?”

The reason that we went with our length, which is on average, 90 minutes, is because we listen to podcasts that long. I enjoy long conversations. I will listen to them on road trips. Even if I’m in the car for ten minutes, I’ll pick up where I left off. I’m grateful that you guys show up the way that you do in all of these ways that we’ve discussed because it does give people like me permission. Permission isn’t even quite the right word, but it feels that way. You’re seeing somebody else doing something that you want to do and you feel it’s okay because you’re not going to be the first and the only person doing it.

Thank you for that because it also reinvigorates us, me specifically. That’s why I want to share. That’s why we want to create things because sometimes you get wrapped up in your own story and you think, “What impact do I have? I’m one person.” You do realize that every person’s story is permission for someone else because they see a possibility that they maybe didn’t know for their life or their business before seeing the way that you did it.

Going back to your podcast example, it spurred for me a quote that I used to have in my head or something I used to say on my Instagram years ago that I haven’t said in a while, it was, “Create from a place of joy. Adapt from a place of business.” I do think that’s how we approach our business. We start with pure creativity, the thing that we want to do. It’s like, “We want to do a podcast that’s longer.” If we do that for six months and we see that we’re not getting traction and we need this podcast to get traction because we need it for our business, then we’ll adapt. I’m not going to get out of the gate and stifle the thing that I want to do because people are telling me it’s bad business practice. I’m going to start off doing the things that I want to do. If I have to adapt down the road, I’ll do that. That’s a weird aside but you reminded me of that, Whitney. Thank you for that.

I have not talked about this publicly. This was the worst year for me, financially, ever in my business. As a result, I started to apply for not contract positions but job jobs. I haven’t had a corporate 9:00 to 5:00 in years before I left that world and went into it. The reason I haven’t talked about this publicly is I felt shame around it. I’ve applied for close to 50 positions. I’ve had three interviews and that was weird because I have not had an interview and I was like, “What is this? Go back to the deep memory banks.” I was like, “Be you. Show up with your Ducky Dale, Jon Cryer, Yahoo Serious hair and be you and wear the nice Hawaiian shirt.”

I realized there’s a framework of a conversation in the entrepreneurial world like, “Leave your 9:00 to 5:00 job and stop making millions for someone else. Make millions for yourself. Only suckers work 9:00 to 5:00 jobs.” There’s so much judgment I see in the entrepreneurial community around 9:00 to 5:00 is bad. Working for someone else is bad. Don’t be a sucker. “Live your dream.” Through necessity, I was like, “I’m struggling this year. It’s been the worst year, financially. What if I dip my toe back in that world by sending out 50 freaking resumes?” Interestingly, I’ve been paying attention to my own judgment around it and my own shame of like, “You failed after doing this for a decade. You’re a piece of crap.” You’re applying for these jobs and I’m noticing how much shame and judgment I felt around it. To take a cue from you guys, admitting it publicly, that’s what I’ve been doing.

I’ve also hit this wall of like, “You’ve sent out 50 resumes and nothing has come through. Maybe this is a sign from God, the universe, Gonzo The Muppet, whatever you believe in, that maybe you ought not to go down that road. Maybe you should grit your teeth and detonate the Lego set and reform it.” I don’t know that I have a question in all this other than have you guys noticed in the entrepreneurial world this 9:00 to 5:00 shaming? Why do you think it’s prevalent? What’s all this about?

This is something that’s been interesting for us as we’ve grown this community of intentional humans who are trying to possibly build online businesses. It’s almost difficult for us to sell Wandering Aimfully to people because we don’t carve out any specific thing where we’re like, “We want you to leave your 9:00 to 5:00 job and start something.” For a lot of people, we don’t want you to leave your 9:00 to 5:00 job. For a lot of people who run a business and you’re stressed out, we want you to get a 9:00 to 5:00 job.

We’ve told people to do that.

It's empowering to be willing to try new things and put yourself out there. Click To Tweet

The thing is, there is no right answer for everybody. There’s a right answer for you right now. Years ago, it may have been a terrible time for you to get a job because you were on the cusp of figuring something out and it was working. That doesn’t mean that’s going to work forever. You’re right. In the online business space, there is this toxic culture of 9:00 to 5:00 bad, running your own business good. It’s such a caveman mentality because it’s not true. It is not true for everybody. It’s not true for the type of person that everybody can be different and at different times in their life. It’s also not true in the fact that you can prosper so much more with a 9:00 to 5:00 job that provides you the cash and the “security” to then explore other things on the side that could then lead you back into working for yourself if that’s what you want to do.

For us, that’s one of the things that people will sign up for Wandering. If you’re like, “My goal is to quit my job in six months and start my own thing.” I’ll write back to you and be like, “That’s a great goal. Also, know that this is a community where you don’t have to do that.” If you want to keep your job and you like your job, we would love for you to do that and then build your thing on the side and have it be a side hustle and enjoy both and that’s okay as well.

Maybe this speaks to how our perspective on everything is colored. In our time here as human beings, in this freaking dimension, wherever we are on this planet Earth, that is the thing that we’re all trying to do. To me, business is a tool for me to be able to do that life in the way that I want to. Getting a 9:00 to 5:00 job is also a tool in order to give me money to have the life that I want. Everything revolves around the life piece and the business or the job. Those are all tools.

It’s awesome that you applied for jobs because it means that you looked around and you said, “I’m not getting the financial means that I need in order to live the life and my time here as a human and the way that I want to. I’m going to put on my thinking cap and go down any avenue that I can in order to solve that problem.” To me, there’s no shame in that. That’s you being a proactive person and taking steps towards living the life that you want to live and not sitting here and going, “Things didn’t turn out the way I thought they would so I’m going to sit here.” That’s proactive. That’s awesome.

This is a pet peeve of mine. We need to stop giving people advice as though there is an objective, right way or wrong way to make choices in your life. Instead say, “Here’s what worked for me. Here’s what could work for you.” One thing that I picked up on what you were saying about, especially sending out the resumes, maybe this is a sign from the universe that I shouldn’t get the job. I feel like we do this thing to ourselves. We like to think that there’s a right path and a wrong path. We think that there’s a right decision and a wrong decision. We extrapolate out the decisions to see where the trajectory is going to take us. When we do that, we put a lot of pressure on the decision-making process instead of erasing that future that your brain is trying to fill in for you.

Back to the experimenters’ mindset thing, it’s not like getting a job is the right decision or getting a job is the wrong decision. These are things that you’re trying at this point in your life and you’re going to keep trying things until something feels like it’s a natural fit for you to move forward. I wanted to add that because I do think I do this a lot in my own life of putting a lot of pressure on these pivotal moments where you feel like one decision is going to take you down the right path or the wrong path and instead of taking a path. Taking it as it comes and going, “I’m confident enough in myself, in my experience, in my skills that whatever opportunity is presented to me and whichever direction that takes me down, I’m going to roll with that set of circumstances and see what happens next.”

I’m feeling inspired because I’ve been on the fence to get a face tattoo. I feel like getting a face tattoo will be like, “You want to do business with me because you like me. You’re going to look past the face tattoo.”

We’re all about giving permission here.

It’ll say, “EEE.” “What is the EEE?”

You’ll forget what the E’s are too.

Also, an elephant on ecstasy and everyone are like, “What?”

That is a great tattoo idea. I am falling in love with you guys. You were joking, Caroline, about collecting Jasons.

You’re my Jason now.

I’m great at taking out the trash.

There is no right answer for everybody. There's a right answer for you right now. Click To Tweet

That’s a requirement for my Jasons.

She doesn’t a lot of domestic chores. We’ll split those. It works for me.

It’s fun talking to you guys. You mentioned the shoulds, Carol. An episode we had was a lot about removing the word should from our language. Her name is Tricia, she’s great, Your Joyologist. If you guys, Jason and Carol, haven’t heard of her, I highly recommend her. You’d resonate. She has a great Instagram that makes me feel good. Her episode is lovely. Another thing that she said was she was trying not to say, “You guys,” and sometimes I catch myself. It’s not always appropriate.

That’s when I have to break myself as well.

What do you say, “You humans, you people, y’all?” Y’all has a nice drawl to it.

That’s what I’ve been trying, friends instead of guys. It’s like, “Hey, guys. Hey, friends.”

I like that. Some people overuse the word love, like, “Hey, love.” I’m not into that one. In my opinion, I like to use love intentionally. It’s all about conscious, intentional language. I digress. I am grateful for each of you because you’re comforting, that’s the best word. This is the reason that I’ve been part of your amazing community for years. I love being a testimonial. I’m excited about Teachery, which we didn’t talk about. It’s being relaunched as an amazing platform and I’m excited about it. I’m going to get inspired to create some new things through that.

It’s nice when you feel so much joy even when you’re doing business and learning new things, which can feel daunting. It’s easy to get burnt out. One of the reasons that I appreciate the way that you two coach is it’s infused with joy. I am grateful that you took the time to come on here because it’s nice to talk in general. You offered many amazing perspectives. Behind the scenes, I was trying to write down all these different quotes that you two were saying because we like to put quotes like that on Instagram. I don’t even know how I’m going to choose one, to be honest. Thank you for giving us so much food for thought, for helping us to remember how to prioritize our mental health, to get back to being humans. Navigating life was the big theme here. You can check out Wandering Aimfully on their social media. I love their Instagram. It brings me joy looking at it. Jason and Caroline, I will see you in the Wandering Aimfully group.

I’ve got the Kool-Aid pumping through my veins.

Thank you so much for having us. The feeling is mutual. We had such a great time chatting with you guys. Remember the three E’s. Do you remember them?

Ecstasy, elephant, and eroticism.

We should have a quiz.

We would fail our own quiz. That’s the problem.

It’s like a little scavenger hunt where you have to go listen to the whole episode mindfully and try to figure out what the three E’s were. I would not be surprised if it ends up in one of your upcoming newsletters.

We’re going to embrace it. There’s a fourth E.

You’ll end up doing an entirely Wandering Aimfully session about this and you make one of your little characters. It will be like Ellie The Elephant. There are also your wonderful visuals of your business practices. I cannot stop thinking about that bridge that you drew. The marketing bridge has solidified in my head. All the curiosity we’re creating amongst the readers and Jason Wrobel, I’m sure that’ll entice them to come and join us on Wandering Aimfully because it’s a magical place.

We do call it Unboring Group Coaching. We call it that for a reason.

You have achieved that. It is anything but boring!


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About Jason and Caroline Zook

MGU 168 | Humans Navigating LifeWe’re Jason and Caroline Zook, a husband and wife team who run the un-boring coaching program at Wandering Aimfully as well as the online course platform for creative biz owners called Teachery. Since we got together in 2010, we’ve made things in a slew of different ways, both together and apart. Caroline was first employed by Jason’s crazy t-shirt marketing company IWearYourShirt, getting her first taste of work-from-home-life (AKA: wearing a robe to work). After that we had separate businesses for a few years. Caroline created Made Vibrant, which started off as a client business doing brand design and transitioned into a digital product business. Jason got even weirder by selling his last name, writing a fully-sponsored book, and then selling his future. We’ve also built software products and sold physical goods.


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