Listen to our full episode on What Are We Doing With Coaching In 2024? below (with full transcript) or find our podcast by searching What is it all for? in your favorite podcast player.
Five Key Takeaways for What Are We Doing With Coaching In 2024?
1. Focusing on Teachery
We’ve made the decision to FINALLY give Teachery the chance it deserves. We asked ourselves, What if WAIM coaching was following our journey of building Teachery next year and working on it full time? We’re calling it Project All In (working title) and we want to focus on Teachery’s untapped potential, its existing user base, and the vast growth opportunities compared to competitors.
2. Recognizing comfort zones vs. growth edges
We want you to take a step back and ask whether you’re fortifying a familiar foundation out of comfort or truly exploring new, potentially more challenging avenues for growth. We realized that, instead of pursuing a seemingly exciting new venture, the more sensible move is to invest time and effort into our existing asset—Teachery (that’s already making money!). The crucial lesson is to resist the allure of novelty and focus on nurturing what already works. This is the exact advice we’d give someone else, so why not take our own business-medicine??
3. Nimble Funness in action
Nimble Funness is a phrase we just came up with, which is a guiding principle for us in decision-making. The idea is to prioritize creativity and uniqueness in every endeavor, particularly in marketing. Especially in this era, there is a need to stand out and be memorable rather than conforming to traditional norms. The example of launching a YouTube channel serves as a case in point, where the goal is not to meet standard SaaS video criteria but to be radically different. Successful marketing is about creativity, fun, and finding a unique niche rather than adhering to conventional strategies. It’s crucial to stay true to your vision, even if it means a shift in focus.
4. Evolving our coaching sessions
We are transitioning WAIM’s monthly coaching sessions from the current format to a more focused approach. The sessions will now center around updates and insights from Teachery, integrating elements from our Un-Boring Business Roadmap, and reflecting on the outcomes of the previous month’s efforts. This aligns with our renewed focus on Teachery while emphasizing a more streamlined and purposeful coaching experience for WAIM.
5. Calm Business Confidential
We each surprise the other on the podcast by bringing a business they know nothing about. The only rule? The business has to be raking in some cash, but not more than a million and a half a year. We chose that number because we wanted a wide spectrum of interesting businesses to chat about.
👩🏻🦰 Carol’s pick: John D Saunders of johndsaunders.co (entrepreneur and agency founder)
👨🏻🦲 Jason’s pick: No biz this month as “his dog ate his homework.”
AND, if you have a calm business you think we should talk about, send us an email and share it!
Show Notes for Episode 179: What Are We Doing With Coaching In 2024?
⭐️ HEADS UP! From October 2 – 17 we’re opening the doors to our un-boring coaching program: WAIM Unlimited. Let us show you exactly WHAT to improve in your online business and in WHAT ORDER, so you can grow your revenue and live a more spacious, satisfying life! ⭐️
This week, we share a pretty big update as it’s the future of our focus in our work!
We sat down last week and had a 3-hour brainstorming meeting that resulted in coming to a decision about our monthly coaching plans for WAIM Unlimited (our un-boring coaching program) AND our small side business Teachery (an online course platform).
In this ep, we share all the conversations we had and how we’re embracing feeling like JCVD straddling those semi trucks! We’re excited about “Project ALL-IN” in 2024 and hope you’re excited to go along on the ride with us.
Full Transcript of Episode 179: What Are We Doing With Coaching In 2024?
⬇️ You can also download the .TXT file of the transcript
Jason: Hello, hello, hello and welcome to the ad read for this episode. And just as a reminder, the ad read is us, and so we’re supporting our own business here. So don’t skip it because it’s not about a mattress.
Caroline: That’s right. So if you are an online business owner, if you are feeling overwhelmed in your business, or you just feel like it’s stagnant and you’re looking for ways to improve it, this is for you.
Jason: Our Wandering Aimfully Unlimited un-boring coaching program is open for Fall enrollment until October 17, and this is the very final enrollment at our current $2,000 price point with our $100 per month pricing plan.
Caroline: It’s open right now, and it is all about making your business more profitable, more predictable, and more peaceful, which is the entire point of running a calm business.
Jason: You’ll enjoy live monthly coaching sessions from us. You get access to a content library covering business growth, creativity, and work life balance. And you’re going to find out what our 2024 coaching plans are as you listen to this episode.
Caroline: It’s especially perfect for you if you are a coach, if you are a client based business owner, or just really any creative solopreneurs, the entire program was created for you.
Jason: And if you’re looking for a welcoming, supportive, and fun community that’s actually active because you all know you join some Facebook groups and ain’t nobody in there, you can join WAIM. We have our Slack Channel, which has monthly accountability through a game we call WAIM of Stones now, but it might adapt into something silly in 2024. You can hang around and find out about that.
Caroline: That’s right. Just a reminder, like Jason said, this will be the last enrollment period that we are offering WAIM Unlimited at our current price. We have not raised the price in five years. It will be the last time we’re offering our $100 a month payment plan option, so definitely want to check that out.
Jason: WanderingAimfully.com/join to learn more and join the adventure.
Caroline: How’d we do? That was a pretty professional ad read.
Jason: Yes. Okay. We just got the money. It cleared our bank account and they paid us.
Caroline: Thanks to our sponsors.
Caroline: Welcome to What Is It All For? A podcast designed to help you grow your online business and pursue a spacious, satisfying life at the same time. We are your hosts, Jason and Caroline Zook, and we run Wandering Aimfully, an un-boring business coaching program. Every week, we bring you advice and conversations to return you to your most intentional self and to help you examine every aspect of your life and business by asking, what is it all for? Thanks for listening. And now let’s get into the show.
Jason: And I’m here, too. Hello and welcome to the podcast. That’s the new one. I’m going to do that one.
Caroline: If someone really had the time, they should just go back and supercut all of our weird…
Jason: Podcasts are cool. Dot, dot, dot.
Caroline: Dot, dot. See, now that really would have taken off.
Jason: It would have.
Caroline: If you’re wondering what would have blasted our podcast.
Jason: What would have what? Would have what? Can I just do a really quick movie chat? Really quick movie chat. Just really quick. We watched Fast X this weekend, and then I listened to the How Did This Get Made? Podcast episode with Seth Rogen as a guest and Evan Goldberg as a guest. And they had all the same questions that we did about this movie. It was very validating.
Caroline: Very validating.
Jason: They also said, upon reflection, like, in the first watch, Jason Momoa’s character is just like, it’s just wild and doesn’t make any sense. But then they were like, you know what, though? If he’s going to be the final big bad, it’s great because memorable. They’re like, talk us through all the big bads of the previous nine movies. They’re all forgettable. Yeah, Charlize, because she’s still in it, but the rest of it’s kind of forgettable. They made some really good points. Also, they really stuck on the scene where he was painting his toenails and the two guards.
Caroline: Yeah. Like, what’s happening there?
Jason: Yeah, they really stuck on talking about that for a while. And I was like, yeah, that was a very interesting scene. But the head of Universal wanted to keep that scene in the movie and everyone else wanted to cut it. She was like, it really shapes his character.
Caroline: I mean, it’s memorable. It goes back to what you said.
Jason: That’s just the short.
Caroline: That’s a marketing lesson for everyone. Be memorable.
Jason: Be memorable.
Caroline: Even if you end up being nonsensical. That’s really what is.
Jason: We used to talk about our classic movie nights many moons ago at the end of our podcast episodes. And we have continued to do them every single Saturday. We watch two movies and we call it Classic Movie Night. But obviously Fast X is not a classic movie. It just came out.
Caroline: No. And also, we have really opened up the criteria. It no longer needs to be classic.
Jason: Right. It just needs to be…
Caroline: We do, a lot of times, choose classic.
Jason: Let’s just very quickly give a shout out to Bottoms then because that’s a movie that’s probably not going to get a lot of buzz. But it was a very fun movie to watch.
Caroline: We enjoyed it.
Jason: It’s like a coming of age story for the current generation.
Caroline: Yeah, it was very like Gen Z high school like, kind of your genre of your superbads and your whatever.
Jason: Book Smart. Another great one.
Caroline: Book Smart is another great… But the plot is so just original.
Jason: Yeah, it’s really good.
Caroline: I loved it. It really poked fun at, like, I think it appropriately had humor that supported ideas like feminism, while also pointing out some of the complexities and the…
Jason: Of how far things can get taken.
Caroline: Exactly. So that’s all I’ll say. I’m trying not to ruin it.
Jason: Yeah. The movie is called Bottoms in case you want to watch it. Of the two movies, everyone’s going to watch Fast X anyway. So watch Bottoms. It’s very well done.
Caroline: We got some lots of good lulls.
Jason: Anyway, I threw that out there, unbeknownst to you. But I just felt like these were two really interesting ones. And I just wanted to have a moment to share about. Let’s talk about the big decision that we made after a three hour whiteboard session, if you will. We don’t even own a whiteboard.
Caroline: You know, these sessions, though, they’re kind of like my favorite thing in our…
Jason: Oh, for sure. Yeah.
Caroline: This happens often to us where it starts with a very simple task, which in this case was, okay, let’s kind of button up the sales page for the enrollment period that’s coming up, which as you’re listening to this is happening right now.
Jason: All happening.
Caroline: And so we were finishing up kind of some changes to the sales page, and then it kind of snowballs into where do we want next year to go? What do we want to be doing? Where do we want to steer the business based on our own internal inner compass? Shout out to the inner compass volume of the Calm Business Encyclopedia.
Caroline: And we made some decisions.
Jason: We really did. And I think this was one of those discussions that it had been lingering and festering for a while. Not in a bad way, but it was just…
Caroline: I mean.
Jason: We were kind of…
Caroline: The word festering is definitely a negative word.
Jason: Let’s just change that.
Caroline: Lingering is a great one.
Jason: You can fester nicely.
Caroline: Uncle Fester.
Jason: You don’t have to fester grossly. It was one of those things we had been talking about for quite a while in different facets, in small chunks. And we really needed to sit down and just tear the conversation apart to figure out what we wanted to do.
Caroline: Yes. And so we thought we would do this whole episode about what that decision was, what we came to, and what lessons that you can learn about making decisions in your own business. And these are our favorite things to bring you on the podcast because I feel like oftentimes even and we’re guilty of this as well, we come on podcasts, business podcasts, and we share the lessons and we share the frameworks and the thoughts and whatever, but the real time. Okay, but tell me what’s going on your business and how you’re changing it or how you’re steering it based on your own desires and what you want the future to look like. I love that stuff.
Jason: Yeah. And I think the big takeaway for this one was we figured out what we’re… twofold really… what we’re going to do with WAIM, our coaching program, every single month for our members. So what’s our focus going to be for coaching? We’ve now done 50 coaching sessions, which is wild. We’ve never missed a month in the time that we’ve been doing this. So four straight years of coaching sessions every single month, and we jam a ton of value into that. But also we were getting to this place where we were feeling like we’ve kind of taught everything we know as it relates to individual topics and even newer things we’re learning about those topics. Just to be totally frank and direct, after 50 of something, you get a little bored. And so for us, we were looking to kind of shake things up, like what would be interesting to us?
Caroline: Because we want to bring our best, most engaged self to coaching. That is the primary kind of benefit of our program. And the moment where we feel like that enthusiasm is waning, that’s not fair to our members. So we’re always trying to think of can we reinvent what we’re bringing so that it adds value and it lights us up at the same time. And I feel like that’s a good question for everyone listening to think about. How can I continue to think about my customer, what value I want to bring them, and also what value do I want to bring myself as the business owner so that I can stay engaged? Because the more engaged you are, the more sustainable your business is.
Jason: Yeah. And we don’t want our energy to be waning. We want it to be WAIM-ing.
Jason: Thank you. So the second part of that that we decided on in this big meeting was, do you want me to hold for applause? No good. The second part of that was we figured out the WAIM coaching monthly next year.
Caroline: Which we are going to share with you.
Jason: Which we are going to share. But it also led to a decision about Teachery, which is our side project online course software that has been around for now ten years. But it has always been just like the redheaded stepchild off to the side of our business.
Caroline: Redheads everywhere are upset about that.
Jason: I know. But they also know that they deserve…
Caroline: Children everywhere.
Jason: They deserve… I’ve been a stepchild multiple times. They deserve the light and the pedestal to stand upon.
Caroline: That’s right, they do.
Jason: And so what we did, we were like, hey, you get to stand on the pedestal.
Caroline: Nobody puts that redheaded stepchild in the corner.
Jason: No, definitely not.
Caroline: You come out of that corner.
Jason: Unless you’re my grandmother and you know what I’m talking about.
Caroline: Can’t bring that to the pod.
Jason: Story for another day. My grandmother does not have stepchildren hidden in her house anywhere. I just want to make sure that’s clear, if any of the different agencies are listening.
Caroline: A little light hearted anecdote that just popped into mind. However, it’s not our story to share.
Jason: No. All right, so let’s talk about where this started. And I think probably the topic of what a lot of people can relate to, which is being a Straddling Strategist and what we mean by that.
Caroline: So this is the term that we have coined for anyone who feels caught between two worlds in their business. So this could be someone who maybe you’re currently serving clients. You have a client business, but you want to move to digital products and so you’re trying to kind of build up your audience and think about what you want to turn… Is it a course? So you feel like you have one foot in the client world and one foot in the product world, right? Or this could be someone… you still have a nine to five gig, but you really want to go work for yourself. You feel like you have one foot in this kind of nine to five world, but one foot in the entrepreneurial world. In our case, we have two businesses. So oftentimes we feel like we have one foot in the Wandering Aimfully world. We have one foot in the Teachery three world. And you’re perpetually in this sort of chicken and egg cycle.
Jason: I mean, the visual that’s perfect for this is our good friend JCVD straddling the two semi trucks in the commercial for what I believe is Volvo. And he’s just straddling those two semi trucks and you’re barely holding on.
Caroline: That’s right. And you’re trying to keep both of these semi trucks going and you can’t have one kind of like outpace the other because it’s a very delicate balance, right? And I think that is a good approach, actually, for many people because a lot of times you can’t take the leap, right? So to use the nine to five example, we wouldn’t tell anyone, just quit your job without building up a little bit of this side business. We would tell you, build it up to where you feel like you have some product market fit, you have a little bit of an audience and then you can transition out of the kind of corporate world, right? That’s what we’d say. Or same with clients, definitely start building up your audience in terms of maybe writing content and people have come to expect your expertise and then launch your first mini product and see how many sales it gets. And then you can transition away from client work. This is always the advice we give is sort of the stepping stone approach. So that means if you’re going to follow that approach, you’re going to find yourself in a season where you’re a Straddling Strategist. That is normal. But there comes a time where you feel and you have to make a decision of I can’t kind of be serving both of these priorities at the same time forever. For us, we’ve been trying to service both of these businesses and it’s never allowed us the time that we need in order to really give Teachery the effort and the try that it needs. This year, I’m really glad we went with this strategy, which was, let’s just carve out more intentionally time to work on the business, which was like our Teachery Fridays. And that’s worked well for us.
Jason: Yeah. And I think it’s a good example of if you are a Straddling Strategist or even what I would consider us before this year is that you have your core business, your core thing that you do and then you have another thing on the side, but it’s just barely on the side. Your heels aren’t even on both. Like you’re standing both feet on one and you’re kind of like…
Caroline: A little toe.
Jason: You touch it with your finger, you’re like, might dabble into that a little. You’re like, Nah, I don’t have time. And so for us, what I think we did was we firmly placed one of our heels on the truck of Teachery this year by…
Caroline: That’s a good metaphor.
Jason: Thank you. By having mandatory non negotiable Friday meetings with Teachery. And so this is where we just spent at least 1 hour to talk about the metrics of Teachery. What are the things we want to change, what are the features we’re prioritizing? What are the things that people are asking about? Where do we want the business to go?
Caroline: How do we want to position it?
Jason: And at least…
Caroline: Our audience.
Jason: At least be moving the ball forward instead of just like I was running Teachery basically on my own, not to make it sound like I was doing it all myself. And then you would pop in and be like, what are we doing? And I’d be like, to be honest, I don’t really know. I’m giving our developers some features that people are asking about. I’m looking at the landscape of courses a little bit and trying to figure it out. And so I think for this year, what we’ve done is we’ve actually established a good rhythm of working on Teachery and that kind of leads us into, I think… do you want to talk about what we want to do moving forward?
Caroline: Yes. So all of this is swirling around. We’re thinking to ourselves, man, we really did a good job of fortifying the foundation of Teachery this year. Again, positioning new features. Our biggest new feature being Themes, which is really important because it allows you to basically have a beautifully designed course right out of the box that you can customize. Fantastic. That was our big win. But we have not been able to carve out time to do any type of outward marketing. And in order for this business to grow, we’ve basically hit the limit on what word of mouth can do for us at this point, which is great. And now it’s time to really put our nose to the grindstone and work on external marketing. Fantastic. That’s swirling around in our minds. We know that. Then, we’re deciding, what should we do with coaching? And if I’m going to be totally honest with you, listening, our first instinct was… It sounds silly now just saying it out loud, but we were going to create new businesses.
Jason: Yeah, well…
Caroline: Micro businesses.
Jason: I’d like to talk about this because I do think this is a trap that a lot of people fall into. And we have been running Wandering Aimfully for five years now. We have taken it from nothing to over 1,500 paying members. It is a great, predictable, profitable business that we love to run. We love our members. The monthly coaching is our favorite time of the month. But what we’ve been doing for coaching, especially this year, we just kind of feel like we’ve been…
Caroline: We tapped it out.
Jason: Yeah. It’s like we’ve done all the things. We said all the things we want to say, and we needed something new. So what we were thinking about was, well, we always have ideas for businesses. Like, there’s never a shortage of ideas.
Caroline: That is our superpower. We have ideas on ideas on ideas.
Jason: Yeah. And I think people listening to this can probably relate, even if they don’t have tons of ideas. They’ve probably been working on one thing and then another idea has popped up and they’ve been like, Ooh, well, that one seems exciting, this one seems like a lot of work. I haven’t really gotten any traction with this one. Maybe I’ll move over to this other one and maybe that’ll be better. And I think for us, what we were looking at was, okay, Teachery has been around for ten years. It is making around $10,000 to $11,000 in monthly recurring revenue, all built through word of mouth. That’s a good side business. But Wandering Aimfully is so much more profitable than that, so much more predictable, and it’s a lot easier to run because we’re in control. And so what we were thinking about was, okay, if Teachery requires so much of us in that business, but also we can’t do everything because we’re not developers. Like, we can’t make new features, whatever, but we do know we need to work on marketing. Maybe there’s an idea aside from that, we just let Teachery be and we just make a whole new business.
Caroline: Yes. And, okay, I want to back up a little bit too, because I want to walk people through this decision making process, because I think they can find their own version of this wherever they are in their business. So to back up, whenever you’re thinking about a new year or where you want to steer your business, I feel like the first step is always to look inward and go, what am I missing right now that I want more of in my business? Or where are the pieces not necessarily a good fit? Because if they’re a good fit, then cool, just keep doing more of what you’re doing. But we all have that point where we’re like, something’s not aligning quite right. And for us, I think going back to what we talked about with the coaching, the misalignment was a little bit of this not having an outlet for our creativity, for our ideas. That newness, that novelty. Like, we’ve really been on a predictability…
Jason: Yeah, a lot of optimization.
Caroline: A lot of optimization in the past like two years. Right. So the itch that we recognized is we have this creative spark that we want to reignite in our businesses. Cool. That’s the thing that we want to look for. When we go to think about how to solve that and how to align our strategy to meet our evolving needs, our first instinct is, well, great, if you want new energy in your business, create something new. Okay, now upon reflection, that makes sense, that’s logical. So we’re like, cool. What if we did this thing where it’s this incubator and for three months we work on a new business and we show people from the ground up using the un-boring business roadmap, which is the five step framework we go through inside of Wandering Aimfully Unlimited. What if we show them how to build a business from scratch? So we think that’s a cool idea, but what it does is it takes the two semi trucks that we’re rattling between and it adds like…
Jason: Here’s the thing. If you add a third truck, you don’t have a third leg.
Caroline: You don’t have a third leg.
Jason: So don’t know what you’re going to do. Don’t know what you’re going to do.
Caroline: We have two legs. And so it became very clear to us, we took a step back, we evaluated that instinct and we realized two things. Number one, we would be falling into a trap that we fall into often, which is…
Jason: This is all of us.
Caroline: Let’s just do more.
Jason: Well, let’s just do more, but also let’s do something new.
Caroline: Let’s do something new. But also, I think us particularly, we always think that we have more capacity than we do. We don’t. The other thing is, when I really thought about it, I was like, oh, you know why we’re doing this? Why we keep going back to this idea of starting a new business? It’s because that’s what we are so confident in. If you tell me to start a business from scratch, I can do it without even thinking. All of those things, the branding, the naming, the offer, the audience, the content, all of that is… We’ve done it so many times now that I feel extremely confident, right? What I don’t feel as confident in is what does it look like to run a SaaS business in a fun way that doesn’t just fall into the same kind of boring things that people do at startups? Are we going to have to build a small team? I’m not that confident in my leadership skills yet because I’ve just been an independent solo creator. What does that look like? I’m going to have to grow these new skills to be able to do all these things right. And so I think it’s really helpful to take a step back and go, I’m falling back on what I’m confident in. I see this a lot in even members in WAIM, who… they are what we call Invisible Innovators. And what they’ll do is they know that in order to take their business to the next level, to make it more profitable, they are going to need to do more marketing. But marketing feels uncomfortable, selling feels uncomfortable. And so what they do is they go, oh, in order to really do marketing well, though, I need to go rebrand my website. And they’ve rebranded for the past three to four years, once a year.
Jason: ShowIt just popped up. I think I need to rebuild.
Caroline: I got to rebuild the site.
Jason: Because it’s like a new thing.
Caroline: And sometimes that’s true. Sometimes you do need to really hone in your message. That’s fine. But I think the thing that I would encourage people to take away from this is to take a step back and ask yourself, do I actually need to fortify my foundation? Or am I falling back to what I’m confident and comfortable doing? The design, the branding, the messaging, in order to protect myself from the more vulnerable thing, which is to put myself in a world, marketing, content, social media, whatever it is, where I’m not as skilled and I’m not as comfortable. And I’m really going to have to develop new skills. And I think that’s a valuable question to ask.
Jason: Yeah, absolutely. And I think the turning point for us in this whiteboard session was I asked the question, okay, if this was not our situation, but we were asked to come in and evaluate what to do moving forward as business coaches, what would our answer be? And our answer immediately would be, you need to work on Teachery. This is an asset that you have. It has an audience of people that have been built through word of mouth, which means it’s good enough that people like how it operates, that you haven’t had to do paid marketing. You haven’t had to do organic growth of any kind. People are like… organic content growth of any kind. People are talking about it on their own to grow this business. And so there’s something there. And also, how much time have you put into marketing this business or tried any type of growth tactics at all? None. So really, the sky is the limit on the growth opportunity for Teachery, and also when you compare it to the market. So the other big players in the space, the Teachables, the Thinkifics, the Podias, et cetera, they have such big audiences because they’ve spent so much money and time on marketing and these things. So I think for us, we kind of had this part of this meeting where we said, you know what? The new business seems sexy and exciting and fun, but also, it really is a bad idea because you’re starting over at scratch. You don’t know if you have product market fit. You don’t even really know what market you’re in. We don’t have one idea that we’re like, we have to build this. We’re just kind of floating around. And I think what we kind of came away from there was, let’s actually give Teachery the chance it deserves. Let’s actually focus on the things that we would tell someone else in our position to focus on, which is stop being an Invisible Innovator with the business. Don’t just build features and send them to the email list of the existing users. You got to go and build things. And what could that look like that’s actually fun?
Jason: And I think this was kind of the big turning point was when we decided on, okay, what if Teachery was this thing? What if WAIM coaching was kind of following our journey of building Teachery next year and working on it full time?
Caroline: We’re calling it Project All In. Working title.
Jason: Yeah. And so the idea would be, in the monthly coaching sessions for WAIM every month, we’re going to basically say, what part of the un-boring business roadmap within WAIM are we applying to Teachery? And what does that look like? So what are the nuts and bolts tasks? What are the results, if we have any? What are the things that we’re trying to do that we want you to take away from this? And then what’s the one thing we’re focusing on that maybe you should also focus on in your business?
Caroline: Exactly. And yeah, like Jason said, a couple of things there. As mentioned at the top of this podcast, we’ve reached the point where the information is all there. Inside of the WAIM dashboard, we have a custom dashboard where you can search by all kinds of keywords, and we’ve done 50 coaching sessions, not to mention all the other courses and resources that we have in there. The information is there. What we think is more powerful now, and it just happens to align with what we’re craving in our business is applying that information. What does this look like when you are actually growing a business and you don’t have to have a SaaS business to be able to translate, okay, oh, that’s your email marketing strategy. I’m going to do my email marketing strategy this month. So we’re excited about that. That’s what coaching is going to be. And of course, it also means accountability, which is what it’s been for a lot of people. So people will say, okay, I’m working through this coaching session this month from the past. Here’s my goal. By the end of the month. It’ll remain that. But what really was a turning point for me as well was not only what you said about how can we do it differently, how can we have fun, how can we think outside of the normal SaaS box? Because to be perfectly honest, I’m not someone who gets really caught up in comparison mode that often, but for some reason in the SaaS world, I really do.
Jason: Well, yeah, and I think it just stems from you don’t have a lot of experience. So there’s, like, imposter syndrome, right?
Caroline: There’s imposter syndrome, exactly. There’s imposter syndrome and SaaS is one of those things where all of us are using so many different software apps on a regular basis. I mean, using software is actually one of the core things that allows someone to have a solo business, right, is you use these platforms, you build your website, you build your courses, all these things. And so I have experience as a consumer, as a user of all these different apps. And so my taste level and my expectation is so high for what I want Teachery to be. But then you run into the constraint of when you’re bootstrapping a business, you can’t do it all. You don’t have a Teachable size team or a Kajabi sized team. So I love that challenge, but it’s also, if I’m just being honest, it is something that I get trapped in a lot where I just go, we’re never going to be able to make that product as slick as X, Y and Z product. But how I’m trying to reframe that for myself is to go, man, the fact that we’ve never really gone all in on Teachery, it’s kind of what they call the regret minimization framework, where it’s like I would always look back and go, what would have happened if…? What would have happened if we really gave it a go? What would have happened if we tried to do more external marketing? If I had fought through my own discomfort and my own mindset blocks in order to give my all to this business? What would happen if we had done it differently and uniquely and what a cool story that would be. So that’s what ultimately for me, decided that I want to focus on this business next year.
Jason: Yeah. And I want to talk just a little bit more about the fun part of it because I think for me, this is the sticking point of moving to focusing on Teachery, what we have talked about a ton. And I think maybe this is a relatable thing for people listening to this is where’s the line in, okay, we need to do content marketing because that’s what all of the SaaS course platforms do and…
Caroline: That’s the playbook succeeds, right.
Jason: You got to have the good FAQs. You got to have all the comparison articles. You need to have…
Caroline: The feature articles.
Jason: The feature articles. But you also need to have your Instagram. You need to have your TikTok. You got to keep up with this stuff. My whole thought on this is, great, everyone’s already doing those things. We’re not going to compete on those things.
Jason: But what we will compete on is creativity and nimble funness because the big companies can’t do this.
Jason: They can’t do what we can do, where it’s just the two of us, and we can just say, here’s a silly idea. Like, what if our mascot Iggy, takes people into outer space and they’re making their courses and has some silly story that they go through, which is actually just a checklist for how you get your course going.
Jason: And it could just be a very simple checklist that you look at. But also if there’s a story attached to it and maybe it’s a comic book, I don’t know. That is not a good idea. We’re not going to do that. But I’m just saying what I want to do is prioritize every turn is Nimble Funness. And so it’s this idea that, okay, well, if we’re going to have a YouTube channel, well, how could it just be so different? How could it just be so out there that it at least stands out and it’s memorable for people? And it may not actually hit all of the key bullet points that you need to hit for a well constructed SaaS video to give the thing. I don’t care about that stuff because people are already doing that. And so I think for us, what I’m most excited about with this Project All In focus is to show people that doing it differently can lead to results and believing in the fact that marketing is just about standing out. That’s all the point of marketing is. While it’s good to rank in Google and do those things, those are things that are really out of your control. What is in your control is being creative, is being fun, is leaning on things that you can do that other people can’t do, and just finding your own kind of unique area of that. And I think the other part of this that I really am excited about with Teachery, just that I want to share real quick, is that our goals for Teachery are very different from everyone else’s goals, and it’s always important to come back to, like, but what are our goals? Don’t compare yourself to, well, this platform sold for $100 million. Like, great, good for them. That’s not going to be us because we don’t want to build a 200 person team that’s around the world, so we’ll never get to there. And that’s all right.
Caroline: Absolutely. I love that. I just wanted to circle back on what you said about Nimble Funness, which we had not come up with until just now, but I think that could be a rallying cry moving forward.
Jason: Did you hear that little thing right there that just popped in? We came up with. Very interesting. Someone jot that down, please. Thank you so much. Just want to leave that there for the jury.
Caroline: I thought you remember how it works, is I get 100% credit for my ideas, and I get 50% credit for your ideas. And we’ve talked about this.
Caroline: No, but Nimble Funness. As you were talking about that, I realized that going back to what I was saying about recognizing, looking inward and going, what are you missing in your business right now? And if you remember, what I said was kind of that spark, like that excitement, that creativity, and what we first thought was going to solve that was new businesses. But now once we realized, okay, actually our problem is not just that we want a creative spark, it’s that we need something that provides us with that spark and something that also does not create more complexity in our business. Right. So those were the two kind of filters that we were thinking, all of these ideas and directions and brainstorming what could it be? And so when we landed on this idea of we go all in with Teachery, what we loved about that direction is that it solves both. It gives us an outlet for our creativity in the form of let’s try to really apply the creativity we’d bring to a new business into how can we make marketing different for this existing business? And it solves the criteria of it doesn’t add more complexity to our already kind of at capacity workload. We still retain our two semi trucks, but maybe we’re shifting our weight to Teachery. That’s what it feels like.
Jason: I think that is what it feels like. I mean, we just have had so much weight on WAIM the entire time that even having a balance of weight is going to put a lot more into Teachery. So to kind of recap what our plans are moving forward is with Wandering Aimfully’s monthly coaching next month, it’s basically going to be what we’ve done for quite a while now, which is what we call Field Notes, which is where we kind of share something that we’re doing in our business and experiment or something else. And we just kind of recap that. And that’s about a ten minute segment of our coaching sessions now. Our coaching sessions next year are basically going to be fully that. So it’s what are we doing in Teachery? What are we applying from the Un-boring Business Roadmap and what are we sharing that has happened based on a previous month’s work?
Caroline: Exactly. And so that will be the nitty gritty. So you will see the numbers, you will see the behind the scenes of how we set up tools. You will see the tactics we’re doing. As opposed to I’m sure we will share the journey, more the narrative journey, on this podcast. But if you’re someone who really wants to see inside of a business and how do you actually do this and how do you strategize and what does it look like in terms of actual tasks? That’s kind of what you get by being inside the member area.
Jason: Yeah, I think it’s going to be really interesting to say, like, all right, this month Teachery never had an email marketing strategy. We literally went into our email list building coaching session, pulled out all the action steps, applied them to Teachery. So if you want to do the same thing that we did for your business, this is the coaching session to follow because we followed it to a T. So I think it’ll be fun to point out all those and be able to use them kind of reflectively based on what we’re doing.
Caroline: So exciting.
Jason: So that is basically the sum up there. As a reminder, if you are listening to this, and it is during the October 2 to October 17 time frame, our Wandering Aimfully Unlimited doors are open and this is our final enrollment period at our $2,000 lifetime pricing. It will be the last time we offer our $100 per month plan. So that is all going to change after this enrollment. So if you want to lock in the best price we’ve ever had, we’re raising our price for the first time in five years. So it’s been a long time that we’ve had this price and we’ve kept it that way and we gave a year’s notice that we were raising the price here to everybody on our email list. So that is happening. You can check out and learn more at WanderingAimfully.com/join if you want to follow along, get all these behind the scenes looks at what we’re doing with Teachery, get all the coaching sessions that we’re applying and just join a community of like minded people. It’ll be there ready for you.
Jason: Do you want to move into the Calm Business Confidential?
Caroline: Let’s do it.
Jason: We have a little bit of drama with the Calm Business Confidential this week.
Caroline: Tell them the drama.
Jason: As of recording this episode, my to do list is about 16 miles long and your to do list is about 16 miles long as well.
Jason: But I thought I had already done my Calm Business Confidential research.
Caroline: Past Jason really let you down.
Jason: He really did. And I did not. And so when we were getting ready to record, I looked at my list and said, huh, there’s not a Calm Business Confidential here.
Caroline: You came to class without your homework done.
Jason: I really did. Well, I had my notebook.
Caroline: You had your notebook?
Jason: And I was like, yeah, I did the homework.
Caroline: And you thought you…
Jason: And then I opened my notebook and apparently someone wrote it with invisible ink because it’s gone.
Caroline: Invisible ink?
Jason: Yeah. I even tried squirting like the lemon juice on it to see if it would appear.
Caroline: Do you have one of the little blue lights?
Jason: I tried, yeah, that light. I didn’t like what I saw, but there were no words there, you know what I mean? So yes, I do not have a Calm Business Confidential this week, so it is just going to be Caroline. Everybody listening, I hope we all feel the same way. It better be good because now she’s carrying the weight of it.
Caroline: Interesting how you turned that around on you. You had a lapse in your duties and you just shifted the attention onto me somehow.
Jason: Can you not talk about my lapse in duty on this podcast? All right.
Caroline: You should get that checked out.
Jason: My lapse in duty? You do it at 45. I’m not there yet. Yeah.
Jason: What? You’re doing a poop joke? And then I was doing, like, a colonoscopy joke is where I went.
Caroline: You do it at 45. I thought you said something like a rating. And I’m like, what is this duty scale that I don’t know about?
Jason: Everyone listening to this is like, what’s happening? Where are we going? What? All right.
Caroline: Welcome to being in our marriage. You just got a yes and. Okay. All right. I am very excited about my Calm Business Confidential today.
Jason: Do I know this business?
Caroline: I don’t think so.
Jason: Ooh. Very exciting.
Caroline: This is a entrepreneur by the name of John D. Saunders. Have you ever heard of John D. Saunders?
Caroline: Okay. I stumbled across John D. Saunders. I don’t even remember how I found this, but he or his web design agency designed Justin Welsh’s new website.
Jason: Okay. Justin Welsh is really making the rounds in the entrepreneur space these days.
Caroline: Justin Welsh is in all the entrepreneurial interview shows, and the reason he stands out is because he’s a solopreneur and does very well selling basically…
Jason: Makes $4 or $5 million a year.
Caroline: LinkedIn. That’s not Calm Business Confidential.
Jason: You’re out of our range, Justin.
Caroline: But what I do love about Justin’s model is it leans into simplicity and it leans into just picking a couple of platforms, going all in on content, and being extremely disciplined in having a very simple…
Jason: Simple, not easy plan.
Caroline: Yeah. But unfortunately, he does make too much money for the Calm Business Confidential. We’re so sorry. Well, John might as well, but I couldn’t tell.
Jason: We’re going to pretend.
Caroline: Yeah, but here’s why John stood out to me. So I found the website, then I went to his agency website. So a little bit about his backstory. So started career as a marketing director and was just, as I think a lot of us do, hustling all the time and really wanted to have more flexibility, have more freedom. So I believe his first kind of foray into entrepreneurship was starting his own full service agency. So a lot of us begin with client work. Right. But one of his big pivots was realizing he needed to focus, really, on just web design and branding. So that’s the first lesson that I want people to take away because this was a pivotal point in my journey of doing clients as well, really deciding I want to be known for this instead of trying to do full service. Right.
Jason: Now did he have a boutique agency like I did?
Caroline: Probably. I think people have now caught on to the old boutique agency.
Jason: Yeah, it’s just you and maybe a friend.
Caroline: Yeah, exactly. So really kind of built up that business, but was still working a ton and kind of racked up… I mean, incredible designs, racked up some really notable clients. Built more than 250 websites for everyone from Land Rover to Amazon, Stanford University, Audi, et cetera. Really got these big name clients. But I think a part of his story, like many of us, just was overextending himself and really could never step back from the business. And so it wasn’t until he figured out kind of scaling what he had learned in… Well, first of all, scaling it up to be able to hire people to deliver a high quality product without necessarily it being him all the time. So that was like, stage one, I think. So he learned a lot about he talks so much about standard operating procedures and hiring and all of these different best practices of kind of building out your roster as a design agency. Then on top of that transitioning to more scalable offers, which is he has an accelerator for people, specifically designers. Who want to build out their own agency. So taking everything that he’s learned and teaching them. And some notes that I love is that he said, being able to pick up my son from school every day at 2:30 is such an amazing feeling. This kind of goes back to what I was saying about your own definition of success, right? The ability to do what I want when I want with my loved ones. And then if you’re interested in, I have so much more. He’s a treasure trove of… He’s a bubble cave. Okay. He has a lot of things going on. So that’s the general story is like, then he was able to scale it, and I think he actually… on the sales page for the accelerator, he shares the profit and loss, and so his profit and loss statement, and what I love about that is you can see that basically it spans two years, from January of 2021 to December of 2022. And in two years, he basically went from like $150,000 in Q1 of January 2021, which is nothing to sneeze at. But then I think the total… Oh, I think this is just the total. Anyway, the total is $1.2 million. And that’s like net profit or gross profit, actually. So, I mean, he makes…
Jason: Great money.
Caroline: He makes fantastic money. He has the ability to have financial freedom and build generational wealth for his family. Okay, but then here’s where it gets into what I think is interesting. He’s also just clearly someone who loves business and just spins up all these businesses and has ideas. Two, that I wanted to… Well, there’s three that I want to highlight. He recently… Actually, I don’t know if it’s recently, but he wrote this book called Borderless. So I think that’s where he shares a lot about hiring, basically, like an international team and what he’s learned about remote work and managing a remote team.
Jason: Sounds like something…
Caroline: Which I think I’m going to need to read, maybe over the winter. He also started a business called BlackIllustrations.com, which are beautiful illustrations of black people for your next digital product. So basically recognize a need in the market for all of these SaaS websites that were not representing black people in their illustrations. And he just thought, let me create that resource to improve representation across SaaS websites. And so I feel like he is someone who recognizes a need and then uses his creativity to kind of meet that need. And then I also love that he started… He said, lastly, I’m building an awesome classic side scrolling game with my six year old son.
Jason: Very fun.
Caroline: Taking his concepts, ideas and more and then packaging them into… And it’s called Pigeon’s Mission. So he’s building this game with his son, and so his son has all the ideas for the stories and then he gets to make them.
Jason: It’s really funny that you mentioned this because Justin Jackson in his email newsletter just shared this past week that he built a side scrolling game with his two teenagers and they kind of treated it like a business.
Caroline: That’s cool.
Jason: And so it was like he was just sharing some of the takeaways. I think he’s going to share a bunch more about it because it wasn’t a ton of information. I was like, oh, give me more about this. This is really fun.
Caroline: Well, I wonder if they know inspired by each other or anything because I know John creates a lot of content on Twitter and I know Justin does as well. So anyway, I love… And he’s done so many more things, ideas and things like that. But I just think here is a person who has definitely followed that roadmap, which is going… starting my own thing, kind of learning the hard way all of the challenges of running a client based business, but finally getting it optimized to the point where it is more scalable. Then, actually taking all that expertise and really scaling it up in the form of digital products. And that finally getting you the financial freedom to be able to explore all of your passions with these fun projects.
Jason: Love that. We’ll leave a link to his website in the show notes.
Caroline: Agency, which still runs, is called 5, the number five, Four written out. FourDigital.com. And then his personal site is johndsaunders.co.
Jason: Cool. Yeah, we’ll leave those links. That’s a fun one. I’ll say it makes up for my lack of having one, I guess, that he has multiple businesses. It’s good. I promise to be back with a vengeance in the next…
Caroline: Please do it.
Jason: All right, you want to wrap up with just some life stuff here? And then we’ll close things out.
Caroline: Tell everyone about the biggest news in our Portugal lives.
Jason: The biggest news in our Portugal lives. Yeah. L-I-F-E-S. That’s a word is that the saga has finally come to a conclusion. We are officially temporary Portuguese residents.
Caroline: Exactly. We finally got our residency cards. And if you have not been following this saga, basically, the way the process works is, yes, you get your visa approved, but then when you get to Portugal, you need to basically have a meeting at this government office so that they can sign off on you. And then you are supposed to receive cards in the mail, which is the final step, so that you can show them to the Border Patrol and things like that to say, like, I’m official. I can be here. And so we did the meeting in the beginning of June, and it’s supposed to take, like, 45 days to get your cards. 45 days came around. No cards. A couple more weeks went by. No cards. Then we hit this August time frame, which is when everyone goes on holiday in Portugal. And we were in this weird limbo where we just didn’t know how to get these cards.
Jason: I emailed every email address I could find for this government office. We tried…
Caroline: We heard nothing.
Jason: Phone numbers, didn’t hear a thing.
Caroline: We finally enlisted the help of a lawyer. Okay, so here’s where it goes off the rails. The lawyer’s like, I will go down to the office and see if they have your cards. We are so grateful. Thank you so much. She does. She says, we got eyes on your cards. They have them here. You just need to come to the office to pick them up. We thought, fantastic. First thing Monday morning, we’re going to go into Lisbon. We’re just going to get this knocked off our plate. We’re going to just walk into the office.
Jason: Get these cards.
Caroline: Show them our passports, get these cards. Bada bing, bada boom.
Caroline: A miscommunication occurred, which was that… couple things. You need to have an appointment if you’re going to go to a government office in Portugal. It doesn’t matter if you’re just picking something up. You need to have an appointment, because we didn’t, and we went there, and we’ve made it up to the office, and we’re like, we’re here to pick up. And they’re like, yeah, do you have an appointment? We said, no. You need to go get a ticket, which is they always use this ticketing system here, which is actually quite helpful, but we go get the ticket. We’re number 13, okay?
Jason: Of one of the nine letters that are available.
Caroline: There’s nine different letters, and then you have numbers of each letter. So we’re “aga.” It’s H. That’s how you say aga. That’s how you say H in Portuguese. So we’re sitting there, and it takes forever for them to even start with aga. Number one. And we’re like, this is not going to go well. Okay. 3 hours later.
Jason: 3 hours later.
Caroline: We have been sitting at this office.
Jason: We did not know that we were going to need to sit and wait. So we brought nothing but our cell phones.
Caroline: Yes. So we just had our cell phones.
Jason: Would have been a whole different experience had we known that this was the process. Get there, take a number, sit, you’re going to be there for 3 hours. Totally fine. I’ll bring a snack, I’ll bring my laptop, we’ll sit, we’ll get some work done. I can sit for 3 hours, easy peasy lemon squeezy, not a big deal. But when I’m under the illusions that I’m just going to pick something up and now I’m waiting 3 hours, this is like the bane of my existence.
Caroline: I also forgot to mention that two people almost hit us twice…
Jason: Driving in.
Caroline: Driving into Lisbon. And you all know my history with driving anxiety.
Jason: Monday morning traffic.
Caroline: So I was already frazzled. But we did a good job of, I think, maintaining our patience. I think we did a great job. We were not frustrated. We were kind. Everyone was kind to us.
Jason: I punched zero babies.
Caroline: Jason did not.
Jason: There were a couple available and I was sizing them up and I was like…
Caroline: Honestly, I was using that as an opportunity to learn more Portuguese. I was listening to the guards. They were talking in Portuguese. I picked up a couple of things. Okay, then we think we’re getting close, right? Then finally they’re at number eleven. The girl sitting next to me was number eleven. And when she got called I was like, this is it. Now we’re down to the wire where it’s almost lunch. And I just knew…
Jason: They’re going to take a break for lunch.
Caroline: They’re going to take a break for lunch at number twelve. And we’re going to sit here and be like, you have to be kidding me. That didn’t happen. But what did happen was the woman who’s like kind of the head of that government office comes out and, in Portuguese, I discern that she is saying that the computer system is down.
Jason: Of course.
Caroline: And that you have to come back another day.
Jason: And a lot of people, it’s funny, over the past kind of almost year of kind of going through this process are like, oh sorry, this is just Portuguese bureaucracy. This is just government bureaucracy. There’s no shade here towards Portuguese government.
Caroline: Not at all.
Jason: This is just archaic government bureaucracy. And when the computers went down, I was like, this is such a government office thing to do.
Caroline: Can we not upgrade the tech for…? I don’t know.
Jason: Can we not just have a better system for all these things? It just seems like we just need to fix a lot of this stuff. Anyhow.
Caroline: Yes. Like we said, we were fine. We weren’t frustrated, but we were definitely disappointed. And thankfully, in my limited Portuguese, the girl came who I knew spoke English and Portuguese. So I asked her and I said even Aga, and I said, we’re just here to pick up. And this is why you do have to have a little bit of without entitlement, without…
Caroline: Anger, without frustration. But you do have to advocate for what you specifically need because they’re seeing a million different types of people in a million different situations. And very easily in our situation, someone could have gone, well, the computer is broken, let’s leave. But you just have to clarify. And she was like, oh no, if you’re just here to pick up, if you wait a little bit, it might come back online and we might be able to get it for you. And so I was like, okay, if I came here for 3 hours, I will wait another half hour. And so we sat there and, about ten minutes later, they called our number, we went back and they had our cards there waiting for us. They must have…
Jason: Oh, the funniest part of this though, is we finally get back there, we’re with the lady who just… She just seems a little bit angry, you know, and I can imagine if you work at a government office, you’re just not like, it’s not a happy place to work. And then she starts messing with us.
Caroline: Yeah, we got like…
Jason: She’s like, oh, I don’t know if they’re here. And then she spoke a little bit of English, a little bit of Portuguese, and then when she got them, she was looking at them, she would like go to hand it to you and then pull them away, like… And I was like, Ma’am, I appreciate that we’re trying to bring some humor into the situation. I am a humorous gentleman myself. I bring nimble fun to a lot of things. However, give me these cards, it’s time to go.
Caroline: I loved it because, based on her angry announcement, I really thought she was going to be very angry. And so I was like, I’m here for the playfulness. I see that card. I’m not leaving here without it.
Jason: Yeah, it was also amazing to look at. And this is what you thought, is that there was probably a pile of 1,000 people’s envelopes.
Caroline: Separated by last name. You could see them, like there was an organization to it, but 1,000 envelopes that had not been delivered.
Jason: And that is the only bummer is that you can tell that they probably tried to deliver it one time. We weren’t here to sign for it. On one of the random days, we were probably over at A Janela getting pizza. And then they don’t try and deliver it again. You don’t get a notification of any kind.
Jason: So you just don’t know. We didn’t know it was there, otherwise we would have gone two months ago to go sit in line and go. But anyway, that wraps up the residency card saga. So we have this. The process now is this lasts for two years, which will actually be May of 2025. So it’s not two years of handing them to us. It’s when they decide to pick the date. And when that comes up, we should be able to renew online. And then we are going to have to get new cards. So we’re going to clear our schedule for 30 to 45 days.
Caroline: We’re going to be home for 30 days.
Jason: leaving the house because they will try and deliver them again. Those will last for three years. And then at the end of that…
Caroline: What if we just put up a sign? Dear CCT, if you’re here, delivering, please…
Jason: We’ll try.
Caroline: Call this number.
Jason: But at the end of that five years, we can then apply for citizenship. And that’s where we’ll have, like, an EU passport if we pass the language test. Yeah. So we have five years to… I think it’s what grade level is it?
Caroline: I don’t remember.
Jason: Third grade or fifth grade, something like that, level Portuguese. So we’ll see. I mean, right now we can barely count to ten, so we’re going to do our best.
Caroline: Stop it. We can count to 20 easily.
Jason: But yeah, that also… getting our residency cards opens up the doors to we opened a new bank account and we can apply for an auto loan now. So we’ve already done that because we’ve been renting a car for the past eleven months, essentially.
Caroline: Like from a rental place.
Jason: From a rental company.
Caroline: Not like, here’s a yearly lease. It’s like no, just every month.
Jason: Just every month. But it is really cute.
Caroline: It’s a local place.
Jason: So yeah, that’s very exciting news for us because it makes us feel like, okay, we’re here. We don’t have to worry about anything. We’re going back to the States here in two months. And that would have been weird, coming back into the country and them asking like, oh, you’re just here for vacation? Like, no.
Caroline: Well, we could have shown them our approved Visa in our passport.
Jason: We could have but it’s expired.
Jason: That’s the only thing. It’s like that would have been a weird thing. But it doesn’t matter now because we have our cards, we can show our cards, we can smile, we can be like bom dia, and then we can leave. So, yeah, I think that wraps up the podcast here. We’ll give you one more shout out to our Wandering Aimfully unlimited enrollment, which again, is open until October 17, final time. You can jump into WAIM and get our un-boring monthly coaching. Get access to a Teachery account as well. That’s included with WAIM. Get access to all the Notion templates that we have available for you for organizing your life and business and lots of other things.
Caroline: Just overall make your business what, Jason?
Jason: Calmer, more clarity, more focus, more peace, more profit, more predictability.
Caroline: There we go. I was looking for the three P’s, man.
Jason: I know you were. Through wanderingaimfully.com/join. Just wanderingaimfully.com/join, actually. I said all of it in one there. That’s wanderingaimfully.com/…?