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178 – 4 Lessons For Your Next Big Project

Wandering Aimfully Through Our Podcast: What is it all for?

178 – 4 Lessons For Your Next Big Project

This week, we wanted to reflect on a few of the biggest takeaways we learned while taking on this monster of a project.
Jason ZookJason Zook Jason ZookJason Zook

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Jason Zook

Listen to our full episode on 4 Lessons For Your Next Big Project below (with full transcript) or find our podcast by searching What is it all for? in your favorite podcast player.

Five Key Takeaways for 4 Lessons For Your Next Big Project

1. Embracing YOUR Work Style

In our Calm Biz Encyclopedia project, the foremost lesson learned is the importance of acknowledging and embracing our own work approach. This includes Caroline’s 👩🏻‍🦰 realization that she thrives when working on tasks just before a launch, as long as it doesn’t compromise her well-being or non-negotiable commitments.

2. The Vital Role of Time Management in Project Success

The second crucial lesson is allocating more time than initially anticipated for projects. This sounds incredibly obvious, but it’s a lesson we have to learn over and over again. Despite allocating an eight-week timeframe, our project wasn’t completed by the launch date. We intentionally didn’t push ourselves to meet our previously set deadline as we’d prefer to work a few extra weeks and keep an overall calm-feeling in our daily lives.

3. Injecting Playfulness for Enhanced Creativity

One of our brand beliefs is “Fun is Fuel.” It’s this belief that work doesn’t have to be boring, mundane, and a chore. Work CAN be fun as long as we prioritize that as a feeling and figure out tangible steps to make it happen. The idea of creating our own (virtual) encyclopedia helped us build this project with more enthusiasm and creativity.

4. Sometimes One Big Step Backward Leads to a Huge LEAP Forward

We recorded a whole episode about being stuck in the video mud and how we got out of that. We are so glad that we were able to take a week to basically fall apart and crumble into a mess of two humans trying to work on a project to then pick ourselves back up and find a new way of doing something. That way, we are not competing with all the YouTubers who make content like we do. The goal of this project was never to get a bunch of YouTube views. The goal is to have something that we’re proud of that’s helpful and the views will sort themselves out. For us, that’s all that really matters.

5. Navigating Business Success on Your Terms

The Calm Biz Encyclopedia project taught us that success is attainable by accepting our working style, managing our time wisely, injecting fun and creativity into our work, and forging our own flavor and path to success.

Show Notes for Episode 178: 4 Lessons For Your Next Big Project

Last week, we announced one of our biggest content projects to date, the Calm Business Encyclopedia: 26 YouTube videos and articles that are an A-Z guide to helping you build a more predictable, profitable, and peaceful business.

This week, we wanted to reflect on a few of the biggest takeaways we learned while taking on this monster of a project. Things like acceptance of how we work, the importance of extra project time, finding your motivators, and ignoring what other people are doing!

We hope this episode is helpful and gives you some useful insights for whatever you’re working on next.

Full Transcript of Episode 178: 4 Lessons For Your Next Big Project

⬇️ You can also download the .TXT file of the transcript

Jason: Hello, and welcome to the before podcast sponsored segment, brought to you by us, Jason and Caroline Zook, sponsored by us, Jason and Caroline Zook, who run an un-boring coaching program by us, Jason and Caroline Zook, called Wandering Aimfully Unlimited. And as of you hearing this, we are just a couple days from opening the doors for our fall enrollment, October 2nd through October 17th. This is our un-boring coaching program that gives you a step by step roadmap to follow, to build an intentional business, especially if you are a creator, a solopreneur, a small business owner who wants to grow, but you’re okay with doing it in a slow and steady pace.

Caroline: That’s right.

Jason: We give you monthly un-boring coaching.

Caroline: You get one thing to focus on. You get the behind the scenes on our business, sharing everything we learn along the way.

Jason: We have an online course platform called Teachery that comes with it if you want to build courses. We also have a bunch of Notion awesomeness if you want to get started with Notion and have a whole template to run your business. If you want a system to transition from digital or from clients to digital products, excuse me. I hope our sponsor doesn’t get mad at me for that little flub, I think they’ll be okay. And also, we have a page template library in Notion if you want to design your next home, about, or sales page. That and so much more is included, along with our weekly accountability game in slack. There’s so much you can check out. Learn at And remember, the doors are only open when, Carol?

Caroline: From October 2 to October 17. And I do want to remind everyone that this is the final enrollment period at our original price point. Next year, the price will be going up. It’s the first time we’ve raised the price in five years. So if you’ve been thinking about joining, now would be a fantastic time. 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’re 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! Let’s kick off the podcast, Caroline. That’s it.

Caroline: Go ahead.

Jason: That’s the kickoff.

Caroline: What is it like inside your brain? Is it just..

Jason: Swirly?

Caroline: Feels swirly?

Jason: Whirly.

Caroline: Mine is swirly, too, but in a different way.

Jason: Yeah, mine just like, swirly with life and ideas.

Caroline: Yeah, like little bits of..

Jason: Nuggets. Tiny nugs.

Caroline: Tiny little nugs of silliness.

Jason: Different than a poop nug that you would find, which is gross, different.

Caroline: Do you regret saying it?

Jason: No. Listen, everyone poops. We’ve all experienced this.

Caroline: But nobody poops nugs.

Jason: That’s not true. Everyone’s had like, a little deer pellet poop where you’re just like, that was interesting. Whatever combination of things I put inside my body, I now am like an animal that forages for berries.

Caroline: I just love the idea of you evaluating your poop..

Jason: I think we have.

Caroline: I don’t think so.

Jason: All been there.

Caroline: Okay.

Jason: We’re not going to talk about that. We’re a serious business podcast.

Caroline: As evidence, by our previous convo.

Jason: This is how you climb the ranks of Apple.

Caroline: Yes.

Jason: Is you’re serious.

Caroline: You’re very serious.

Jason: So..

Caroline: Very important things that we discuss.

Jason: Strap in to the serious car.

Caroline: What are we talking about on this episode?

Jason: We’re going to talk about this big project that we’ve been working on for the past seven weeks.

Caroline: Big project.

Jason: And it’s like, kind of done, but kind of not done. It’s a very weird feeling. This is what I wrote in our recap email.

Caroline: Because you’re used to.. When we launch a project, usually that’s the most exciting moment, because the thing is done. It’s a launch of a new product.

Jason: There might be a couple of..

Caroline: It’s a rebrand..

Jason: Tiny little nuggets you got to clean up. Just tiny.

Caroline: I honestly, for the rest of the podcast, can’t hear you say nuggets. You ruined it.

Jason: What about chicken nuggets? You definitely want to hear about those.

Caroline: Okay.

Jason: All right.

Caroline: But you got to be careful because I don’t want you..

Jason: Combining the two.

Caroline: Soiling my chicken nuggets.

Jason: I don’t think anybody wants those combined.

Caroline: So normally the launch day is the big day. In this particular case, it’s a content series that’s being released a day at a time. So the first day, there had only been one thing. So it kind of builds. It’s a slow burn. It’s a different excitement.

Jason: It was a very weird, kind of like, quote unquote launch day because we’ve been building it up. So it feels like there’s like, a thing that’s coming. And obviously there was in the Calm Business Encyclopedia. And if you have not heard us talk about that in the previous episodes, it’s an A to Z guide to running a predictable, profitable, and more peaceful business. So we have 26 different pieces of content in the form of an article or a YouTube video, and it’s a lot of work, but when we released it last Monday. It was just one, it was just one six minute video. And one, like, thousand word article. That’s it.

Caroline: Yeah.

Jason: And people have been reading like, okay, well, I’ll come back tomorrow.

Caroline: Come back tomorrow.

Jason: Because I felt the same way. I went to the page, and I was like, this feels underwhelming, but there’s so much more to come. So just it’s kind of a weird feeling. Anyway, just sharing that.

Caroline: Yeah, I’m glad you’re sharing that because I think something that has fascinated me about this project, maybe it’s because it’s not something we’ve ever done before. I’ve had lots of feelings about it, but they’ve all been different feelings than you’ve had.

Jason: Yeah.

Caroline: I didn’t even think about that, like the anticlimactic kind of feeling?

Jason: Right.

Caroline: But then again, you’re the one who’s like, pressing publish on the articles. You’re the one who. You’re sort of interfacing..

Jason: I’m like closer to it.

Caroline: With the public, so to speak. And I feel like. I’m just like, I got to get more of these done, so I have to still be focused so much on creation instead of the publishing of it because there’s more to do. So when it was like the announcement, I was like, I don’t even have time to care.

Jason: Yeah. Well, and I think it goes back to we’ve done so many different 30 day kind of project challenges like this in the past, but almost all of them were done, kind of in, like you did the thing? And then you talked about it more afterwards than you did in the beginning.

Caroline: Right.

Jason: And I was thinking back to, like, I did a 30 day challenge of working at my desk with a stand sit bike, basically. And I was thinking about that and I was like, oh! I didn’t tell anybody about that until it was done. And, that’s very much like the thing on YouTube. And we’ve been doing that for years as well. But it’s like, I did this for 30 days. Now let me talk to you about it. Whereas opposed to this was like, we’re going to do this for 30 days. Here’s day one.

Caroline: Well, can I tell you kind of an interesting emotion, a positive emotion that has come up about the 30 day challenges or whatever?

Jason: I would love to hear it.

Caroline: Is, man! There’s something so satisfying to me about being able to publish something daily and stack the installments and have that consistency and be able to follow through on the consistency of something. Man, does that feel good. Because we haven’t done something like that.

Jason: No.

Caroline: It was so long.

Jason: I mean, we haven’t done it for WAIM at all.

Caroline: Yeah.

Jason: What’s really interesting is, as we embarked on this, basically, we’re just going to call it 30 days, 26 days of content. But I was thinking about it and I was like, oh! The most videos we’ve ever published on our YouTube channel is seven in a month. So we’re going to obviously outpace that. The most articles we had ever written in a short amount of time, I think was like four in a month because they’re so long and so in depth. When we did the Build series, I think we probably had a little bit more, but even still, it was maybe like nine of those articles in a month. So it’s just wild to think about in the entirety of five years of WAIM. We’ve never done a 30 day kind of, content project.

Caroline: Side note, you forget this often. When we did do the building WAIM thing in the beginning, for the first, like, five weeks. We posted every day, Monday through Friday.

Jason: That was daily?

Caroline: Yeah.

Jason: Oh, okay.

Caroline: Yeah. I just wanted to remind you.

Jason: I went back and I thought I counted the dates. Maybe I looked at the dates wrong then. That’s probably..

Caroline: I think probably after week three, we got pretty quickly off that wagon because we were doing it in real time. So that is something. Talking about lessons. We didn’t write this down, but here’s a lesson about this project. If you are going to do something of this magnitude with content, don’t force yourself to do it in real time.

Jason: Yeah, I think that we have four lessons that we want to share while building this project, because the project obviously isn’t completed. So maybe we’ll do another episode in like, six months from now. Where we say, okay, now we’re looking back and how do we do on our three pronged goal approach to this project, which we’ve talked about in previous episodes. But just very quickly, our three pronged goals are. First goal, immediate. Just drum up some buzz for our enrollment period that’s coming up. That comes next Monday.

Caroline: Thank you to our sponsors.

Jason: Which is October 2. Yes. Thank you to our sponsors, but then also us for promoting our sponsor, doing the ad read. We did a great job. Anyway, first goal, drum up some buzz. Second goal, have like a short term, not short term, but have a start here experience on our website that’s just like an awesome group of content of everything we’ve learned in the online business space here in the past five years, specifically with kind of digital product businesses. And then the third thing is long tail trying to get discoverability organic traffic through YouTube or through Google. So we’ll check back on those goals in six months, but we have four that we wanted to talk about as far as lessons go throughout the build process. But what I was going to say is a bonus. Fifth one here is what you just said, which is if you’re doing a 30 day challenge and you’re kind of embarking on a journey like this, maybe just give yourself a little bit more space for the emotions of it, for the time of it. There’s just a lot that goes into a thing like this. It’s very big, it’s very difficult. So just saying that’s like a bonus. Like, ride the emotional roller coaster is what I was getting at. All right, let’s get into the first real one here.

Caroline: Okay.

Jason: All right, go ahead. I moved it from two to one because I thought it was more important.

Caroline: Wow. Interesting.

Jason: Yeah!

Caroline: This is a big, I don’t know if it’s just hitting me at this point in my life, or this point in our business journey, but I told Jason my biggest takeaway personally from this project is accepting the way that I get projects done. More specifically, I’m someone who, I’ve gotten better over the years, but I used to be a procrastinator. I’m not as bad anymore, but I’m always going to be the person who’s working the day before the launch date. Do you know what I mean?

Jason: I do know, yes. I’ve lived with you and worked with you for years.

Caroline: It’s gone through periods of time where that has been really under the wire, like, oh, there’s too much to get done and I can’t even possibly get it done the day before. And now I’m to the place where it’s an appropriate amount of things that need to be done the day before the launch. But I used to just kind of beat myself up over that. I used to judge myself and be like, why can’t I pace myself better and blah, blah. And the truth is I’m just a person with high quality standards. I’m a person who, you know. Estimating time is difficult for me even with all, and a lot of my time strategies have worked. My Pomodoro timers, my time estimations, all of that which we teach inside of WAIM Unlimited has helped tremendously. I can’t even tell you how much it’s helped, but I just am so over beating myself up over those things about me. Why can I not just embrace the fact of like, oh yeah, I love working on projects, even in the moment if it feels like, oh, there’s pressure here, if I’m really honest with myself, it’s part of what I love about being an entrepreneur.

Jason: Yeah, well, I just think there’s something interesting like, where you thrive in a project is very different for other people. I thrive in the like, beating all of my own deadlines because I want the previous me set a time and a date and like, well, I want to prove that I could do previous me wrong. I’m better than that. But I think, what’s interesting about watching you in this project and in other projects is you thrive in the last chunk of time on a project.

Caroline: I do.

Jason: In the early time of the project. I think it’s just very difficult for you to get the intrinsic motivation. Like you’re motivated, you’re working, but you don’t have that push and that drive.

Caroline: Well, it’s also a little bit of Parkinson’s Law, right. Where it’s like the time is always going to expand to fit the container. That’s just human nature. But you’re right, there’s something and maybe this is what it is too, now that we’re digging into.

Jason: Let’s just do it. We’re on the couch here.

Caroline: You are a very decisive person.

Jason: Right.

Caroline: And it’s not that I struggle to be decisive, but I’m certainly less decisive than you are. And something about the hard container of a deadline helps me be so much more decisive in doing things. And so I find that boundary is really helpful for me. So anyway, the difference is, where it becomes, I don’t know what has helped me accept myself in this way is, I’ve at least changed my ways to the point where it doesn’t impede my anxiety levels to a high degree anymore. It doesn’t impede, meaning like, on the last day before a product launch, I’m not at all time anxiety high and feeling like I’m on the verge of a breakdown. That doesn’t happen anymore and I’m still able to get exercise in. Or like, for example, the night before this launch, we stopped working at 06:00 P.M, which is to me a mark of like, okay, if I can fit the amount of work in the work hours, for me that feels like a win. Even if I’m still scrambling the day before, and it’s a little bit of like, I got to put a lot of focus in on that day. If I’m able to cut it off at 06:00 P.M, and feel like I did a good job, then that to me, is my measure of success. And so it brings up this notion that we’ve talked about before on this podcast, which is, how do you know when some aspect of yourself is something that it’s time to just accept or when it’s an aspect of yourself that you still want to work on changing. And for whatever reason, I think for all the reasons I just described, I’ve just finally come to this place of like, well, if the only thing left telling me that I need to change this about myself is just that I think I should be doing it a different way. If that’s the only thing, if it’s not actually impeding my life, if it’s not actually making me more anxious, then who gives a crap?

Jason: Well, and I think the other part of it is it’d be different if you were working at the 11th hour every project and the project wasn’t getting completed. So I think that would be the big, maybe red flag for someone who’s listening to this or like, oh, I’m like that too, but I don’t actually ever get the project completed. I’m always late on things or they’re not getting done. I think that’s when you might need to make some sort of change in things and maybe you have a previous deadline that you set that’s like a week in advance. Like, this is the deadline, and then you have a week to kind of play catch up on things. But I think for you and this is just what I’ve seen over the years is like, we get to the end of a project, but it always gets done. So there’s a big difference between it always getting done, or it always getting pushed. And I think that’s the big change that might need to happen.

Caroline: Another way that this shows up in our business. We make jokes about it on this podcast all the time when we do projects, and we’re like, we’re going to bite off more than we can chew. And there’s just been times where I thought, man, we really need to change this about the way that we work and we’ve done things to maybe avoid putting too much on our plates, but what if that’s just always going to be us?

Jason: We just like a full plate.

Caroline: We love a full plate. We love challenging ourselves, that’s definitely part of it. We love making things, that’s a huge part of it. We just love making things and we love challenging ourselves. And so, what if the way that we work is always going to be ambitious and that’s okay?

Jason: Yeah, I like to think about it. Like, a butler is coming out of the kitchen with, like, a big old plate full of cinnamon rolls. And as he’s walking to the table, it’s so full of cinnamon rolls that they’re just falling off on the floor. And it’s really sad. But by the time the plate lands in front of us, there’s plenty of cinnamon rolls left. And that’s kind of how we work on a project. We pile too much on our plate and there’s just, like, things that have to fall off the plate for it to finally get to the place where it lands in the hands of our email subscribers and our viewers and etc. And by the time they get it, they’re like, wow! This is a very full plate of things. We’re like, yeah, you should have seen it when it came out of the kitchen. There was so much more on this plate, but that all fell off because we just couldn’t get it done. But that’s kind of how we operate. It’s like, too full of plate, but by the time the plate arrives, I don’t think anybody would really notice. And I think even for this project, one thing we can share is there’s an article template for the way the articles look on our website. So if you go to Click into any of the Calm Business Encyclopedia volumes, you’ll see this kind of like, really fun template. But that wasn’t done until like, five days after the project was released. And that was actually more to do with our developer than us. But that’s just part of the project, right? It still falls on our, like..

Caroline: Totally, and if we had finished the design two weeks before we had given it to him, or if we had been better managers in terms of telling him what to prioritize, ultimately the accountability comes to us. But yeah, I love actually, I did not know where you were going with the cinnamon roll plate. I was like, I don’t get it. But I love visualizing that because again, it’s about just going like, okay.

Jason: Yeah.

Caroline: Okay. That’s how we work.

Jason: The plate didn’t land in front of you empty. That’s the most important part. It landed in front of you with, like a well balanced meal there’s just like, the perfect amount of food.

Caroline: So it’s two things to me. It’s did the plate land with something on it, and can I laugh about and enjoy the process of getting from the kitchen to the table? And to me, if those things are true, then who cares how many cinnamon rolls started on the plate? That’s okay. And that’s always going to be the way it is.

Jason: Just be totally clear in this metaphor. I would go back and pick up all the cinnamon rolls.

Caroline: Of course.

Jason: Now, if it was like roasted zucchini, I’d just leave it on the floor. Screw that zucchini. I don’t want it.

Caroline: That’s the spectrum from zucchini to cinnamon roll.

Jason: Yeah, exactly. All right, let’s talk about the second lesson that we learned here. And this one, I think it’s kind of obvious, which is why I moved it to number two. But it is definitely worth talking about over and over again whenever you’re working on a project which is. Giving yourself lots of time, more than you think.

Caroline: And actually, this is, I would say, one of the areas of the project that I would consider a success, which is we started it eight weeks out. And I think the only reason why I was able to go to sleep or to stop working at 06:00 P.M on the night before the launch was because we started it eight weeks out. And that’s something that also is like a big takeaway for me, is because we started it so much earlier. We had that one week that was basically a wash because we tried to do the videos a certain way, and I spent all that time scripting, and we didn’t even use the scripts. And that was, quote unquote, wasted time, but forever in a day. From now on, I will bake in a week of basically wasted time into a project.

Jason: Yeah, and I think we talked about this in one of the previous episodes, but there was a moment where the Friday before the project was going to go live on the Monday. I think you were really feeling the pressure of the project and getting it out and going, and I actually wasn’t feeling the pressure because I looked at what was left and I was like, this is all doable. It’s not anything that’s going to make or break the project. And I think that’s just kind of like a real moment of the way our two brains work differently, where you still see this huge list of things to do. But I kind of see it from a macro sense where I’m like, yeah, but because we had so much more time on this project, you’ve already done the bulk of what needs to be done. Now the rest of this is just kind of like making things look better. It’s like applying the frosting to the cinnamon roll. It’s not going to be perfect, but there will be a little bit of cream cheese frosting on there for everybody.

Caroline: Yeah. And I find that difference in perspective so valuable. I also find and this goes back to point number one. It’s always the thing that is going to bring tension between us, right? Because you’re seeing it from a macro sense where you’re not looking in all the details and you’re going, It’s fine, it’s doable. And I, because I’m the one that’s mainly in the creative production, am seeing all the little like, there’s so many more little micro to do’s in these bigger to do’s that you don’t see. And I think sometimes in the past I’ve been like, no, but you don’t understand. There’s so much but I wouldn’t want you to understand because your kind of macro view is what can calm me down in those moments and go, it’s going to be okay, you can do this. And I value your perspective in not getting overwhelmed so much. It’s just if you work with a partner or you work with a spouse or you work with a teammate or something, it’s a challenge to be intentional about seeing the value in their different perspective and not using their different perspective as a point of conflict.

Jason: Yeah, I think just an actionable takeaway. For those of you listening to this, is the next three months of your business planning that you’re looking at. Just review all of your self imposed deadlines. What needs one more week cushion? What do you just need to be like. Ooh! I’ve got that client that’s like a big client. They need one more week in the project than what I’ve estimated. I’ve got this project I want to launch before X. Add one more week into the planning. So just like, do that right now. It’s a really good exercise just to add in a little bit of buffer for future you to feel a little bit less frantic.

Caroline: Love it.

Jason: All right, lesson number three here, and this is really one that we’re trying to come back to a lot these days and moving forward, which is just to look for ways to bring the silly and to really bring the un-boring to a project.

Caroline: And this might be, you can insert whatever value you want to replace for fun or silly, if that’s not your vibe. But for us, this is like a core value of us as people and as doing business together is we’re just sort of like, if we’re not enjoying it, what is it all for? Ding, ding, ding.

Jason: Nice.

Caroline: The name of the podcast.

Jason: That was the bingo.

Caroline: And it’s funny, I was working on something else this morning and I found a list of our brand beliefs that I wrote down, like a couple of months ago and one of them was Fun is Fuel. And we don’t really say it like this, but maybe we should start saying it. But it’s just this belief that for us, the reason behind making things fun is because that is what energizes us. That is what makes us want to get up in the morning and work on our business is if we’re having a good time, because it’s not about the destination, it’s about the journey. You’re going to spend so much more time on the journey than you are ever at any destination. So is it enjoyable? And I think we did a good job of that during this project of just sort of whenever the other person suggested something that was a little bit silly, a little bit left of center, the other person was just like, yeah, let’s throw that into the project. So whether it was you really wanting to make the images and the branding for it a little bit more absurd by, you know..

Jason: Adding in fuzzy donut.

Caroline: Fuzzy donut.

Jason: Weird spirals and 3D blobs.

Caroline: Weird emojis. Like all those things, I really value that because I think it made the project feel uniquely ours as a brand. Or whether it was me just really loving this encyclopedia concept and being like, I don’t care if people don’t get it. I don’t care if it feels like such a stretch. I would so much rather than just say we’re going to make 30 videos and articles for a month, I would rather wrap it up in a concept that I can get excited about, which was this encyclopedia idea. And so for me, that was embracing the fun.

Jason: Yeah, I remember writing this article a long time ago that was called Find Your Motivators. And it was like, in anything that you do, what’s the thing that’s going to take you one step forward to take action on that thing.

Caroline: Right.

Jason: So it’s like going to the gym. If it’s buying a new pair of gym shoes or pants or whatever that is, if that motivates you to put that thing on and go to the gym and do the exercise, then invest in that because that’s investing in the motivation. So for us, I think what we’re really trying to lean into and what we have for the past couple of years with WAIM is just fun. I remember when we were sitting and having a meeting like five years ago, and we were talking about all these to do’s we have for whatever we were working on at the time. And I took a moment, I just threw my notebook on the floor. I was like, this isn’t fun. Why are we doing this to ourselves?

Caroline: Totally.

Jason: And I think anybody listeners who runs a business where, it’s not going to feel fun all the time.

Caroline: Exactly.

Jason: But it is in your ability to take a step back every week and go, what could make this more fun? What could make this more motivating? What am I missing here that’s not helping me move forward? And you’re maybe not always going to have an answer to that question, but I think it’s just one of those things that whatever that identifying belief is for your business, that stands out to you, come back to it as often as you can. And I think for us, that’s what we’re trying to come back to a lot more these days. Because I think the truth of the matter is we don’t want to be working for another 20 years. So it’s like maybe we have ten more years of work in us to get to a finish line of having enough savings and retirement to not be working. I want those years to be fun. We’ve done the hard work of building the skills and the experiments and all the things. Now I want to lean on the fun and figure out how do we get to our goals, but also prioritizing fun over everything else.

Caroline: Yeah, and I think it’s so interesting. I do a lot of research on businesses, startups, like how big businesses are doing it to try and glean anything that we can bring into our business to make it more efficient or make it more organized or whatever. And the thing that I always wind up thinking when I go do this research is like, how did this become so blah and vanilla and dry and devoid of any whimsy whatsoever? And I think when you imagine being a kid and how everything is like this wide open imagination, you’re comfortable being silly, you’re comfortable being sort of out of the box and adulthood just has this way of stripping you of all of that. I don’t know why? Because you think it doesn’t matter.

Jason: Well, I think in business it’s because it’s safer too. So it’s like you design a homepage and you’re like, well, we could put like fuzzy donuts and 3D blobs and this stuff on it. But if that’s not going to move the needle with profit, why are we adding that in?

Caroline: Yeah, exactly. It feels nonsensical. It feels superfluous, it feels unnecessary. And the irony is that for us, there couldn’t be a more necessary thing than absurdity.

Jason: Yeah, absolutely. And we talk about this all the time and we’ve said it in so many podcast episodes. We love leaving money on the table, just like we’ll take the cinnamon rolls off the table, but we will leave the money on the table. And that is with so many decisions we make in our business. And I know that might sound like coming from a privileged place, but even when we weren’t making enough money to sustain ourselves and we were pulling from savings, we were still making those decisions. Because for us, it’s not about profit over everything else or capitalism above all. It’s enjoyment. It’s having a business that feels calm, it feels peaceful, it feels like you want to wake up and work on it every day. And if you’re listening to this and you don’t feel like that with your business, it’s time to take a step back. And hopefully that’s what the Calm Business Encyclopedia will do for you, is to go through when it’s done, 26 different topics of business and reevaluate every single one of them and just be like, what is the thing I want more out of, each of these different parts of my business and what am I not getting now?

Caroline: Yeah. And to me, that is a part of the core mission of Wandering Aimfully is to show people that they can use running an independent solo or small business as a means of having a more enjoyable life. Because a lot of working for someone else or working for a big company, it is devoid of some joy. And when you work for yourself, you’re responsible for it and you’re in control of infusing that joy and that fun and that absurdity and that weirdness into everything you do. And again, replace fun for whatever your motivating factor is. But I think we’ve done a good job, this project of keeping that at the forefront.

Jason: Definitely. With Fuzzy Donuts, it’s impossible not to. All right, the last lesson we wanted to kind of share here is not forcing someone else’s blueprint. And I hope this is one of those moments where you hear us say it and you maybe listen to this podcast and think like, yeah, those are experienced business owners that I’m listening to. We still fall into these comparison traps and it’s just like natural for you to go. Okay, let’s talk about making YouTube videos. Let’s go look at YouTube here’s.. Oh, this is what a video is supposed to look like. This is the quality I’m supposed to see. This is the way it’s supposed to be delivered.

Caroline: These are the tips for storytelling. This is how you intrigue somebody.

Jason: Yeah, here’s how you structure a video, all this stuff. And you go, okay, well. This is how I have to make YouTube videos. And you sit back and you go, that doesn’t feel good to me. I don’t like that. We recorded a whole episode about being stuck in the video mud and how we got out of that. And I’m so glad that we were able to take that week to basically fall apart and crumble into a mess of two humans trying to work on a project to then pick ourselves back up and find a new way of doing something. And that way it’s not going to compete with all the YouTubers who make content like we do that get a ton more views than we do. But that’s not the goal of this project, is to get a bunch of YouTube views. It’s to have something that we’re proud of, that’s helpful and the views will sort themselves out and that’s it. That’s all that really matters.

Caroline: Yeah. And I also want to take a second to say there’s nothing wrong with wanting to learn from someone who has come before you, who has picked up lessons and go, okay, let me start there, right. I think that’s what we’re really looking for. When we look for a blueprint. We’re asking someone else to go okay, save me the headaches of figuring this out the hard way. Save me the time, save me the effort by just telling me what worked for you so I can start with something, cool. That’s an instinct that we’re all going to have. And in a lot of ways, it’s really smart because it’s like the idea of work smarter, not harder. Right? Great. But for me, I think it’s start with that blueprint, sure. But the second that you realize that you’re forcing it, the second that you realize like, this doesn’t feel aligned with the way that I should do something, that’s when I think it’s worth taking a step back and going man, I got to go my own way. It’s kind of like okay, now I know that didn’t work. And I also wrote something down here, which is that, it’s actually when you find yourself at that moment where you go, whoa! This blueprint isn’t going to work for me. It’s actually an opportunity because what it makes you realize is you’re never going to develop your own voice by going down a well lit path. And so I think about that with YouTube. It’s like, I don’t know if these keynote videos are our thing or if they’re something that we could do for years or if it’s going to resonate with people. But what I know is the keynote videos are a stepping stone to creating more, and creating more is the only path to find out a voice of video making that is uniquely ours.

Jason: Yeah.

Caroline: So I’m glad that we blew up the blueprint. I’m glad that we didn’t use the familiar tactics. We still experimented with certain things. Like you may have noticed in the videos, we start with like a little what you would call a hook, like kind of asking a question or a statement that kind of tells the viewer, are you interested in this? Great! That’s something we picked up from someone else that requires no forcing on our part.

Jason: Yeah, same with like, the YouTube thumbnail design.

Caroline: With the thumbnails, we’re trying a new thumbnail design to just like, see..

Jason: Be more enticing.

Caroline: Yeah, exactly. Great! All of those things are tidbits, but the filming of the videos themselves, the creative voice again, we’ll never get to what is a Wandering Aimfully unique video, if we don’t sort of like, allow ourselves to go down this path that is more aligned with us and our skill sets rather than what we see working for someone else.

Jason: Yeah. And I think the actionable takeaway for you listening to this is, is there something that you’re currently doing in your business that feels like you’re forcing a way that you’re seeing other people do it? And it just feels really incongruent to how you would actually want to do it? Do it in a way that feels right to you and then kind of experiment and see what works and what doesn’t work. And however you’re going to measure the success of making that change, do that. And for us, it’s really easy. It’s publishing the videos. So we do have a goal of you know, we’d like to get 500 new email subscribers by the end of the project being live on YouTube, I don’t necessarily think we’re going to get there, and I’m not going to be upset that we didn’t. But that was just a number to answer that question, because that was a question that was kind of spinning around in our minds. But really the truth of the matter is just publishing the videos and not hating the process was the target or the goal. And we figured that out. And so that’s a win for this project, which I think is really great.

Caroline: And the bigger goal for me is the long term prong of seeding our website and our channel with evergreen content that can organically bring people into our audience for the long term, for years. Because, if we’ve learned anything, it’s that. The thing that allows us to take time off of social media and not rely on that for marketing is you need some type of ongoing lead source that is organic. And so we knew that our goal for 2023 was going to have to be to create new articles and new content. And so that’s the win.

Jason: Yeah, absolutely. All right, those are our four lessons. Now, normally we would be transitioning into the Calm Business Confidential.

Caroline: Correct.

Jason: However, we’re throwing you all a curveball if you’re listening to this, I would like everyone who’s currently driving to pull over. Put your hazards on very safely, pull over. If you’re on a treadmill, step your feet sees off to the side. If you’re currently cooking, put down the knife. We’re just asking for one thing. Send us an email and tell us that you want the Calm Business Confidential to continue. We just want to get some emails about it. And if we don’t, then we’ll just take that as a.. This was not a segment that you all wanted, and we’ll stop doing it. And that’s totally fine. But this is how we’re going to find out that information that we wanted to do it. If you’re on Spotify, I’ll throw a poll up so it’s even easier on Spotify. You can go into this app, there’ll be a poll that pops up, and you can click, yes, I want more, or you can click, no, I don’t want that. But most of our audience is not on Spotify. So again, pull over, step to the side of the treadmill, put your knife down.

Caroline: And if you do love that segment, then in your email where you tell us that so that we and keep doing it. Also, just think of one or two businesses off the top of your dome.

Jason: Yeah, but if you don’t have one, we understand how much work that is, too. So if that’s going to hold you back from hitting send on an email, I’d rather get a bunch of emails. And people are like.

Caroline: Obviously.

Jason: This is the best thing in the world. I’ve never seen anything better than this. Oh, my gosh.

Caroline: That’s what you’re looking for?

Jason: You know like that.

Caroline: Of course.

Jason: It would be fantastic.

Caroline: That’s what I’m looking for.

Jason: But yes, would love some calm business confidential ideas as well to move forward with. All right! Do you want wrap up this episode there and keep it just short and sweet, or do you want to talk about life in Portugal?

Caroline: Life in Portugal.

Jason: Okay. Yeah. Well, we have kind of an announcement, but not quite an announcement about our lives in Portugal.

Caroline: Okay.

Jason: Which is thing, that’s. It’s been a cliffhanger for quite a while.

Caroline: Big cliffhanger.

Jason: But it doesn’t happen until tomorrow. So there’s like a 7% of me that doesn’t believe it to be true yet, which is..

Caroline: Our residency cards have been located.

Jason: So, we are.. Right now, two year, temporary, long term, however you want to describe it, Portuguese residents. But the problem is we don’t have the cards in our hands.

Caroline: Exactly.

Jason: We just know that they exist at the office.

Caroline: To give you a recap on the saga. We had our appointment at the government office in early June, where they go through our paperwork, and it’s basically just like the meeting on this side to say, you’re good to go. You can stay here for two years. We’re already technically, we’re legal. We have the visas, but it’s sort of like the confirmation stamp. All of that seemed to go well. Then they’re like, you’ll probably get it in..

Jason: 30 to 45 days.

Caroline: 30 to 45 days. Then, we didn’t hear after 45 days, we email, we don’t hear anything, we’re trying to track it down. Then, it’s August. So it was just like, kind of bad timing, but August here is where everyone goes on holiday. And, also the government office is in the midst of this shakeup where they’re rolling up another government office into it, yada yada. And so a couple of weeks are going by, and I’m telling Jason, and I’m like, I just have this feeling that they’ve already processed us. It’s just they have not gotten into the mail. They’re sitting somewhere in someone’s pile of something, and we just have not been able to track them down. And, you know luckily, when September kicked back up again, we lit a fire to kind of track these down. You did a lot of the hard work to contact a lawyer, and she was able to go to the office. We located them.

Jason: Yeah. She said, I don’t have power of attorney for you, so I couldn’t pick them up myself, which is totally fine. But she said, you can go in on Monday at 09:00 A.M, and be there, and they can hand them to you. So you better believe it. We’re recording this actually on Sunday the morning before. So tomorrow morning, we are hopping in the car, we’re driving to Lisbon, we’re going to park at that office, we’re going to walk in with our hands outstretched. Say, Bom dia tudo bem? And then hope that they hand us our cards. So, that is the kind of big news which is exciting for us because it just takes like a big breath of you know like, removes a piece of stress from our minds of you know, we were going to leave in November to go back to the US. It may have been a little bit tricky coming back in if they had a question of like, why are you here? How long are you here for? So this makes it a lot easier because we just go. Residency card, what’s up?

Caroline: And then also, we were.. The hold up with getting our car.

Jason: Finally get to buy a car. Eleven months of renting a car from the tiny little car rental place down the road.

Caroline: Every month we go to the cutest little rental place in Leiria, and we talk to the folks there, and they’re like, Again? And we’re like again.

Jason: So, yeah, we’ll finally be buying a car. Maybe we’ll share what that process is like, but we don’t know that yet.

Caroline: Speaking of cars, I don’t think I shared this on the podcast.

Jason: Yeah, you did something with our car that wasn’t bad. It was good.

Caroline: I’ve been driving again.

Jason: Wow.

Caroline: I feel like a real adult woman.

Jason: Yeah. And just very quickly, for everyone to know, you haven’t driven a car in like, two years.

Caroline: I have not driven a car in two years.

Jason: And the last time you drove, you had a panic attack.

Caroline: Exactly, so it was a little bit not a good track record. I mean, I drove for many, many years. And then kind of what happened was.. It was, coincided with my eye issue but also, it was all my anxiety stuff in 2019. So then I wasn’t driving. Then the pandemic happens, then we’re not going anywhere.

Jason: I was the sole grocery store runner.

Caroline: Exactly. And then it’s like, if we are ever going anywhere, we have one car. So you’re driving because of my eyes and my anxiety. Then I was trying to get back into the habit before we left for our Europe trip, and I had a couple really bad experiences. My glasses prescription was still not correct, and it makes with my eye condition driving, extremely anxiety inducing, so panic attack. Then it was sort of a mental game because it was like, oh, crap. Driving is really scary because when I drive, I have panic attacks. And so anyway, it built up to be this whole thing. We’re traveling all of last year. Of course I’m not going to.. If I’m not driving in the US, I’m not driving in different.. Definitely not Italy. So, long story short, it has been this big thing that has sort of built up into a bit of a hurdle in my mind. And I just thought, you know. For my freedom and my ability and also for us to have kids and for me to be able to go places and take the places, I got to know how to drive and I got to feel comfortable. So, we are finally diving back into the deep end. And I drove for the second time yesterday.

Jason: Drove to the grocery store.

Caroline: Navigated those roundabouts like a champ.

Jason: Sure did.

Caroline: And so that’s just my big personal win.

Jason: If anybody cares too, just for people who are living in Portugal sharing what it’s like. Our US driver’s license basically give us a driver’s license here. And we don’t have to get a Portuguese driver’s license. So it’s as long as our US driver’s license is active, it works here. So that’s actually one of our to do’s when we go back in November, is to actually transfer our licenses from California to Florida because we don’t have an address in California anymore. So we do have a little bit of DMV homework that we have to do when we go back, woof. But yeah, that’s that other update. And then one final update that was just a fun one is our little local restaurant that’s just right down the road from us had another themed night.

Caroline: Yes.

Jason: And this one was Bollywood.

Caroline: It was a Bollywood night with Indian dishes. And this has just become such a delightful thing that happens in our neighborhood. And the whole neighborhood comes together and they have a guest chef come in and they just basically do an entire menu that’s based on a specific cuisine and a specific culture and region. They have dancers, it’s just exciting. And it really does feel like a celebration of culture, it feels like a celebration of community and neighbors. And we get to sit at the community table and just chat with our neighbors. And it always leaves me feeling immensely grateful that we picked this place to stay in, that we have been able to build community here. We’re coming up on a year of living here, and one of my biggest fears moving here was that we were going to feel so alone and so isolated. And it’s been the exact opposite. I’ve never felt like I had more of an immediate community around me than here. And I feel really grateful for that.

Jason: Yeah, what’s also really fun about these themed nights at this restaurant is we just basically get introduced to a lot of different cultural and cuisine things that we never would I don’t know anything about Bollywood besides what I see on TV or in movies or whatever. And so to be around a bunch of Indian people who are talking about like, oh, this is the music that we used to listen to in our small village.

Caroline: Right?

Jason: When it came on.

Caroline: The biryani that my mom makes is different from it in this way

Jason: In this way, yeah. It was just like, it’s a very unique thing.

Caroline: Also, one of my favorite cultural moments was.. At the very end of our meal, they brought around what looks like these little nerds.

Jason: It looks like the candy nerds.

Caroline: Right.

Jason: Not like a bunch of computer geeks.

Caroline: No, these little pebbles, almost. And they scooped them into my hand, and I’m like, what is this? And so they’re saying they’re fennel seeds, and I guess this is supposed to aid with digestion, like, at the end of your meal. And so I’ve never seen this before. And so I go to kind of like.. I have it in my left hand, imagine a little pile of what looks like nerds, and I’m going to pick them up with my right hand. And I look over at our friend Rajan, who is Indian. And he sort of sees me almost about to peck at it with my fingers, and he just gestures to me very subtly with a smile, like, smash it to your smash it to your mouth at one time, sort of. And I was like, oh, okay, got it. And so I just threw it back into my mind. But I don’t know, it’s just like, little interactions like that where you feel these cultures coming together, you feel like you’re learning something, you feel like it’s a very welcoming, inclusive experience, and I just enjoyed that.

Jason: And also you got up and danced. They did some dancing circles. I blame it on my knee. Not that I don’t like to dance.

Caroline: That was another favorite part. I mean, I was like, a little bit self conscious.

Jason: But there were like, 20 people dancing.

Caroline: Exactly. And also there was like, another Indian friend of ours has her mother here, and seeing them dance together.

Jason: Yeah, and she’s like, 82 or 83. Like, she’s older, so she was moving and grooving.

Caroline: And it warmed my heart because they were just jubilant. They were having such a great time.

Jason: Good time. And also, this was like, right at the end of a super busy week, getting the project out there, and we almost didn’t go. We were like no, we need to do something, we got to get out of the house. This is one of the things you got to force yourself, and once you do it, you’re like, yes. Okay, this was worth it, it feels good to step away from all the to do’s and the tasks and the thinking of all the things we’re working on.

Caroline: Yeah, it was wonderful.

Jason: Fun night, fun way to wrap up the week, hope you enjoyed hearing about it. Next week, keep your eyeballs peeled for WAIM Unlimited, opening October 2nd to the 17th. As you heard at the beginning of this episode, if you want to join our un-boring coaching program, you can find out more at

178 – 4 Lessons For Your Next Big Project

(Big Fat Takeaway)

If you’re embarking on a big project, we have 4 lessons to share from our experience building and launching our Calm Business Encyclopedia.


This article written by

Jason Zook

I'm all about that Cinnamon Roll life (that just seemed like a "cool" way to say I love baking and eating cinnamon rolls). Also, I co-run this WAIM thing as well as Teachery. Currently, 75ish% completion of Tears of the Kingdom 🧝‍♀️⚔️.

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