129 - Reflecting on 40 years in life and 4 years in biz

This episode is a dual celebration! Jason turned 40 years young this year AND WAIM turned 4 years old this year. They were close enough in proximity we decided to record an episode sharing lessons from each.

Show Notes

Every “milestone” birthday has you reflecting on life and your previous years. Jason left his 30s behind and moved into the 40s, sharing five life/biz lessons with you.

For WAIM, our little entrepreneurial endeavor passed the 4-year mark and it’s hard for us to believe! But, during these past 4 years, we’ve learned some well-worn lessons we wanted to share with you that we hope you can apply to your business.

And, of course, there are lots of silly stories and walks down memory lane shared this week!

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What is Growing Steady | Intentional Creative Business Podcast?

We’re Jason and Caroline Zook, a husband and wife team running two businesses together and trying to live out our version of a good life in the process. In this business podcast, we share with you our lessons learned about how to run a calm, sustainable business—one that is predictable, profitable AND peaceful. Join us every Thursday if you’re an online creator who wants to reach your goals without sacrificing your well-being in the process.

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.

Caroline: Back in the saddle.

Jason: Here we are in the saddle, in your ears, being podcasters. Do you ever just think about...

Caroline: Two weeks in a row.

Jason: ...how odd it is to be a human right now? And that like we're just talking into these small metal devices and people are just listening in their ears?

Caroline: Yeah.

Jason: But I guess that's been going on for quite a long time.

Caroline: Just like, on purpose, recording our conversations and then publishing it for literally the entire world to hear.

Jason: Right. The entire world to hear, but only nine people in the world.

Caroline: Do my feet smell?

Jason: I'm not going to comment on that because that's... I just took a shower.

Caroline: No, I know you did.

Jason: Yeah. You're looking at my feet. Just want everyone to know, you're looking at my feet.

Caroline: I know. When I asked you if my feet smell, it was really my way of saying, "I don't know, it just kind of smells like feet over here." It's fine. I'll just face this way. Just so you know, listeners, the way that we record these is always actually for years now on a couch, and we're in like a little...

Jason: Leg puzzle.

Caroline: Like a little leg puzzle.

Jason: Yeah.

Caroline: Where we're facing each other, but my legs are stretched out and then his legs are stretched out and they fall together. But that means that everyone's feet are in everybody else's face.

Jason: Yes, it's called feet face.

Caroline: It's called feet face.

Jason: That's how we do it.

Caroline: Try it sometimes.

Jason: That's how we do it. All right. This episode is hopefully going to be a fun one for you listeners because we're looking back on the entirety of my life, all of it.

Caroline: We're going to take you through every year.

Jason: Every smoldering detail, and then we're going to look at every detail of WAIM for the past four years, because WAIM basically turned four years old in March of this year.

Caroline: You told me that, and I could not believe it.

Jason: You know what's really weird to me?

Caroline: COVID is a time-ass warp.

Jason: I do a manual payment tracking for every single one of our customers.

Caroline: Yeah, I know that.

Jason: I know every single payment that they do.

Caroline: You're telling listeners because I know that.

Jason: I'm telling you, too, just to remember that I do this every single day of our lives.

Caroline: I know.

Jason: And I realized this in January was the first time it happened. Or maybe it was March was the first time it happened. I think March had been the first time. Anyway, I'm doing the payments right now as of recording this. And it's a June, and it's the fourth June that's in the list of Junes. It's so weird to see four Junes.

Caroline: So you have, like, June 2018, June 2019.

Jason: June 2019.

Caroline: That feels weird.

Jason: Wild. All right, so where do we want to go from here? We're going to do...

Caroline: Don't skip the pramvel?

Jason: Oh, okay. Sorry. I was just going to say we're going to talk about forty-four things. Right. Because we have so many or we can tell them about our math.

Caroline: Okay.

Jason: Yeah.

Caroline: So originally our idea was 40 things that Jason's learned about life because he's turning 40. And then we were like, that's so many things. So what we decided is since Jason is forty and WAIM is four, we're going to do ten things.

Jason: Right. That's how it works.

Caroline: Because forty divided by four equals ten and also math.

Jason: That's what seems right.

Caroline: And all of you who remember the episode where we miscalculated the number of fights that we've had over the course of our relationship will remember that math is our strong suit?

Jason: Yeah. You know, what we hadn't done when we recorded that episode? We hadn't traveled full time together.

Caroline: That's right. We're really racking up the totals.

Jason: The numbers are getting real.

Caroline: We're kidding. Are we?

Jason: Okay, pramvel, we're doing some travel updates before we get into that.

Caroline: Yes. So don't forget. So before we get into the meat of the episode, those of you who just like to tune in for the travel updates, this is your...

Jason: Time.

Caroline: Segment.

Jason: Great job.

Caroline: The pramvel. Where we last left you off in last episode, that was a huge catch up episode.

Jason: Recapped.

Caroline: Holy cow. Those of you...

Jason: Hope you enjoyed it.

Caroline: ...who got into that one? Congratulations.

Jason: I mean, it wasn't that long, though. It was just a lot of things.

Caroline: Four countries, many weeks. Where we last left you off, we had just spent a week in Crete at a resort called the Royal Senses Resort and Spa, which we booked specifically for your 40th birthday. So it ties in well.

Jason: We have a YouTube video coming if you want.

Caroline: And we have a YouTube video... because I don't think we went into too many details, but, boy, we just enjoyed that week so much. We have an entire video just dedicated to what the experience was like at the resort.

Jason: Yeah.

Caroline: Because when we looked up quite a few videos and there weren't a lot about the resort.

Jason: There was a drone footage. There was a woman who carried a GoPro throughout the room, and that was it. And then there was the hotel's video, which made it look like the best hotel in the entire world.

Caroline: Exactly. I don't know if anyone listening does this, but this is our thing. I feel like if I told people that we do this, they'd be like, what?

Jason: Yeah.

Caroline: But this is just a very normal part of our travel planning process is, if you're going to look at a resort, and it's pricey, I immediately go to YouTube, and I look for videos so I can understand what I'm getting into.

Jason: Getting a real vibe.

Caroline: Exactly, because like Jason just said, the promo videos are like... a professional videographer just did a glamor shot of...

Jason: Yeah, there's two models who are like the most attractive humans in the world.

Caroline: Right. And I'm like, oh, so do I just turn into that model when I set foot on the premises?

Jason: And there's not a single person at the place? You're like, okay, so when I book here for $226 a night...

Caroline: You clear out everybody. You turn me into this model. And then you slowly have the breeze below my luscious dress in the sunset? Long story short, do you do this listener? Because this is what we do. We go look for videos. So we want to be one of those videos.

Jason: It wasn't just videos, by the way. It's TripAdvisor.

Caroline: Of course.

Jason: Like trying to find Google Reviews, because a lot of times those are like, you're just getting real people leaving those reviews.

Caroline: We should do an entire episode on some of our travel hacking planning tips because, when I met up with my friends in Paris and told them about our extensive How to Look Through Google Reviews to Find the Best Restaurants, they were blown away. They were like, "How do you keep nailing these restaurant recommendations?" I'm like, "Oh, I just have this very specific thing in Google Reviews." I should tell everyone about my Google Street View hack, about how to look up where things are.

Jason: Oh, yeah. And our WAIMers, when we show our Airbnbs, because we do like Airbnb tours and our WAIM update videos, we have like, a very, very--I mean, calling it a vlog is kind of silly--but it is that, it's a weekly video update that we give to our WAIMers and we do a tour of the Airbnb at the end of those updates. And everyone's always like, "How are you finding these places?" And I think if they only knew it's like ten to twenty hours can go into finding one place. It's a lot of work.

Caroline: We're just, we're such nerds. And also we have no children. And this is what we spend our time doing.

Jason: Speaking of spending ten to twenty hours, when we were looking at kind of filling out the itinerary, we had talked about, "Okay, we're going to be on the island of Crete."

Caroline: Yes.

Jason: Obviously, the Greek Isles. There's Mykonos, there's Santorini, there's all these other isles. Do we want to go to another one? And the more we talked about it... and we were planning this before the whole recap that we just gave you in last episode, which was a lot.

Caroline: A lot.

Jason: And so when we were planning, we're like, "Carol is probably going to need some recharge time. Maybe let's not travel to another island. Maybe let's try and just stay in the island of Crete and see what we can find." And also, if possible, the island is not huge. It takes probably like four to five hours to drive coast to coast or edge to edge to the island. But maybe let's not go all the way to the edge because long car rides don't do well for you either.

Caroline: Yes. And boy, am I so glad that we fought the FOMO because as much as I would love... it gives us something to go back to and do the whole Greek Isles experience. But for that point in our trip, it was so clutch for us to just not waste time and anxiety on the transportation and to just be able to stay put. And so what I was going to tell everyone is like this week... So let's just first start with where we stayed. So we left the resort and we found this incredible Airbnb listing that was basically only like a 25-minute drive from the resort to... It was actually a drive towards the airport, which was even better because then it shortened our ride to the airport. But anyway, in this little kind of like, bungalow beach villa up on this huge hill at the top of the hill of this little, what would you call it? A beach town or a fishing village...

Jason: Agia Pelagia.

Caroline: Agia Pelagia, I think, is the little beach town. And by beach town, I mean, there's like five restaurants and a cove, and that's it. But it was perfect because what we loved about this is that it had a view and it had a pool. And again, as we told you, this was our vacation time. So all I wanted was to, like, read my book at a pool. That's what I wanted. And I was thinking about it. And this week, I think is one of my favorite weeks of this whole trip where I just felt really good and we loved the place so much.

Jason: Yeah, the place. There were three villas that were not connected. So that was kind of nice, too, because you're not sharing any walls, which is always like an adventure if you're sharing walls. And they all have their own pools. They were slightly different layouts. You could look them up online, but this was the only one that was available. And when we showed up, we met Despina, who was the owner of them, and she was also the designer, an engineer, and she was so lovely. And the second we walked in, this is one of those... the photos of this place. And I think if I can remember, I'll put the Airbnb link in the description. We'll also have a video coming out so you'll be able to see it as well. But this is one of those where the photos look so good. And so we're like, "Is this going to live up to the reality?" Because you've stayed in a couple of... as anybody who's traveled to Airbnbs, you know, like, this doesn't match up.

Caroline: Right.

Jason: But we... it absolutely matched up.

Caroline: My gosh. It was perfect for us.

Jason: Like in person it felt as great. And we told her that, and she just seemed like we were the kindest people to say that to her. I think most people just, like, get in there, like, "See you later."

Caroline: No, she was so perfect.

Jason: She was wonderful. So, yeah, we really spent this week hanging out at this place. We walked down the hill, which is like a ten minute walk down to...

Caroline: My favorite thing.

Jason: The beach.

Caroline: I thought this walk was going to be like... because it was pretty high up. And I was like, "It looks very rugged." But it turns out it was just a very easy walk ten minutes down the hill. And then you have all these restaurants. One restaurant in particular which we absolutely loved, I couldn't believe it. Basically found, like, a Southern California restaurant in...

Jason: Incredible.

Caroline: Agia Pelagia. It was this cool restaurant called Liber. So if you stay anywhere near there, definitely head there. And you could tell that that restaurant is built for the summertime because it's humongous. And it was a little bit, like we said, off season.

Jason: They had just opened, like, two days before we got there.

Caroline: Exactly.

Jason: And if you listen to last week's episode, when we were talking about the restaurant at the hotel and, like... we've just run into this where we've been getting to places right as seasons were starting, and we've just had this fortune of showing up, and they're like, "Yeah, you're the only people here, but we'd love to serve you."

Caroline: And we get this very personalized experience. And we chatted with the owner, and it was just really, or manager, and it was fantastic.

Jason: One of our favorite things that we did, we went, I think we went to this place three times or two times?

Caroline: Three times.

Jason: Three times. We did the most digital nomad thing ever.

Caroline: We were like, "We're such a cliche right now." After going there one day and really enjoying the food, we decided a couple of days later, and they had really good WiFi too. We decided to walk down the hill, get a little bit of exercise, bring our laptops, and we had to do some travel planning. So we ate lunch there and then hopped on the WiFi.

Jason: We had a view of this little inlet of water and this beach.

Caroline: And the water was so blue.

Jason: And we were just having, like, mixed drinks. I was like, "This is the most..." Like, the only way this could be more digital nomad is if we were in Bali. That would be it.

Caroline: Right.

Jason: That's like, Bali is at the top of this. And then you have where we were just like...

Caroline: We just felt like we were living that cliche, but it was so lovely and it was just so nice to recharge the batteries. So that was definitely a week that will stand out to me.

Jason: What was the other highlight of Kokomo Villas?

Caroline: Uno.

Jason: Uno Deluxe.

Caroline: Uno Deluxe.

Jason: Yeah. We got into Uno Deluxe.

Caroline: We got heavy into Uno Deluxe.

Jason: It was one of the games that were there. Jengga was there, and we played one game in Jengga. I lost. So...

Caroline: Uno Deluxe. I swear this round went on for like two and a half hours.

Jason: If any of you have played Uno Deluxe, please send us an email and tell us that you have also gotten stuck in like a 1-hour round.

Caroline: We were like in a warp where one of us would get in there and then the other one would get a couple of wilds.

Jason: We shuffled like a hundred times.

Caroline: Anyway, you don't care. But it was very fun.

Jason: I think it's fun. I do think people care. I think people are interested in when you're doing this full time travel life and when you're not just sightseeing because you just can't sightsee all the time, what are you doing? And so this is like a fun thing. We just picked up this habit of Uno Deluxe.

Caroline: Okay, Uno Deluxe.

Jason: And we really got into it. Yeah. So that was the Kokomo Villas. It was a very relaxing time. Every single person we interact with was like, "What are you going to go see? What are you going to go do?" We're like, "We're going to stay here."

Caroline: Wait. We forgot about the one downside of the Kokomo Villas. The only downside of the Kokomo Villas. Tell everybody what it is.

Jason: Oikos, the stray cat.

Caroline: The stray cat.

Jason: Yeah.

Caroline: So immediately upon arriving, we noticed that there is not one cat but two cats that have no collars that decide to pop up and like, "New people who might feed us." And you're in a country where you've never been before and you don't know if this cat is friendly, not friendly.

Jason: Friendly, ferral.

Caroline: Yeah, exactly. So I was like very hesitant. Of course, after a couple of days go by, I'm like, "Okay, this cat is perfectly friendly. It's just they're hungry." But I don't want to feed the cat because then the cat will come back.

Jason: The cat came back no matter what. This cat was so stubborn.

Caroline: We tried not feeding the cat. We tried feeding the cat. The cat got bold and at one point, we were having a lovely, nice prepared dinner on the balcony and the cat jumped up on our table...

Jason: By the second plate.

Caroline: Went inside.

Jason: The cat was like, I'm not having it. Also, we named the cat Oikos in case you were curious, because he was Greek and we'd had to give him a name.

Caroline: But I know that Oikos is like an Americanized version of a Greek word.

Jason: No, I didn't name a person that. I named a cat that. That's okay to name a cat that.

Caroline: Yeah.

Jason: Again, we share the realities of this travel things. It was uncomfortable for you to be outside with this cat roaming around. Do I think this cat was probably just super friendly and would have loved on us and, if we petted, him he would have been very happy? Absolutely. But also we're in a foreign place. We don't know where any emergency services are. If he scratched you for some reason...

Caroline: Exactly. That's my thing is, I'm like, I'm not going to get taken down by a cat scratch. I'm just not doing it.

Jason: Yeah. You've tried to get taken down by shingles. You've tried to get taken down by COVID.

Caroline: Exactly. And I was just feeling better with my shingles. I was not about to risk it on a cat.

Jason: Yeah. So from there, we got a taxi, we got taken to the airport, and we waited in the airport to get on a flight to go to our next destination, which we will talk about next week.

Caroline: That's right.

Jason: That's the pramvel. And we will leave you hanging with... Do you have any hanging information at the airport that you want to share with them?

Caroline: Any hanging information?

Jason: Yeah. Like anything. Like a story that you want to share. Like, we'll pick that back up next week?

Caroline: I do not.

Jason: Great. Cool thing, bro.

Caroline: Say that to yourself.

Jason: Great job.

Caroline: Where were you leading me?

Jason: Anywhere you wanted to go.

Caroline: I didn't want to go anywhere.

Jason: Thank you. Appreciate you. I think that's lovely for everybody to get to enjoy. Yeah.

Caroline: Let's get to the meat of this episode, Jason.

Jason: All right, let's do it. We do have a hard stop on this episode. We have to stop at a certain time because we got a thing going on which is not going to be here. I'm just letting you know because I literally do have to close this thing down.

Caroline: I know that.

Jason: Yeah. I'm just sharing.

Caroline: Okay.

Jason: Let's roll.

Caroline: So we have ten lessons that Jason's learned from his 40 years on this Earth and then sprinkled in, we also have lessons that...

Jason: Listen, these are our lessons. You could say they're my lessons. I think, like, half of them are my lessons. Half of them are like combined lessons.

Caroline: Yeah. And I think our thought with this episode is just we hope that some of these resonate with you and might be helpful reminders for (a) two people who have been running a business together for four years and (b) a person of your age who is entering a new decade.

Jason: Trying to say something nice there but...

Caroline: What's that? Age isn't a bad thing. Aging is a lovely thing.

Jason: Yeah, I know. But the way that you kind of, like, looked at me and then said those words...?

Caroline: Why do people take aging to be a bad thing?

Jason: I'm not taking it. I'm just the inference with your eyes and your face was like you were, like, looking at me as the old man emoji. Like, I went from the bald guy emoji that I use. And I like...

Caroline: No, that's an insecurity.

Jason: I saw your face.

Caroline: Show me what my face did.

Jason: I turned into the old man emoji. All right, let's get to thing number one.

Caroline: Cool, I didn't know my face could turn into emojis.

Jason: Yeah.

Caroline: So number one, you wrote this one. You said, "I'd rather have a calm business than a visible business." What did you mean by that, Jason?

Jason: Yeah. I think this is something that as you get older, too. This is just a natural progression of you just want to do less things that are taxing energy wise. You want to do less things that maybe put you out in the public eye. You just kind of want a quieter, calmer existence. And I think as far as business stuff goes, all of my businesses, my businesses that I created and were online, they were all a lot of flash. They were a lot of effort. They were a lot of my face everywhere. And you got to be on news segments and things and getting mentioned by all these different outlets and whatever. And while that's great for the ego, it's just exhausting.

Caroline: Totally.

Jason: And also, it doesn't really get you that far. I am one of the few people who can say my business was promoted on the Today Show, which you could argue for those of us who are in the US who have businesses like maybe ten years ago, maybe it's completely different now. But that was a huge thing.

Caroline: It's still a big thing. Yeah.

Jason: My business was featured on the homepage of Yahoo!. That sounds hilarious right now. Yahoo! was basically the number one website in 2009.

Caroline: Right.

Jason: And those things, they're cool in the moment, but they don't necessarily actually do much. And the repercussions of you getting introduced and being in the public eye and having people see you and more access to you, it's not as rewarding as you might think the alternate of it might be, which is just to run a business that's profitable, that you just have to spend X amount of time running every single week or day of your life. And that's it.

Caroline: Yes. The juxtaposition of the most visibility that you had on your business was also the most unhappy that you ever were.

Jason: 100% and the most in debt and the most I was working like hours in the day and just all of it.

Caroline: Yeah. And I think something interesting of the way that I relate to this as well is we've never really made a huge push on social media with Wandering Aimfully. We've been consistent with it. We've not been... but from the beginning, it was just never like a big priority of ours. But now this year going completely dark while we're doing this adventure. So we've never been less visible as two people or with our business in terms of in the public and engaging in that way. And yet I just can't emphasize enough how much more at peace I feel in my own skin.

Jason: Yeah.

Caroline: I think maybe this is something that only comes with age, right? Because you just go, "Oh, you get to this point where you're exhausted about caring what other people think of you."

Jason: Yeah. This year for us could not be more worth sharing. This year, if we were... I'm not going to say strategic because we've already thought this through and we just decided not to do it. But it's like, if we really wanted Wandering Aimfully to grow, this would have been the year.

Caroline: Exactly.

Jason: We could make reels from every destination. We could make all this content. We could be posting so many more videos, we could be doing all this other stuff. But you know what? It's already an exhausting trip.

Caroline: Yeah.

Jason: And it's already really hard for you, and that makes it hard for me. And so it's like, What is It All For? Like, why would we do this? Why would we make this trip stressful? Why would we make this part of running... like we're already keeping two businesses afloat and keeping customers happy this year. Why add a compounding thing, for what? What are you really trying to do?

Caroline: So ultimately, I think the lesson with that one is just if you are someone who values your own mental health, who values having quality time, who values having space and margin in your life, take it from someone who's gone down both paths. I guess it's just validation of knowing that it's okay to not be the most visible business or to be the most flashy business, or to be the business that everyone...

Jason: Be a boring business.

Caroline: Be a boring business.

Jason: It is 100% okay to be a boring business.

Caroline: We're un-boring coaches but be a boring business.

Jason: That doesn't mean your business isn't helpful. It doesn't mean your business isn't awesome. It doesn't mean your customers won't love you. It just means that from the outside looking in, you're not going to be on the home page of Yahoo!. Okay. I'm so sorry. So that's it. That's number one.

Caroline: So number two. And this one was something that I've learned from working on WAIM for four years. And I don't know a more eloquent way to say this, but I wrote down, "The only way you'll find out what works is by being okay with finding out what doesn't." And what I really want to hit home with that is it's so easy for us four years in now that we have a coaching program that works and we do launches and it all works, right? We have an email list growth strategy that works. We have a sales strategy that works. We have a customer care plan that works. But it took us YEARS to get there. And I think of how many things we tried. Like first starting with building the entire business in public and then that getting off the ground and then having it really be... changing up different plans and different pricing, pivoting our positioning, doing Build Without Burnout as like a cornerstone product, building an entire six month curriculum. Then we moved on to un-boring business... You know what I mean? Like, we tried so many things. And I just think if we would have been afraid to try things because they might fail, we would never have hit on the thing that actually finally worked.

Jason: Yeah. And I think this is one of those lessons that it's so hard for you as a person to hear if you're at the beginning stage of your business. But it's just that it will take time and it will take experimentation and no one can give you the fast track pass to get your business to be successful. Your business is so unique to you and how you want to run it and what you want to do and what your unique things are about it that you have to figure all that stuff out. Even if you're someone who's like, "I want to design Squarespace websites for yoga instructors." It's going to be different for you than it is for the 3000 other people that do that. And you have to figure out your own way of trying to find clients, of trying to work with them and building processes, because you can't take a bunch of other processes and ways of doing things and just slap them onto yourself and think that they're going to work perfectly.

Caroline: Totally. And I think as a caveat to that as well, or like, as an addendum, I think not becoming too wrapped up in what your next idea will be. Not too wrapped up, almost like too romantic about it or too invested in it. Yes, be invested in it. But don't try to hinge all of the hopes and dreams of your business on this next idea that you're working on because it may not work out. So I guess what I'm trying to say is have a little bit of an objective perspective on this experimentation mindset so that it's like, "All right, I'm going to try this launch, and for this launch, I'm going to really hit home on this particular feature of my offer. And if it works, great, and if it doesn't, I'll move on and I'll try something next launch."

Jason: And the thing that we always tend to talk about with this is like, you got to think about all the things you're doing in your business like a scientist. This is an experiment. Fail or succeed, I'm not going to be emotional about it. I'm just going to, "Okay, great. That's awesome. I learned something, move forward." But the thing is you're going to learn the most from all the failed experiments.

Caroline: That's the truth.

Jason: And they do hurt.

Caroline: They do hurt.

Jason: And they are uncomfortable. But you know what? The more that you do, the easier it gets to deal with the ones that don't work out and the less misses that you have going forward. Like, we're very fortunate now, four years in, we know who our audience is, we know what they care about. We know what they're looking to get from us.

Caroline: But only because we got through so many of those misses. And if there's one thing I wish that you would take away, it's that the next time that it doesn't, an experiment that you run doesn't go your way, a launch that you have zero sales or you gauge interest of a new course idea and nobody cares. Like, whatever that, quote, unquote failure is, I want you to just take a second to just be grateful to yourself that you tried something. Call it a win. You tried something. You can cross that off the list of things, of ideas and move on to the next one.

Jason: Absolutely. Speaking of moving on to the next one.

Caroline: Moving on to the next one. We're just going to bot back and forth. This is one of Jason's lessons.

Jason: Bot bot bot.

Caroline: From being 40. "The way things have always been done is not the way that things have to be done."

Jason: I mean, this is just something that is in my DNA.

Caroline: Correct.

Jason: And so I think for a lot of people, it can feel very uncomfortable to go against the grain, to do things differently, to own your weird, to use the phrase that ended up as the title of my book, my second book. And it's just one of those things that I have continued to see the value in seeing how someone's doing something and just going, "I'm going to do that differently" because number one, I'm not going to feel personally satisfied if I just copy and paste what someone else has done. But number two, I also know that, "Okay, well, that person is already doing that. So how can I do it differently?" Because no one needs that again.

Caroline: Not to mention a lot of the ways that we do things that goes for business, that goes for society, that goes for cultural norms. It doesn't work for everyone.

Jason: For sure.

Caroline: And so it's taking a look at the way that things are customarily and going, "Can I make that better? Can I make that unique? Can I make that different?" Like, I think about your first book, Creativity for Sale, and you just said...

Jason: Oh, yeah.

Caroline: "You know what? How could I do this differently? Instead of a publishing company giving me a book advance, how could I write my own book advance basically?"

Jason: I think the most linchpin moment of my first book, Creativity for Sale. And if you don't know anything about that, I wrote a book. I essentially crowdfunded the book, if you will, by having little sponsored ads at the bottom of every page, little text ads, like 140 characters. And I ended up making $75,000 in those ads for the book. And the reason that that happened is not because I had this genius idea to do it. It's because I reached out to a bunch of entrepreneurial friends who are authors and said, "Hey, what can I expect as a first time author from a publisher as far as an advance? Like, I want to make money writing a book." Like, "Oh, you're not going to make money writing your first book. All this is a marketing tool." And so my brain heard like, "Hold on a second. The way that you all are doing this is not the way that I have to do it. I don't want to just see it this way. What's a creative angle I could find in this?"

Caroline: If you would have just accepted that and said, "Oh, there's no way I'm going to make any money. I can't. I'm a first time author. That's not the way that things work." Guess what? You figured out a way.

Jason: And was it easy? Absolutely not. Was it a lot of work to make $75,000 on my first book? Absolutely. Is my first book embarrassing for me to go back and read? 100%. But you know what? It got done, and it opened up a whole new set of doors for me on understanding what was possible and believing in myself and my ideas and knowing especially for me at that time, I had just come off my I Wear Your Shirt project. I thought I was a one hit wonder at that time. So this was really helpful to me to be like, "Oh, okay. I can come up with more ideas that are really interesting and different and unique."

Caroline: Yeah. And you've just continued to do that, and you will continue to do that for the rest of your life. It's just always asking, "How can I do it differently?"

Jason: As an old man emoji, you know I will.

Caroline: Did my face turn into the old man emoji when I said that?

Jason: Yeah.

Caroline: Moving on, number four. So this is bumping it back to me, something I've learned from four years running WAIM, "Take the risk and lean into growth." So going back to when Jason, in case you don't know the backstory of how wondering if he came to be. Jason had a business called Jason Does Stuff. He was doing online courses and things like that on marketing. I had a business called Made Vibrant. I was doing design things, hand lettering, more creative stuff. And Jason basically was like, we're kind of doing the same thing with... There's a lot of overlap in the things we talk about, even though we come at it from different angles. What do you think about combining businesses? And it took about a year to convince me to do this.

Jason: I remember so many walks, just, like, trying to get you to see the opportunity for us to do this. And you clearly knew that we were better together as a team.

Caroline: Totally.

Jason: But I think there was definitely this resistance from your side of like, "Well, I don't want to give up my independence."

Caroline: Totally.

Jason: Which I understand, for sure.

Caroline: Yeah. But the bigger point here that I want to make is it was just such a big move. It was such a big decision. It felt so, like shaking up everything that I knew about what I was working on day in and day out to take a risk on this thing that I didn't even know what it was going to be. But the thing that actually ultimately convinced me because I was going back and forth for so long of like, should I or shouldn't I? Is this the right thing? Is this the wrong thing?

Jason: Meanwhile, I was interviewing other people, and...

Caroline: What I was really asking myself was, "Will this work or will it not?" But ultimately what I realized is it's not about will it work or will it not. It's about, am I going to learn something by doing it? Am I going to put myself out there and be uncomfortable and take a risk? And is that going to make me grow, whether it works or it doesn't? And that's what ultimately made the decision for me, because even though the irony is that I'm such a "afraid person," I'm such a person who resists uncertainty. I'm such a person who just likes my comfort. But at the heart of me is someone who just wants to grow no matter what.

Jason: Right.

Caroline: And so I think I'll always put myself in a situation to take the risk. It just takes a while.

Jason: It's just not always going to come right away. And I think that's a really important note just for anybody who's listening to this that doesn't feel like a risk taker themselves is that you don't have to feel comfortable taking risks. The difference between the two of us is I am very comfortable taking risks. It's just how I'm wired or what have you or it's privilege. It's all those things that come along with being a white male in the society that we are in right now. And so I just don't worry about those things. But for you, there's a lot more resistance, there's a lot more apprehension. And I think that anybody listening to this who might have that same resistance and apprehension, it's just helpful to hear someone say, like, "I still want to do those things. It's just going to take me longer to get there."

Caroline: Yeah. And as you were just talking, I had sort of a little bit of an epiphany of realizing, when you just phrased it like that. I'm not comfortable taking risks in the micro sense, but I'm comfortable taking risks in the macro sense. So what I mean by that is in the moment, in the tiny measured in minutes and days and maybe even weeks, I'm so uncomfortable taking risks, like taking this trip or moving to California or any of these things. But if I zoom the lens out to my whole life, I can't imagine a life where I look at the macro view and I don't see that I took any risks or I didn't try something new. In the macro view, I actually quite like upheaving my life and feeling totally out of my element and doing something different because I like the growth that it brings on. And I like feeling like my life isn't just one note, if that makes sense. So I just wanted to share that in case anyone is sort of wired like me in that sense. And maybe if you're fumbling through a big decision right now and wondering, should you take the risk. Maybe that realization will help you clarify that answer.

Jason: And I think one of the ways to do that is also just to write out all the worst case scenarios, which is exactly what we did with Wandering Aimfully. We're like, "If this doesn't work after a year or whatever, we can just go back to our previous businesses."

Caroline: Yeah.

Jason: It's okay. No one's going to be like, "Whoa, whoa, hold on! You're not allowed to go back to Jason Does Stuff. You're now Jason Doesn't Stop." And I'm like, what?

Caroline: What?

Jason: How do I put a contraction in the URL? Okay, what's next?

Caroline: Talking about taking risks, number five is your advice of, "You don't get what you don't ask for."

Jason: Yes. And this kind of curtails off of the Creativity for Sale story. But it's basically like every business that I've started since 2008 has been about doing things and asking for things that most people probably wouldn't ask for. Like, I asked people to pay me to wear a T-shirt every single day of the year for a year with this weird pricing structure at a dollar per day. And I was just thinking about this. I was thinking in the shower before this. Do you remember the question that I used to get asked all the time?

Caroline: What do you do?

Jason: Which was like, "Where are people going to see me in your shirt?"

Caroline: Oh, that's right.

Jason: That was the question people could not... and reminded me...

Caroline: They were like, "Where are you going to go in my shirt?"

Jason: This is 2009. So social media was not yet prevalent everywhere.

Caroline: You were like, "What do you mean, 'Where am I going to go?' I'm going to post a YouTube video and I'm going to post about it on social media, and hundreds of people are going to see it versus if I went to the grocery store."

Jason: And it's just so funny to think, like, just now, 13 years ago, or however long it is, the mindset was you have to go out in public for people to see you. Now the mindset is like, "Why would you go out in public? Like, put it on Twitter, put it on TikTok, put it on this, like, you're going to go viral. You got to get it online." And so, yeah, you don't get what you don't ask for thing has been so prevalent in so many different things. Selling my last name, what a bizarre thing to do.

Caroline: Yes. Also tell people about because I think this really illustrates it about the Bus Time tour that we did just because from a business perspective, I want people to really hit home this idea of, like, pitch... If you have an idea, if you can just get over the fear of pitching that idea to businesses, you can create your own opportunities.

Jason: Yeah. There was a sponsor who I had worked with, like, one or two times before, and they came back and they're like, "Oh, we really love working with you. This is still the I Wear Your Shirt time but I Wear Your Shirt has kind of just come to an end. And they're like, "We want to do something that we've got this much of a budget. Like, is there anything you want to do?" And I was like, "All right, well, they probably just want a couple of videos. Like, I'll just dance around the neighborhood like I always do and be silly." I was like, "Wait, what if we just do something weird?"

Caroline: You were like, "What would I want to do?"

Jason: Exactly. And I think we all cobbled together. There was another guy, Sean, who was working with us at the time. And we're like, "What if we did this road trip? We went to a bunch of different cities. We had this vehicle, like an SUV that was just wrapped in this weird brand that we made up. And we just shared this whole trivia."

Caroline: Basically, we just played trivia, drank beer, and went to different cities and then made videos about it. And basically it was a sponsored road trip. It was so fun. And it just came from us being like, "They'll never go for this, right?" But we wrote it all out. We explained what the value proposition was, and they totally went for it. And we got paid to drink beer and play trivia and different Buffalo Wild wings around the country.

Jason: They also loved it because... And again, this just goes back to like, you don't get what you asked for. So many people just regurgitate the same things, right? It's like, "Oh, I'm going to tweet about you a couple of times. I'm going to make a YouTube video." Like, we're going to get a car. We're going to wrap it in this weird branding we're going to make up. We're going to make this little website. People can meet us at these other places. We're going to have these little things, these little goody bags, like whatever. They're like, yeah. Hundred percent.

Caroline: And so many people say no for the other person before they ever get a chance to get the no. So you don't get what you don't ask for. All right, number six, I think what I've learned is, "Take people on the journey and let yourself be vulnerable." So this is a huge thing that Wandering Aimfully has taught me along the way through the past four years. We have not had it all figured out.

Jason: Wait, what do you mean?

Caroline: Oh, no? You didn't know that?

Jason: Oh, no.

Caroline: But no. I think in this time, people are so concerned with the fact that they need to have all their shit together to be, like, a leader or a thought leader in their industry or whatever. And you and I have just never had any interest in pretending that we have shit figured out. We just have not.

Jason: And I think for the folks listening to this, you watch and consume so much content from people who live an imperfect life. And I think that the thing there is in business if you can take people on the journey with you. We've seen this work out so many times. Like, the perfect example of this is when we were building Wandering Aimfully, we had a site. It's actually still up. You can still see at build.wanderingaimfully.com. And we thought it was going to be this like five weeks. We're going to get Wandering Aimfully up. It ends up taking five months. We ended up spending $30,000, which is basically like three times more than we wanted to spend. It drained all of our savings at the time. We had this developer that basically screwed us over, but it finally worked out. And it was just like there were multiple times when we both were just like an emotional wreck with this business, but we just shared that and we were just honest. And what we found is that so many of you who are listening to this found us through there, and it became this relatable moment where you were like, "Oh, they're just like, I am. It's not perfect. You're not just going to start a business and it's going to be successful."

Caroline: Yeah. And my favorite reason also, by letting people in a little bit and being vulnerable about the things you're going through, or like when I went through all of my anxiety stuff in 2019, by letting people into that, you also let them into your reasoning behind wanting to pivot the business or do different things or it really gets them invested in your journey as customers, as customers of your business. And so people ask us all the time like, "Oh, well, I'm afraid to piss off my customers if I pivot." And it's like if you take your people along on the journey with you, they will support you. They will rally behind you because they know you. You have let them know you. And so when I did my anxiety stuff or when we said we're going to scale back because of my energy levels or because of this or that. And it's like people are always rallying behind us and being like, "Great, good for you." And it's because they know why and they know us.

Jason: And I think the other thing, like, a lesson there for especially client-based business owners is if you deal with chronic illness, anxiety, depression, anything that just makes work hard for you on a consistent basis is for you to let your clients know ahead of time that you have those things that might derail a project slightly so that when something comes up because it will, you can let them know. And they go, "Oh, I understand. I know that you deal with this. This is a difficult thing. Please take all the time you need." As opposed to you hiding those things. And then when the shit hits the fan and you can't respond and they're like, "Hey, you're ghosting me? What's going on?" So no, you were honest with them upfront about who you are as a person and what you do.

Caroline: And what also happens when you do that and you reveal those things upfront, let's say. Let's say your biggest fear is that a client then goes, "Well, I can't I need someone who's like 100% reliable all the time." Great. They can go.

Jason: That's not a good client.

Caroline: That is not a good client for you.

Jason: If they're not going to see you as a human being and be okay with it, yeah, it's not good. All right. What's next?

Caroline: Well, funny you touched on this, but yours for number seven was just, "Be less perfect."

Jason: Yeah. This is definitely something that I have had to fight forever. And I would argue that you could look back at all the content that I made over the years and none of it's perfect, but I had my own level of proof.

Caroline: Yeah. I guess it's less "Be less perfect" because that's like insinuating that you think you're perfect, but it's like "Care less about being perfect."

Jason: Exactly. And I think that the pining over the quality of footage, caring about the layout of things. I'll tell you, there have been so many features of Teachery, the software application that we now run together that I wish went a whole different direction or a layout that I really wanted that just didn't happen. And I can actually tell you today we are releasing a feature and I wanted it to go completely differently, but there were just technical limitations. And I've now learned over the years just to be like, all right.

Caroline: Yeah. And you could never get to version seven if you don't go through versions one, two, three, four, five, and six.

Jason: Exactly. Yeah. And if you get held up in this idea of, like, this thing that I'm creating has to be perfect and has to be the best I can do right now, it might not get done for years as opposed to just, like, rolling out something crappy and just being like, "Hey, I'm going to do my best and we're going to just see how it goes."

Caroline: Yes. I told you this story about in 2011, before I had ever run a business or started online anything, I just wanted to start a blog. And for a year, I didn't start a blog, even though I really wanted to, because I couldn't think of the perfect name.

Jason: One year.

Caroline: For a full freaking year until finally I was so fed up with myself, a year rolled around and I was like, this is stupid. And I just came up with a stupid name.

Jason: What did you end up with?

Caroline: Clumsy, Crafty, Happy.

Jason: Dot Blogspot?

Caroline: Dot Blogspot.com. And guess what? That got my entire online business career started because I just finally said, "I'm not going to wait for it to be perfect anymore." All right. Moving on to number eight: "You are the one in control of your life and business. So don't make it shitty."

Jason: Don't make it shitty.

Caroline: Don't make it shitty. If you are someone who has your own business. And basically this all boils down to control what you can control. And don't put yourself in a position to be your own shitty boss.

Jason: This is something that we run into all the time where we like, pile all this work on ourselves. And I think we've gotten a lot better at it over the years. And I give you a lot of credit for helping us build systems and processes, but we pile on all this stuff and we're just like, "Who is doing this stuff?"

Caroline: "Who did this?"

Jason: You like, look around. You're like, "Who is the asshole that is around here giving me all this work?"

Caroline: "This is too much work for one person."

Jason: And then you realize as you look at all the walls, they're all mirrors. You're like, "Shit, shit, shit, it's only me." And I think this is something again, it's like a lot of these pieces of advice. No one can give this to you, and you can know exactly how to fix this other than you just have to understand over and over again, keep telling yourself that, "Hey, don't be a shitty boss to yourself."

Caroline: Set your own boundaries to yourself.

Jason: Exactly.

Caroline: If you're tired of working till midnight...

Jason: Stop working till midnight.

Caroline: Tell yourself that you need to quit working at 6PM. You have to be your own advocate. And sometimes there's like two forces within your body. It's like the worker and the boss. And sometimes you have to stand up to your inner boss and be like, "This is a shitty work environment."

Jason: Exactly. Yeah.

Caroline: And, "We're going to make some changes around here."

Jason: 100%

Caroline: "We're not going to do calls on Monday mornings when I hate it. We're not going to work on the weekends when I'd rather be at my kids baseball game than doing it."

Jason: Those actually are the simple things of not being a shitty boss and not being shitty to yourself that matter. So if you don't want to take calls on Mondays, don't take calls on Mondays. If you don't want to do client emails on Fridays, tell your clients you're not available on Fridays. Like you set the tone for your business. Make it work for you, and pick the things that you want to make it a better work environment for you.

Caroline: Okay, that's a good one. Number nine, we have two left. This is for you, "Try and have some fun."

Jason: Very much coming off of that last one on not being a shitty boss. The other part of that, and we've run into this many times where we have all this stuff that we're trying to do and we'll be in this stressful thing because we're feeling overwhelmed and all this stuff. And I'll just throw a journal on the floor and I'm like, "This is not fun."

Caroline: Yes.

Jason: And it just comes back to this idea of like, listen, we get it. Work is not always going to be fun. Working for your clients, getting things done for them creating products for your customers, sending out the email, posting the social media content, like all the stuff, it's not always going to be fun. Obviously. Let's not even talk about taxes and all that crap. But there are a lot of opportunities where you can sit back and go, "But also, how can I make this fun?" Maybe my content creation day is like I listen to Whitney Houston's best hits for an hour, then I get into content creation for 3 hours and that's my content creation day. What I'm not going to do is get up at 6AM, slog through my emails, then sit down and try and rack my brain for ideas. It's like you're setting yourself up for failure. A, you're being a shitty boss, and then B, is that fun? Are you actually having fun? Have fun doing these things.

Caroline: Yeah. And I think the bigger concept there also is just about, What is It All For? Not to be meta about the podcast, but it's really about enjoying the journey. And so you have to take a step back every so often and go, "In pursuit of whatever my goals are, am I doing this in a way that I am enjoying? Am I enjoying this?" And so that's really what you're talking about is every so often we get in these little ruts where we have to take a step back and go, "Are we enjoying this? Because it doesn't feel like we are."

Jason: Yeah. And perfect example is this podcast. We know that we could make this podcast so much more, maybe shareable and story driven and a whole high concept business podcast that a lot more people would find. But you know what? It probably wouldn't be fun. You know what's fun? Sitting with our legs.

Caroline: Just chit chatting.

Jason: Inter-tangled on a couch.

Caroline: And getting some foot face.

Jason: And just like shooting the shit. How are my feet smelling? Not great.

Caroline: You've kind of moved them and I appreciate you.

Jason: Yeah. All right. What's our last thing here to wrap it up?

Caroline: Over four years of having Wandering Aimfully, I just have to say, I have just learned and it's super simple, but just actually care about your customers. Like really actually care about the people who you're serving and that will continue to fuel you for years to come. I think even in moments where either I'm less motivated or I fall out of love with the business because that happens, all I have to do is just remind myself of actual real people who we've helped. And I read some of their messages and I remind myself that even if some of the things are like old hat to me, somebody in WAIM just came across this for the first time and it changed their perspective. And I'm instantly re-energized. And I just think it's because I actually care that people's lives are being impacted and also just they're the reason that WAIM is and continues to be successful because we never have had, like, super a ton of marketing. But it's like people. It's word of mouth marketing. It's people just enjoying the experience. That's what fuels the business. And so that care does go a long way. I mean, that's not the reason to do it, but it is just a result of caring about people.

Jason: I would say a lot of people could look at their businesses and go, "The number one driver of all revenue for my business is Facebook ads, is Instagram marketing, is B2B networking or whatever." For us, the number one driver is word of mouth. It always has been. It always will be. We also love word of mouth because it's not an algorithm. It's not going to change. You know what we do? We care about people. Those people understand that we care about them. And then when we ask them to do something, typically they're ready to raise their hand to do it for us in some way, or they raise their hand without us even asking. And it helps us grow our businesses. And that doesn't happen through some slick strategy of the psychology of people and how we're training them to do things for us. No, it's us caring. It's someone saying, like, "Hey, I can't make my monthly payment this month because I'm going through a tough divorce and it really sucks." And it's us going, "You know what? You're done paying WAIM." We just did this for someone a couple of weeks ago. It's fine. You owe us $200 more. It doesn't matter. I would rather you not have to worry about your divorce. That sucks. That's so hard to go through. And it's just being a human. And I think for so many people, the humanity of business gets lost when profit is so much the driver of what you're doing every single day. And why is it the driver? Because that's all we see. When you hop on your Instagram feed and you start clicking through stories, it's people telling you how to 10X this and 5X that. But you know what none of those X's relate to?

Caroline: People.

Jason: Being better to people. And that actually pays off. And we've seen it pay off over and over and over again. And again, it's not some strategy. We don't think about it that way. We just think about in the moment, "Oh, this person needs just like a high five in their life. Let's give that to them in some way in whatever way that looks like." So I think those are those things that are the unscalable business things that we've done. And thankfully, they've come to us naturally. Like, no one said to tell them this, but maybe you're listening this and you're like, "Oh, you know what? I have really been stuck in the Facebook ads world or the this or that. And I haven't just emailed 20 of my customers individually just to say, like, "Hey, how are you doing?" I just started a conversation with people to see what's going on in their lives because that stuff doesn't scale, but it does go a long way.

Caroline: Definitely. Those are ten lessons. It was five lessons from Jason's 40 years. It was five lessons from four years of WAIM. It's a lot of math, honestly.

Jason: I want to give one more bonus lesson.

Caroline: Okay, you've got three minutes.

Jason: Eat cinnamon rolls.

Caroline: Oh, wow. Yeah, yeah, yeah.

Jason: You know what I mean? Whatever type...

Caroline: Let's change it. Find your cinnamon roll.

Jason: Oh, wow. Nice.

Caroline: Because it's, remember, Embracing You. For those of you who are along with our Embracing You journey.

Jason: Oh, yeah. That's true.

Caroline: Not everybody is a cinnamon roll gal or girl or non-binary person.

Jason: They're wrong, for sure. Like the fact that they're not choosing cinnamon rolls. They are incorrect. But I will say that if a cinnamon roll is not your favorite, I guess you could pick some other pastry if you want and enjoy it. You know what I mean? Find your thing.

Caroline: Find your thing that brings you joy.

Jason: Share it. Talk about it. This is not actually an extra tip. It's just me being silly.

Caroline: It is a little bit of a tip, though.

Jason: Hey, I wanted to say just a big thank you to you, and I'm so glad we're on this journey together. That's you listening. But I also pointed directly and made eye contact with Carol.

Caroline: Who are you talking to?

Jason: It's for you.

Caroline: Are you talking to the person listening or me?

Jason: Right now, you have the confused face.

Caroline: Is it me?

Jason: It's for you.

Caroline: Oh, that's sweet.

Jason: The listener.

Caroline: Jason! Stop it.

Jason: Yeah. It's been great to be on this journey with you.

Caroline: Also, instead of saying, like, this trip, you said journey, which can be like anything.

Jason: Exactly.

Caroline: Are you talking to me?

Jason: I'm always talking to you.

Caroline: The listener.

Jason: Everybody. All right. We thank you for listening, so much. That's them who are on the other end. Carol listens to me about half the time throughout the day and about half my life so far.

Caroline: It's true.

Jason: And here's to another 40 years.

Caroline: Yeah. Happy birthday.

Jason: Oh, thanks so much. It was like a month ago, so I really appreciated that. Thanks for making me feel special.

Caroline: Aw, you're special. You're my favorite person in the whole world, and you know that.

Jason: Even though I'm now an old man emoji.

Caroline: I like you better.

Jason: We really need to get a new cinnamon roll emoji. I'm so tired...

Caroline: Every year that goes by, you get better.

Jason: Of not having a cinnamon roll emoji. What Senator do I have to call to do this? Is that a thing? Is there a cinnamon roll person who could take care of that?

Caroline: A Senator roll?

Jason: Nice. Great way to end it. All right, that's it, everybody. You're fantastic. We love your faces. We hope you're glad to have us back in your ears.

Caroline: We're glad to be in your ears.

Jason: We'll be back next week with another episode. Give them the cliffhanger of the travel. Tell them about it.

Caroline: We went to an airport, and you'll never guess what we saw.

Jason: Nice.

Caroline: Airplanes.

Jason: It was a dog in a suitcase. Okay, bye.