241 - 5 signs it's time to pivot your business
How do you really know when it’s time to move on from an offer you’ve built your business around? In this episode, we’re sharing the four indicators that helped us make the decision to wind down WAIM Unlimited—insights we hope will help you reflect on your own path.
We dive into:
- What it feels like to fall out of love with your offer (and why that’s not a failure)
- When your results no longer match your effort—and why that’s worth paying attention to
- How a strong pull toward something new can be a signal, not just a distraction
- Why shifting life circumstances (hello, parenthood!) require more sustainable, aligned business models
If you’ve been feeling stuck, disconnected, or daydreaming about a new chapter, this one’s for you. We’ll help you ask the questions that matter and maybe, just maybe, give you the nudge to take that leap.
💬 If you have questions you want to ask us about our decision to retire WAIM Unlimited, send them through our contact page.
***
😏 If you’ve been thinking about using Teachery to build your online courses, take advantage of our Lifetime Deal at https://teachery.com/limited-time
💌 Want practical tips to help you grow your creator business-without burning out? Join our Growing Steady newsletter and every Monday you'll get 3 actionable tips for growing a Calm Business—one that is predictable, profitable, and peaceful: https://wanderingaimfully.com/newsletter
[0:00:06] Caroline: Welcome to Growing Steady, the show where we help online creators like you build a calm business, one that's predictable, profitable, and peaceful. We're your hosts, Jason and Caroline Zook, and we run Wandering Aimfully, an un-boring business coaching program, and Teachery, an online course platform for designers. Join us each week as we help you reach your business goals without sacrificing your well-being in the process. Slow and steady is the way we do things around here, baby.
[0:00:30] Jason: All right, cinnamon rollers, that's you. Let's get into the show. Here we are, back on the podcast. 241 episodes of this podcast.
[0:00:44] Caroline: Of this podcast.
[0:00:45] Jason: Wow.
[0:00:45] Caroline: And that's not even the other podcasts we've done.
[0:00:48] Jason: It's pretty crazy. I was watching, I can't remember what podcast it was, but they were at like episode 940 something.
[0:00:53] Caroline: Yeah.
[0:00:53] Jason: And I was like, wow, that's a lot of podcast episodes.
[0:00:57] Caroline: Yeah.
[0:00:58] Jason: We have been in the podcast era enough for someone to have like over a thousand podcast... Obviously, be like a daily show, but a weekly show. That's pretty incredible.
[0:01:06] Caroline: Very incredible.
[0:01:06] Jason: Also, what is that? It's like 52...
[0:01:12] Caroline: That's...
[0:01:12] Jason: 950 divided by 52. We should do some public math real quick. 18 years. If you did one a week.
[0:01:18] Caroline: That doesn't seem right. Yeah, but so it's more than one week.
[0:01:21] Jason: That would be like 20 years' worth of podcasting.
[0:01:23] Caroline: Not that they're having... I mean, at this point, they're might have been people who've been doing it for... Not 18 years, but...
[0:01:28] Jason: Yeah. Probably a rare few, but yeah.
[0:01:30] Caroline: ...15 years.
[0:01:31] Jason: But yeah, 15 years. I mean, we started podcasting 15 years ago, for sure. At least, I did.
[0:01:36] Caroline: Yeah.
[0:01:36] Jason: Yeah. Anyway, that was random. I don't have like a life pramble, but I have a fun fact pramble that I was given to via Instagram.
[0:01:46] Caroline: You love a fun fact. Share with us please.
[0:01:47] Jason: Love a fun fact. Love a fun fact. There's really nothing going on in the tennis world right now for this to be a timely thing. If the season had just kicked off and the Aussie Open was going on hey...
[0:01:57] Caroline: Tell people you like tennis. I don't know if they know that.
[0:01:59] Jason: I do. I like tennis. I worked my first job out of college was I was a graphic designer for the men's governing body of tennis, which is called the ATP.
[0:02:07] Caroline: Yes.
[0:02:07] Jason: So like the MBA or the MLB or like any of these governing bodies, their ATP is the one that runs tennis. I got a job as a designer. I knew nothing about tennis when I went in. In fact, during the job interview... This is our pramble, I guess. I had my portfolio, and I showed off my design work and whatever. And again, this is 2004, 2005. And they were like, "Oh, can you name five active tennis players?"
[0:02:34] Caroline: You had a pop quiz. Any research.
[0:02:35] Jason: I didn't think to do any research about tennis because, again...
[0:02:37] Caroline: You're like, they certainly they won't pop quiz.
[0:02:39] Jason: I'm a graphic designer.
[0:02:40] Caroline: Yeah.
[0:02:40] Jason: I don't need to know about tennis. I'm not...
[0:02:42] Caroline: I'm not. It's...
[0:02:42] Jason: I'm not a rules expert. I'm not...
[0:02:44] Caroline: You tell me what to design, and I'm going to design it.
[0:02:45] Jason: Exactly. I knew at the time, Andre Agassi. Again, 2005.
[0:02:50] Caroline: Was he actively playing at that time?
[0:02:51] Jason: He was winding his career down, for sure.
[0:02:53] Caroline: Okay. But he was still in the mix.
[0:02:54] Jason: He was still playing.
[0:02:55] Caroline: Okay.
[0:02:56] Jason: That was it.
[0:02:56] Caroline: Cool.
[0:02:57] Jason: I knew nobody else. And they were like, "What about Andy Roddick?"
[0:02:59] Caroline: That's a big one.
[0:03:00] Jason: He's one of the more well-known men players...
[0:03:02] Caroline: He's just a baby at that time, probably.
[0:03:03] Jason: ...out of America. Also, Roger Federer was just coming on the scene in his own. Rafael Nadal was just coming on the scene his own. These are two of the greatest tennis players of all time. Djokovic wasn't even in the conversation yet. So I was like, that's the best I can do. And I was like, "Can you guys name five graphic design tools?" Yeah.
[0:03:22] Caroline: That's such a Jason thing to do in an interview.
[0:03:23] Jason: Yeah. And I'm in an interview, and I remember...
[0:03:25] Caroline: Power move.
[0:03:26] Jason: ...my boss that I didn't know he's going to be my boss at the time. His name was Philippe. And I remember after that, he was like, "I just knew you were the right fit for the job." When he said that, like... And I was like, I mean, it's a fair question I thought.
[0:03:37] Caroline: Okay. Side note, whatever that quality is, I would like to figure out how to raise our child with a little bit of that. Just a little bit of like...
[0:03:47] Jason: A little bit of white male confidence.
[0:03:48] Caroline: No. A little bit of white male confidence. No, I just think...
[0:03:53] Jason: Isn't that moment, though?
[0:03:54] Caroline: It's less that. It's less the...
[0:03:55] Jason: Yeah.
[0:03:55] Caroline: It's less the audacity.
[0:03:56] Jason: Yeah.
[0:03:57] Caroline: And obviously, you got to feel out the respectfulness of the situation.
[0:04:00] Jason: Of course.
[0:04:00] Caroline: But it's less...
[0:04:01] Jason: It was a very jovial interview. Yeah.
[0:04:02] Caroline: Yeah, yeah, yeah. It's less the audacity, and it's more just like the curveball. It's like the not cowering to the power dynamic and being like, we're just two people here.
[0:04:11] Jason: Yeah. Exactly. Also, you asked me a question. I didn't know, so I'm going to ask you a question I know you don't know.
[0:04:14] Caroline: Yeah. I just think a little bit of healthy defiance like that is like a really good quality to have.
[0:04:20] Jason: Also, the fun fact that I wanted to share.
[0:04:22] Caroline: Yes.
[0:04:22] Jason: So players that were born in the 80s. So this is like your Federer's, your Nadal's, your Djokovic. They were all born in the 80s, as we were. We were children of the 80s.
[0:04:32] Caroline: We were children in the 80s.
[0:04:33] Jason: How many Grand Slam titles do you think those players have made up?
[0:04:38] Caroline: Only male players that were born in the 80s.
[0:04:40] Jason: Yes.
[0:04:41] Caroline: Grand Slam titles.
[0:04:42] Jason: Oh, yeah. Women were not included in this. I apologize. But also, Serena Williams was born in that time, so this would be part of that as well.
[0:04:48] Caroline: Okay. But we're not...
[0:04:49] Jason: We'll just go with male players.
[0:04:49] Caroline: We're not counting Serena?
[0:04:50] Jason: Yeah.
[0:04:50] Caroline: Okay. Grand Slam titles? 40.
[0:04:54] Jason: So it was four year... Yeah.
[0:04:55] Caroline: Yeah. 40.
[0:04:55] Jason: Okay. 60 plus.
[0:04:58] Caroline: Wow.
[0:04:58] Jason: I don't know what the exact number was.
[0:04:58] Caroline: The fact that I was even in the ballpark of the right sort of size of number is a miracle.
[0:05:03] Jason: How many Grand Slam titles have been won by players born in the 90s?
[0:05:08] Caroline: 13.
[0:05:09] Jason: 2.
[0:05:10] Caroline: What? What was happening in the 80s?
[0:05:13] Jason: Well, what happened in the 80s...
[0:05:14] Caroline: Well, the 90s, really.
[0:05:14] Jason: ...was the fact that those players were born, but players that came up being born in the 90s...
[0:05:20] Caroline: Yeah.
[0:05:20] Jason: ...that sport has been so dominant by those three players.
[0:05:23] Caroline: Right.
[0:05:24] Jason: Now, born in the 2000s...
[0:05:26] Caroline: Oh, I see what you're saying. So then the 90s players didn't have a chance.
[0:05:28] Jason: Never had a chance. Never had a chance.
[0:05:29] Caroline: So in the early 2000s, it was all the 80s players who were winning Grand Slams, not the 90s.
[0:05:33] Jason: Exactly. Exactly. And then even in the 2000s, the 80s players were still dominant. Like they're still incredibly good.
[0:05:40] Caroline: Nice.
[0:05:41] Jason: So players born in the 2000s, how many Slams?
[0:05:44] Caroline: Well, they're just so young.
[0:05:45] Jason: Exactly.
[0:05:47] Caroline: 10.
[0:05:47] Jason: Five.
[0:05:48] Caroline: Yeah. More than the 90s.
[0:05:49] Jason: Exactly.
[0:05:50] Caroline: Yeah, I knew that's we were heading.
[0:05:50] Jason: So it's very surprising. When I was listening to this, it blew my mind because as someone who, again, used to work in the tennis world and I watched these players come into their careers and be so dominant and then just continue to watch tennis after I left that world.
[0:06:04] Caroline: Fascinating.
[0:06:06] Jason: I thought that was a fun fact.
[0:06:07] Caroline: It is a fun fact.
[0:06:07] Jason: Even if you don't love tennis, it's just incredible to think about like an era of players...
[0:06:10] Caroline: I love stuff like that because I love the curiosity that it peaks of going like, what happened? Why?
[0:06:16] Jason: Yeah. Let me very quickly...
[0:06:17] Caroline: ...
[0:06:18] Jason: Let me very quickly, just extremely quickly while you talk about name...
[0:06:22] Caroline: I can't. Oh, don't do this.
[0:06:22] Jason: Name five active men's tennis players right now.
[0:06:24] Caroline: Five active men. Active, Jason?
[0:06:28] Jason: I'm going to see if we can find women.
[0:06:30] Caroline: Djokovic is still active. No? Yes, no?
[0:06:33] Jason: I think he's still active, but he's on the way out. Yeah.
[0:06:35] Caroline: Okay. Nadal, he's retired. Didn't he retire at the Olympics or something? And...
[0:06:42] Jason: Yeah, Nadal's retired.
[0:06:43] Caroline: Okay. Federer is retired.
[0:06:44] Jason: Federer is retired.
[0:06:45] Caroline: Okay. Those were words.
[0:06:46] Jason: You're not doing great.
[0:06:47] Caroline: Buddy.
[0:06:48] Jason: Okay.
[0:06:49] Caroline: Who's the...
[0:06:49] Jason: As I'm getting...
[0:06:50] Caroline: Wait, wait, I got it, I got it. Who's the British guy?
[0:06:52] Jason: Andy Murray?
[0:06:53] Caroline: Yeah.
[0:06:54] Jason: Yeah, he's retired.
[0:06:55] Caroline: Oh, no.
[0:06:56] Jason: Again, also born in the 80s, and yeah.
[0:06:58] Caroline: Who's the...
[0:06:59] Jason: Female tennis players born in the 80s who've won Grand Slam titles, you have a total of 35 as listed by my quick research here.
[0:07:05] Caroline: Okay.
[0:07:06] Jason: Which is incredible because Serena Williams makes up 23 of those.
[0:07:08] Caroline: Jeez Louise.
[0:07:09] Jason: Venus William makes up seven. So it's like just the Williams sisters make up 90% of that, which is incredible.
[0:07:14] Caroline: That is wild.
[0:07:15] Jason: So yeah, if you look at the total between the two sports, the two male and female versions of the sport, it's over 100 Slam titles...
[0:07:25] Caroline: Of the 80s.
[0:07:25] Jason: ...of the 80s. Players born the 80s. So like really that was like a golden era of tennis players. Anyway. That's that silly thing no one really asked for.
[0:07:33] Caroline: Hmm. Do you think that also, I wonder how many... I don't know how you'd measure this, but I wonder if just like less... Yeah. The question I'm trying to get to is people born in the 90s, they saw these dominant players, were they like, oh, I can be that. Or were some like, there's no use trying because they're just killing the game?
[0:07:55] Jason: Yeah. I mean, it's also... Yeah, it's a very interesting conundrum because you could argue that players born in the 90s and especially now in the 2000s, they have much better technology to become better.
[0:08:06] Caroline: Or they have much better technology to distract them. And they're not willing to put in the discipline to be out there and play...
[0:08:11] Jason: Well, and physically, I think those players are much more physically gifted. Like you see this in the NBA right now. There are so many seven-foot players that can play all positions. Like they're positionless players. They're incredibly agile and...
[0:08:24] Caroline: Because they are taught from the beginning that you need to be...
[0:08:26] Jason: How to move your body, you're training in a whole different way.
[0:08:29] Caroline: Well, yeah, it's just the natural optimization over time you get more strategic.
[0:08:32] Jason: But in that, what they might not be doing is what players born in the 80s where like you mentally have to tough through so much more because you don't have all the physical gifts.
[0:08:41] Caroline: Huh?
[0:08:42] Jason: A lot of people have argued, like Roger Federer is the perfect tennis player.
[0:08:45] Caroline: Huh?
[0:08:46] Jason: Nadal is not the perfect tennis player, but physically, he's more gifted than most tennis players. He creates more power from less than any other player.
[0:08:53] Caroline: I see. Okay.
[0:08:54] Jason: And then Djokovic is kind of like, he's just a weird anomaly of a human being. And the way his body can move and how quick he can be.
[0:09:01] Caroline: But how does that relate to them being better than the 90s kids?
[0:09:04] Jason: Well, I'm saying Nadal is the perfect embodiment of that. Like he's mentally just tougher than most players. Djokovic, mentally tougher than most players. Federer, I don't necessarily think it's the mental toughness. I think his game is just like he's the perfect tennis player.
[0:09:16] Caroline: Okay. He's the anomaly.
[0:09:17] Jason: Anyway, that's 10 minutes of tennis talk no one wanted on the podcast where we never talked about tennis before.
[0:09:21] Caroline: I have more thoughts. I also do wonder if there is a technology story there about the impact that suddenly you have more things to have as hobbies, you have computers, and things like that. It's like...
[0:09:36] Jason: There's less to do when you're born in the 80s.
[0:09:38] Caroline: When you're born in the 80s, it's like, oh, I'll pick up a sport and I'll be like an elite athlete.
[0:09:40] Jason: Yeah. All you do is play tennis.
[0:09:41] Caroline: Exactly.
[0:09:42] Jason: You're born in the 90s, you're like all I do is send dick pics on Snapchat.
[0:09:46] Caroline: Oh, God, I hope not.
[0:09:47] Jason: But they're other people's. They're not yours. You're just finding them online. It's like a curated account.
[0:09:50] Caroline: That's a federal offense.
[0:09:53] Jason: Well, that's open source. So it's like...
[0:09:54] Caroline: That's not.
[0:09:55] Jason: You know what Unsplash is?
[0:09:57] Caroline: Yeah. Okay.
[0:09:59] Jason: Yeah.
[0:10:00] Caroline: We need to move on. Okay.
[0:10:01] Jason: Okay. Yeah, let's move on. That's what you get with this podcast. Random tennis facts, a little bit of my history of...
[0:10:07] Caroline: I'm very sorry if you are listening to this with a small child. We do put the explicit on the episodes for a reason.
[0:10:14] Jason: It is. It is, yes. And you know that there are some language and things that pop up.
[0:10:18] Caroline: There's some landmines.
[0:10:19] Jason: Also, if your child right now is like, what's a dick pic? You just say it's pictures of people named Richard. That's all you're saying. Like I didn't say it was anything else.
[0:10:25] Caroline: No. What do we say?
[0:10:26] Jason: Also, I got to give credit to my friend, Matt D'Avella, that's where I first saw that joke embodied and he did a great job.
[0:10:31] Caroline: Wow. Way to give joke credit.
[0:10:32] Jason: Yeah. Remember when he did that on a video and like we died because it was like Dick Cheney and...
[0:10:36] Caroline: Oh, yeah.
[0:10:37] Jason: Yeah. It was really funny. Okay. Let's get into this episode because this is a follow up after last week's episode.
[0:10:43] Caroline: Yes.
[0:10:44] Jason: And going to be a little bit shorter this week just because we want to be respectful of your time and there's not as much to talk about in this part of it, but we did want to focus on the pivoting of it all.
[0:10:53] Caroline: Yeah. Because last episode we really focused on us, us, us. Like what are we doing to pivot? And I thought to myself, I always like to deliver value. And so, I wanted to do a follow up episode on maybe someone listened to last week's episode, and they got their wheels turning and they were like, oh, is it time for me to do take a big leap and pivot my business? And so, I think in this episode we want to explore what were the five main things? I said four, but I added one at the end. I don't know if you saw the notes.
[0:11:19] Jason: Nice.
[0:11:20] Caroline: But what are the five main indicators that we knew it was time to actually do this big drastic change with our offer structure and pivot. And in the hopes that it can give you some questions to ask yourself to see if maybe it's the right time for you.
[0:11:34] Jason: Yeah. Yeah. I think this is really helpful for a lot of people listening to this, who... Even if you've just been doing something for like a year, but you're just having that feeling where it's like it's frictionful to sit down and do the work. Like it's not frictionless.
[0:11:52] Caroline: Yeah. You're experiencing a level of resistance that is more than is usual for you.
[0:11:58] Jason: Right. Because just so everyone knows, to build a business and do anything online...
[0:12:02] Caroline: Yeah.
[0:12:03] Jason: ...you will experience resistance.
[0:12:04] Caroline: Of course.
[0:12:04] Jason: Even if you absolutely love it to death.
[0:12:05] Caroline: To do anything, in this day and age you'll experience resistance.
[0:12:07] Jason: There are certain parts of it that you're just not going to do. But that's just a part of doing business, y'all. And I think one of the things that we try to do is push that as far as possible. Because if you stop at the first sign of resistance, a lot of times you're stopping before you actually get to the good part.
[0:12:24] Caroline: Totally.
[0:12:24] Jason: And I think we all know that when you give something like three months of effort and you're even less than that, you're not really giving yourself a full try. There's a lot more that you need to experience.
[0:12:34] Caroline: So there's a balance here is what you're saying. Where it's like you don't just want to give up if you're experiencing any resistance at all. It's like business shouldn't be like completely frictionless. Like I don't think that's realistic. But there comes this moment where when something major feels... And the best way I can describe it is like out of alignment. Like where something just feels like I have been swimming upstream for so long now that I'm starting to wonder if I'm just like in the wrong stream.
[0:12:58] Jason: Yeah.
[0:13:00] Caroline: That's kind of the feeling that you have.
[0:13:01] Jason: For sure. Okay. So the first little note here, if you will, is that you've fallen out of love with the offer.
[0:13:07] Caroline: Yeah. This is the first indicator for you to look out for if... And maybe that means that it's time for a big pivot is, like Jason said, you've fallen out of love with the offer, the main offer that you're trying to sell. Your main program, your main digital product, your online course.
[0:13:22] Jason: The way you work with clients.
[0:13:24] Caroline: The way you work with clients. Like you're just no longer enthused in the way that you once were. Not in a way of like the honeymoon period is over because that's going to happen. But truly, like Jason said, like you're experiencing a level of resistance that is not normal.
[0:13:37] Jason: Yeah.
[0:13:38] Caroline: And we wrote down here that like parts that you used to love start to feel like you have to do them and not you get to do them.
[0:13:45] Jason: Yeah. And I think like as we talked about last week and I pointed out about the like the 70 plus number of months doing the same type of business that we have been doing.
[0:13:54] Caroline: Uh-huh.
[0:13:56] Jason: That it takes a toll. Like it's a long time to do anything. And so, it is very natural. Like in a relationship, you're only going to get five to six good years of loving.
[0:14:05] Caroline: Jason, how dare you?
[0:14:07] Jason: Before you just yet... You're looking for something new, something fresh.
[0:14:10] Caroline: You got to switch it up. It's like a seven-year itch or something.
[0:14:14] Jason: Exactly. But I do think there is something very important here to realize that, yeah. If you look back on it and you have really given something a good try and you've done things a bunch, like you wrote down the notes here. We've done 13 live launches of WAIM Unlimited with pretty much kind of like the same setup. And I would really argue only one of them has really been that different, and it was the live cohort one that we did last fall. Because that's the only one that like, it felt new to me and that we were going to do something after that was like...
[0:14:42] Caroline: Yeah, it's been largely the same configuration. I mean, it's been different things we highlight, different sales pages, a little changes to the pricing and like the payment options, whatever. But in general, it's been the same formula, which is, by the way, why we have a Calm Launch Formula. Is that anything that you can do for 13 times and have successful results? That's a repeatable formula and it makes your life so much easier. However, the balance of that and the caveat to that is you do come to this place where you go, man, I just am looking for a new set of challenges. And I think this very much is just the entrepreneurial mindset. Like if you're trying to create your own business, you're probably someone who loves that building from scratch feeling, and you arrive at this place in your business where predictability is great, but then you just start to feel like the passion is gone.
[0:15:38] Jason: Yeah. There was a clip going around I think is one of the Google founders or early investors, couldn't remember exactly who it was. Doesn't really matter for this the thing that he said, but I really appreciate it because I think we all know this intrinsically, but you don't necessarily put it into practice. And I think I mentioned this in last episode too, where he was like, "Every five years and now it's even getting shorter in that time span. Everything is different."
[0:16:03] Caroline: Yeah.
[0:16:03] Jason: So it's like if you're Google, it's like what we were in 2005 when we got started is so different than when we were in 2010, is so different than 2015, is so different than 2020 and 2025. And I think as smaller business owners, we tend to think like, oh, I'm going to create an Etsy store and I'm going to sell these beautiful art prints that I am creating and I'm going to do that for 20 years. But it's like what you don't realize is Etsy may not exist in five years.
[0:16:29] Caroline: Yeah.
[0:16:30] Jason: And I think that's not to scare you, but it is just, I think even for us and looking at WAIM Unlimited, it's like what we taught five years ago and the way we were thinking about online business has drastically shifted. But it's the first-time kind of in our lives where we really noticed that shift in the same business. I think it's very different when we look at like in 2010, when I was still doing IWearYourShirt stuff.
[0:16:52] Caroline: Well, because we were basically changing and pivoting every two years or so.
[0:16:54] Jason: Yeah. But it wasn't because we were sticking with the same business. It's because we were starting new businesses because they weren't viable, and they weren't working.
[0:17:01] Caroline: Exactly. This is the first thing that really had enough legs that we were able to run the clock to the point where we were like, okay, yeah, now we actually are sensing.
[0:17:09] Jason: Yeah. Which is just... Sorry to hog the mic here, but it is interesting as I'm working more on Teachery myself and the task that I'm working on right now is actually thinking through a new course editor interface and template to build courses. And it's actually making me really excited about Teachery. But I also don't know, like I'm finding this push and pull of but how long is this going to last? This investment of design time, development time, teaching people how to use this new way of building courses. Are we on the era out of this type of way of learning and through courses? Or is it still viable for another five to 10 years and it's just going to require technological pivots where AI is going to have to be involved at some point?
[0:17:50] Caroline: Yeah. And I think there's no right answer to that question. Because none of us can predict the future, right? So you do have to go with your gut, which is what this point is all about is recognizing in your gut, do you feel like you have lost the passion for your offer? Because I think it's really worth noting if you're... And this speaks to like the next point. So I don't want to jump ahead. But it's like...
[0:18:12] Jason: Oh, let's just jump.
[0:18:13] Caroline: If you're getting less results from selling an offer that you've been selling for a long time, don't discount the fact that it really might just be that you're tired of it. Because if you're falling out of love with the offer, it means you're promoting less. It means you're wanting to create content around it less. It means you're just less invested in the outcomes. And you and I would still say that we are so invested in our WAIMers and helping them and all this stuff, but it's like that can be true and we can recognize that we were getting to this place where, like trying to create coaching sessions, I started to realize like, oh, this is like dread is too strong of a word. It's not that, but it was like, oh, I wasn't looking forward. They used to be my favorite thing to do in our business because I love curriculums, I love teaching, I love educating, I love helping. It used to be my favorite thing. And I started being like, there we go again. Like I got to do that again. And it's like, I think that's when you really have to pay attention.
[0:19:10] Jason: Yeah. I think there's two things here when it comes to the results not reflecting the effort anymore. Number one is...
[0:19:15] Caroline: Wait, we didn't even really intro that. So in case you missed it, we did move on to indicator number two...
[0:19:21] Jason: Fantastic.
[0:19:21] Caroline: ...which is that the results don't reflect your effort that you're putting in anymore. And I alluded to the fact that that is related to number one, which is you might just have been falling out of love with your offer, which means you're not quite putting in that much effort. But if you feel like, in our case with our launches, the effort is largely the same and the results are waning.
[0:19:40] Jason: Exactly. So the thing I was going to say two things here that I think you should really take stock of. Number one, you need to be really honest with yourself. If you are doing launches or little periods of pushes to get new customers or clients, are you actually doing marketing?
[0:19:56] Caroline: Right.
[0:19:57] Jason: Or are you just staying stuck in the talking about the making of the thing, but you're not actually ever really promoting like the problem that it solves and the benefits of it and those things? So it's like what I see often through some of our WAIM members is they go, "Oh, no one wanted to buy my thing." And it's like, "I don't think anybody wants this anymore. Like someone bought it in my first launch." And you look at, you go, "Okay. Well, what did you do marketing-wise?" "Oh, well, I just kind of like I emailed my list right before for like a week or two, saying that it was coming." Not talking about the problem. "And then I did post on Instagram one time." It's like you didn't give a fair shake at marketing to help promote the launch of then thing.
[0:20:36] Caroline: Right. Which is the other side, the flip side of this, which is you have to ask yourself, okay, am I actually putting in effort?
[0:20:43] Jason: That's what I'm saying. So it's like the part one of this is the results matter on the reflection of how much effort you actually put in. And if you're honest with yourself and you go, I actually didn't put in that much effort, then I can't trust these results to say that my offer is not worth buying.
[0:20:59] Caroline: Exactly. So maybe I shouldn't pivot and maybe I should just be honest.
[0:21:01] Jason: Exactly.
[0:21:02] Caroline: And I should, the next launch or the next time that I'm promoting this, use those insights and put in the more effort. But then it's like...
[0:21:11] Jason: The other side of...
[0:21:12] Caroline: And then it's like see step number one, which is did you not put in that effort because you are truly just misaligned with wanting to create this anymore?
[0:21:17] Jason: Right. And then the other thing I want to talk about in this one is you might be in the place where you're like us, where you are putting in the same amount of marketing effort for the most part, but you are not seeing the results that you saw before. And that is an indicator that human behavior has changed. And what people are willing to pay for has changed.
[0:21:38] Caroline: Exactly. And so, for us, in our case it's not like we saw for... So the past three launches, we've seen this decline in sales, right? And it's not just that we saw one less launch and thought we'll pivot our whole business, right? We gave it three different launches to really see. And even some of them had less effort than others, which we were honest about in the launch recap, if you're interested in that. But we've done low lift launches before and the results were much better. And so, what that indicates to us is yes, there is just a mismatch with this offer now. Like we have outgrown the offer, not to mention the fact that we're ready for something new.
[0:22:17] Jason: Yeah.
[0:22:17] Caroline: But we could just see that the results are waning. It is headed in a direction where the marketing efforts are no longer sustainable. And then we ask ourselves, okay, well, could we still use the same offer, not change a thing about it, but change our marketing strategy? And the question that we then ask ourselves is, do we want to do that? It's like, are we still excited to promote this thing? Again, it all goes back to number one. The answer for us was no. And it was like, Jason and I often talk about this metaphor of climbing a hill of sand versus climbing a hill of concrete. Which one of those activities would you rather do? Anyone who has tried to walk in sand knows it's just, it makes everything harder.
[0:22:56] Jason: Yeah.
[0:22:56] Caroline: And so, I always think of that metaphor when I think of is my offer right? Because if your offer is wrong, you can still sell it. You can still climb a mountain of sand, but everything's harder.
[0:23:09] Jason: Yeah.
[0:23:10] Caroline: Versus a mountain of concrete is like your foundation is solid.
[0:23:13] Jason: Yeah.
[0:23:14] Caroline: And this offer is just, you're excited about it and it's well-tailored to your audience. And in this online industry climate, it's highly specific. It's outcome based. It's all these things. That's what a offer looks like that is going to be a mountain of concrete and not of sand. And I just felt like we got to this place where it's like WAIM Unlimited is a mountain of sand.
[0:23:34] Jason: Yeah. And it's still a great and helpful community, and online business resource to help people get where they want to go and help them build the predictability, profitability, and peacefulness in their business. But it has become so difficult for us to be able to like hone in on the exact thing and make it easier for ourselves as opposed to saying like, this is how you make social content using Canva by this course. It's just so simple. It's so direct. Like you know exactly what you want to do.
[0:24:04] Caroline: Totally.
[0:24:04] Jason: All right. Let's move on to indicator three. You feel a strong pull toward something new. And this is where all of our multi-passionates are our friends who get really excited by new shiny ideas. You have to be very careful here because we are two people who have unlimited ideas, and we get very excited about a lot of them. But you have to be very discerning, and you have to be very...
[0:24:34] Caroline: Disciplined?
[0:24:34] Jason: Disciplined. You need to be an adult. You need to put your big adult pants on. And you need to say, am I jumping to a new thing too early? And that I didn't give the existing thing that I've been putting effort and time into the chance to actually succeed.
[0:24:49] Caroline: Yeah.
[0:24:49] Jason: And I think that it's very easy to get lost in the shiny excitement of a new thing. And I think for a lot of people listening to this podcast, you're a lot like us. You love building. You could spend all of your time building, but having to do marketing and having to do sales is like the most frictionful thing you feel in your life as a business owner. But unfortunately, it is a very important part. And we've talked about this before, like for a lot of us, it's like 90% building, 10% marketing and sales, but it should be 50% building, 50% marketing and sales.
[0:25:22] Caroline: Definitely. And I think for us, our approach to this, since we are people who do get excited about ideas, love building things. The way that we approach this is we give ourselves like a tinker period where we allow ourselves...
[0:25:34] Jason: Different than a tinkle period.
[0:25:35] Caroline: It's different than a tinkle period. Okay. A tinker period where we give ourselves this amount of time where we let ourselves indulge those ideas. Like we brainstorm, we like work on stuff.
[0:25:46] Jason: Yeah, we had a... Not last summer, but two summers ago. No, maybe it was last summer. Whenever we had the idea for income Iceberg. You remember this?
[0:25:53] Caroline: Yeah, this was two summers ago.
[0:25:55] Jason: We literally were like we were down like a three-week rabbit hole of thinking of this like new like app or thing or whatever. And we just were like, let's just play. Let's be in the tinkle period. That's all I can think about it now.
[0:26:07] Caroline: Okay. Well, now it's a tinkle period, so I don't know what to tell you.
[0:26:12]
Jason: But let's not do anything.
[0:26:13] Caroline: Let's not do anything.
[0:26:14] Jason: Let's not build anything. Let's not put anything out. Let's just keep talking about it and like see what happens.
[0:26:17] Caroline: Like really do the thought experiment of, okay, but when I have this idea, what does it really mean? What really is it? We're brainstorming, we're talking, we're fleshing it out in our minds and then we're giving it time.
[0:26:30] Jason: Yes.
[0:26:30] Caroline: Because the time is where you start to see is the luster wearing off. Your brain's going to start to chew on it in like it's a background task mode where you're in the shower and suddenly you're thinking about that idea. You're brushing your teeth, you're thinking about that idea. And what that's going to do is it's either going to, A, show you some maybe pitfalls you hadn't thought of. It's going to start to make the idea more real where you can really evaluate is this something I'm interested in? Or you're going to stop thinking about it, you're going to lose interest in it and you're going to go, oh, I was never that excited to begin with. But I really think that the tinkle period is really important.
[0:27:06] Jason: Yeah. And I think for us as we've been talking about, we are just so excited by these no code AI building tools, like Lovable is the one we've talked about a ton, and now there are even more of them popping up that are getting popular. But it's the first time in a while where that tinkle period has gone from three weeks on a thing to there's not a day that goes by that I wish I had an hour that I could play in Lovable.
[0:27:31] Caroline: Exactly.
[0:27:31] Jason: And it's every single day I'm fighting the urge to do that because I need to do all the actual work that's making us money, and it's helping our customers. And that, I know is the feeling I should be having after an extended period of time. Like we only started using Lovable in November of last year.
[0:27:47] Caroline: Yeah.
[0:27:47] Jason: I started using it first, and then you got really into it in December. And we both have since then, continued to want to work on it.
[0:27:56] Caroline: Yeah.
[0:27:56] Jason: And that's why, for us, this pivot in 2026 that we're thinking about is building apps using Lovable and actually diving in on this idea, because it has stuck with us in an every day since that beginning honeymoon period. We still want to be in this relationship together with it.
[0:28:11] Caroline: Exactly. And it's like, isn't that what you want to feel about your business? Going back to your original point, you're not going to love every activity you do in your business. It's not going to be super passionate about every single aspect of it. It's not going to be frictionless every aspect of it. But aren't we all searching for that thing that you wake up and you spring out of bed in the morning, and you go, oh, my God, I can't wait to fire up my laptop and work on this thing. And this is the first thing that you and I have felt in a long time where we're super excited to work on it.
[0:28:42] Jason: And I do think there are different... There are varying levels of need to be energized by your business for different people.
[0:28:49] Caroline: Yes.
[0:28:49] Jason: There are some people who just are like, I just want the predictability of income. And so, I want to wake up and know that I'm either working for another company or another person, and I'm just totally fine to do that work because I don't have to solve every problem to run this business. And that's okay.
[0:29:02] Caroline: Totally. The predictability is really what they love.
[0:29:05] Jason: Is more important. And then there is a whole other group of people, which I think is us, where it's like, we have enough talent and skill and ideas that what I don't want to do is get up and waste the precious time that we have on things that aren't exciting and that aren't interesting. And I would say for the first four years of running Wandering Aimfully, that's how we felt every day.
[0:29:26] Caroline: Totally.
[0:29:26] Jason: We're like, oh, this is so fun. Like we get to help everyone navigate the online business space in a way that we're navigating it and we're just trying to do it differently. We're trying not to hustle. We're trying not to take on every marketing tactic or trend that pops up. We're ignoring TikTok completely. Like can we still survive? And I think that you get to a certain place in doing that over time and you just realize like, okay, we did that for long enough. It is no longer energizing. It doesn't mean its crappy. Like actually, one of my favorite things that I do in the morning, and this has been this way for probably the past year, is I have my coffee, I do the morning routine, I watch YouTube or whatever. And then when I open my laptop and I start to work, I do all of the shitty tasks first. So it's like email just combing through that and not really replying anything, just cleaning it up. No one asked for my morning achievement, I'm sure...
[0:30:13] Caroline: I'm actually, I've never asked you this before, so this is really fascinating for me.
[0:30:16] Jason: It does change, but this is what it's been recently. Then I do Teachery customer support. Usually that's like the worst part of my day because inevitably there's one person who asked the most dumb question ever, and it's okay that they asked that question, but it just, after doing customer support for 10 years, I'm like, really? We're still asking this question? And then after that my dessert, my morning routine dessert is our Wandering Aimfully Slack.
[0:30:37] Caroline: Yeah.
[0:30:37] Jason: So it's like I look forward. I still look forward to what are people saying in there?
[0:30:41] Caroline: How can I help?
[0:30:41] Jason: What are they sharing? What are they working on? What has someone DMed me that they sound or whatever?
[0:30:44] Caroline: It's the best.
[0:30:46] Jason: And I think that to me is a good signal of I am not unhappy in what we've built with Wandering Aimfully. And I do still look forward to some parts of it. But it's as we talked about last episode. What I don't look forward to is the monthly coaching session.
[0:30:59] Caroline: Yeah.
[0:31:00] Jason: I actually like the live interaction part of it.
[0:31:03] Caroline: But not the teaching aspect of it.
[0:31:04] Jason: But not the teaching part of It. Because I feel like what we are teaching is a little bit of like a dying dinosaur in the world of online business. And that's why we want to pivot to talking about Lovable. Because as much as we all resist or whatever when it comes to the idea of AI, I think we really are running in the direction of a business in five years is not going to be created by going online and buying a website domain and whatever. It is going to be typing into a chat or talking into a chat that you want to speak something into existence. And there's enough technology that it just exists.
[0:31:38] Caroline: Yeah. And to be clear, we're not saying that businesses without AI won't exist. Like there's definitely an opportunity for that. And if someone came along and they were like, we want to be the coaching program for businesses who don't want to use AI, I definitely think that there's a market for that.
[0:31:53] Jason: Sure. But it is a shrinking market.
[0:31:56] Caroline: It is a shrinking market. And the question is, do we want to be those people? And as I've said before, but how excited I am about AI, it would be disingenuous and hypocritical for me to try to be that person instead of the authentic person that I am, which is, oh, my gosh, we are on the precipice of this moment where ideas, people have never been more empowered to be able to create the things that they want to exist in the world. And how exciting is that? And again, I'm not naive to the pitfalls and the downfalls and everything like that. It's not black and white. But yeah, again, you have to create the business that you feel authentically represents who you are and the stuff you want to put out into the world and what excites you. And that's what excites us. So that is the third indicator is that you feel this strong pull towards something new. And again, we're going to take you along the journey on... We don't know exactly how that looks or how we're monetizing it or any of those things, but we're going to figure it out and you're going to come along for the ride. And that's why we have a podcast. And number four, an indicator that it might be time to pivot is your life circumstances are shifting in a big way. The biggest way that our life circumstances are shifting is that we are going to be a family of three.
[0:33:03] Jason: We are. And yeah, I think this one is the easiest indicator to take note of. Because there are so many of you listening to this, who you have health challenges or your family dynamic is changing in some way, or there's some type of medical emergency that you now have to take on the financial burden of. And you're kind of like playing in business is not going to serve you anymore because you actually need more predictable income. So you have to figure out something.
[0:33:26] Caroline: You have to make different decisions based on different circumstances.
[0:33:28] Jason: Exactly. And I think that as we have looked at it, there's not a lot that we're tied to when it comes to Wandering Aimfully as a business, like things that we have to do every single day or the business crumbles apart. But I will say that the idea of having a kid running around our house and wanting to play with them for hours in the day and like figuring out how to enrich their lives and be a part of those really fun formative years early on, do I want to also be thinking about, oh, I should go check Slack and make sure no one's asked any questions or whatever. And I totally get like, yeah, Slack could... You could just take longer for me to reply. But also, I want one less thing in my brain that I have to think about in my daily routine as a business owner. And so, I think when you think about the circumstances shifting, it's also a little bit about like, where do you spend your time every day? And when those circumstances shift, are you just ready for some things to be left behind that give you a lot more flexibility and freedom? So that you are in more in control of like, oh, the way my business runs, I've set up a bunch of systems, I batch a bunch of content. I do one day a week replying to certain things. I do another day a week where I reply to other things. It's less of like I have to do it at a timely and more of like, I get to do it in a timeframe that works best for me.
[0:34:42] Caroline: Yeah, for sure. I just think any big life shift, it's a moment to reevaluate and go, how are my needs going to change?
[0:34:50] Jason: Yeah.
[0:34:52] Caroline: How are the constraints on my time going to change? How are the constraints on my energy going to change? And is the way that I'm operating currently going to fit into those new changes? Or do I need to shift some things? And I think also there's something very clarifying about parenthood, specifically becoming a parent. I think I've said this before, but knowing based on other people's experiences that I am those first few years are so precious, and that I'm going to want to spend my time with our kid, means I also know myself well enough to know that I believe that I'll be the type of mom who also needs that work outlet. Because work is almost like... I heard this on a podcast this morning. I was like, oh, that resonates for me. Like, work in a interesting way is almost an act of self-care for me in some ways, because it's where my creativity thrives. Yes, I have my art, which is like a whole different thing. But work is where I love seeing my ideas come to life. And that makes me feel like an individual person apart from being a mother. And so, I want to try to maintain some level of blended identity, right? I don't think it exists in these hardcore buckets. But for me personally, I want to be able to hold the complexity of Caroline the person, Caroline the mother, Caroline the business owner. I just, I want that all in there. And so, I know that I'm going to want to work on stuff, but I also know I'm going to have this incredible pull to want to spend time with our kid. And so, if I am going to spend time on work, it better be on things that I am super passionate about and really want to spend that time. Because I'm choosing, I'm trading off that time for spending time with our kid.
[0:36:31] Jason: Yeah. And we're trying to do that now. Trying to make that decision now. Yeah.
[0:36:34] Caroline: Exactly. So I'm trying to... Exactly. That's what I mean about it being very clarifying because you go, okay, what do I want to spend my time on? And that's what we're trying to figure out.
[0:36:43] Jason: Yeah. All right. Getting into the final indicator here, the fear of the unknown isn't as great as the fear of staying stuck.
[0:36:51] Caroline: This is the last, to me, moment of asking yourself if it's time for a pivot where you just go, you know what? I don't actually know if this pivot is going to be the "right move", but the way that I'm feeling right now in my business is that it feels worse to stay stuck in the current position than it does to step into the unknown. And I think if that's true for you, if it feels worse to stay where you are than it does to change things up, if that prospect and that fear of what might come isn't enough to scare you away, then I think that's probably a good indicator that that pain of doing things the way that you've always done them is just, it's run its course.
[0:37:29] Jason: Yeah. And I think that in this one, you don't have to completely undo an entire business or quit an entire business without any other plan of attack, right? I think the idea is for us, we don't know if we're going to be able to build apps that people want to buy using Lovable. However, what we do have a history of is I've been a part of building small apps that people have purchased both as customers and as buying the app from me. And there's not a lot of difference in building the app with Lovable. It's just that you remove a developer from the equation, and we can do it ourselves. And so, what I'm saying is, if you're in this position where you're afraid of what the next move might be, but you do have some history or you do see some examples of people doing things, it lessens the fear because you can say, oh, this isn't as scary. I can see that there's a path forward here, and maybe I can even test that path a little bit before I completely stop working on whatever I'm working on.
[0:38:30] Caroline: And I think it's like, you don't know what's going to happen. So it's like, do you trust yourself to figure it out?
[0:38:34] Jason: Yeah.
[0:38:35] Caroline: We have no idea if this building apps, things like that will... We know we're excited about it, but will it actually make any money? We have no idea. But I do trust our ability to continue to pivot if it doesn't work. Like if it's not making money, if people are like, we don't want this. We have so much experience with building digital products, coaching, building membership communities, like designing. Like we have so many skills and so many things that we've done that I just have no qualms about the fact that we'll figure it out. And that's the type of confidence that you only gain from actually taking big leaps like this over and over again where you can build that confidence, but...
[0:39:16] Jason: It's also, you build that confidence in honing skills.
[0:39:19] Caroline: Yeah.
[0:39:20] Jason: So I think the reality is, and we've talked about this on multiple episodes, I really believe we're in an era right now. Maybe we need to do a whole episode on this where like, soft skills are harder to sell, hard skills are easier to sell. And maybe it's always been that way, but it's definitely feeling that way right now where people are like, I want you to solve my problem with a thing immediately. I'm not looking to like necessarily join like a six-month program where I'm going through a huge life change. Yes, there are people who are selling that, but I just think we're seeing a big decline in people being willing to just pay for more nebulous results. And so, I think if you're listening to this, like we've said this for years though, if you don't have any skills that you can fall back on, there's never been a better time to hone those skills, to become a Canva expert, to become a CapCut video editor, to become a Framer website builder. Like, these things are skills that will always be worth something to someone.
[0:40:15] Caroline: Because they take time to hone.
[0:40:16] Jason: Because they take time to hone. And...
[0:40:16] Caroline: And you can accelerate that for someone.
[0:40:18] Jason: Exactly. And I'm not saying that like being a compassionate coach for emotional entrepreneurs isn't valuable, but I'm just saying it is a much harder thing to sell when times get tough, and you need to scrounge some money together.
[0:40:32] Caroline: Totally.
[0:40:32] Jason: And so, yeah, I just think, as we look at making a pivot, if you're someone listening to this and you've only ever focused on the soft skills, I'm not saying that you need to abandon those, but I'm saying it might be a good time to lean into something where you're like, you know what? I really do love making social media graphics on Canva. Just an example. But like great. So maybe get really good at that so that you have a separate skill that you can lean back on if things don't go so well. And that might lead itself to be something where, again, like I was saying, you may not jump out of bed to work on that every single day, but you might also be the person who's like, I just need some financial stability for the next six months to two years. Let me just lean on this harder skill that people are willing to pay for. And then I can build up a buffer to then do some of the work that I want to do that I'm more energized about.
[0:41:20] Caroline: Totally. All right. The wrap up here. So here are some guiding questions as you just listened to all of that, to ask yourself to really figure out if a bigger pivot is right for you in this moment. And these relate back to all of our indicators. So number one, do I still love my main offer? Am I excited to promote it and create content around it? Number two, are my results, my sales numbers, my opt-in numbers declining from effort that used to bring better results? And if so, am I willing to do what it takes to improve this for this offer or not?
[0:41:53] Jason: Mm-hmm.
[0:41:55] Caroline: Number three, do I have something else that I feel a strong pull toward to do instead? Number four, are my life circumstances calling for something different, a different level of flexibility, a different level of time commitment? And does my life feel out of alignment with my business? And then finally, number five, am I more afraid of staying stuck than of stepping into the unknown? Do I trust myself that I'll figure it out? And does that kind of excite me a little bit?
[0:42:26] Jason: Yeah. And just like a final note here, I think a lot of times maybe it's looked down upon to pivot. Like you're afraid to tell people that you're going to change something because it makes you look...
[0:42:37] Caroline: Yeah. We should probably do a whole episode on like the fears of that.
[0:42:40] Jason: Yeah. I think there's a lot of...
[0:42:42] Caroline: Or how to do it.
[0:42:43] Jason: ...possible negative feelings and a lot of worry that people are going to see you as like flaky or whatever you can't stick with things. And I think it's more you should feel empowered to make these changes and you should feel good about them. I think the careful line to draw is that, again, you need to get past the tinkle period so that you're not always every three months saying you're doing a new thing.
[0:43:04] Caroline: Yes. Yes.
[0:43:05] Jason: Then you do look a little bit like your thing because you're not putting, again, back to the very beginning of this conversation, you have to give something more than three months of effort to see if it will work. Like it's just business requires those things. And so, I think that's just a very important part of this where there is a little bit of a fine line to walk in the always be pivoting or be pivoting consciously when you have put enough time and effort into doing things that they've had the time and effort to succeed.
[0:43:31] Caroline: Mm-hmm. And recognize when you are caught in a cycle of avoiding marketing by just creating new things all the time.
[0:43:39] Jason: Exactly. Yeah. All right. That's it for this episode. Hope you enjoyed it, and it helped you think about some things. And if nothing else, you now know a bunch of fun facts about tennis Grand Slam winners.
[0:43:48] Caroline: Right. That was the real value of the episode.
[0:43:50] Jason: That's really it. Okay. Bye.
[0:43:51] Caroline: Bye.