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158 – Learning The Same Lessons Over And Over (Is Okay!)

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

158 – Learning The Same Lessons Over And Over (Is Okay!)

Normally our over-ambition leads to a project taking longer to complete, but with only ONE day to complete our latest project, it spurred some additional thoughts about a lesson we continue to learn.
Jason ZookJason Zook Jason ZookJason Zook

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Jason Zook

Listen to our full episode on Learning The Same Lessons Over And Over (Is Okay!) below (with full transcript) or find our podcast by searching What is it all for? in your favorite podcast player.

Five Key Takeaways for Learning The Same Lessons Over And Over (Is Okay!)

Quick wrap-up on Behind the Build (see episode 156): We found building our new lead magnet and home page live quite fun! It taught us the power of constraints, but that said, we bumped into a lesson we continue to learn all the time which is biting off more than we can chew. That brings us to today’s topic!

1. We all have lessons we have to learn over and over again

What’s the lesson you have to keep learning? And what is the emotional experience of finding yourself in the same loop over and over? For us, it’s being too ambitious and overestimating what we can accomplish. We are never short on ideas and we love what we do, so we always are putting too much on our plates 😬😬😬.

Has there been a time recently in business, or maybe in life where you feel like, “Here I am again, right back here, learning this same damn lesson”? While that’s a thought that may come up, try changing it and asking yourself, “How can you reframe having to learn the same lesson all over again?” We like to think about this reframing as opportunities, not obstacles. Instead of seeing the bad in something you may have to do over, can it be a good thing?

2. What is the positive part of you that finds yourself here?

It’s not necessarily like you can never fix this part of your personality. It doesn’t necessarily need to be fixed as much as it’s just understanding you run into the same hurdles again and again. And so for us, we always have things we want to do, we always want to make them different or unique or better, and that leads to us thinking we can get more done than we can.

For you, maybe for example you love collaborating, but you constantly find yourself getting burned by those relationships or people letting you down? Rather than focusing on the negative outcome, take a moment to focus on the positive quality that gets you to that negative outcome. This can help you start from a place of self-acceptance, self-love, and self-compassion rather than self-criticism.

3. Get a little better each time

The goal is not to never be ambitious again or to never challenge ourselves again or establish a project that we don’t know if we can totally do. There’s tremendous value in challenging ourselves and pushing our limits. The goal is just to get a little bit better each time so you never get to that extreme place where the results are so terrible or feel so defeating.

The next time you encounter setbacks, ask yourself how you can avoid cranking it to twelve. How can you aim for an eleven and then a ten and then a nine until you get to a place where you might still encounter that problem but the consequences aren’t quite so dire? If you’re a person who runs into repeating the same lesson over and over again, it may be that you haven’t done that thing enough to actually understand the totality of what it takes to do it.

A lot of times we beat ourselves up for encountering the same lesson over and over, but the circumstances are different or the variables are different. We think this needs to be acknowledged so that you can give yourselves compassion to say maybe you have to learn this lesson in a new way this time, but basically, in this particular scenario, you were doing something new for the very first time.

4. Being mindful of the antidotes or bumpers and balancing traits

If you think about being ambitious, for example, that’s a good trait to have! But if you crank ambition up to twelve, it can bring a negative outcome if you don’t hit your goals (which may be impossible to hit given time constraints). What are the bumpers and the balancing traits that you need to be mindful of as you lean towards your most natural state, which in this example is being overly ambitious? For us, it’s patience or practicality. It’s a trait we have to be mindful of all the time, balancing that ambition with real facts, such as how much time we actually have to complete a project or task.

5. Digging into the deeper story BEHIND the behaviors you don’t want to repeat

Whenever you run into this repeating lesson loop, it can be helpful to ask yourself, “What is the deeper driving motivation or the root cause, the root belief, the story I’m telling myself about what is driving this behavior?”

We asked ourselves why we over-deliver and kept asking deeper questions. We want to let people see how we build things and how it’s different and unique. In digging into this deeper, you can start to trust in that quality more often. For example, instead of going so hard on the quantity of the things that we’re trying to do, can we trust that each one of the things that we are doing is un-boring and really rely on our individuality and attention to detail?

Personal growth should be rooted in loving yourself. You have a future version that you want to grow into and it’s a different posture than trying to run away from the person that you are now.

Show Notes for Episode 158: Learning The Same Lessons Over And Over (Is Okay!)

This week, we share how our Behind The Build LIVE project went. In that project we ran into a familiar friend: Being too ambitious and not being able to achieve what we’d set out to do. Now, normally our over-ambition just leads to a project taking longer to complete, but with only ONE day to complete our live project, it spurred some additional thoughts about a lesson we continue to learn over and over again.

We’re certain there’s a lesson in life or business that you continually run into. We hope in this episode, we share a few nuggets to help you EMBRACE learning the same lesson over and over and lessening the negative shameful thoughts that can come with it!

🌘✨ Also, do you agree, the phrase should be: Shoot for the stars and end up on the moon? C’mon, space engineers, let us know!

Links mentioned in the episode:

Noah Surf House:

Full Transcript of Episode 158: Learning The Same Lessons Over And Over (Is Okay!)

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

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 unboring business coaching program. Every week, we bring you advice and conversations to return you to your most intentional self and to help you examine every aspect of your life and business by asking, What is it all for? Thanks for listening. And now let’s get into the show.

Jason: And I’m here too. Hello there and welcome to…

Caroline: I wish you wouldn’t. He never told me.

Jason: You wish I would or wouldn’t?

Caroline: Can’t decide. He never tells me I was going to start it.

Jason: Did you get the tone of what I was singing there? I won’t remember you. That’s what. I don’t know.

Caroline: Oh, no, no. I don’t think you executed that properly.

Jason: The people at home, in their car, on their walks are like, Yeah.

Caroline: Yeah, nobody got that.

Jason: Stick to the online biz stuff.

Caroline: One of the true delights in our relationship and the fact that I found you as my life partner is that we are both, I would say, equally…

Jason: Horrible.

Caroline: Not talented in the voice department.

Jason: Terrible.

Caroline: And so one of my favorite activities is us trying to go back and forth, trying to hit a note. And it’s truly awful to listen to, but man, does it get us into giggle fits.

Jason: But also one of my favorite things to do is when you’ll be singing like, we’re in the car and be like, wow, babe, that was really good.

Caroline: Sorry.

Jason: Yeah.

Caroline: Just the sincerity that you deliver that always is just like the more sincere you are, the more I’m like, you asshole.

Jason: But I’m equally as bad.

Caroline: I know. That’s why it’s fine. I’m like, Oh, yeah, let’s see what you got.

Jason: What we do not have is singing.

Caroline: Yeah.

Jason: Hey, last week we did some stuff in Portugal. We’re going to give you that in the pramble. And I would say the highlight of the week for life things was our little valentine’s date dinner. We’re not big valentine’s celebrators.

Caroline: We never have been big valentine’s people. But since we moved to a new country, we’ve been trying to at least do one little date night a week, I would say. Kind of where we’re at, in case you’re curious, is like one little social engagement a week and one little just the two of us date. Aside from our Saturday movie nights, which is our sacred date night, which…

Jason: Never changes.

Caroline: Watching movies is not exactly like…

Jason: But you would think that moving to in a country, like, we wouldn’t have a social event every week, but actually they’ve been piling up.

Caroline: Well, yeah, just because we’re in the dating phase of…


Caroline: Adult Friend Finder first dates. And just like we’ll talk about that.

Jason: That has turned into just a porn site, right? Like…

Caroline: Adult friend finder?

Jason: I’m assuming. Right?

Caroline: I always thought it was made up. That’s a real thing?

Jason: Oh, no. Yeah, that’s a real thing. Yeah. Hundred percent.

Caroline: Every time you make that joke, I thought it was fake.

Jason: No, that’s a real website. I’m just not sure if it’s porn, so please don’t go there. I have no idea. I just know that it used to be a site for adults to find friends.

Caroline: Friends?

Jason: Friends.

Caroline: Which is fine. You do you.

Jason: So we did a valentine’s dinner and we found this hotel that’s right on the beach. It’s actually right around the corner from one of the first places that we had a bite to eat at here in the Silver Coast of Portugal when we were here in August of last year. And it was such a cool place.

Caroline: It was so neat, and the food was delicious. My favorite part about it is you all know, we just like all types of culinary experiences. We like the super casual, taco place that we found where you’re sitting at picnic benches, and we like Michelin star dinners where it’s like fine dining. We like it all for different reasons. But what I liked about this one is I feel like a valentine’s dinner, special dinner thing, could become very sort of like, high brow. And it was very approachable and casual. And I really liked that.

Jason: It was very mid brow.

Caroline: Mid brow.

Jason: I would say.

Caroline: It was very mid brow.

Jason: It wasn’t low brow.

Caroline: Flavors were high brow. High brow flavors. Mid brow presentation.

Jason: Yes. I’ll actually see if I can remember to add a link in the description for the show notes here so you can check out the place because just it’s a really cool place called Noah’s Surf House. And we would 100% go back. We were talking about them, like, let’s come back here, like, often because the prices were pretty good. The atmosphere was fantastic, and the food was super tasty.

Caroline: And people were very wonderfully kind.

Jason: Yeah. So that was a very enjoyable adventure. One that… it’s fine. It is enjoyable, but it’s me addressing one of the harder things that I have to do.

Caroline: Oh. Please.

Jason: That I just don’t like being bad at things.

Caroline: You didn’t really segue. I thought we were still talking about a restaurant.

Jason: No, we’ve moved on. I was going to get there. You just didn’t let me get there. I will remember. Sorry, everybody. Caroline’s under her blanket. Record from under there. The sounds going to be better.

Caroline: You went definitely a second and a half longer than I thought you would. So I had to get under my blanket. But good for you.

Jason: Oh, just a question for everybody who listens to this and likes to send us emails when we ask this, Are you the type of person when you’re watching something and it’s so embarrassing on, like, a show or a TV?

Caroline: The kids call that cringe, Jason.

Jason: It’s so cringe that you physically cringe? Are you that person? Or can you just watch and you’re fine? Caroline is the she will hide under her blanket.

Caroline: This, I think, is the most scientifically accurate measure of empathy that we have. I think that we should do some testing on this because, yeah, I physically feel like it’s happening to me.

Jason: You will almost leave the room when we’re watching something you’re like, I cannot deal with this.

Caroline: It’s hurting my heart.

Jason: And I’m just watching it and I’m like, it’s fine. Everything’s fine.

Caroline: And that’s because.

Jason: The kid’s embarrassed. But, like, it’s fine. It’ll be fine. It’s a movie. It’s made up.

Caroline: And that’s how all humans are different.

Jason: Anyway, let us know. Are you a person who hides under the blanket when things get weird or you just sit there and it’s fine?

Caroline: It’s not real.

Jason: Anyway, what I was going to say, my segue, which was perfect and very much everyone followed along, is we had our second week of Portuguese language lessons last week. Our wonderful teacher, Anna, is just so lovely.

Caroline: We love her.

Jason: We laugh for, like, the entire hour.

Caroline: Every terça is just the best.

Jason: Which is Tuesday.

Caroline: It’s Tuesday.

Jason: And I will say that it’s just one of those things that I am not good at. And definitely I have realized I am not good at auditory learning.

Caroline: Yes. This is a revelation for us.

Jason: Yeah. So I need to see it. If I was taking an online course, I need a video lesson and I need a written lesson. I don’t actually really need to hear that much. I mean, I think the hearing is helpful for pronunciation, specifically in language, and I need that. But I’m just saying, when Anna says a sentence, I’m like, no, I got one of those words. And I think that this is a very interesting thing about how my brain processes information, especially new, difficult information. So it’s just a realization for me. Also admitting that I’m not good at it, but I’m still sticking with it. And my goal is that if we’re going to do a language lesson every single week for this year, I want to commit and be here for it. But I also got the sinking suspicion I’m going to get left behind.

Caroline: You’re not going to get left behind. I have told you many times. I am so proud of you because I know that it’s not easy for you to do something that you’re not good at. And then secondly, I know that school and academic related things have a lot of baggage for you.

Jason: I just don’t like it.

Caroline: I think that’s a lot of people.

Jason: When you go to 14 different schools and you get bullied a lot…

Caroline: You go to 14 schools and you get

Jason: bullied.

You really don’t want to do homework.

Caroline: Yeah. And you just associate this school environment with negative feelings and emotions. And so I’m proud of you for sitting in that discomfort. And also, it’s also, to me, such an act of love because I enjoy doing it with you so much. I enjoy it for myself because I like language learning. I like learning in general, but every time we do our homework together.

Jason: Yeah. This is where it’s a very eye opening difference. For you, this is a hobby. For me, this is like, hard work.

Caroline: I understand.

Jason: Yeah, it’s not enjoyable. I won’t say it’s enjoyable, but I’m doing it not just because I want to do it for you, but also just because we moved to a foreign country and a foreign country to us from the US. I want to show the people that live here that I’m trying not just to move here and speak my language. I want to move here and try and speak their language, even though I know they’re just going to be like, let’s just speak English. So anyway, that’s just my… I wanted to share that little personal update.

Caroline: Oh, and just speaking of that, though, it was such a highlight of my week when we had a delivery. And it’s a 50-50 shot on whether…

Jason: This is our first phone call on our Portuguese phone, by the way.

Caroline: We got a phone call on our Portuguese phone and it was a person who…

Jason: It does not ever ring.

Caroline: It doesn’t ring. And I was like, what’s this? And it was a delivery and they only spoke Portuguese. And the fact that I felt confident enough where I didn’t just freeze up and I was able to communicate enough in order to have a nice interaction with this person and try to be helpful and not just be like, agh, and thank God I know the word aqui, and like, sim. That’s here and yes. And I was able to deduce enough of what he was saying and like, that…

Jason: I loved that at the end of that conversation, you were like, okay, it’s coming on Wednesday. And I was like, because I was listening to what you were saying. And I was like, I heard you say até já.

Caroline: He said, Dois. And I was like and I thought he said two days because I thought this was the delivery where it was… whatever. And Jason was like, Didn’t you just say he said he was in Ribamar?

Jason: And that’s when you said até já, which is the more like, see you soon, not like, see you in a couple of days.

Caroline: Exactly. He said até já at the end. And I said, Até já. And then Jason goes…

Jason: I think it might be today.

Caroline: I think maybe he said 2 hours. And I was, like, probably 2 hours.

Jason: 2 hours later, the truck shows up. It was great.

Caroline: And that’s the perfect example of you don’t have to be… like, you’re not going to get it 100% right. But it was such a high to me to be like after just a couple of lessons, I can see the results of it actually impacting my life in a positive way, which is so motivating for any habit that you’re trying to form or anything that you’re engaging in. So that was really exciting. And we’re still very early on and rudimentary in our Portuguese, but I really give you a lot of credit and I am enjoying doing it.

Jason: Well, let’s see how you feel in six months when I’m still trying to conjugate two verbs. Segue. Here’s a segue, everybody, into our final topic of our Portugal pramble, which is the ongoing car saga. Just wanted to give you folks an update because I know some of you actually are interested in this, and it is that we have not yet purchased a car. We are still trying to see if we can secure an auto loan through the bank that we signed up for and put money into when we first moved here. I will say the hardest thing that I’m now realizing that they don’t understand is we don’t have like a salary or a wage that comes through our bank account because we own our own business. We don’t pay ourselves a salary.

Caroline: Into the…?

Jason: No, into our bank account, our US bank accounts. So the way that… because we own our own businesses, we don’t get paid every month.

Caroline: But we do do the payroll.

Jason: I know, but we don’t get…

Caroline: It’s not consistent and it’s not a statement.

Jason: For them. And I finally realized this this morning when I got an email from another Anna.

Caroline: That’s the hold up.

Jason: She was like, Is there any way you can show this in monthly transactions in your bank account that we can see this money coming in? This is just a tip for anybody who might be moving to a foreign country where you’re not establishing any credit. It’s something to think about. Into a new country is something to think about, which is, is there a way for you to get your money situation where it looks like your business is paying you in some way? Because I think that would have really benefited us. And now I’m thinking about it. If we do end up buying a home here, if that’s something in our future, I want to get that going sooner rather than later so that we can show that. So anyway, all that to say, we still don’t have a car. We did find a local rental company that had some good prices, so we’ve got a small, little, very European feeling car that we can scoot around and…

Caroline: Which has worked perfectly for us, honestly. It might have us rethinking what we end up purchasing because it’s like, do we need something that’s different than that? I don’t know.

Jason: Right. All right, that’s your Portugal update. And just sharing behind the scenes of what life is like here and the things we’re going through.

Caroline: Great. Now, shifting gears. Let’s get into the topic.

Jason: Because we just talked about cars. So you said shifting gears? What happened at the end?

Caroline: I stopped.

Jason: Like, real quick.

Caroline: Yeah.

Jason: Was there someone in the road?

Caroline: Uh-huh.

Jason: I will…

Caroline: Don’t. And so the topic of this week’s episode is something that we, Jason and I, have been talking about recently, and it really stems from actually Behind the Build Live.

Jason: Yes.

Caroline: Which we… let’s just give them a quick kind of wrap up of how that went.

Jason: Let’s do it.

Caroline: So you heard us. Maybe you did, maybe you didn’t if you were on this podcast. But the past few weeks, we were talking about a little experiment that we did called Behind the Build Live. And this was an opportunity to basically for one day, we set an ambitious goal of trying to create an entirely new lead magnet for our website, to capture new email subscribers, and then also to redesign the home page of our website. And this was a project that we had put off. We thought we were going to have to wait until like, maybe Q2 or even Q3 in order to do this. And then Jason had the idea of what if we just constrained it quite a bit, tried to limit it to one day? And then we allowed people to watch our process of how we take an idea like that and break it down into tasks and execute on it, which I thought was super fun. And we haven’t done any a lot of experiments and creative things like this. As of recording this, last Thursday, we did that. And first of all, just to tell you how it went, went great. It was very fun to just do something new again.

Jason: In our final video thumbnail, it was like, we failed and we succeeded.

Caroline: We didn’t complete all the tasks that we had on our to do. So that was the like, we failed. But it was also like, wow, we got 90% of the way there, which was really cool, which is something that it taught us, as well as just a reminder for you listening about the power of constraints and just saying, I’m only going to do this thing on this day. How far can I get? There’s something very motivating about that type of challenge. Now, that said, we bumped up against a lesson that we learned all the time in our business, which is we just bit off more than we could chew. We tried to be too ambitious. It was too much to try to do both of those things in one day. And we’re very much a shoot for the moon and land among the stars kind of a couple. We do that often. But that actually brings me to the topic of this episode, which is I told Jason I wanted to talk about the feelings around this idea of when you keep running into the same lesson over and over and the emotions of that.

Jason: Just real quick, before we get into that, can I just ask a question for all the space engineers that listen to our show? Which is…

Caroline: The big contingency of space engineers?

Jason: So when you say shoot for the moon and end up in the stars, technically…

Caroline: The stars are farther away than the…

Jason: The stars are… I mean, exponentially farther away. Like you can get to the moon. So it should be…

Caroline: I’ve never thought about that.

Jason: It should be shoot for the stars.

Caroline: Stars and land on the moon. Jason, I’ve never thought about that. That’s a good point.

Jason: That’s what I’m saying. So I just, if any space engineers are listening to this, like you work for NASA or you’re, like, currently in space, it would be helpful if you could kind of…

Caroline: Jason, my mind is blown right now. That makes so much more sense. Shoot for the stars and land on the moon.

Jason: Stars are hundreds of millions of…

Caroline: They’re so far away.

Jason: Light years away. They happened in the past, too.

Caroline: Or maybe shoot for the moon and land back down to Earth and crash and burn because that’s the only thing between here and the moon.

Jason: Or shoot for the moon and just end up in the dark space between.

Caroline: I don’t like that one bit.

Jason: Which doesn’t sound good.

Caroline: Space a top five fear of mine.

Jason: I know. So let’s get back to this lesson that we keep learning over and over. And so for us, this lesson, and we hope you’ll have one that you can kind of relate to as you listen to this, which is for us, it’s being too ambitious and overestimating what we can accomplish. All the time, every single day, every hour, every minute. I think the only thing that I’m not over ambitious about, that I actually do achieve in my daily life is my baked goods. I set out to bake some cookies, I end up with cookies and then I eat them.

Caroline: To be fair, there’s not a lot of other ways for you to stuff that.

Jason: Let’s see you get in there and bake some cookies.

Caroline: Just saying, like, what would an ambitious chocolate chip cookie feel like? I say that, and now I’m like, I watch a lot of cooking shows, and actually the parallels are quite… we all know those cooking shows where you’re like, that was too ambitious.

Jason: I’ve also made some…

Caroline: Great British Baking.

Jason: Real shitty cookies in my day. Anyway.

Caroline: The whole point also is that I want you listening to this episode to think of like, has there been a time recently in business, but also in life where you feel like, here I am again, right back here, learning this lesson? And what is the emotional experience of finding yourself in the same loop over and over? And I don’t know, I just was thinking because I had this, like, little bit of a debriefing after Behind the Build, I was like, Gosh, why do we always do this to ourselves? And then I was like, you know what? I’m not going to beat myself up over this. I’m not going to fall into this sha-. I mean, this is a very strong word for it, but I know those of you out there will resonate. I’m not going to fall in a shame spiral about why do I always do this to myself, of biting off more than I can chew? Because it’s just not helpful. It’s not helpful to find yourself in a situation where you have to A, learn a lesson, but then you’re going to shame yourself for having to learn that lesson. Like that’s not helpful. And so I wanted to do an entire episode on what went through my mind when I had that first gut reaction of like here we are again, and how did I actively in that moment reframe having to learn the same lesson over again?

Jason: Yeah. And I think a big part of this and I think personally, this is what I tend to bring to a lot of these situations that we run into just because I think it’s my natural outlook and some of these things is like, it’s no big deal. Let’s look at the positives of this. What do we get from this? Opportunities not obstacles, is something that I have said for many years in our relationship. It’s probably something I’ve got from somebody else, but it’s just this idea of like…

Caroline: Wasn’t that Ryan Holiday’s book Obstacle Is The Way?

Jason: Yeah, but I don’t know that he said that specific phrase in there. But sure we can give it to Ryan, he’s very smart. But I think part of this is realizing that it’s not necessarily a bad thing. It’s not necessarily like, Oh, I can just never fix this part of my personality or what have you. It doesn’t necessarily need to be fixed as much as it’s just understanding that it is a part of your personality. And so for us, it’s like we’re never short on ideas, we always have things we want to do, we always want to make them different or unique or better. And that leads to us thinking we can get more done than we can.

Caroline: Right. So I think that’s where I went as well, which is trying to unpack it and understand, okay, why do I find myself in a similar position? Or we find ourselves in a similar position over and over and what is the positive part of our personality traits that get us in that position? Right? Because I just am a big believer of this whole idea of like there’s always a flip side of every flaw. And so something that you consider to be a flaw is actually the flip side of a positive quality that you embody. And so for us, yes, like you just described, we always have ideas, we have a strong vision, we are very goal oriented, we’re very oriented towards action. And so sometimes those great qualities, if cranked up to twelve, are going to get us into a situation where we bite off more than we can chew. But rather than focusing on the negative outcome just for a second, taking a moment to focus on the positive quality that gets you to that negative outcome I think is helpful because you go, okay, I’m actually not just like a bad person. Like let me focus, you know what I’m saying? Not a bad person, but let me…

Jason: We do extrapolate those things out.

Caroline: I do think humans have a tendency to do that.

Jason: I think even just to give a very specific example in Behind the Build, when we were at the 4:00 pm of the day and we had like two and a half hours left and we knew we weren’t going to accomplish it. I think we both had this moment where we were just like, I thought we were going to be able to do this. And you kind of beat yourself up about it and it’s like, what is that? That doesn’t accomplish anything.

Caroline: Totally. And I do think that this is especially a trap that you can fall into if you’re someone who is trying to impart some type of wisdom or advice, is you start to think that you’re somehow immune from the same problems that all humans fall into.

Jason: Right.

Caroline: And I think that 4:00 pm thing is like, part of that frustration is us going, Man, we really wanted to show people how you can set out a goal and accomplish it. And so by not doing that or finding us in that, you sort of have this moment of like, Oh, am I not qualified to tell someone? And then you go, No, I’m actually the most qualified because we’re all human beings. And the most helpful thing that we could tell people is that we encountered a challenge and here’s how we thought through it, which is hopefully what we’re doing in this episode. Right. And so I’m saying that also because I know a lot of you listening have your own audiences and you’re sharing wisdom and you’re sharing value, but just remember, the ultimate goal is not for you to never encounter a problem again or never have to learn a lesson again. If anything, those are all opportunities for you to continue to share your wisdom and continue to show people how you work through that. But yeah, by focusing on, I think, the positive qualities that lead to that outcome, I think at first can help you start from a place of self acceptance and self love and self compassion rather than self criticism. So that’s a good place to start.

Jason: Yeah. I also think specifically for our example, I think at the 4:00 pm mark of Behind the Build Day, if you would have asked us, and maybe more specifically you than me, would you ever want to do this again? At that exact moment, you’d be like, No, I don’t want to do this again. But then you get to the end of the day and you’re like, Okay, yeah, I don’t feel as bad as it did a couple of hours ago because we’re now past the time and I’ve come to grips with the fact that we put too much on our plate and I was over ambitious and like, it’s okay. And now like a week removed from it, I’m like, yeah, heck yeah, let’s do it again.

Caroline: Totally.

Jason: But it’s do it again understanding let’s be a little bit less ambitious. Maybe we can be a little bit more prepared than we want it to be. And I think for anybody listening to this, it’s like, okay, what’s the thing that you run into often? And it’s just how told the next time that you know you’re going to run into that thing, can you just be, like, a little bit better at understanding that you’re probably going to run into a similar problem? But you can be better at working through that or you can at least acknowledge it’s going to happen, but it’s going to be okay.

Caroline: Exactly. Which I think does bring us to the next place where I kind of landed, which was remembering that the goal is not to eradicate this behavior from your life forever, that you’re never going to run into it again. It’s just to get a little bit better each time. So you never get to that extreme place where the results are so terrible, right? And so just to bring more tangible details to this, what I mean is like we would never look at Behind the Build and go, Oh, you know what, the goal is to just never be ambitious again.

Jason: Right, of course.

Caroline: Or to never try to challenge ourselves again. Or to never establish a project that we don’t know if we can totally do because there’s parts of that that have value in challenging yourself and pushing your limits. Right. But what we what we can say is like, oh, you know, maybe I never want to get to the point where that cranks up to such a twelve that I burn myself out or that I crash and burn. Or that a good measure to me is I might have had that little 4:00 pm mini meltdown, but I didn’t scrap the whole thing.

Jason: Exactly.

Caroline: And I didn’t totally push myself to a place that was irreparable. Right. So I think changing the goalpost from being, oh, I never have to learn this lesson again to the next time I do encounter this challenge, which is probably always going to be some present to some degree, because I’m an ambitious person or I’m whatever. That places that you find yourself falling into. Instead of saying, oh, I’m never going to encounter that again. Going, the next time I do encounter it, how can I just not crank it to twelve? How can I aim for an eleven and then a ten and then a nine until you get to a place where you might still encounter that problem but the consequences aren’t quite so dire?

Jason: Yeah, I think there’s also a very interesting part of this. If you’re a person who runs into the repeating the same lesson over and over again, there might even be some angle on this. It’s just like you haven’t done that thing enough to actually understand the totality of what it takes to do it. So I was just thinking as you were talking. If we did Behind the Build every month for the rest of this year and it was always a lead magnet and a home page redesign, and we just said, maybe this is going to be like something, something that we do an experiment every single month. We’re going to change our lead magnet, change our home page and just look at the year and like, which one did the best? By the 12th month and probably by the 6th month or even by the fourth month, we would probably get it done every single time in the day. And we would feel really confident that we could do that.

Caroline: Yeah, but here’s what’s so interesting about what you just said, which brings up a really good point. You said something very interesting, which is…

Jason: You could say it’s interesting one more time. I don’t mind that was too…

Caroline: The way that your face just lit up when I said you were interesting.

Jason: Well, maybe you should compliment me more because apparently…

Caroline: I’ve never seen you that lit up.

Jason: Apparently, I don’t get a lot of com-.

Caroline: What you just said was interesting. What you said was interesting, which was if we did it once a month, every month and did the homepage and lead magnet. So if we did the same thing.

Jason: Exactly.

Caroline: Right.

Jason: Exactly.

Caroline: And so the reason you said that is because you acknowledged the fact that if we tried to do it again with a different project, the variable is different. Right?

Jason: Totally.

Caroline: And so this brings up a good point that we didn’t write down, which is a lot of times we beat ourselves up for encountering the same lesson over and over, but the circumstances are different, the variables are different. And so I just think that needs to be acknowledged so that we can give ourselves some compassion to say, yes, I maybe have to learn this lesson in a new way this time, but basically in this particular scenario, I was doing something new for the very first time.

Jason: This is for all of you client service folks out there. If you’re a designer, if you’re a writer, if you’re a copywriter, if you’re a virtual assistant, anything, and you constantly find yourself going, Why is it that every client that I run into, I just can’t get them to work in my process? It’s probably not you, it’s the client. And it’s the fact that every single one of them is different. And I think this is something that as I’ve interacted with a ton of our Wandering Aimfully members who have client businesses, I will see this thing where they’re like, I don’t understand. I have my processes honed in, but yet like this new client and I’m like, hold on. What are the variables that are changing? This new client. You can’t control that person. You can’t control when they pay their bills, when they get you feedback, how they give you feedback. You can have the best process in the world. Like the Behind the Build Live. We could have the streamlined version, but as soon as we said, it’s not a lead magnet and a home page, now it’s a whole online course like, oh, well, shit, that’s going to be a whole different bunch of variables that we’re going to run into. So I think it is really important in this bumping up into I’m learning the same lesson again. Are there variables that are changing that you just need to understand and appreciate that you can’t control all of them? And as you move forward and run into these things and go, oh, okay, this is not actually me not learning this lesson, maybe specifically, it’s that there are additional variables I have to have more experience with to get through this.

Caroline: Definitely. And that also, I think, helps you reframe the situation that you encounter as like, Great, this is a new opportunity for me to add to the reps, if you will, to say, okay, what did I learn in that rep? Like, what did I learn in that rep? And you’re almost like, compiling this list of wisdom of, yes, it might be the same lesson that you’re having to learn over and over again, but you’re going to learn new things because the variables are different. You’re going to have interpreted that lesson in a new way so that you can try different techniques going forward of how to at least… I think it’s just about trying to lessen the dire consequences of whatever that lesson is. Right. And so for us, like I was just describing, if we can just lessen the fallout of maybe overextending ourselves. For me, the goal would be just to never get to a place where I’m so physically and mentally spent that it wrecks my mental health, that it impacts my physical health.

Jason: Yeah, you need a whole day to recover.

Caroline: Exactly.

Jason: Which you actually didn’t the next day.

Caroline: I didn’t.

Jason: So I think that just shows your ability to recover.

Caroline: Which is, I know, and I was happy with that. And I think that was also about appreciating and going, okay, you can very easily tell yourself, here I am again learning this lesson, but really look at the scenario and go, but did I behave in a way that actually the consequences weren’t quite so bad as the last time? And if the answer is yes, then I think it’s worth appreciating that about the way that you handled it and about the fact that you are learning the lesson. It’s just learning the lesson doesn’t mean you never have to encounter the challenge again.

Jason: Yeah, I think the other thing that I try to remind us of, and I think you do this now too, is like, we are making all this up. So a lot of times when you run your own business and you create your own deadlines and you create your own projects and you create your own daily task list, you’re doing it to yourself.

Caroline: Totally.

Jason: So you have to have compassion for your own previous version of yourself, your future version of yourself, where you go, I did this to myself, so it’s not a big deal. It’s okay that… this was all made up anyway. This was a whole arbitrary thing that we did in like a one day thing.

Caroline: Yeah. It’s like if you imagine yourself as, just for simple terms as the boss and the employee, sometimes we can be a real dick of a boss. It’s like as the employee, as the person who is executing on the vision that my previous self has set forth, let’s say I didn’t get all the tasks done or whatever. The way that I’m behaving as the employee is almost as if my boss was really going to come down hard on me for not finishing this. What if in that situation, I can just go, but I can choose to be an empathetic boss right now. I can choose to be a compassionate boss. I can choose to treat myself the way that I would treat an employee who just said like, Hey, and of course, yes, there’s accountability and there’s self accountability and there’s discipline and all that good stuff too. But it’s like I just think there’s something about the mental framework of going like, am I being a dick of a boss right now?

Jason: Exactly.

Caroline: Maybe don’t do that.

Jason: Yeah, like previous me, why’d you do this to me?

Caroline: And then so another thing that I think is really helpful, which we kind of touched on a little bit, but I’ve been thinking about this a lot because we’re putting together the coaching session for this month, which is all about kind of entrepreneurial mindset. And a framework that I have found helpful is that if you think about this lesson that you’re having to learn over and over again, we already talked about what is the positive trait that is associated with maybe getting you in that situation. For us, let’s just call it ambition, which I don’t totally resonate with, but I think it’s what you describe this most succinctly. We’re over ambitious, right? Like, we just think we set out to do way more than we can practically do. I think it’s worth going like, okay, that’s a good quality. But again, if I crank that up to twelve, it gets me into a negative outcome. So what are the bumpers and the balancing traits that I need to be mindful of as I lean towards my most natural state, which is my overly ambitious self? What are those bumpers that can just prevent me from hitting a twelve on the ambition scale? And for us, it’s like I think patience is one of them that I have to be mindful of all the time. It’s like part of what the ambition is, is I want to do it all right now. And so if I can just employ a little bit more patience. It’s probably why we talk about slow growth so much because it’s like we teach the thing we most need in our lives. Patience or practicality, like, balancing that ambition with, like, okay, but real facts. How much time do we actually have?

Jason: Real facts, like the moon being closer than the stars.

Caroline: That’s a real fact.

Jason: The space engineers, you let me know. Yeah. One of the things that we talked about for this that I think is a good example for folks, because we’ve run into this and I think everybody can kind of relate to this is like, you know, you want to get back on the exercise and working out train and you haven’t done it for a while and you go hard for like a week and then your body is so sore or you’re so tired or you just really hate it because you went intense. You’re just like, I got to get back into this. I’m doing, like, the YouTube workouts that I saw. I’m doing the Apple Plus, whatever workouts that keep coming up my watch. I’m like no, thank you. No, thank you. No, thank you. And then all of a sudden, you don’t want to do it, and it’s because you went too intense to start. As opposed to just like, what if I just worked out for 10 minutes a day? Like, I just did some squats and, like, jumping jacks and, like, went for a walk around my neighborhood, and, like, that was good enough. And then by the second week, when I’m not super sore and like, oh, you know what? I might do, like, a 15 minutes workout and then, you know… so it’s it’s actually, like, starting slow, taking it a little bit easier.

Caroline: And if you know that you’re someone who finds himself in this place where you… intensity is maybe, like, a thing that you use a lot of times, right. So that would be sort of the trait, is like, okay, I know that I can sometimes drift towards this intensity where I start things really fast and I go really hard, and then I kind of fizzle out. Then one of your bumpers might just be, like, pacing yourself, and it’s like, oh, I always know in the back of my mind, since I know I’m, like, an intense person, I just might need to temper that a little bit with pacing myself. And so I think it’s valuable for every one of us to go, okay, what are those handful of, like, five traits that are positive, but that maybe I have a tendency to crank it up to twelve? And what are the bumpers that I can keep myself? Maybe like, a ten or a nine or an eight?

Jason: Yeah. And I think for anybody listening to this, whatever the trait is for you that you see for yourself or the lesson you keep bumping into. It’s like, how can you take the weight that you run into that at a level of twelve and run into it at a level of three moving forward? And just, like, see what it feels like. Just for it to be like, this is going to be so easy when I do this. It’s going to be so much less pressure. It’s going to be so much less actual investment of time. Let me just see what that feels like.

Caroline: Yeah, just so that you almost have like a lower limit too.

Jason: Yeah. You’re like, okay, I could have done twice as much as I did, but that’s a good place, how about get you there?

Caroline: And what were all the positive feelings that I had associated with cranking it way back?

Jason: Exactly.

Caroline: Right. Like if we did a Behind the Build and you’re like, okay, our goal today is… I almost can’t even come up with an idea.

Jason: Let’s design three slides.

Caroline: Yeah. Three slides and let me write an opt in form. I just think it would be an interesting experiment just to see how it would feel. So maybe that’s a goal for our next Behind the Build Live is we almost forced ourselves to scale it way back and just see how that would feel. The last point that we wanted to dig in here… into here is also something we go into. We did a previous mindset coaching session and this is something that has helped me, which is whenever there’s some type of thing that you run into, mindset that you want to shift, it’s asking yourself, like, What is the deeper driving motivation or the root cause, the root belief, the story I’m telling myself about what is maybe driving this behavior? And I posed that question to Jason and we didn’t come up with a super clear answer, but I thought it would be fun to just talk through on the podcast.

Jason: Right.

Caroline: Do you think that there is a deeper driving force or belief or root cause of why we tend to be over ambitious?

Jason: Yeah, I mean, I personally think it’s because we want people to watch us do things and know that we didn’t phone it in and that it seemed very unique or it seemed very different, or they watched and they’re like, Wow, I didn’t expect them to do that much. I always want to over deliver, I think is the thing. And I’m sure this stems from something in my childhood.

Caroline: Well, exactly. It’s the five questions to go deeper, right. So then I’m like, that resonates with me. And then I’m like, well, I wonder why we both have that quality. What is it in us? Is it coming from a place of not just trusting that our unique perspectives are enough? Is it just that we need it to be our unique perspective plus ten times more than anyone would ever expect? Because then that’s so different and I don’t know, but I think it’s worth just talking that through even if you don’t arrive at like a clear answer so that you can be aware of like, what is the deeper reasoning behind my behavior.

Jason: Yeah. Well, and I, I think one way to it’s not necessarily to combat that, but it’s to think about it. It’s really helpful to have like a guiding word or principle in your business that I believe stands out from other people to help with this. So it’s like you can always fall back on it. So my example for us is unboring. So I really try to always, in everything that we’re doing because online business stuff is so boring and over talked about and everyone said the same thing so many different ways but I’m like, but we’re not boring people. Like we can make this fun, we can make it interesting, we can make silly jokes, I can sing a song out of tune.

Caroline: Weird metaphors.

Jason: Yeah. It’s those things that stand out because it’s the same information but it’s packaged in a way that someone’s like, yeah, but I actually had fun listening to that or whatever.

Caroline: And so maybe in digging into this deeper, it’s like can we just trust in that quality more often?

Jason: Exactly.

Caroline: Instead of going so hard on the quantity of the things that we’re trying to do, can we trust that each one of the things that we are doing is unboring and really rely on that sort of individuality?

Jason: And you may have this in your business, person listening to this of like, Oh, mine is like punctuality. I really hated growing up that I felt like I was always late to things or whatever. And in my business that I run, I’m always punctual. I’m always getting my clients, their stuff at the deadlines, I’m always getting whatever those things are and so you know that you’re kind of like maybe good enough value that you’re falling back on that hopefully is not overworking you in any way whatsoever is I’m just going to be punctual. I’m just like that is a trait that I want someone to, when they think of me, they go, Oh, I’m going to get that stuff on time every single time.

Caroline: Yeah. And that’s going to be different for every single person and it depends on your own values and as all of this stuff does, right? But I hope that in this episode, just by understanding that these are still things, we still have lessons that we learn all the time. This was just one. Over ambitious or like turning our ambition up to twelve is just one of the many, many things that we fall into. And that’s just part of being a human being, is you’re always going to be falling back on your patterns and your habits and your things until you have some sort of negative consequence of that or outcome of that and you just go, Okay, how can I do better next time? And I want to end on something that, again, I talk about in the coaching session, but I think it’s really important for us to remember is not trying to shift any of these things or change anything about yourself or learn these lessons from a perspective of self criticism, but instead have it be a motivation out of self love. So what I mean by that is I always have this paradox in my head of like, is it possible for us to say that we’re good enough? Because we all know that that’s important, to love ourselves as we are in this moment, exactly as we are, and to want to be better? And how do those two things coexist? It feels to me like they’re antithetical, but I think they can coexist. I think it’s part of a paradox of being a human when you root them both in self love and you say self love means that I accept myself as I am today, that I don’t need to change in order to reach some metric of worthiness to myself. And I also love myself enough to know that I’m evolving and there’s a future version that I feel like is truer of the way that I want to show up in the world and I can pursue that at the same time. And so as long as I’m doing both self acceptance and self growth from a place of self love and not self criticism, of, like, trying to be what other people want me to be or saying that I’m not worthy or saying that I’ll only be good enough when I grow into this X, Y and Z, when I don’t run into this problem again, that’s only when. Then I can love myself.

Jason: Right.

Caroline: It’s like I think any of this stuff with personal growth really needs to always be rooted back into, no, this is a way that I am loving myself is I have a future version that I want to grow into and it’s a different posture than trying to run away from the person that you are now.

Jason: Facts.

Caroline: That’s it.

Jason: Great job. That’s a great place to end it. I don’t have anything to say. Otherwise, if we keep talking, I’m just going to sing more. And I don’t think anybody is interested in that whatsoever.

Caroline: I really am not.

Jason: Oh, I thought you were going to say you really are. And then I was going to, like, just go for 3 minutes.

Caroline: I don’t think so.

Jason: I think I could just try and do it.

Caroline: I dare you. I dare you to sing for 3 minutes.

Jason: Really?

Caroline: Yeah.

Jason: You would become that blanket. You wouldn’t be under the blanket, you would be a blanket. And you would just be…

Caroline: A little bit of a game of chicken right now because I did just dare you. And I’m like, yeah, but if there’s any person you’re daring in life, don’t dare, Jason.

Jason: Don’t do it. I’m not going to subject everybody to that.

Caroline: I won the game of chicken. Just kidding.

Jason: All right, everybody, that’s it for this week’s episode. We’ll be back next week. We appreciate.

Caroline: Thanks for listening.

Jason: Okay, bye.

158 – Learning The Same Lessons Over And Over (Is Okay!)

(Big Fat Takeaway)

EMBRACE learning the same lesson over and over and lessening the negative shameful thoughts that can come with it!


This article written by

Jason Zook

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

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