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169 – Jason Interviews Caroline!

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

169 – Jason Interviews Caroline!

In this interview, we talk about Caroline's early life and career. We share about the importance of taking the extra step to stand out.
Jason ZookJason Zook Jason ZookJason Zook

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Jason Zook

Listen to our full episode where Jason Interviews Caroline! below (with full transcript) or find our podcast by searching What is it all for? in your favorite podcast player.

Five Key Takeaways from Caroline’s Interview

1. Working for myself is my greatest accomplishment

When I hear the word accomplishment, I tie it directly to a societal external validation thing. To me, having the flexibility to spend my days exactly how I want to spend them is a big accomplishment.

2. Living with a blended, loving family, and being highly sensitive

I did have a loving family, though it was blended and complicated. When you’re in a house with three older brothers and none of them are in touch with their sensitive side, your being sensitive becomes the thing that makes you different. I had this weird thing where my coping mechanism, in order to fit in or to get validation within my family unit, was to get good grades and became very focused on school and excelling.

3. Taking the extra step

I think the act of going out and having to get a job is what helped me build confidence. Having to do the application process multiple times, nail an interview, and figure out what to wear and what your skills are, that whole process is very helpful. I give credit to all of the parental figures in my life who said, “If you want to go out and get a job, you need to be the best candidate, and you need to go and take the extra step that people wouldn’t take.”

4. Lessons from being the President of Ad Society in college

When you see something you want to make happen, you go out and make it happen. I ran for president of University of Florida’s Ad Society and it was a good leadership opportunity. Looking back now, I learned processes and organization to run that group, and I get to bring those skill sets to our current businesses, Wandering Aimfully and Teachery.

5. Don’t sacrifice a relationship for a career

Most people would say, don’t sacrifice a career for a relationship that may or may not work out. And my life philosophy has always been, don’t sacrifice a relationship that might work out for a career. I’m aware that other paradigms exist, but for me, I wanted one partner and I thought, there was not going to be one decision that I make in my life that affects more of my life’s trajectory than who I pick to be my person.

Bonus #1: Learning curve on how to get things done and be a self-starter

There was a little bit of a learning curve in terms of how to actually get things done and be my own self-starter. For the first six months of working for Jason’s business (IWearYourShirt), I remember eventually discovering an app called Teux Deux and started making a to-do list to set what I’m going to do every day. I started to really like it because I started to put my strategy hat on. Being willing to learn new things, new apps, new processes, etc, continue to help me to this day.

Bonus #2: Lessons from doing a daily art challenge in 2016 (Abstract Affirmations)

You have to know when to push on and when to quit. Doing a daily challenge helped me fight perfectionism, which helped me build confidence, find my creative voice, build my audience, etc. The daily challenge gave me the permission to prioritize my art, even though I stopped short of the full 365-day goal (which is OKAY!)

Show Notes for Episode 169: Jason Interviews Caroline!

We hope you enjoyed hearing us ask each other questions we didn’t know about the other person OR just wanted to go a bit deeper on. Even after 13 years together, we’re constantly learning new things about one another.

Did you enjoy us interviewing ourselves? Would you like to see us do this again in the future? Any questions you want us to answer?

Full Transcript of Episode 169: Jason Interviews Caroline!

⬇️ 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, and welcome back to…

Caroline: The interview series everyone’s been clamoring for.

Jason: Oh, okay. Clamors. What’s up, clamors? Welcome back to the show, and we are on round two of part two of this two part series where we interview each other.

Caroline: Yeah.

Jason: Last week, if you missed it, would highly go back and listen to last week.

Caroline: You would highly go back.

Jason: I would highly recommend that you go back.

Caroline: Sorry. It’s rude of me to just come on this podcast and be correcting you.

Jason: Highly. This is my show. And listen to your show that you had where you interviewed me.

Caroline: What was the name of my show?

Jason: Podcast…

Caroline: Feelings.

Jason: Podcast interviews are cool, dot dot dot, because of intro. Yeah. So that was fun.

Caroline: It was really fun.

Jason: Hope you all enjoyed that.

Caroline: If people like this, I would like to do more because there was so much we didn’t cover.

Jason: Oh, wow.

Caroline: We didn’t even get to any current events, really.

Jason: We didn’t get to current events? Like, maybe just public policy.

Caroline: Yeah. No.

Jason: Okay, so this week, we will be turning the microphone tables around, and I will be interviewing you. So for those of you who didn’t listen, last week, Caroline interviewed me. I answered all the questions truthfully and honestly to the best of my abilities. And now this week…

Caroline: The podcast is not under oath. You’re not under oath.

Jason: Are you sure?

Caroline: No.

Jason: That’s not a thing about podcast?

Caroline: I’m not sure.

Jason: They’re not under oath? Are you ready?

Caroline: I’m so ready.

Jason: Okay. There’s a lot less preamble because we’re just, like, getting into it.

Caroline: Great.

Jason: All right.

Caroline: Wait. You need to do an intro for me.

Jason: Oh, I’m so sorry. Right. I’ll do an intro the same quality you did of an intro for me.

Caroline: Excellent. Thank you.

Jason: Caroline Kelso Zook, born nay, Caroline Kelso Winegeart. Winegeart.

Caroline: Geart.

Jason: Born in Jacksonville, Florida at one…

Caroline: I almost said, Sim, in Portuguese.

Jason: Baptist Medical.

Caroline: Why would you know that?

Jason: Were you born at Baptist?

Caroline: Yes. Why would you know that?

Jason: Because I did my research. Found your Wikipedia.

Caroline: It’s on my Wikipedia?

Jason: Yep.

Caroline: Okay.

Jason: Back in 1988, a great year, and grew up, was a child for a while, and then was a teenager, and then became an adult, and then that’s where we are today.

Caroline: Love it.

Jason: Not that tall.

Caroline:: Not that tall.

Jason: But not that short.

Caroline: Not that short.

Jason: Average height.

Caroline: Definitely.

Jason: That’s my intro, folks.

Caroline: That’s actually my tagline. Caroline Zook. Average height.

Jason: My best feature is my height. Your best feature is…?

Caroline: My hair.

Jason: Your hair. Congratulations.

Caroline: Thank you.

Jason: All right, that’s the intro.

Caroline: Okay.

Jason: Okay, here’s my first question. Kick things off. What’s your greatest accomplishment?

Caroline: What is my greatest accomplishment? Something that I’ve done. I mean, the first thing that just comes to mind is creating a career where I don’t have to work for someone else. That, to me, feels like the greatest accomplishment. And having the flexibility to spend my days and exactly how I want to spend them. To me, that’s a big accomplishment. And it’s kind of funny because even hearing your question, I immediately go to my first thought was, it’s been a long time since I accomplished anything. And then I was like, I went through this internal battle in my head. I was like, no, you do. You accomplish things all the time. But I think it’s because when I hear the word accomplishment, I tie it so directly to a societal external validation thing.

Jason: Trophies, awards.

Caroline: Like, for example, my book. It doesn’t even cross my mind as an accomplishment.

Jason: Right.

Caroline: Which that’s not to belittle the doing of the thing. It’s just that I decided a long time before I did that that it was not for anyone else, and it wasn’t to be an author. It was an opportunity at the right time, and it was a vehicle for self expression. So I don’t even think of it as an accomplishment.

Jason: Yeah.

Caroline: Which is funny.

Jason: As a good interview host, kind of had an inkling that was going to be your answer, which leads me to my second question, which is…

Caroline: Wait, you had an inkling that my answer was going to be being able to work for myself?

Jason: Yeah. Which leads me to my second question. Did you ever think you would work for yourself?

Caroline: Oh my god. Are you a mentalist?

Jason: I might be a medium. I don’t know. I don’t know the difference between those two things.

Caroline: Wait. What’s the question? Did I ever think…?

Jason: Did you ever think you would work for yourself or on your own business?

Caroline: I would work for myself? No. In fact, it never even dawned on me that it was a career path until I met you.

Jason: Wow.

Caroline: Which, to be fair, was early on in my life. We met when I was 21. But, I mean, my entire life, I only knew about these more traditional career paths. And we were joking the other day about, I think, about the game of life, like the actual board game of life. And it teaches you so early on, you have these cards that have your occupation, right? And it’s like doctor, lawyer, and maybe there’s a business person one. I doubt it.

Jason: Maybe there is now, there wasn’t 20 years ago.

Caroline: And if so, that’s one path out of all these other…

Jason: Probably, salesmen.

Caroline: Salesmen? Maybe, but that’s a man and I’m not a man.

Jason: Good call.

Caroline: No, it’s just like so it never even dawned on me. I always thought of this traditional career path, and I don’t know if this was told to me directly from my parents, but in terms of, like, oh, you need to be a doctor or lawyer. I don’t remember them ever saying that. But I think indirectly, the message that I received was, you need to find a path that is going to allow you to be financially secure, and the only way to do that is through these jobs, like being a lawyer or being a doctor. And so I just had my eye on that prize because I just thought, I got to do whatever it takes in order to have more options in my life than my parents do. And I saw that money, lack of money was, like, a big factor in that. And so it’s not like I thought about money all the time, but I definitely thought about, quote unquote, success in a traditional path and just getting myself to a job where I could make enough money to not feel stressed about money.

Jason: Yeah. When you were little, what did being rich look like? What did you think it was?

Caroline: Well, first of all, the first time I went to a friend’s house who had a second storey, I was like…?

Jason: In Florida, in Florida, that’s like…

Caroline: Yeah. I was like, what? Yeah. Also, something that sticks out so distinctly in my mind is, like, friends that had a… whose parents had a beverage fridge in the garage.

Jason: Oh, yeah.

Caroline: Well, and first of all, a garage. We didn’t have a garage.

Jason: Carport.

Caroline:: We had a carport. And so when I went to friends houses who had, like, a garage where you could go out into the garage and get a soda out of their fridge, I was like, what is happening here? You guys are millionaires. And I remember I would go over to my friend’s house in fifth grade after school, and they always had… They had a drink fridge in the garage, and then they had a… what do you call those, like, ice chest or something?

Jason: Like a cooler?

Caroline: Yeah, like a cooler where they just had, like, every frozen food from the grocery store you can imagine.

Jason: Oh, I see what you’re saying.

Caroline: Yeah, in the freezer. Pizza rolls, Hot Pockets. It would just, like, come home, grab a snack after school, and pop it in the microwave. And I was just like, you have endless freezer food. And first of all, freezer food was expensive, so we didn’t actually have that much freezer food, and that felt rich to me.

Jason: Mine was the pool either way. So it was a pool table.

Caroline: I remember a friend who had a pool table, and I was like, whoa.

Jason: Also, as a person who… I’m sorry, too, on my interview show, I’m sharing some of my own stories.

Caroline: That’s okay. I knew this coming onto this show. It’s a very fluid…

Jason: I do that. I do that with my guests. I also like to be here. I remember when I was however old I was, maybe 14 or 15, that we moved into the house, and this was, like, the big house.

Caroline: This is where you jumped in terms of money.

Jason: We didn’t have a pool, but we had a pool table.

Caroline: Wow.

Jason: And I’ll just never forget, I was like, oh, this is what I grew up thinking rich was.

Caroline: You were like, I made it.

Jason: Like, we’re here, and then it’s like, we out here.

Caroline: The Kevin Hart joke of like, oh, no, I’m rich.

Jason: I’m rich.

Caroline: You’re not.

Jason: Yeah. So that was a fun thing for me growing up. I was thinking about that. When you were growing up, you had a big blended family.

Caroline: Yes.

Jason: What was that like?

Caroline: What was that like?

Jason: Because I didn’t really have a blended family. I just had multiple iterations of different types.

Caroline: Right. Yours was… yeah. As far back as I can remember, it was like that. So I actually just don’t even know any other way. So for anyone listening, my parents split up when I was like, something like nine months old or something. And so meaning divorced. And so my dad was always in my life but never married, so I never thought of them as together. And then pretty shortly after, my mom met my stepdad when I was like, three. And so he had two kids, so then they all moved in together. So then sometimes the boys would come visit. So then I had two step brothers, and then I had myself and my older brother Matt. Matt and I would stay at my mom’s house. The boys would come over.

Jason: But they predominantly lived with their mom.

Caroline: But they predominantly lived with their mom. Then on the other side, my dad got remarried, and she, his second wife, had a boy and a girl. So then I had a new stepsister and a new step brother. And then my dad and his second wife had a baby, my little sister, my little half sister. And then they got divorced, and then my dad got remarried again and had my little half brother. So at any given moment, I was predominantly at my mom’s house. So I did have sort of like a stable home base. But then people were kind of coming in, and then I would go over to my dad’s house and stay. And then so then I had like a different kid sibling dynamic there. And then when all of that kind of ended, then there was a new dynamic where it was like visiting my dad while he was single. And then when he had my little brother, that was a new dynamic. So it was always sort of these changing social dynamics in my family. But I do remember growing up having a sense of pride. Like, I think my parents did a really good job. I don’t know if this was just like the narrative that they pushed or if it was true, but they did get along fairly well. My dad and my stepdad at least respected each other. I’m sure there were things that really, especially money. Money was the thing that caused problems.

Jason: Too many pool tables.

Caroline: Because my dad was a lawyer, but he was always in between things. So it was always like, he was, like, working at this firm, and then he would do that for, like, a year or two, and then it was like, oh, I’m on my own. I’m starting my own firm. I just always remember that always being in flux. And even though he was in this career that I feel like you would associate with having money, he was incredibly unreliable for my mom in terms of child support and things like that. I mean, I can remember very formative memories of being at the Publix grocery store and my dad having written my mom, like, a bad check. And so then she’s trying to buy groceries, and the check is bouncing, and then it’s embarrassing. I don’t really even know how the finances work where they can check that at the counter or something. Something’s happening where we’re trying to buy groceries. We don’t have money. It’s embarrassing my mom. Then the loop is like, then the phone call happens, and then Lamar.

Jason: Yeah.

Caroline: We could bleep it out. That was difficult. But going back to what I was saying before, I remember being mostly happy, and I remember having a sense of pride that though it was blended and though it was complicated, I mean, I do remember having a sense of embarrassment a little bit of explaining to people my family tree, like I just did.

Jason: Yeah. It’s hard to explain.

Caroline: Because it’s hard to explain, but I do remember having equal parts embarrassment, but also equal parts pride of, like, yes, it’s chaotic and it’s different and it’s unconventional, but we all love each other, and for the most part, we get along, and there is love in my house. And I really liked all of my siblings, and it was difficult, I will say, at times, because especially on my mom’s side, it was basically three boys against one girl, and that’s exactly how it felt. They were all older boys. And I think, as a way, I don’t know this to be true. Like, I’ve never had a true conversation with my brother about this, but it became easy for him to kind of fall in with the two older step brothers and get along. And they all got along really well, but it always left me on the outside. And a lot of my childhood, the negative parts of my childhood very much became colored by this feeling of being on the outside and being different than everyone in my family.

Jason: Which I think we have in common, right?

Caroline: Totally.

Jason: I accepted that I was the black sheep and kind of wore it as a badge of honor. I would go on a limb and say that you were a little bit of the black sheep in your family, but it wasn’t really a badge of honor.

Caroline: Totally.

Jason: Yeah. And I think that probably boils down to the peacekeeping person in you and trying to keep the family, keep all the branches of the family happy.

Caroline: Yeah, because what happened was deep down, I felt like the black sheep, especially for being sensitive, because when you’re in a house with three older brothers and none of them are really super in touch with their sensitive side, you being sensitive becomes the thing that makes you different. Not only are you younger and you’re just sort of like the annoying little sister, but I was also deeply sensitive. So things hurt my feelings, and I felt the energy of people around me. I felt the energy when there was conflict about money. So it’s like deep down, I felt like a black sheep. But then I had this weird thing where my coping mechanism, in order to fit in or to get validation within my family unit, was to get good grades and to become very focused on school and excelling. And it’s like I found this way in, which was every time I remember a very early formative memory is going to take this gifted test right now. Right. Now, you look back and you’re like, how many of the kids were quote unquote, gifted? Like, I don’t know, but I remember going to take the gifted test and passing and the pride that my mom had talking about how good at puzzles I was and how advanced, and she’s so smart, and the joy and the happiness that she got from my excelling, that was almost like a thing early on of teaching me, like, when there’s turmoil and there’s chaos, your academics and your ability to excel actually are a tool that you can use in order to make your mom happy and that can please other people and that can create more safety within your family. And so it’s taken me years of therapy to understand this, but that’s why academics and achievement became such a trap for me, because to me, that was my only means to safety.

Jason: Yeah.

Caroline: And acceptance.

Jason: And approval. Exactly.

Caroline: And acceptance. Yeah.

Jason: And I’m not trying to paint any picture of your family growing up, but I think in a family that is as kind of like, detached in a lot of different ways, there’s a lot of different family members of different places, but we’re all intermingling because we’re all still together. I think it’s one of the ways you could stand out in the family. Right. So it’s like you kind of fall into the trap of being maybe like the young, sensitive one who isn’t loud. You’re one of the few girls in many of the situations or the only. And so this was a way for you to stand out amongst all of these louder personalities.

Caroline: To feel significant.

Jason: And it was really the way for, I think, for you to probably feel a sense of pride in yourself in your family.

Caroline: Totally. But then it’s weird because it had a different effect as well where it made me feel like more of a black sheep kind of because then… And all of my siblings did well in school but I really was like your straight A student kind of thing. And it made me feel then disconnected from my family members because it made me feel like now they see me as this teacher’s pet. Do you know what I mean?

Jason: So we’ll skip out of some family dynamics and move into some job stuff.

Caroline: Okay.

Jason: Through my research.

Caroline: Yeah.

Jason: I know you worked at Rita’s Italian Ice, which is like a dessert…

Caroline: Shaved ice.

Jason: Shaved ice place. I know that you worked at Outback Steakhouse.

Caroline: I did.

Jason: I know you did some data entry…

Caroline: I did.

Jason: Thing. My question was, what do you think was the most formative job you had, growing up, just to help you learn skills as a person who would eventually start your own businesses?

Caroline: Honestly, I don’t think the skills themselves are what helped me. I think the act of going out and having to get a job is what helped me because none of the actual stuff I’m doing is… And I was never at a job, honestly, long enough for it to really sink in.

Jason: Because they were like summer jobs.

Caroline: They were sort of summer jobs. And, yeah, I was never at a job for very long enough to really cultivate skills. But I do think that the act of going, a lot of times, it was out of a place of necessity. So it’s like, I got my job at Rita’s because I needed…

Jason: That’s the Italian ice place.

Caroline: Italian ice. Because I had just gotten this hand me down car, and in order to get to school, I needed gas. And my family can’t even totally give me gas money, right? So it’s like, I got to go get gas money.

Jason: Should have made a deal with your mom in these good grades. Like, if you got a good grade, give me a 20, mom.

Caroline: Yeah, but when you don’t have the money, my mom’s like, I need 20 to pay groceries for us. They gave me gas money, too.

Jason: I think we all know…

Caroline: When finances are tight…

Jason: And you just want your own money.

Caroline: Yeah, it’s true. So that was sort of that. And then having to go and seek out a place that I wanted to go get a job at. Go ask for the application, fill out the application, that whole process. And having to do that multiple times and nail an interview and what do you wear and what are your skills? And that whole process, I think, is very helpful. And I never had this approach of, like, let me just submit my resume online and hope it works out. And I give credit to all of the parental figures in my life really said, if you want to go out and get a job, you need to be the best candidate, and you need to go and kind of going back to what we said in your thing of go take the extra step that people wouldn’t take.

Jason: Exactly.

Caroline: Overdress. Ask questions about them.

Jason: Know your strengths and weaknesses.

Caroline: Don’t be afraid to speak to… because a lot of these owners or a lot of the people are older than you and how to speak to someone who’s older than you. These things. That’s what I learned. But as far as, like, I don’t think those kinds of jobs teach you how to be an entrepreneur. They teach you how to follow instructions.

Jason: Yeah, I would say that definitely is a helpful skill. It’s kind of like the you have to put in the work to see the results.

Caroline: Exactly.

Jason: That’s a skill that you take to entrepreneurship. But I would also say the people interaction is probably a big thing that is helpful that it may not seem that way, where it’s like in the Outback Steakhouse where you’re the hostess, you’re greeting people. And it’s kind of funny because it’s actually related to those two jobs that you had are very related to your spot in your family where it’s like you have to manage the…

Caroline: Emotions of people.

Jason: A family walks up to eat and they’re like having a fight. You have to be like, hey, who wants a rainbow snow cone?

Caroline: And a lot of times when you’re the hostess, you have no control over how fast the staff is turning tables, but you’re the first line of defense that gets yelled at, basically. And you’re so right. I never thought of it this way, but same with Rita’s. I think it’s interesting that I got promoted at both of those jobs extremely fast. Like two weeks of working as a hostess at Outback, and I was just the only one who didn’t miss a day of work without calling in.

Jason: You sold the most bloomin onions.

Caroline: And I was, I think, okay under stress, and they were like head hostess.

Jason: Yeah.

Caroline: And so it’s just like I think you’re right. This, like, skill of a little bit being able to smooth things over, keep the peace, was a skill set that I brought to those jobs where you’re interfacing with people a lot.

Jason: Yeah. Moving on to college, because I don’t know that I’ve ever asked you this.

Caroline: That’s what this is for.

Jason: You went to University of Florida, Go Gator, and I want to know about the Advertising society experience, like where that started and where that came from. Because to me, that’s also an example of a little bit of entrepreneurial spirit in taking the charge of that, becoming the president of that.

Caroline: Well, actually, I don’t know if I’ve ever told you this story, so let me know if I have. But funny story about that. Naturally, I switched majors. So my first year in college, I was premed because aforementioned got to be a doctor. And then I was like, this is a really bad idea. I don’t like these classes, and I hate blood, and so this is not going to work out. And so I took an elective for Advertising 101. And I loved the business strategy part of it. I loved the creative strategy part of it. And so I just said, I’m going to change my major to advertising. And that started me on the track. And then, of course, being the overachiever that I am, I thought, let me join Ad Society. Let me join some clubs that will look good for getting a job after this. So the advertising club was called Ad Society. I joined as a junior, actually, I think, or no, maybe a sophomore, I joined kind of late. I don’t remember when the timeline was, but I joined a little late by the standards, and I didn’t really get involved.

Jason: Well, it wasn’t your major either, so I’m sure that’s why you joined late.

Caroline: Well, exactly, because I had changed. Yeah, but then I just sort of like, went to the things. They had guest speakers come in, so I always liked going to the meetings to hear the speakers, but I just didn’t get very involved, I should say. But then I’m a junior, I’m in a meeting, and they talk about elections coming up because they elect the senior, like, the next president, I think, at the end of the year or whatever. And there was one girl who was running for the president of Ad Society, and she was running unopposed.

Jason: She had a pretty good chance of winning.

Caroline: And I looked around and I was like, you can’t let her win unopposed. Like, it bugged me. And I was like, this makes no sense for me to run. I am not… Typically, the way it works is very like in real life where you get on a committee, then you become a committee head, then you become like one of the upper officers of the club or whatever. Have not been a part of a committee, have not run a committee, have not done anything in the club. But it was more about me being like… And it was nothing against her. It just was like, I think I can do a better job. She was the party planner for the thing, which I was like, cool, you need a lot of skills to do that. But as far as running the meetings and keeping the budget, like, all the things I was like, I don’t know, I think I could do this. And so that part, I think, ties back to what we were saying about like, you see something that you want to happen, go out and make it happen. So I run for president against her, and I feel a little silly doing it because I’m like people are like, who is this girl? And I won.

Jason: Nice. How many people were in the Ad Society? Just for all of us who have no idea.

Caroline: At meetings, I would say it’s probably anywhere from like 50 to 70 people.

Jason: Okay, cool. So it’s not three people.

Caroline: It’s not three people, no. It was a popular club because it was a popular major, and maybe I mean, it was definitely dozens, I would say. And yeah, so my role was to run the meetings and kind of manage all of the upper officers and everything, and it was fun, and it was a really good leadership opportunity. And you know me, like, looking back now, I love processes, and I love organization, and I got to bring those skill sets to that experience. And also, it made me get up in front of… I had to run meetings. So I look back at what we’re doing with coaching.

Jason: Coaching sessions, yeah.

Caroline: And it’s so much that. It’s like preparing a curriculum, kind of having an agenda for what I think would be valuable.

Jason: We have our own version of an overhead projector.

Caroline: There was always this weird ten minutes before the meeting started where I had to mingle, because it’s like, I’m standing at the podium, like, I’m running the meeting, but I got to go and mingle with people and be like, oh, how are you liking it? And blah, blah, blah. It was just weird. I don’t know.

Jason: Yeah, I think it teaches you a lot of life lessons because it puts you in a lot of uncomfortable positions. But then how many meetings did you run?

Caroline: Over the course of the year? I mean, I think they were, like, either once a month or so. Not that many, but, like, ten.

Jason: Yeah, but I think it’s like the first one’s probably super scary, and the second one is a little less scary, but then by the 8th one, you’re like, oh, I got this.

Caroline: I still remember walking from my sorority house to the place where we’d have the meetings for my first meeting, and that nervousness. It wasn’t anxiety. It was, like, nervousness.

Jason: I have nervousness thinking about it for you.

Caroline: The first time I stand behind a podium, and I’m like, hey, I’m your president. And you’re like, what do I even do here?

Jason: What do I do with my hands? That curtails nicely into that’s actually how we met.

Caroline: Yes.

Jason: But I’m curious to know, in the roster of ten speakers, where did I fit in there, and, like, which number was I, and were any of the other speakers really, like, memorable or impactful for you, personally?

Caroline: I don’t remember a single other speaker.

Jason: Okay, good.

Caroline: But also, what you have to know.

Jason: You married one of them.

Caroline: I married… Man…

Jason: That’s funny.

Caroline: I wish I would know what the lineup is so I could go, you will marry one of these people. But the funny thing about that is the president was not supposed to pick the speakers. So that’s probably why I don’t remember because it wasn’t actually my job. I forget the name of the position, but their entire job was to outreach and get speakers to come to meetings. But what happened was a speaker pulled out last minute, and this person, I think, was also going to be like, out of town or something. There was some reason why they couldn’t do it, couldn’t find someone last minute. And I said, as you do, because you’re the president. And you’re like, I got to make this meeting work. So I’ll put feelers out. I sent an email to all the Ad Society people who had just graduated the year before and said, hey, I’m in a tough spot. Do you know anyone? Because now they’re all out in the industry, right? Like, any of your bosses, would they be willing to speak or whatever? And Jessica Ryan at the time, I don’t know what her married last name is, but she was like, yeah, she was working in Jacksonville. And she was like, I just went to marketing… an AMA, American Marketing Association, meeting or something with this guy who has this T-shirt business. And he was really a good speaker. He was engaging and funny. He would be great for Ad Society. And I was like, cool. Can you give me his email? And she’s like, oh gosh, he’s got so many emails coming in. It’s like the height of I Wear Your Shirt.

Jason: This is Jiffy Lube time.

Caroline: He’s a J list celebrity. Those of you who listened to last week’s episode will get that. He’s actually a J list celebrity. So you’re probably not going to be able to reach him via email. But he’s on Twitter all the time, so try to get him there. And that’s what led to me DMing you. So I don’t know who the other speakers were and who I almost married.

Jason: Well, I didn’t know that you didn’t coordinate the speakers, so that’s even funnier too.

Caroline: And when you were telling your story about how you just happened to go to J.U. for basketball, I’m like all these things, which is how life works, right? All these things had to fall into place. You had to randomly choose Jacksonville University to come down and play basketball at.

Jason: It was either that or Arizona State. So like, wow. Would have been a whole world of difference.

Caroline: We need to find out who that speaker was that dropped out and send them a card and say, just so you know…

Jason: You know who it was? Dr. Swanson.

Caroline: Dr. Swanson.

Jason: The knee urologist.

Caroline: The knee urologist.

Jason: Yeah.

Caroline: Again, throwback to last episode.

Jason: Last episode. Just for everyone who hasn’t necessarily heard that story. What care about…

Caroline: Not the knee urologist.

Jason: Not the knee urologist. This is my selfish question of your interview. You had a selfish question for me.

Caroline: Did I fall in love with you immediately?

Jason: What was your initial impression of me? Because we exchanged some DMs, you convinced me to be a speaker. You haggled me down from the price because at that point, I was now getting asked to do so many things that I had to start charging because I just couldn’t do them all. And so that was for me. I was like, listen, even if it’s on Skype, which is what it was. I was like, I just have to charge because I got to weed through these things, and my time is super precious at that moment. Yeah.

Caroline: Do you want me to tell you honestly?

Jason: Oh, yeah, sure. Yeah.

Caroline: Two things. I, first of all, had such a creative crush on you. I was dating someone at the time, so I didn’t have an initial romantic inclination towards you in any type of way. But I was in this mode in my life where by the time we had you come speak, it was my last semester of my senior year because I got elected junior year. And then you come back, and that’s your year where you govern. And so I was gearing up to go find a job in the workplace and graduate from college. So I was very much in this very early 20s. Like, creative, I can go a million different directions with my life. And so you just had this way of speaking so differently about creativity as you do now. But I just was very infatuated with how your brain worked. And so those are two impressions. The number one creative crush, I just was like, this guy thinks so differently, and I just want to be around that energy when you meet somebody like that, where you’re just like, well, how do they think? And then the second thing was I thought, this guy is arrogant as fuck. The way that you spoke, I was like, you just spoke with an assertiveness. And going back to what we talked about last episode of, like, I don’t care what you think of me, you spoke with that that I read as arrogance. But once I got to know you better, I knew that it was just that I wasn’t used to people talking like that and not caring what other people think.

Jason: This was in 2010 or 2009?

Caroline: 2010.

Jason: Yeah. So the funny thing about this is, like, had you reached out to me in 2009, I probably would not have been that confident, and I wouldn’t have had that much experience. But I had the entire experience of 2009 going from a literal nobody who nobody paid attention to, and I had zero following on the Internet, and nothing at the beginning of that year to fast forward, like, six or seven months. I’m now on almost every major news outlet, answering questions, doing things. Then I start getting into the speaking things. So I’m doing like AMAs. I’m Skyping in all this stuff. I’m Skyping into interviews.

Caroline: So to be fair, you kind of had a reason to be arrogant. It was boosting your ego.

Jason: Exactly. Totally.

Caroline: You were in, like, an ego boosted space.

Jason: And it was just like and not to belittle the Florida Advertising Society, but that was, like, the lowest it was, like, the lowest thing on my list to do, so I didn’t even have to get anxious about it because I’m like, all I need to do is show up, tell my story, and, like, I’m good. Like, I know they’ll appreciate because I’ve done this now, like, 30 times.

Caroline: Totally.

Jason: Yeah. So it’s kind of funny. It’s not surprising at all.

Caroline: I remember so distinctly after I think it was on the way after you Skyped in, we would always go to get pizza afterwards. Like, we would meet up afterwards.

Jason: Not the speaker.

Caroline: No, not the speaker. The group would go to a pizza place and have, like, beer and pizza or whatever. And I remember riding in the car with this guy named Jamie, and I was like, I don’t know. I just thought that dude was so cool. And he was like, that guy? Kind of, like, commenting on how you kind of came across very confidently. And I’m like, I don’t know. He seems like a good guy to me. That’s what I said. I was like, I get it, but he’s done a cool thing, and he just seems like I don’t think he means it that way.

Jason: Well, and that’s the thing, right? Confidence comes off as cockiness a lot of times.

Caroline: Totally.

Jason: And especially even just some of the standard gender norms. Right. A guy seeing another guy can feel very jealous or competitive, and so you actually can’t even remove your ego from it. All you see is, like, ego clashing.

Caroline: And it’s both, right? It’s that there is some truth to it where you were kind of peacocking. But then it’s also that then that makes that guy want to be… it’s just kind of funny, but there was something about you that I just was like, there’s so much more to who he is than this persona. And I was just so much more fascinated by your brain and your creativity.

Jason: Well, thank you. So you graduate college. Did you have a job before you graduated, like, lined up, that was ready to go?

Caroline: No. If you remember correctly, I had interviews right after I graduated, so I wasn’t interviewing for jobs before I graduated. I was in the midst of trying to set up interviews.

Jason: That’s right because I remember we were having phone calls.

Caroline: We were having phone calls. And you were kind of…

Jason: Coaching you up a little bit.

Caroline: Coaching me up a little bit. And kind of…

Jason: Probably telling you not to take the jobs or telling you to ask for more money.

Caroline: Yes, both of those things. And so I had an interview at an agency in Atlanta, and then I was really seeking out… I had decided I didn’t want to go to New York. Like, I could have parlayed. I had an advertising internship between my junior and senior year in New York at a very prestigious advertising agency, like, one of the top ones in the world. And I hated it, and I hated living in New York, and so I knew I didn’t want to go back there, but I thought I want the fun of working on big name clients. I don’t want to work at a regional agency where I have, like no…

Jason: Which is funny because…

Caroline: Which is funny because that’s what I ended up doing. But at the time, I just was right out of college, and I still had this idea for my path of wanting to be, quote unquote, successful, right? Like, wanting to go… Again, remember, at this point, everything in my life that is good has come out of me achieving and validating, getting external validation. And so I thought, okay, well, the most external validation would be go take this big name job in New York City and be a NYC Madison Avenue Mad Men girl.

Jason: Yeah.

Caroline: But I was like, I actually can’t physically allow myself to do that because I hate it. So what’s the next biggest step? And so I thought I had found this perfect fit at this agency that was technically an independent agency, so it wasn’t with one of the big holding companies, which was like, kind of the more soul sucking stuff. It was an independent agency in Durham, North Carolina, which was like a small thing, but I had grown up going to North Carolina, and I really liked that area, but it was big name clients, so they had clients that you would recognize. And the kicker was that the person that I was dating at the time was going to law school in Chapel Hill, which is right next to Durham. And so I thought I’ve found the perfect out of college thing because, right, I’m going to be with this person for the rest of my life. That’s what you think when you’re 21.

Jason: We were just casual…

Caroline: We were friends.

Jason: Friends, yeah.

Caroline: And then, of course, what happened was I had set up that interview at that agency. Meanwhile, you and I are now figuring out that we like each other. I end that relationship with that person. I still have the interview in Durham. I go to the interview. I love the interview. I love the agency. They offered to pay me $5,000… No, $10,000 more than the Atlanta agency. I think it’s… I think it’s twelve.

Jason: Which, truthfully, the Atlanta… I remember chatting with you about the Atlanta agency job offer, and I was like, this is not enough money to live off of.

Caroline: It’s literally not enough money to live off of. Yeah, I think it was like $22,000 right off of college.

Jason: Which is ridiculous.

Caroline: I was just like, objectively, no. And Atlanta is not a low cost of living place. But anyway, so I loved the whole thing, and I just thought, well, this is weird because I no longer have a boyfriend that lives anywhere near here, but I really like this job opportunity. So I said yes, and you and I did long distance for six months. And yes, I broke up with my current boyfriend, and we immediately started dating. And I know that that’s probably not conventionally good advice.

Jason: Thirteen years later, I think we made the right choice.

Caroline: Same.

Jason: Yeah. I think it’s fun to hear that story of you getting that job. And I remember back to us having those phone calls. I was traveling for I Wear Your Shirt when we were having those phone calls. So I remember I was in Denver, Colorado, and I remember being at, like I just filmed a YouTube video for whatever shirt I was wearing.

Caroline: Weren’t you at a farm? No, warehouse.

Jason: One of the places I was staying was, like, near a warehouse because that was part of the nonprofit that you helped me with.

Caroline: Right. You were scouting.

Jason: I was, like, figuring that out. But I remember being at a playground, no kids were around, and I had, like, filmed a stupid video, danced around, doing my thing, and then I was, like, on a swing, sitting on a phone call with you.

Caroline: Really.

Jason: Chatting about life. And that’s one of those memories.

Caroline: It’s kind of funny because I can remember pacing around the parking lot of my sorority house on the phone with you, too. And looking back, it’s so obvious that we were just, like, literally in love with each other. But at the time, convincing myself that it was just a creative crush or like a friend, a mentor or whatever, it’s like, no, you dumb dumb. You were, like, really liked this guy.

Jason: Yeah, I mean, the fact that we could spend hours on the phone and it quickly went away from the standard surface level discussion stuff of the advertising industry. We never even talked about that. It was like we talked about our favorite movies, and we talked about our family histories, and we talked about what we were doing in life, and that type of thing. So it was fun. Okay, cool. So you work at the agency in Durham. I’m coming up. I’m flying every other weekend or so. Luckily, the flight was like, $120.

Caroline: Yeah, you’re flying up, I’m flying down.

Jason: You don’t love flying, but you don’t know that you hate flying as much as you do at that time.

Caroline: It wasn’t as bad as I got.

Jason: And then I think you were there for like six months and you realized that just…

Caroline: I realized three months into it.

Jason: Yeah, our relationship was blossoming. But also the job.

Caroline: Yeah, a couple of things with the job. Number one, I was under the impression… This was my thought about advertising and my career. I thought it matters more what agency I work for than what my position is. So I took any position possible at that agency, which was a junior media planner. For my skill set, that was the worst thing I could have done. I mean, maybe, but I really wanted to be in strategy. I really wanted to be in creative, and I was just going to try to parlay my way over there. But the problem is I hated media planning so much that I could never even get there. And then the other thing that happened was I joined and they put me on two accounts, and I was the only junior planner that stayed on two accounts. And I was working for Sherwin Williams, and I was working for some financial company, and I was totally overworked. And me being me, I just didn’t say anything, and I just hustled and hustled and hustled to meet the expectation. And I think they probably were like, well, look, we’re not paying this girl very much, but she’s, like, really delivering. And they just gave me more and more, and that was my fault for being young and not speaking up for myself and saying, this is too much. And when I did my exit interview, I told them that, but meanwhile, you’re flying up, I’m flying down. And now my eyes are being opened to a world of creativity that I do not feel every day at my job. And I hated it, and I started hated going into the office. So I just kind of reached this crossroads where I was like, is this really what I want to do? And I just had this feeling about us, and I know it doesn’t make any sense. It doesn’t make any sense at all. But I just knew that what we had was really rare. And this is maybe unconventional advice, but most people would say, don’t sacrifice a career for a relationship that may or may not work out. And to me, my life philosophy has always been, don’t sacrifice a relationship that might work out for a career because, to me, the one thing that is going to shape… And I know this isn’t everyone, and I know that many people don’t even believe that you need to be with one person for your whole life. So I’m aware that other paradigms exist, but for me, I wanted one partner. And I thought, there’s not going to be one decision that I make in my life that affects more of my life’s trajectory than who I pick to be my person. And so I was like, if I let this relationship die, even though I know it’s rare and I know it’s special because of some idea of where I want my career to go, I’ll regret it. And so I took the unconventional advice, which was, I quit my job. I found a different job in Jacksonville, where you lived.

Jason: But you found a job before you quit your job.

Caroline: I found a job before I quit my job. I started putting feelers out about three months in. I started emailing. I used your network. I started emailing people that you knew in the advertising and marketing world in Jacksonville and said, do you know of any positions available?

Jason: Which Jacksonville was so small, I pretty much knew everybody at that point.

Caroline: Exactly. There was kind of like the top local agency in town. They were starting a social media department, and they were looking for people. And so I said, I’m into social media. I can do this. And I flew down to visit you and interview for the job, got the job. Then I went and quit my other job, and I took a huge pay cut for the time. But I just thought to myself, A, I have a good feeling about this relationship. If it doesn’t work out, I’ll be okay, but B, it’s worth taking a risk on this relationship because I trust myself that I can figure out something with my career and it’ll be fine.

Jason: So you worked at the Durham agency for, like, six months, then you moved to Jacksonville, and you worked for that agency for…?

Caroline: A year.

Jason: A year.

Caroline: Yeah. I quit the week after I got employee of the month.

Jason: Yeah. Fantastic. What I was going to bring up that I thought was interesting was you mentioned, like, I didn’t want to work in an agency where I only worked on local accounts. But I would say the funny thing about that is it was probably less stressful to work at the agency with the local accounts than it was to work at the big agency. Right. So it’s like the dream is, like, I want to work on these big accounts, but that was actually more stressful than the smaller agency that was actually an easier job.

Caroline: It was less creative in some ways, but it was less stressful as well, for sure. Although I still had that chip on my shoulder of, like, I want to be able to tell people I work for clients that they’ve heard of. And so part of the draw of that job was that I got to run social media for the regional McDonald’s co-op.

Jason: Yeah.

Caroline: And now I look back and I’m like, that’s not something to be, like, super proud of.

Jason: Yeah. You were tweeting about Big Macs.

Caroline: I was tweeting about Big Macs, but I still was just kind of married to this idea of wanting to do something that got me validation.

Jason: Yeah. And I think that’s a thing that we have seen throughout our lives together is, like, your not need for validation, but, like, your drive for validation.

Caroline: Yeah. It took me a while, and I definitely feel like I’ve broken that habit, but it took enough time to pass of me going my own way. I think, honestly, the first big fork in the road where I chose myself over validation was when I said I don’t want to go back to New York. That was a crucial decision in my life where I listened to my body, I listened to my soul, and I said, this does not make me feel good. It is not worth it to work on. I was working for Mars, which is like, I’m in meetings about M&M’s ads. I’m working on AT&T commercials when that was, like, a big thing. I’m working on really cool stuff, but it’s not worth it for me to feel this anxiety and this pit in my stomach and, like, I worked in this dark office with sad people.

Jason: There was a Ronald McDonald’s statue in the building.

Caroline: No, I’m talking about New York.

Jason: Oh, sorry. Yeah, sorry. I was moving forward to the other dark building that you worked in, the basement.

Caroline: That building was dark as well. Durham was a cool building.

Jason: Durham was awesome.

Caroline: Like, great building.

Jason: That was awesome.

Caroline: And honestly sold me on it.

Jason: All right, let’s move out of the advertising agency years and you started working for me. I’m curious to know from your side what you can remember of what that felt like. So you went from commuting to an office, working around other people in cubicles, doing meetings, like, all the standard nine to five-y things, to now literally working in the upstairs bedroom that I had converted into a quote unquote office and helping me put on a T-shirt every day.

Caroline: Yeah. Do you know what’s funny that what I remember about that time? So if you recall, you didn’t actually have that upstairs as an office. Like, we did that together. You would just work from the couch and from the dining room table, and you would just work wherever.

Jason: But I had that office set up as a live studio.

Caroline: Studio, yeah, exactly. But you didn’t have desks, yeah.

Jason: I was like, what was that room?

Caroline: And the reason that that’s important to mention is because what I remember about that first six months is you were still speaking all the time and traveling for videos and traveling for stuff, and so you’d be gone for, like, days at a time. And I would stay in my pajamas and sit on the floor of our living room, using the coffee table as my desk, pretend to work, and I would watch full seasons of Dawson’s Creek. And I just remember hitting this point because and the reason I share that is because I don’t think enough people talk about what a strange transition it is, and maybe there’s enough content now where people say, like, how to structure your day and how to be productive. At the time, productivity was not a thing.

Jason: In 2011.

Caroline: No one’s telling me how to actually get shit done. I was so confused. I was going from this world of academics and early career stuff where people are like, here’s what you do every day, to me being like, what do I do?

Jason: And also, you convinced me to hire you to help solve some of my problems. So I was like, I don’t have time to tell you. You know what you need to do. I have to get on a plane, figure it out.

Caroline: And I mean, I was doing some stuff, but I certainly didn’t need to take a full day to email five clients for their logos and then watch Dawson’s Creek all day. But I think I needed that time to almost like and I’ve always been like this, I have to take it so far. I had to be so unproductive in order to almost like the hot stove of feeling how not good that feels in order to bounce back and be like, productive again. Does that make sense?

Jason: Yeah.

Caroline: So I learned how to I remember discovering Teux Deux, the app or whatever.

Jason: T-E-U-X D-E-U-X.

Caroline: Yeah. I remember discovering that and being like, I’m going to make a to do list and then I’m going to set what I’m going to do every day. And then I started to really like it because I started to put my strategy hat on and then we would have brainstorm meetings about coming up with really unique concepts for different sponsorships. There was a little bit of a learning curve in terms of how to actually get things done and being my own self starter, but I think I picked it up pretty quickly. But that’s what I remember about that time.

Jason: Yeah. Do you remember being more fun or as fun as you thought, leaving the agency world to work for my company?

Caroline: A million times for fun.

Jason: Yeah.

Caroline: I also remember the high of going to a movie in the middle of the day or going to the grocery store on off hours, or being able to go leave for lunch and spend as much time as we wanted at lunch. This is something that always really made me feel unhappy in the corporate world, was like this weird feeling of being like, you have babysitters, you’re just like, what? And I remember one time I had to leave. This is still I’m working at the agency in Jacksonville, and I think we were getting ready for a party or something, and I had to go get props. And so I got to leave in the middle of the day and take my car and go drive to like, Old Navy or something to pick up a prop. And I remember the freedom of driving in the middle of a workday, not at the times of the morning or the evening. And the absolute high of that feeling and being like, oh, I can’t be just a cog in a machine. Not when this exists.

Jason: Also, this freedom in the middle of the day to drive around is amazing.

Caroline: Is amazing. Yeah, I was just never going to be cut out for that world.

Jason: Yeah, I definitely remember. I mean, when you started working for I Wear Your shirt, that is when I had already hired the multiple shirt wearers. So I was managing four other people. I was still wearing a shirt. Then we had an operations person. And then you were helping with kind of like client relations, but also just like a bunch of other creative and strategy stuff. And at that point, I remember the luster had worn off for me on the daily freedom and doing things. And I was just then so overwhelmed by all the stuff that I had to do that, when we would go to movies in the middle of the day, I couldn’t shut my brain off. All I could think about was like, oh, I hope this person got their video up today, and you’re probably on the other side. You’re like, this is amazing.

Caroline: Yeah. And I did honestly have it kind of made in the shade because, going into to me working for you, we had lots of conversations about and I think I was really the spearhead of this conversation.

Jason: I was literally the spearhead of no conversation.

Caroline: Yeah.

Jason: I was so overwhelmed that I was just like, thank you for helping in any way whatsoever.

Caroline: I said, here’s what’s going to happen. You’re going to hire me, and you don’t have to pay me very much because I already live with you, so I’m not paying rent. So cool. You get a discount on my rate. Great. And here’s what I’m going to help you with. And here’s how I think it should work. I think you should still be the boss. I think you should treat me when we’re at work like I am here to support your vision. I think… I was just, like, setting the boundary really clear early on because I thought that if I stepped in and started suddenly like you and I acting as though we were as we do now, which is we’re partners in the business, that it would create problems between us.

Jason: Oh, and it probably would have just because of my ego would have been so fragile at that time.

Caroline: And also, I was so new, so I honestly would have been talking out of my butt. And so I think I had the emotional awareness to be like, I think this is going to work better for us. So at the end of the day, every decision is yours and you can own it. And I think that was the right move. But I imagine looking back, that must have been really hard for you because you didn’t have anyone you could share the burden with, really.

Jason: Yeah.

Caroline: You know what I mean? It was a gift and a curse because on the one hand, there wasn’t a lot of conflict because you could just bulldoze forward and make decisions. But on the back end, you didn’t have anyone that you were in the trenches with, taking on the burden of the business. Maybe I’m selling myself short in saying that I don’t know how helpful I would have been at that time, but I was so green, I just didn’t know anything about business.

Jason: I feel like I was still so green, too, just because I was so in the business. And I think this is what a lot of people fall fall into, is, like, you’re in the day to day that you can’t zoom the lens out and see what’s the bigger picture here? What am I actually trying to get to? As opposed to just like, I’m just, like, slogging through some tasks to tomorrow when I have more tasks, to the next day when I have more tasks. And it’s like, but what am I actually trying to do? What’s going to actually get me to the freedom that I thought this whole way of working would accomplish? So let’s move from the I Wear Your Shirt years because we talked about that in the J list time. We talked about that in my interview. Now…

Caroline: Did we just call it the J List episode?

Jason: The J List episode. You started a little company called Made Vibrant.

Caroline: I did.

Jason: So this actually was you started this while I Wear Your Shirt was still going.

Caroline: I did not.

Jason: Oh, no, it was at the end.

Caroline: No. Yeah. The way that it happened was…

Jason: You had Clumsy Crafty Happy.

Caroline: I had Clumsy Crafty Happy, which was my Blogspot blog.

Jason: Nice.

Caroline: Which I actually started when I still worked for Dalton, which was the agency. And I had a blog. And it was just like, DIY projects and creativity and thoughts and things like that. But I do think that was so crucial to just getting my writing voice and being creative and practicing, like, publishing something online. But then what happened was when I Wear Your Shirt closed and you said, hey, I can’t pay you anymore, meaning me and Sean.

Jason: The last two survivors.

Caroline: The last two survivors. I looked around for a job I thought I’ll do, like, a remote job. I remember actually Marie Forleo was hiring a customer success person. I was like, I could do this. At least it’ll be sort of in the same world and whatever. And you’re like, don’t do that.

Jason: Yeah.

Caroline: You were like, you’re creative. You can do things. I had taught myself design, A, in order to make cooler header images for my Blogspot. I taught myself a little HTML to do that. I remember I taught myself design because I put together, like, our media kit for I Wear Your Shirt and things like that, Photoshop. And so you were like, you have these skills, why don’t you try to do something with it? And so what I did was I started a portfolio site called Caroline Kelso Design and Illustration. And I was big into, like this was, like, me becoming, like, an artist. And I was getting into hand lettering, and I was getting into illustration and things. And so for about a year, I took all kinds of weird, odd design projects. Like, do you remember a friend of a friend paid me $500 to design the designs for Etsy Decals that she wanted to sell on Etsy? The Etsy market was big at the time. So I did that job. I did some illustrations for a friend of a friend’s book. I made a hand drawn blog header for a friend’s sister. Like these types of little…

Jason: Just small things, yeah.

Caroline: I did a custom hand illustrated baby shower invite for a high school friend. These are the things I was doing. Right. And I’m charging, like, $100, $200. $500 was, like, really a big deal. And then I decided okay, I’ve got a little bit under my belt. I want to create a brand that is bigger than just a design, freelance design. I want it to be a blog. I want it to be a brand. Right? Which actually was like me getting into branding. And so that’s when I launched Made Vibrant, I wanted it to be this bigger story where I could mix my love of personal development and creativity. And that’s what Made Vibrant was all about. It was like becoming your brightest self. And I did design as well.

Jason: And you did that through three separate websites so you could really keep it.

Caroline: I couldn’t find a theme, Jason’s referring to I couldn’t find, like, a WordPress theme that I liked that would have these three things. I wanted a cool blog layout that I liked. I wanted a cool portfolio layout for my design site. And I wanted a shop because I thought I was going to sell, like, art prints.

Jason: Now, this is 2013.

Caroline: What I did was I bought three themes, and I made,

Jason: You figured it all out.

Caroline: And I then bought a fourth theme in order to make a website to pull it all together.

Jason: Yeah.

Caroline: And it worked.

Jason: It’s fine.

Caroline: It’s fine.

Jason: Everything’s fine. But these are the funny things that I think folks who start a business now or, like, pivot to a new idea, they’re like, oh, I got to do this perfect. It’s like, no, you can have three separate different entities.

Caroline: Also, looking back, what I didn’t realize was that, no, you use your blog. It makes no sense to separate your studio site from your blog because you use your blog to get eyeballs on your studio site. And if you separate them…

Jason: Seems like it worked out for you.

Caroline: It did work out for me.

Jason: All right, so this is like 2014 time. You’re doing Made Vibrant stuff. You’re starting to do hand lettering things. You’re working on Better Branding Course. You’re working with a couple of different clients. But I’m finding my way. We decide to move to California.

Caroline: Yes.

Jason: How did that feel and where did that come from? And did you see that happening for us?

Caroline: I did because we were both aligned in wanting to move, for sure. I remember that much. I remember us both looking around and being like, this was right after I Wear Your Shirt. We just needed a fresh start. And we were starting to really feel the limitations of being entrepreneurial in a city that didn’t always… There were things happening. There were entrepreneurial things happening. But it was like such a small percentage compared to what we wanted. And so we just wanted to move to a place where there are more people like us. We had landed on San Diego. We’re going to move in with our friends who are also coming from New York and entrepreneurial.

Jason: Just adult roommates.

Caroline: Just adult roommates.

Jason: Yeah.

Caroline: But to answer your question of how did that feel? Exciting. Exciting. I don’t remember feeling scared, actually.

Jason: Yeah.

Caroline: I don’t. I remember feeling like I’m ready for a fresh start. I remember the only fear I remember experiencing was when we sat down with our friends before we had made the decision, and how this all came about was actually at, like, a conference.

Jason: Yeah. At a breakfast at a…

Caroline: Brunch spot where a Margarita was involved. And they were like, we’re thinking of moving. We were like, we’re thinking of moving. They were like, Tell me your cities, and we were, like, telling, we’ll tell you our cities. And we all landed on San Diego. And Jason, like, over Margaritas is like, let’s move in together. And then before I know it, we’re doing a Zoom call a month after that to actually pick out places together.

Jason: We’re saving Zillows.

Caroline: This is so true about our relationship, but Jason is the gas, and I’m the brakes.

Jason: Accelerator. We say accelerator because it’s electric movement.

Caroline: Okay. Jason is the accelerator, and I’m the brakes. Way to really…

Jason: Yeah.

Caroline: Do your part to fight climate change one metaphor at a time.

Jason: You know what I’m doing.

Caroline: He’s the accelerator, I’m the brakes. And I remember the fear of how quickly things were moving because I need time to process.

Jason: See. You were afraid.

Caroline: I was afraid, but by the time that I just sort of surrendered to the moment.

Jason: I think this is a good metaphor for our lives together, which is like, I’m always pushing to do a drastic thing or, like, a big thing, and I’m just because I just see it as like, none of these things are ever permanent. Right. It’s like you can always undo these things, whether it’s moving across the country and selling all your things, we could go buy all the same crap again. We could move back to where we were. Whether it’s starting a business together and closing our two businesses, we could undo it, and we could moving to Europe, like, tomorrow, we could pack up our things in our two suitcases. I don’t know how we’d fit it all, and we would just move back to where we want to go. All of these decisions have some sense of impermanence.

Caroline: Which is so funny because going back to the conversation about when I decided to quit my job and move back to Jacksonville, that’s absolutely how I felt. So that’s why it’s like, deep down, there’s deep alignment in that philosophy. It’s just funny because me against someone else in the world, I’m the accelerator, they’re the brakes. Me versus you. You’re the accelerator, I’m the braked. So it’s like I have the same adventurous spirit that you do. It’s just that you move at a quicker pace than I do.

Jason: I’m just faster. I’m the dual motor. I’m the dual motor, model three.

Caroline: You’re the dual motor. And so by relative standards, I feel like I seem like the brakes, but I’m really not.

Jason: Yeah.

Caroline: I wouldn’t do all of this…

Jason: Just in comparison.

Caroline: Just in comparison. And I wouldn’t say yes to all these things if I wasn’t actually aligned on them because I think you know me well enough to know by now that I don’t do anything I don’t want to do. But every decision in our lives that you have pushed for, even if I felt the instinct to slow us down, and I have slowed us down in all the best ways, I think, to say, like, let’s really think about this.

Jason: Do we really want to buy Bitcoin in 2011? No, we don’t.

Caroline: But every decision that you have, every unknown frontier that you have pushed us towards, has been immeasurably wonderful for our lives.

Jason: Yeah. And I wasn’t trying to take credit for that in any way whatsoever.

Caroline: Oh, no. I give you credit for that.

Jason: I was more just sharing the…

Caroline: Dynamic.

Jason: Yeah. How they come together. So Made Vibrant is going. And the one part of it that I wanted to highlight here before we start to get into the round down round is the Abstract Affirmations project.

Caroline: Okay.

Jason: Because I think…

Caroline: I forget I did that.

Jason: This project is similar in a lot of ways to my I Wear Your Shirt project in the daily challenge for an extended period of time. And I’m curious, looking back on it, A, if you want to quickly describe it, B, what you think your biggest kind of takeaways were from it moving forward, and if you still use any of those lessons today.

Caroline: So Abstract Affirmations was a project that I decided to do. I think it was the year 2016 where…

Jason: I have it in my notes here.

Caroline: Yeah. Every day, I wanted to do a painting and sort of a hand lettered…

Jason: But this is a physical painting.

Caroline: A physical painting. It did end up being digital because I got an iPad. You surprised me with an iPad, but a painting mixed with a hand lettered message, affirmation. And I by that point, I had been doing that already, like, on my Instagram and kind of sharing these little, like, life lessons, which now seems so obvious because that’s, like, all people do on Instagram now, but, like, 2014 to 2016, not that many people were doing that. And then I also, on top of that, wanted to sell the print. So it was also an exercise in selling my art as well as and really the point of it was, like, I wanted to develop my artistic voice. I wanted to develop an artistic style that was on my own. And I felt like daily doing a daily challenge was the best way to get me there. I had been doing monthly hand lettering challenges for people and hosting those, and so I was a big believer in challenges. But a daily challenge was really scary, and it was an incredible project. And so I would share each piece on Instagram every day, and I would write kind of a long piece about it. And so it was this beautiful body of work where I got to hone my skills as a writer, I got to hone my skills as an artist. I did find what I believed to be kind of my style and my voice. And so it was ultimately a really positive thing. I learned how to sell my art. I made some good money with it. It’s actually what ultimately brought my book deal as an opportunity because my book agent found me through that project. And so it was really great. The downside of a daily project is that it’s going to burn you out. It just will if you don’t build in breaks. And so I didn’t even make it the full year. I think I made it 280 days or something like that. But I just started to get so bored with it all. And it went from being something that was pushing me forward to something that was holding me back. And the moment that I’ve recognized that change, I decided it doesn’t matter that I’ve given myself this challenge, like, I know myself the best. And it’s that classic thing of you have to know when to push on and you have to know when to quit. And it’s just nobody can tell you that except for you. But I’m still so glad that I did it, especially because I can look back and I have this body of work that I’m really proud of, and maybe I’ll come back to some type of daily project in the future. But yeah, it gave me a sense of it did a lot of things for me. It helped me fight perfectionism because every day, even if the piece, I didn’t love it, I had to put it up there because I had to move on. And that is the best way to get over perfectionism and to build a body of work which builds confidence, because you just go like, you’re not going to look at all the couple ones that I don’t like. You’re going to look at the general amalgamation of the entire body of work together. And I’m really proud of that. So it taught me to kind of fight that perfectionism, taught me what my creative voice is. It allowed me to connect with a lot of people who loved my art. It built my audience, like, all these things that were really positive from it.

Jason: Yeah, I always think back on that project, and I’m like, I think this was such an interesting project because you got to see what the daily creation thing was like that I did for so many years. But I also look back on it and I remember when you kind of committed to it, and I was like, don’t do it. I know how hard this is going to be, even if it’s just making a piece of art is still a ton of work every single day of your life. Plus, you’re still running a business like you’re still doing a bunch of other things. But I look back. And I’m like, I wonder if it was, like, a 90 day project, if that would have been, like, enough.

Caroline: Probably.

Jason: But it’s hard to know. And it’s also like, we talk about this a lot. We’ve both had burnouts multiple times throughout our entrepreneurial journeys now, and I think every single one of those is kind of necessary because it’s the hot stove moments where you realize, like, okay, now I know not to push to do this. And then you do something else, and it’s like it seems similar, but it’s actually, like, a different way of burning out where you go, okay, now I know not to do this.

Caroline: Yeah. And to your point about, like, would it have worked at 90 days? Probably. But this is where we’re a little bit similar in that I always want to do the thing that most people won’t do. Most people won’t commit to a year long project because they can’t stick with it that long. And there’s a good reason for that, right? Because burnout. But I was still at that place where I was like, if I’m going to do this, I want to really do it, and I want to challenge myself. Again, this is another place where I think you and I have overlap, is ultimately, we do like to challenge ourselves. I’m a believer that you do find out the most about yourself when you bump up against something that is very challenging. And so I’m always on the lookout for things that are a little bit scary to me, but with the flexibility of going, I can walk away at 280 days and not feel any type of failure whatsoever. Like, was it a hard decision? Yes. Because there was something about that clean 365 days that I wanted to do, but I don’t feel like that project was a failure by any means.

Jason: Yeah, I don’t look at it that way either. Obviously, you’ve got a book deal out of it.

Caroline: Yeah, exactly.

Jason: You have 280 pieces of original art.

Caroline: Exactly. And so that’s my advice to some people sometimes, is, like, shoot for the hard thing and really give it your best shot, but then know when to walk away and just kind of hold it loosely.

Jason: As we say around here, shoot for the stars and you end up on the moon because the stars are further away.

Caroline: Right. Shoot for the star. Yeah, exactly. Shoot for the stars and land among the moon. It actually, though, brought up another point, which I think we’ll do a podcast about this at some point, but it reminded me of that…

Jason: On my interview show?

Caroline: No.

Jason: On your interview show?

Caroline: That other show, What Is It All For? You know that one?

Jason: Got it.

Caroline: But we had a conversation the other day about the site of commitment. And so what that project did for me was that it made me go all in on a commitment to myself, which then gave me permission to carve out an hour every single day for my art. And I have not done an hour on my art for that many days in a row since that project. And so there’s something about a big commitment, a big thing that you’re aiming for that gives you mentally the reason to go, I’m going to prioritize this and carve out time in my day to do my art. And that’s the part I miss. The part I miss is giving myself a reason to spend an hour doing art every day.

Jason: Yeah. All right, you want to get to the round down round?

Caroline: Round down round.

Jason: I have more round down round…

Caroline: You have a rounddown round on your show as well?

Jason: Yeah.

Caroline: That’s so interesting.

Jason: I have more round down round questions than you did.

Caroline: Okay, so go faster.

Jason: Because I just had a bunch of random things I wanted to ask.

Caroline: Oh, great. I can’t wait.

Jason: These are kind of all over the place.

Caroline: That’s what random means, actually.

Jason: The woven journey of your life that has come to…

Caroline: That has come to…? Okay, great.

Jason: That’s come to an end.

Caroline: Great.

Jason: What’s a popular business idea you wish you’d have come up with? So not like, I wish I’d invented Instagram. What’s one that’s, like, realistic, that you’re like, oh, I had that idea, and I…

Caroline: I know there’s an answer to this, but I have to come back to it.

Jason: I can give you mine if you want.

Caroline: Okay. Go ahead. Yeah.

Jason: Mine is Wirecutter because I had this idea in 2006 and it was a website called Piqul. It was P-I-Q-U-L. This is back when, like, Flickr was a domain and Twittr was, like, with no E-R. And the idea was you would fill out a search box and it would say, I’m looking for the best blank while blank. So, like, headphones while running or knife while cooking or whatever. We thought through, like, a whole bunch of stuff. This is just me explaining it now, 17 years later. So I don’t remember the nuances of it, but Wirecutter basically became this exact thing where you’re like, I’m looking for the best vacuum. And so they just go through and they do, like, a full rundown of the best vacuums and they’ll just tell you the top three.

Caroline: I’m just now realizing that the name is related to the idea of picking something.

Jason: Of picking something, yeah.

Caroline: But you decided to take all the letters that actually make the word pick, P-I-C-K, and remove them.

Jason: Well, because it was cool at the time. So here was the reason for the name.

Caroline: I know, but when you add the Q, suddenly I’m not thinking about the word, pick, P-I-C-K.

Jason: But also it was a pickle. You’re in a pickle to decide what you’re choosing.

Caroline: Okay.

Jason: That was also…

Caroline: Oh, I do like that.

Jason: Thank you.

Caroline: Okay. I do like it.

Jason: Yeah, I let that domain go a long time ago, unfortunately. Do you have your popular business idea you wish you’d have come up with? It doesn’t have to be something you thought about. Just more like, Ooh, that’s one, like, I wish I would have done.

Caroline: I’m thinking I was going to say one, but I still want to keep it for myself, even though it kind of exists out there. Oh, this is not my idea.

Jason: That’s what I’m saying.

Caroline: I still think of your idea of Yimi. Yimi, that was, like, way ahead of its time.

Jason: What was that?

Caroline: Okay.

Jason: I even had shirts made of this.

Caroline: It was an overlay. It was like a Chrome extension type style thing. It was an overlay where you could kind of like Pinterest, where you could add things to your Yimi, but it was public wish list, so it’s like I could… It’s a little bit like Pinterest now, but it wasn’t really big at the time, where it’s like, as I’m shopping, I add things to, like, Caroline’s birthday Yimi or whatever, and then I send the link to all my friends where it’s like…

Jason: Yimi that.

Caroline: Yimi that.

Jason: Yeah. Oh, that’s funny. I forgot about that idea. There’s so many of those little things I’ve forgotten about.

Caroline: The amount of ideas in our idea graveyard is just… So I don’t know. Go ahead.

Jason: Okay, great. Next question. Again, round down round. That’s very random. It’s the round down random round. That’s what mine is. Yours is the round down round. Mine’s the round down random round.

Caroline: Cool. That’s really different.

Jason: What’s the most memorable moment that comes to your mind in our 13 years together that’s not our elopement?

Caroline: Impossible.

Jason: Just like what’s… It doesn’t be the most. I’m sorry. It could just be like when I ask you right now, what’s just like a really memorable…? And also I’ll caveat to this, like, a mundane moment.

Caroline: Okay. Because my immediate thought was arriving in Tahiti.

Jason: Okay, well, then it comes to you. Like, the most memorable moment is walking on that.

Caroline: That’s definitely…

Jason: The overwater bungalows. We’re looking at a screen saver.

Caroline: One of the most surreal feelings I’ve ever had in my life.

Jason: Yeah.

Caroline: Also, we were just, like, very sleep deprived. It takes a long time to get there, but a mundane moment. I love these.

Jason: I know. I know you do.

Caroline: A mundane moment. You know what’s one that I just have been thinking about lately because your birthday?

Jason: Go ahead.

Caroline: Maybe this is mundane, but it’s actually quite recent. But your birthday during the pandemic.

Jason: Oh, with my Lamborghini?

Caroline: Yeah. It was really fun.

Jason: When I say my Lamborghini, I mean the one that you made me out of paper.

Caroline: Yeah, I made you… Jason wanted to do, for this birthday, this driving experience thing, but obviously it was during lockdown.

Jason: This was like, ten years of thinking about this.

Caroline: Yeah. Leading up to the pandemic, I was like, this is the birthday where I’m going to do it. I was doing all this research of this exotic car thing and whatever, and it didn’t work out because of the pandemic. And so where did I get the paper for that poster board? Did I just tape a bunch of paper together?

Jason: I think you did.

Caroline: I think I taped a bunch of printer paper together.

Jason: No, no, it was your watercolor paper.

Caroline: Because I remember it was my watercolor paper. You’re right. And I drew this Lamborghini, and I set up two chairs in our living room, and I found a YouTube video of, like, a Lamborghini point of view Lamborghini Drive. And there was other surprises I had for that birthday, but anyway.

Jason: The charcuterie board was great.

Caroline: The charcuterie board.

Jason: But yeah, you found a YouTube clip that was driving through Italy in, like, a point of view clip. So you set me up and you brought my sunglasses out of the closet, and you’re like, all right. And you started the video. If you go to my Instagram, which I’m not on anymore, but it’s still there, @JasonDoesStuff on Instagram. You can see a photo of this. It’s not too far back because I didn’t post much in the past four years or three years. So there’s a photo of me. You can see the setup that you did.

Caroline: My favorite mundane stuff with us is just, like, almost like the kid-like stuff that we do. Like, the weird stuff like that where we just…

Jason: Do you want to know mine?

Caroline: Play games.

Jason: It’s also car-related.

Caroline: Okay.

Jason: 2013, I’m at rock bottom. We have no money financially. I buy a 1947 Chevy 3100 truck.

Caroline: Yeah, that was a bad financial decision.

Jason: Bad financial decision.

Caroline: Good life decision.

Jason: And this truck is super old. It barely runs. It smells like gas when you fire it up. But I will never forget those drives that we would just take on this little small highway behind where our house was, with Plax, our dog.

Caroline: And we put Plax in the front seat.

Jason: He would sit in the middle seat, but it was just a big bench seat. It was just three of us. He would sit in the middle of the bench seat.

Caroline: The dash has holes in it, so the heat from the engine is coming into the cab.

Jason: You had to drive with the windows down.

Caroline: It was great when it was Fall or Winter because it was, like, kind of a heater.

Jason: Yeah, windows didn’t work, so the windows were always down.

Caroline: It was very low to the ground. So if you went to any driveway that was like… You would just hear metal onto concrete.

Jason: But just like, there’s no stereo. So it’s just like us, like, driving and just, like, chatting, and it’s just loud. Not like, super loud, but it’s just, like, just rumbling. And I’ll just never forget. That was just such a special, those little mundane moments of that.

Caroline: I totally agree.

Jason: What does our life look like in five years?

Caroline: Interesting that I ended on, like, a future planning thing as well.

Jason: Yeah.

Caroline: In five years from now, I think we’re still living in Portugal. I think it’s entirely possible we live even in our… Even this house.

Jason: Wow.

Caroline: I don’t know. I want to find a way to make that happen.

Jason: Yeah. There’s a book called The Secret. I think it might help you.

Caroline: Okay, I’ll check it out. Never heard of it. I think we have one child.

Jason: Okay.

Caroline: At the time. I think they are an angel. They never have…

Jason: Children are the best.

Caroline: Honestly, never have needs.

Jason: Transcendent.

Caroline: Transcendent.

Jason: They also help make pour over coffee.

Caroline: Yeah. They actually never cry when Jason’s making coffee. It’s the weirdest thing. They just are like a sweet baby angel while he just makes peaceful coffee. Those of you who listen to the end of last episode will get that. No, yeah. I think we’re learning what it’s like to be new parents, but I also see for us, still loving business and just enjoying the process of building businesses. I think it’s going to be an adjustment, of course, to figure that out. But when I envision it in my head, it’s like a really fun period of life where I think of… This is bad, but I think of some of the most fun that we had being parents to Plax and just some of the chaos of that, of trying to get his nails done. And I’m doing wall sits while I’m holding him and you’re trying to get his nails and I’m like singing to him and us figuring that out or when we got to the point where we had to bathe him every day. And I’m in the bathtub with him and we’re trying to figure out every way that we can so he doesn’t jump out of the tub and stuff. That type of chaos, that joyful chaos, is like what I imagine five years from now is like.

Jason: Okay. That made me think, do they have business nannies? They have like, a nanny that could come and watch our kids?

Caroline: Yeah.

Jason: Is there a nanny that can come and watch our businesses?

Caroline: I think that’s just called, like, an operations person.

Jason: Okay, cool.

Caroline: So we’ll get a business nanny.

Jason: A business nanny.

Caroline: Yeah.

Jason: Shout out to business nannies out there.

Caroline: I don’t think they like being called that… is the thing.

Jason: Okay. I don’t want to belittle their… like that’s a big deal. They are very helpful.

Caroline: Yeah.

Jason: Also, like, strong believer in nannies around here.

Caroline: Very pro nanny.

Jason: Very pro nanny. Do you want our kids to go to college?

Caroline: I don’t think that I have restrictions around that. Do I want them to go to college? College was a positive experience for me, socially. I think it was it’s this, like, time period where you’re, like, kind of suspended between…

Jason: College was also a positive experience for me, socially.

Caroline: I know it was. So if they can, the pitch that I would give them to college is like, don’t go to college because you think you need to do X, Y, and Z for us, go to college because you’ll never get this period of your life back where you’re sort of caught, as Britney Spears would say, what is it? I’m not a girl, not yet a woman. So that’s what I want for them. I want them to have that time in life where they can figure out who they are and what path they want to go down. But I also could very easily see them if they are sort of more entrepreneurial like you. I mean, we’re both entrepreneurial, but I would say you.

Jason: More predisposed to.

Caroline: More rejecting of convention that yeah, if they came to me, I was like, hey, I don’t think this is the right path for me. I want to go do X, Y and Z. Like, I’m certainly not going to stop them. So I guess it all depends on the kid is my answer.

Jason: Yeah, I think my vote would be even if they want to go to college, which I’m totally for, if they want to. I think my caveat would be take a gap year or two first to travel, to get an internship with a company in an industry that you’re interested in and just experience life before going to college and kind of getting sucked into that system because it’s very easy just to get there and then think like, well, I got to be here for four or five years to finish this out. Especially because I think our kid will probably… kids… will probably end up being a completionist by nature just through growing up parents who are completionists.

Caroline: You think so? Or they could totally go the opposite.

Jason: They could rebel. And I know all the parents that are out there that are like, you can’t have your kids do the thing. They’re going to do the opposite way you think. But I’m just saying let’s just assume that they are completionists like we are.

Caroline: They would want to finish.

Jason: They would want to finish college. Maybe not. Maybe would leave, but I’m just saying, like, I would want them to experience some other type of life before that just to see what that’s like.

Caroline: You don’t want to get caught in the trap.

Jason: Exactly.

Caroline: I get that.

Jason: I have two more questions for you. They’re silly questions.

Caroline: Great.

Jason: Number one, you have to get rid of one piece of technology. iPad, laptop, iPhone.

Caroline: Babe, this is a great question. Phone.

Jason: Wow. Right away.

Caroline: Absolutely, phone.

Jason: Interesting.

Caroline: Because think about it.

Jason: You can’t post on social media on your iPad.

Caroline: Yes, you can.

Jason: Can you?

Caroline: I think you can. I don’t care.

Jason: Okay.

Caroline: Because I’m always posting on social media?

Jason: Well, you just have your private account for our family now.

Caroline: But do I really care that much? No. I’m already bad at texting, which you can do on your computer. But the device I’m on the least out of those three things is my phone.

Jason: This is true.

Caroline: So, easy.

Jason: Okay. I almost put Apple Watch in there, but I was like, that’s probably the easiest one to get rid of because your phone can do like, everything your watch can, but your watch…

Caroline: I really like my watch, but yeah, it’s probably the least.

Jason: So your iPhone? I don’t use an iPad, so if I had to choose between laptop and phone, I’d get rid of the phone, and that would just be laptop only. All right, final question. If you were a candy, what candy would you be? And then you can also say what candy…

Caroline: This is very hard to detach from what kind of candy is your favorite? Because I’m my favorite.

Jason: Yeah.

Caroline: And then so it’s like, I would just be my favorite.

Jason: But what candy are you? Like if you think about, like…

Caroline: Okay. What comes to mind… Now, I don’t care if you like this candy or not.

Jason: No, it doesn’t matter. It doesn’t matter.

Caroline: Okay. So I’m going to go with an Almond Joy.

Jason: Oh, okay.

Caroline: Which one is the…?

Jason: Almond Joy has nothing…

Caroline: The dark chocolate? Yeah.

Jason: Yeah.

Caroline: But Almond Joy is dark chocolate?

Jason: I think it comes with both, to be honest.

Caroline: Okay. I’m a dark chocolate Almond Joy because the dark chocolate because it’s like I love deep, rich experiences and just, like, a depth of, like, tell me your soul. A little bit of coconut because it’s, like, a little sweet.

Jason: Okay.

Caroline: I’m sweetie pie and an almond because a little crunchy. Okay.

Jason: You can crunch.

Caroline: I have a little crunch to me sometimes.

Jason: Okay.

Caroline: And also just all three flavors together, like, interesting and not the total norm. It’s not your average. It’s not your Snickers, it’s not your Reese’s cups.

Jason: Not some M&Ms.

Caroline: It’s a little bit out of left field, a little left to center, but, like, delicious, none the same.

Jason: Do you want to know what candy I picked for you?

Caroline: Yeah.

Jason: You’re a Blow Pop because you have a sweet exterior, but then, like, a surprise fun interior.

Caroline: Surprise fun interior.

Jason: So it’s like the fun keeps going. It’s not like you take a bite, and it’s like, oh, this is all. It’s like a whole change. It’s like a whole different adventure.

Caroline: Babe, that’s very cute.

Jason: Thank you.

Caroline: That’s great.

Jason: You know what candy I thought you would have picked for me?

Caroline: I didn’t pick one yet.

Jason: Okay, go ahead. And you don’t have to sugarcoat it. Pun intended. You can just pick the candy you want.

Caroline: You are Pop Rocks because you put it in your mouth, and you’re like, Whoa, didn’t see that coming. No, you’re a surprise. You’re just like you… Always exciting. Nobody is being your friend or your partner in life and is, like, in for, like, a smooth ride.

Jason: Right.

Caroline: It’s always fun. It’s always exciting. It’s always something new. Keeps you on your toes, and sometimes it hurts a little bit.

Jason: Which is similar to the one that I thought that you would pick for me is a Warhead.

Caroline: Warhead?

Jason: Yeah. Super sour. It hits you, like, first impression. You’re like, I don’t know if I like this. But then you work through all that.

Caroline: You’re like, aggressive.

Jason: Then you work through all that. You’re like, no, I kind of like this. I would probably have this again.

Caroline: Yeah. You’re like, I’m glad I bought that pack of 28.

Jason: Yeah.

Caroline: I’ll pop another one.

Jason: Yeah. Kind of close, kind of the same thing.

Caroline: Honestly?

Jason: Yeah.

Caroline: That’s funny. Both of our answers, I mean, in the explanation, it’s kind of funny. Pop Rocks is, like, not that far removed from Warheads.

Jason: That’s true.

Caroline: Okay.

Jason: Yeah. All right, well, thanks for coming on my show. I appreciate it.

Caroline: I’m so happy to be here. Thank you for the invite. I’ve just been listening for a long time. I really respect what you do here.

Jason: I hope you don’t mind. I’ve got, like, an outro that I always do.

Caroline: Okay, go ahead.

Jason: All right, Cinnamon Rollers. It’s been good layering the cinnamon on your bodies and frosting you with cream cheese and love.

Caroline: No, thank you. Thank you so much.

Jason: Sweetening your soul with a proofed batch of delicious goodness.

Caroline: Okay.

Jason: That’s what we do around here.

Caroline: Wow.

Jason: Yeah.

Caroline: I can’t believe I’ve missed that every episode. I haven’t heard you say that at the end.

Jason: Yeah, well, sometimes I forget. All right, that’s it. We hope you enjoyed this. Definitely, let us know if you want us to do this again. Maybe in another 166 and seven episodes, we’ll do another.

Caroline: We’ll see you in four years. Bye.

Jason: Okay, that’s it. Goodbye.

169 – Jason Interviews Caroline!

(Big Fat Takeaway)

In this interview, we talk about Caroline's early life and career. We share about the importance of taking the extra step to stand out.


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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