114. Finding Fulfillment Via Travel with Kyle Kroeger

Many of the stories my guests share here on Fine is a 4-Letter Word involve dramatic downfalls, tumultuous transformations, and earth-turning evolutions.

Even if you haven’t really had one of those, I’m willing to bet there’s something going on that’s not fine. Let’s put it to the test.

Kyle Kroeger was raised in an entrepreneurial environment with four core values – work hard, do your job and be passionate about it, have your own life and be with your friends, and always ask what else you could be doing.

He went to college, graduated, and started a career working in finance. This is an industry that supports some of Kyle’s core values – work hard, do your job and be passionate about it – but it’s also a structured work environment where you’re not supposed to ask any “what else” questions. Kyle actually enjoyed it to an extent, the money was good, and everything seemed fine.

But fine is a 4-letter word.

Something was missing for Kyle.

He had a passion for exploring and travel. He spent much of his life in Minnesota but had visited Amsterdam while studying abroad and felt like it was home. So he started a side hustle, a travel journal site where he documented his journeys and shared resources to help others who wanted to see more of the word.

He asked himself a question you may have asked yourself: How could he make enough money doing it so that it could replace his finance job and let him truly live his passion?

Along the way, Kyle’s values have been tested, at one point realizing that adhering to Google’s content guidelines was stifling his creativity and passion. What’s more, after all his hard work to comply, Google changed their algorithms and brought him new challenges. This is where I found him when we sat down to chat.

In a moment, when you meet Kyle, you’ll learn more about his philosophy of pursuing your passion and maintaining your authenticity, even when compromising on your core values can make you more money faster. For him, it’s all about sharing his experiences, and one of his great joys is being a resource and guide for others who want to travel more.

Oh, and he lives in Amsterdam now – a dream come true!

Kyle’s hype song is “Lose Yourself” by Eminem.


Invitation from Lori:

Like Kyle, you may find yourself torn between living a life of purpose with passion and leaving an incredible legacy, or doing what seems fine because it brings you wealth and appears to be in alignment with your core values.

If what you’re doing, if how you’re living today, isn’t bringing you joy, it’s time to change.

That’s why I created the F*ck Being Fine Experience.

It’s a life-changing program that gives you the strategies, tools, and encouragement to create new habits that will help you feel more alive, confident, and purposeful.

Discover how it works at https://zenrabbit.com/f-being-fine-program/

The first step is to take a step. Do it now!


Lori: Hello, and welcome to FINE is a 4-Letter Word. My guest today is Kyle Kroeger. Welcome to the show, Kyle.

Kyle: Thank you, yeah. Thanks for having me, Lori.

Lori: We were just talking because at the beginning, when you hit record for recording, it has a countdown of, like, five. And I always feel like there should be "Jeopardy" music running. So that's what we were just laughing about because, run it in your head, "Jeopardy" music. And here we are.

Kyle: A picture of Alex Trebek maybe, too, to complement it. Yeah.

Lori: Right. Because it doesn't matter who they get to fill in for him now that he's gone. It's not the same.

Kyle: Right, yeah.

Lori: Yeah. He's just always that—that's who "Jeopardy" is.

Kyle: Yeah.

Lori: Anyway. Did you watch "Jeopardy" when you were growing up?

Kyle: Not a ton. It would be on every once in a while visiting grandma's house for something, but I didn't go out of my way too much watch it. I was always so immersed into sports. But, yeah, when it was on, it was always a kick. I always liked it.

Lori: Yeah. I love "Jeopardy." And my favorite category is Business and Industry. Or Music.

Kyle: Yeah, Music. That was my jam. And Sports. Those two sections is when I would shine.

Lori: Yeah. So speaking of growing up, what were the values and the beliefs that you were raised with that were instilled into you as you were growing up?

Kyle: I grew up under an entrepreneurial family. Both my parents were entrepreneurs, which, yeah, I feel like that instilled some hard-workingness. Very middle-class entrepreneurs where, yeah, do your job and be passionate about what you do, too. And so growing up and learning, for more of a professional perspective, that was big. But then outside of professionally and those type of values, a lot of independence was important and being active, but also having your own life and being with your friends. No limits of, like, hey, if you want to be with your friends, you should go live and enjoy that. So, yeah, those were big parts of my early years and even to today.

Lori: And then how did those values develop or contribute to who you became as a young adult when you were choosing a career or choosing what to do with your life?

Kyle: I've been looking back on that now a lot lately, being that I love change or being challenged or having uncomfortableness and learning from that. So, yeah, that's really there.

Now I travel quite a bit or even move super far away and write and love those type of things and those challenges. And then even entrepreneurially, always thinking of something else you could be doing. Or the sky's the limit, I guess. And yeah, input is output. Right? If you work hard at something, you should see the results.

Lori: Maybe.

Kyle: Maybe.

Lori: We talk a lot about the whole hard work equals success, but that's not necessarily true. That's what we're taught. And that's what's instilled in us. So everybody's working as hard as they can, but they're not necessarily seeing the success because they also have other beliefs that are wired in there that are contradictory to that.

Kyle: Yeah, that's true.

Lori: Maybe money is evil or being an entrepreneur, you just end up failing because somebody in the family did it, and they failed. Okay, now we're going to go down the rabbit hole of what is failure? Like, they didn't get the result they thought they were going to get and so now—

Kyle: Yeah. It's—

Lori: Yeah.

Kyle: It's a very complex formula. There's that equal by any means. There's pluses, minuses, and maybe dividers that even go into some of that, too.

Lori: Yeah. We talk a lot—and I want to get into it with you, too, because of what your business is, in that it's not just hard work. Yes, you have to do some work, but it's about taking inspired action. And then it's about allowing yourself to recharge and to go have fun and to play, and how important that is. Was that always a factor in what you were doing? Because you weren't always talking about travel.

Kyle: Yeah. In my professional background, I was always in finance and working in very a traditional environment, a traditional office environment. And, yeah, I really wanted to work on something that didn't feel like it was work and felt like I was just having fun all the time. And that's what I do now. So at ViaTravelers.com, a travel website that I run, exploring, which was my huge hobby, and seeing new worlds and cultures, that was what I wanted to do. I didn't have a background in it, but I knew I was passionate about it, so I want to just follow that journey a bit. And so I kind of ran with it, and that's been a great ride so far, obviously. And, yeah, it's a lot more to come.

Lori: What inspired you to go after turning something that you loved into a career? Because a lot of people are at jobs that they're okay. They're fine, and they have something they're passionate about, but they don't see a clear path to how they could turn that into money.

Kyle: Right. In my finance stuff, I felt like I was fine. There was always something. That was the goal when I graduated school. I wanted to do this. This was the job. And I was sitting there working very long hours, and I'm like, "This isn't actually what I'm passionate about. I like it. I do have passion, I guess, for it, but there's more out there, too. And so, yeah, I had that aha moment of, like, it wasn't really all that fine. And so I think testing the waters a bit on the side to truly answer those questions: what do I truly want to be doing?

A lot of people can do anything. It's a matter of what you want to do and staying focused to the trials and tribulations of your passion because it might not be a straight line. And it definitely won't. But when you have that fire, that passion about it, that's when you follow that path. And before you know it, you unlock and learn so many things about it and about yourself along the way. So testing the waters was huge.

Lori: What did you do specifically to test the waters?

Kyle: I went on a handful of trips. I used to love taking photos with my iPhone, but then I stepped it up to digital camera, and then the GoPro, and then to a drone. And so every time I was traveling for a vacation or had PTO, I started with that digital camera. And I was like, okay, this is great. This is fun. I like this. I like capturing the memories. And then I stepped into video. And then I'm like, well, why don't I just build a journal of my experiences and memories that just lives on the Internet that other people could also see? So then I just kind of kept stepping it up, and, eventually, it was freeing enough where I felt like there's enough balance that it was something that was actually sustainable for the future. And I loved doing it along the way, so it ended up being a no-brainer to transition.

Lori: Okay. So you had this journal that you have online, so that's all cool. And then you probably started getting a lot of followers because people are interested in travel. Then how did you monetize that to be able to leave your full-time job?

Kyle: The monetization angle is always very hard with this, but that's okay. Initially, it's not going to be right away. It takes some time. But display advertising is one part, and then affiliate marketing. So that's basically a toll road of the Internet. A lot of people don't realize how many affiliate links exist, but it's a way to compensate me sending people to a different site where they take an action. So if somebody booked a hotel, we get a small commission. And that helps us fund our operations and all of that.

Lori: Yeah. So when you're talking about affiliate, you're talking about you are the affiliate for a hotel, for example.

Kyle: Yes.

Lori: Because when you first started talking about it, just because of my frame of reference, I'm thinking you have affiliates sharing your information, and they're getting paid, which could also be happening because you don't have necessarily a large list on your own, and so you'd use other people's lists or audiences.

Kyle: Yep. It's mainly, yeah, we send people to trusted products that we use to help us travel smarter. And that's why it's an easy monetization per se. It's easy to naturally speak about it. If you're going through the travel rhythm, you know, "This is literally what I use all the time." So, yeah, it just becomes that much easier to talk about it within your journaling of your experiences.

Lori: Yeah, exactly. We're talking about getting some sponsorship for the podcast, actually, and I'm working with somebody. It's only going to be products or services that I use. You're never going to—I was about to say a company that you will never hear me talking about, but because you'll never hear me talking about it, I'm not going to say it.

Kyle: Right.

Lori: But it's some fast food companies that I would never eat at, so those would never be—

Kyle: Exactly.

Lori: It's just a natural extension. Right? Affiliate marketing is about—you're talking about products that you would be talking about anyway.

Kyle: Right. Exactly. And you don't want to be talking about—like, if I had a green living site or something, or sustainability, and I'm recommending them to go with fossil fuels. It just aligns your audience, too, and you're providing helpful information, too, along the way. So that's what makes it a great business, too, as well. It's why I even pursued it more, because you have this alignment of interests amongst your tribe and all of the people that want to share in that journey with you.

Lori: Yeah. How long did it take you from when you got the idea to create an online travel journal until you left your full-time job and this was replacing your income?

Kyle: About a year and a half or so? Yeah, about a year and a half. I'll say that. Yeah, a year and a half. So ViaTravelers started. The name came out when I was in Italy on my honeymoon. Via is "street" in Italian. It's also connection between journey, destinations. So the concept's like street travelers or finding ways to go off the beaten path. So I was trying to think of honeymoon time to leaving. It was probably more like two years, two and a half.

Lori: Yeah, okay. All right. It's interesting, and it's realistic to say that it was two and a half years because sometimes people are like, "Oh, yeah. I left my full-time job, and I just started doing this." And it seems like it's overnight. And people are like, "Okay. Well, if it's going to"—like, it's not realistic for other people to go and think that they could do that same thing. It takes time to build sometimes.

Kyle: Yeah, it really does. I think that's my one thing that I've always talked about to a number of different people that want to go on a similar path. You want to know what you're getting into, and the rhythm, and almost act like, on the side, it's going to take a lot of work because you're going to be doing two full-time jobs. But testing it in a way and acting like, "Oh, this is what my day would be like," can really have some mental clarity and a good level-setting when you do make the switch of being like, "This is now what I do." So, yeah, I always encourage trying it out. And it doesn't have to be right, right away. You can always try something else. And that's the part of testing the waters.

Lori: Yeah, exactly. What advice would you give to people who are like, "I want to do it, but ..."? They have a million different reasons why they can't.

Kyle: Yeah. I always love this one. I think it's as simple as two words, just start. Right? I think "just start" is like—yeah, it's hard to explain, but it's like stepping outside of your house. If you want to go for a run, you have to go and you have to take the first step out of your house. So it can be as simple as that. If you have that mindset and you maintain it, before you know it, reward yourself for the small things. Right? So first dollar of revenue. There you go. That's milestone one. Before you know it, then it's, again, more, something else. Right? Kind of leveling up from ground zero of "just start" to, now, you have a little ladder to climb.

Lori: I love that you just recommended that people celebrate even the smallest wins. The first dollar. So I talk about that a lot, too. It's about celebrating. When you celebrate even the smallest things, the universe rewards you with more.

Kyle: Exactly.

Lori: More things to celebrate.

Kyle: Yes.

Lori: Now, you took the travel thing, and you actually are living overseas now. How did that happen? Is that because you have more access to traveling to different places that you wanted to go, easier? That didn't even come out right.

Kyle: I get it.

Lori: What was your decision there?

Kyle: I totally get it. It was a multiple-angled thing. So I live in Amsterdam now. I grew up in Minnesota. I studied abroad when I was young, and I visited Amsterdam. And I left the city, and I was like, "I really like this city. I want to live here someday," and visited multiple times and still reiterated that point, I felt like, every time I visited. So that was kind of a goal, to be like, hey, live in a whole new place.

And then beyond that, during COVID, I started a travel blog during COVID. It was when I was really focusing on it. A hard time to start a travel site.

Lori: Yeah.

Kyle: But I did a lot of day trips: a lot of nature, a lot of national parks, a lot of state parks; day trips around the Twin Cities of Minnesota and covered a lot of ground there. Covered almost every tourist town in Minnesota. So going to Europe where you can train travel pretty easily and see so many different cultures, so many different places, that certainly helps. So why not give that a try? So it was a little bit personal, a little bit business.

Lori: Yeah, that's cool. And your wife was on board, obviously, because she's living with you.

Kyle: Yes. And our two-year-old toddler did not have a say, unfortunately, because she was young. We told her, and she knows what she's doing now, obviously. I always joke about that, but she's living her best life, and she speaks more Dutch than both of us combined.

Lori: I bet. I was just going to say it'll be really easy for her to learn Dutch.

Kyle: Yeah.

Lori: Yeah, awesome. So I had some notes from our first conversation about creativity and personal development and growth. Let's talk a little bit. What was the path of your personal development?

Kyle: I think the path for development was really focused on expanding your thought process beyond what you're traditionally told is the only way to be. That's a very common thing in very high-level, professional service-type jobs like finance where, you know, "This is the way we do things. Don't stray outside the box," to really wanting to embrace something that's completely different than that where it's more creativity-driven and not numbers and not spreadsheet. So I traded in my spreadsheets for GoPros and things like that. And that was a huge learning curve and was kind of intimidating at times, for sure. But sort of embracing some of that to become more personally developed and learning those to round out your personal knowledge base of yourself, round out your knowledge base by knowing. You can kind of know some of the creative side, but then, at the end of the day, you still have, in your back pocket, some of the things you've learned in other expertise areas.

Lori: Yeah, absolutely. What kind of support did you have? Were people around you supportive of your move, or were they kind of, like, "Dude, what are you doing? You have this amazing job in finance, and you're going to leave that for this?" Didn't you get a lot of that?

Kyle: It was generally neutral, which is actually interesting. Right?

Lori: Yeah.

Kyle: People would be like, "So you're doing this now?" Or people will ask why Amsterdam, I guess. And that answer was pretty clear for me. But in terms of what I was doing, no one really commented on it. Maybe it's the Minnesotan of my friend base. It's like, avoid anything bad or any conflict as much as possible.

Lori: Yeah. We're just not talking about it. It's okay.

Kyle: Yeah.

Lori: It's fine.

Kyle: Yeah. Everything's fine. So, yeah, generally, everyone's come to visit, and that's been really cool to see. And they probably wouldn't have come to visit this area. And, hopefully, helping others take that first step of going on a completely new trip that they might not have otherwise done.

Lori: Yeah. So you're on a personal mission to introduce Minnesotans to Europe.

Kyle: Exactly. One by one.

Lori: I love it. What's coming up next? What are you excited about working on these days?

Kyle: We're working on creating our own products and being more immersed with our community of readers. So anyone that's listening, I encourage you, if you love travel, join our newsletter. You can interact directly with me via email. I respond to all emails. But another example of a new "everything was fine" moment was actually within the last three weeks.

Lori: Oh, good. Tell us about it.

Kyle: Well, so we spent so much time. We have a team of 10 to 12 writers, all with different perspectives of travel and all in different parts of the world as expats. We spent a lot of time reading Google's guidelines for what quality content is and worked really hard to focus on that and develop really good. And we love our content, for sure. But in the last three weeks a lot of the algorithm has changed, and that's impacted us a lot.

So over the last year, we thought everything was fine because we were relying on someone else's guidance, which guidance changes now quite frequently. And so it wasn't fine because we were relying on this one entity and kind of getting jerked around a bit by it. And so we need to stop focusing on that. We need to focus on our people that want to hear our travel stories. We didn't go to 12 countries in the last year for no reason. Right? And so we want to share and help people. That's the biggest thing. We want to solve travel problems and help people. So that is our number one focus going forward now.

Lori: Cool.

Kyle: A lot to unpack there.

Lori: Yes, there is. What is the most interesting travel problem you have solved?

Kyle: I think the ability to see more with less. That's a big part of mine, maximizing your dollar on experiences. It's not really quantifiable, I guess. Probably through our number of people on our newsletter. But one thing we offer is different travel hacking guides where it's simple hacks of ways to find very cheap flights, how to see more in places without—you don't need a massive budget to take that trip across the globe. Right? And so I think helping some people, and I've gotten feedback directly from the newsletter of some of those things like, "Wow, I would have never thought I was going to go to Japan ever in my life, and some of those things that you've provided helped me do that." So one of those is, like, all I need.

Lori: When you said that, I was thinking that people send you questions or challenges that they're facing and that you help them solve it. So I was wondering if you had a story from somebody specifically.

Kyle: No.

Lori: But you just mentioned you helped somebody go to Japan who never thought they would be able to go.

Kyle: Yep. We are going to do a little bit more of that feedback loop, actually, and try to understand. So that's one thing we're doing, actually this week, just interacting and figuring out where that exists. And we're going to do whatever we can to solve that gap.

Lori: Do you have a crazy travel story of your own like, "I can't believe this happened," or "I can't believe I made it out of this situation"?

Kyle: Yes, in a way. One was crazy. I was at a wedding in Outer Banks, and I had a layover. It was the day after the wedding, so a late start to the day. Flew out, had a layover, and then went to Minneapolis. We were supposed to fly the next day to Amsterdam, direct. Instead, we got this crazy idea of, "Let's just keep it going, and why go back home and sleep?" So we got to the airport, figured it all out. Didn't have to pay or anything like that. That was the crazy part, is they allowed us to be on standby, and they told us there were seats available. So we went back home, took a 15-minute cab, dropped off our old stuff. Packed in 10 minutes because we only had, like, 30 to 45 minutes to get back to the airport. But we needed to get all of our other stuff, and so we went back. Just through the old stuff and grabbed a bunch of random stuff. Didn't even know what we grabbed, really, but figured it was enough. And went back and jumped on, and it was back at the airport and ended up in Amsterdam.

Lori: Okay. So you were supposed to go to Amsterdam anyway, but you were supposed to have more time in between.

Kyle: Basically, yeah. And we crunched it. Made it. We figured it out, and it ended up being a whirlwind because it felt like we were in Outer Banks, like, hours ago.

Lori: Right, right.

Kyle: It was pretty wild.

Lori: You definitely cannot fly from the Outer Banks directly to Amsterdam, though.

Kyle: No.

Lori: There's no international there.

Kyle: Yeah.

Lori: Yeah. What's been the biggest difference you've noticed between living in Europe versus living in the United States?

Kyle: Great question. Some of the stuff I kind of knew going in. It was more lifestyle over work. I think one thing, conversation with a lot of people, if you're meeting somebody, or even your friends that you know very closely here. It's like, the first conversation is never work, if at all.

Lori: Right.

Kyle: And if you're meeting somebody for the first time, usually, you generally aren't asking what their profession is, or their job, or status, or anything like that. And maybe it was more my culture before when living back at the States, but that was always the first line of conversation.

Lori: Yeah, absolutely. I mean, I'm in the—well, now I'm being the digital nomad that I mentioned. My home base has, for a long time, been the Washington, D.C. metro area, and that's always. I thought it was just our area, too. But you're saying, Minneapolis, is it? I think it's the same throughout the country. Although I've heard some people in Denver and California, that's not necessarily the first question. But for most of them it’s "What do you do?" And they're not asking what do you do like, "Do you like snowboarding? Are you a skier? Do you play paddleboard? Do you play pickleball or do whatever?" It's, "What do you do as a profession?"

Kyle: Right, exactly.

Lori: It's always the thing. And it throws people off if you are like, "No, but I mean what do you enjoy doing for fun?"

Kyle: Right.

Lori: And they're like, "Oh, oh." But, right. What you're saying in Europe is they don't even talk about business really.

Kyle: Yeah. There's a few people I'm familiar with. I still don't even know what they do or what their job is. And I know them pretty well, enough to text. And I don't know. I didn't ask, and I haven't looked up. I'm not good on social media and stuff like that, so that might contribute as well. But yeah, kind of wild for me. A little bit of an adjustment.

Lori: Yeah. It's a whole different perspective of how to live life. Right? Because, again, it just—what's the word I'm looking for—illustrates, illuminates, highlights how work-focused Americans are. And the rest of your life, that's your side gig—the rest of your life. But your life is really your work. But that's so twisted. That's where we need to rewire the brain, to be like, yeah, work is a part of life, but it's not your life.

Kyle: Yeah, it really is.

Lori: When people talk about work-life balance, I'm like, no, it's work-life integration [? 30:31]. Everything is integrated together. It's not one is one thing, and one is another thing. They're not two different lives.

Kyle: Exactly. That's right. Yeah. And there's a saying. I don't know if it's a Dutch saying, but one of my Dutch friends just told me. When you leave, end the day, or if you're at a dinner table, and the only thing that you can say that you learned that day is something related to work or is work, that kind of like a fail. Or not a fail. So it's like the goal every day is to go to the table knowing what you learned that is outside of work. And you see that a lot. You can hear a lot of people doing music practice before dinner, or playing the piano. Reading. There's a big culture here. That really blew my mind because so many times, that would be the start. And it goes into my point of creativity and personal growth. It was like, hey, maybe you are spending the next three weeks learning an instrument or a language or something. And that can be pretty powerful. It's iterative between rational and personal.

Lori: Oh, my gosh That is gold right there.

Kyle: Yeah.

Lori: This whole conversation, that is a key takeaway. I love it. That's fantastic. All right. So we'll leave that nugget right where it is as we wrap up our conversation. But first, what is the song that you listen to when you need an extra boost of energy? Because you seem pretty chill.

Kyle: Yeah. So I typed it up. "Lose Yourself" by Eminem. It's a little cliché. Right? But I typed it up, and then I gave it a listen. I was like, "Is this going to be the one?" And I turned it on. And I was like, "I'm going to give it a listen." I'm like, "Yeah, that's it. That's the one." It's a little cliche, but I was a little Eminem fan growing up.

Lori: Sure.

Kyle: Kinda loved that. And every time I listen to it, I kind of get back into that younger generation mode of being excited and ready to rock. So, yeah, it works every time.

Lori: Awesome. Love it. And then lastly, if somebody wants to get in touch with you to continue the conversation, where can they do that? And how do they sign up for your newsletter? Because I'm going to go do that.

Kyle: Yeah. You can access the newsletter on our homepage ViaTravelers.com. There's a little button, Join Our Newsletter. It'll open up to an opt-in page where you can subscribe. And then we also have other guides where if you want an Amsterdam guide, just go to any of our Amsterdam articles. And we have a whole specific guide for that. That's free.

You can check us out on socials: @viatravelers with an S at the end. ViaTravelers on all of our social platforms—Instagram, Facebook. You know all of the platforms. TikTok. And then YouTube if you love seeing stuff. And you can see my personal videography. I'm not always doing the vlog style, but most of all of the footage, if not all of the footage, is from me on our YouTube channel, ViaTravelers.

Lori: Awesome. Okay. I will put links to that website in the show notes. Cool. Kyle, thank you so much for joining me today on "Fine is a 4-Letter Word."

Kyle: Yeah. Thanks again for having me, Lori. This was great.

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