How to Earn a Freelance Income to Travel More or Move Abroad

Jenn: [00:00:00] Hey everyone and welcome back to the Travel Mug Podcast. So for people who love to travel, which is obviously us, we are always typically trying to find a way to travel more, and for many of us, the main issues come down to money and time off from work. So this week we are talking to Jen, from Jen on the Run.

Jen has moved from America to Europe and built a successful freelance career that lets her control her time so she can travel more. Jennifer, thanks, uh, for coming on the show. We're excited to have you.

Jen: Thank you so much for having me here. It's great to be here.

Jenn: Yeah. So Jen, tell us about yourself and when your love of travel started.

Jen: Yeah, so I would say my love of travel really started. From an early age, I was very lucky. My parents took me, uh, when I was a [00:01:00] little kid, to Europe. So that was like my first exposure to somewhere completely different. And I don't think I really knew at the time like what much of the historical significance was or anything, but at least I had the exposure. And then from there, like as I got older, my mom drove us, uh, my sister and I, from Michigan to Oregon on a road trip, and then the next summer from Michigan to South Dakota. So like, there was just like a lot of travel from an early age, and I think that just like really inspired a, a lifelong love of travel.

Jenn: Yeah. I love that. I, I think, you know, similar for Meggan and I, you just, you kind of, you get the bug, like people who travel, they know.

Meggan: Yes,

Jen: Yeah.

Meggan: Europe is my favorite. So imagine going there first and seeing that first and then being like, this is how life should be lived. I think that every time I go to [00:02:00] Europe. So that was your first trip? That's amazing.

Jen: Yeah, I was so lucky. I mean, like, you know, like a little kid with gelato, like sitting in a piazza, like running after pigeons. Like that was basically me. And um, yeah, I like just had so much nostalgia about that for a long time.

Jenn: Yeah. Yeah, yeah. So let's like fast forward a little bit to your, um, growing up and, and choosing a career. So did you always plan to work as a freelancer or did you originally have a more like traditional quote unquote career path in mind?

Jen: Um, I actually really wanted to be like high powered corporate executive, like wear like a pants suit, you know, like come home with a briefcase. That's what I wanted to be, is like wild because I did like pretty much the opposite of that. you know, so [00:03:00] like I either wanted that or I wanted to get a job at a advertising agency or a creative agency, you know? So I really wanted like the traditional, like just work hard, to the office, but it didn't really turn out that way at all. So, yeah.

Meggan: how did that lead, how did that, like career path, how did that diversion happen? How are, how did you sort of get into freelancing sort of. Of walk us through, like you sort of went in this direction.

Jen: Yeah. So my first job out of college was working for a woman who had her own business and she worked from home and like given like this was 2013, so it was unusual at that time to be working from home and also being a solopreneur, basically. So I was her marketing assistant and I worked from home and I would come to her home for [00:04:00] meetings and we would go to like onsite client meetings as well. But basically like I didn't know it at the time, but like it was an excellent example. And then through her I met my now mentor who also worked in a similar fashion. So like, I feel like I stumbled so fortunately into the space because I had these examples of women business owners who were, know, running their own show and, and kind of taught me like, oh, this is how you can do it.

This is how it works.

Jenn: Hmm. Yeah, that's, that's awesome. I remember for me, in, I don't know, grade nine, I think when you do like, take your kids to workday, I went to work with my stepmom and my stepmom at the time, so this would've been like. Oh, 2000, let's say five or something around there. And my stepmom worked from home, which in 2005 was a very, very, um, uncommon [00:05:00] and she was a work from home travel agent. So we, um, we planned a fake Disney trip together and then we went to the grocery store and got ingredients and we came home and made soup. And I was like, this is the life. I love this life.

Jen: Yeah,

Jenn: Yeah.

Jen: exactly.

Meggan: life

Jen: know?

Meggan: to be lived.

Jenn: Yeah,

Jen: Right. It's like you can work and make soup at the same time. It's like, yeah, perfect.

Jenn: yeah, yeah. Amazing. So, , a lot of people get overwhelmed with the first steps of starting to freelance. So how did you kind of get over, I'm gonna say like limiting beliefs about like starting a freelancing job. 'cause I know for myself, I've worked corporate, I've worked freelance. There's a big mental barrier to like going it on your own, let's say. So how did that work out for you?

Jen: Yeah, definitely. I think that that is such a [00:06:00] common experience that we all face. Um, and especially in the freelancing space, you know, and if you're new to freelancing, there are those, you know, limiting beliefs like why would a client choose to go with me? Or how do I set my rates? Or are my rates too low or are they too high? So I think a lot of those roadblocks come up in doing mindset work and really knowing your value, I realized that when I did an exercise of, I worked with a business coach for um, I think almost a year, and doing that, working with a coach really helped me see, like I journaled about what is my value, what are the unique things that I bring to the table? by identifying those strengths I [00:07:00] saw like yes. Like everyone may be a writer or a social media manager there, there may be other people like offering those services, but there's a reason why like my particular clients continue to keep working with me month to month. It's because they like the experience of working with me.

They like the, you know, the, the certain strengths that I bring to the table. So I think that doing an exercise where you are really defining your unique value and really believing in that in yourself. It just, you know, it's, it's, it's always an evolving process. It's never perfect. You know, like there's still things I'm learning now. You know, it's, it's always an evolution, but I think that that is really like such a, a helpful exercise, especially in this space.

Jenn: Yeah.

Meggan: Could see that. And I think too, [00:08:00] like, I think that's a helpful exercise honestly in life is sort of like writing down, you know, things that you know, to be positives or strengths and how you could be utilizing that. And I think if you're starting your own business and putting yourself out into the world, that's kind of like a really strong and important foundation to have.

Because if you don't believe in yourself, how are other people going to believe and what you're going to offer them? So I think that obviously the business coach, you know, instilled a lot of really, great things for you to do. But I guess, how did you then make that transition to start putting yourself out there? I'm sure that was a scary step to start actually marketing yourself and, and putting yourself out there. So walk us through, uh, walk us through that.

Jen: Yeah, so how it happened was I did have a full-time job where I was working in an office space, um, and I had a really long commute and I do think it was a bit of good fortune that came my way that I got my first client. So, from there I [00:09:00] was able to start pitching clients. So once I got that first client, then was like, okay, how can I go through this process of building on the momentum? So I think like continuing to pitch is what really like led me to, you know, having more stability.

Jenn: I think so for context, I um, used to be in 2020 when, you know, crazy things happened around the world. I was a full-time massage therapist and, uh, my job was shut down for several months and I could not work. And at that time I'd had a travel blog for quite a few years. So I, I had some skills there and one of, uh, my friends posted online, Hey, I am looking for a virtual assistant. I need them to be able to do this, this, this, and this. And I was like, I can do all of those things. And I basically started a virtual assistant [00:10:00] business based on that, because my friend needed a client and I was like, Hey, I can do this. So I think it's, if you want to start a freelance business or, or even just to have it as a side gig and not have it even as your, your whole gig, uh, it just, you need to like keep an eye out.

You know, what are your business friends looking for? What do they need? Do you have those skills? And really, network has always been the biggest thing for me. Whenever I've been freelancing, it's always been someone I know or a friend of a friend of a friend kind of thing. And so really like leaning in on your network and, and messaging people and saying, Hey, I'm starting this freelance business. These are my skills. Like if you know anyone that's looking like, please pass along, my name is, it's scary to do. It's scary to put yourself out there, right? But I think that it's a really important [00:11:00] step when you're trying to get your foot in the door in this business.

Jen: That's exactly it What I found was it was the personal connections that I had had made with people, just genuine connections like where I wanted to meet for a coffee and have conversation and maybe it led to something where we worked together. Maybe it didn't. Maybe it was just like conversation and you know, a nice, a nice out after, you know, a day out, you know? like, that's what I found is like I connected with other people in my space and then, you know, people started referring me. And I think you become known as, oh, that's the, that's the person who does social media management. You know, then people think of you when they hear of opportunities and they like. It's just mutually beneficial. Like it just [00:12:00] becomes like a really positive, like, oh, I saw this. I'm passing it your way. Or you know, if you know someone who's interested, like you just kind of create that exchange and it's just, it's a beautiful thing. I think

Jenn: Yeah. Yeah. And like you said, you know, when you meet people, it, it might not lead to a direct, you know, business relationship with them, but it leads to them, uh, thinking of you when they see opportunities. And, uh, I think that's something really important to keep in mind. 'cause I think some people have the mindset that if like, oh, I connected to this person and it didn't lead to them being a client, then it was a failure. But like, it a hundred percent wasn't.

Jen: Right. Right. And well, and I think also, like I do wanna add on that is like, how you, how you, your personal branding, like what you choose to become known for is also so important. And I think there's this, this concept that I feel like many of us have heard of now [00:13:00] that like where you, you manifest or you attract, like, what is it again? It's like if you present yourself a certain way, you're going to attract, it's going to come to you instead of chasing after it, you know, like. You kind of just become magnetic based on like what you're putting out into the world will come, will gravitate back towards you. And you know, like out of fear of sounding too woowoo. You know, like I do believe in that. You know, like, I think

Meggan: Hmm.

Jen: like if you, you share your message in a genuine, authentic way, people will just gravitate towards you and they'll know that, oh, like. You know, she's the one who does social media management. Like

Jenn: Mm-hmm.

Jen: you and they'll think of you.

Jenn: Yeah.

Meggan: More. I think it's really important to sort of put yourself out there in a way that you want to receive people. Um, and I think that it's really important that people know [00:14:00] who you are authentically, because I think you can't start any relationship, whether it's business or personal, with, with a, with a front. So I think if you're putting yourself out there and you're being authentic with people, that will come back to you. And I completely, um, agree with that. And that's exactly sort of what you're needing to do as a freelancer. And I think that that leads really well into the next question because there's probably people, you know, potentially thinking of doing this. And from your own experience, or even maybe other freelancers, you know, what do you think are some of the biggest mistakes that new freelancers make?

Jen: Yeah, that is such a good question. Because I think when you're new, the most common mistake that people make is, one not signing a contract and two charging too low, setting your rates too low or working for free. So I would say, I'll start with the first one, [00:15:00] and I think the contract is a big one because I understand where it comes from. You're like, well, I feel like I can trust this person. You know, you kind of tell yourself like, oh, like, I'm not too worried, they're gonna pay me. Or like, I don't wanna, you know, we have this deal and I don't wanna send this a contract and scare them away. You know, like, it looks so legal, you know? So I feel like all of these thought processes, I've had a million times. But when I talk to friends who are starting out in freelancing, like it can cause so much grief later on by not clearly stating like, okay, these are the deliverables, this is what you're getting. We have it written down. This is the payment structure. You know, work, this is the deadline for the payment, or we're dividing into two payments, you know, however you wanna structure your contract. [00:16:00] Just having that piece of paper can just save you so much like time and hours that like cost you more in the long run with the amount of time you're spending, you know, on the admin of like getting paid, you know? So I think having a contract is just a must no matter what you're doing. , So that's a big thing. Then the second I would say starting out, like if you're new yes, you do want to have a sample portfolio, like you want to be able to show the work that you've done. So I do think, it is fair to to gradually increase your rates over time. But that said, like, do research before you throw out a number and, you know, do you, do be competitive in this space. Don't, don't undersell yourself.

Jenn: Hmm. Yeah, I think that's really [00:17:00] important and I'm, I think it's a um, almost like a rite of passage mistake that most freelancers make is like starting too low and then being like, oh no, I need to increase my rates, like in order to cover it. Because when you're self-employed, um, you have way more costs. Like it's not the same as like your hourly rate. At your, your nine to five corporate job, right? Like you need to account for all of the costs that you have, any, um, like programs and systems that you're using. So you really, it, you can't just throw out a number. You do really need to put some time into figuring out what that number needs to be for you.

Jen: Exactly. Exactly. And I do think like the right kind of client or the client that you wanna be working with is also going to understand that that's baked into your rate. You know, your rate is also including the cost of your health insurance that you have to pay, you know, on your [00:18:00] own. Your rate is also including the cost of like, the taxes that you'll need to pay. Um, and like you mentioned, will be the cost of equipment. If you're a freelance photographer, that's camera gear, you know, lenses, flashes, everything, so all of that goes into your rate, and the client will see that. So you, you should be charging more than you know what you might imagine.

Jenn: Yeah, a hundred percent. I think another thing that people, you know, before they start freelancing, one of the things they get hung up on is they feel like they need to have everything figured out in advance before they get that first client. And you do need to have some things figured out, but there's, there's so many things that you figure out along the way and, and you change your systems to make them work better once you're you're working with with clients, and I think [00:19:00] that it stops a lot of people from getting started thinking like, oh, I need to figure out 50 million things, when really you need to figure out five and just get going.

Jen: Yeah. No, that's, and that's so true because. You, you know, I am definitely one to overthink everything in any possible way that I can to avoid

Meggan: club.

Jen: Yeah. You know, like, that is definitely me, um, overcomplicate everything. Um, but that said, I think that. At some point, yeah, just do the thing.

Jenn: Yeah.

Jen: Just try, just outreach. Outreach. Like initiate and, and reach out to the client. Like pitch the client you want, you know?

Meggan: Yeah. I think going even back to the contract for a second, I think if people can reframe that and see is it,, it as a [00:20:00] protection for themselves rather than a burden on the client, I think is a, is a way that you should probably look at it like this is your livelihood and this is your business. So if you sort of set that precedent and have that piece of paper, which seems scary to present or, or scary to think about, I think it's really important protection for yourself. And so if you're trying to make this a serious business. I think that's one way to reframe it in your mind and just say, you know what, I'm just, I'm just protecting myself going forward. If I need to be paid to live and this is the work I'm doing.

Jen: Yeah, exactly. Exactly. And you know. Most things. I feel like there's, there's so many things we sign contracts for, you know, in, in

Jenn: Yeah.

Jen: ways like Yes,

Meggan: all

Jen: I, I think

Meggan: like, sure.

Jenn: Yeah. I accept. Yeah.

Jen: exactly.

Jenn: Yeah.

Jen: it, it's mutually beneficial. It protects you and the client and,

Jenn: Yeah. Yeah. I wanna go back [00:21:00] to, talking about like identifying skills that you, that people out there, listeners out there might have that they, uh, that they could turn into a freelance business. So how did you think like, oh, I have these skills actually I could be doing this for myself instead of working for someone else.

Jen: Yeah, so in my particular experience, there are a lot of realms now that exist that you can do as a freelancer. In my experience, what I have done is copywriting and social media marketing. so the creative art, like anything creative, I mean that I can think of at the moment. You know, generally the creative industries, like can be done freelance, you know, you have graphic design. So I think [00:22:00] there are certain skills that are a bit more adaptable to having a freelance career there are challenges, like if you physically need to be in a location, you know, if you're a school teacher for example, that would be very hard, but you could, well, I guess there's online teaching now, so,

Jenn: Yeah.

Jen: um, yeah. See, I mean, there's just so many things, you know,

Jenn: Yeah.

Jen: um, but I guess like. If you really want to make a hard pivot and go into a different career path, I guess what I would recommend is look at the skills that you have and look at like what exists in the freelance space and see like what fits best. I'm forgetting the term right now, but there's like a new like business manager, um, type of like service offering that I find absolutely [00:23:00] fascinating and like can work with someone who will like, organize your whole business operations and I find that absolutely incredible and people are offering that and it's amazing. yeah.

Meggan: takes all kinds. I mean, that's for sure, and I think you're right, like there's so many different creative spaces and people just have to maybe make a list of what do I do best and what can I prove that I'm able to do, and then sort of see where that slots in to what they could do potentially for freelancing.

Jen: Exactly. Exactly.

Jenn: So, like we said, you, um, have been living abroad. So let's talk to us and our listeners about the realities of like working and living abroad. Obviously, like Instagram makes it look so glamorous and lovely, but like what does it really take to live, uh, that kind of life?

Jen: Yeah, definitely. I think Instagram makes it look so easy and like you could just like [00:24:00] pick up and move and when in actuality like there is a lot more work behind the scenes that goes on, that isn't always, uh, obvious from the surface level. So I would say my experience, you know, there's, every day is a little different and I think that it's exciting and challenging at the same time, I am navigating cultural differences. I'm navigating learning a new language. So the actual puzzle pieces of making a move abroad, like you need to prepare logistically, like how am I gonna move my things? What do I wanna do with the things that exist already, you know, where I'm living? You know, so just between the finances, logistics, like practicalities, and then like [00:25:00] the emotional side of everything, like. You know, all of this.

Jenn: Yeah. Yeah.

Jen: much, you know there, there's quite a lot that goes into making a move abroad. But I truly believe like if you want it, then like it is definitely like go after it, you know.

Jenn: Yeah. Yeah. How did you find, as a, a freelancer who kind of works from anywhere, how did you find like a community of other people. Like I would, I am such an extrovert, I'd be so lonely. Like I don't wanna just sit in my apartment on my laptop all day, like I need to get out there. So how did you find, like meeting new people and finding your community?

Jen: Yeah, and that's exactly it. I'm like restarting completely from scratch. So, finding people actually, I have found fairly easy. I'm based in Florence, so here [00:26:00] there are a million opportunities. There are meetups, there are language exchanges, I joined a coworking space. Um, there's, like, Facebook groups, like I've met people through Facebook groups, um, or sports like, I just joined a touch rugby league. Like I never saw that one coming. You know, like I'm still learning how to, how to play rugby, but, um, it's, you know, it's like that's what I do love in living in like, um, a larger city abroad, is that there are several ways to connect with people.

I also lived, last year I was living in Sardinia and that was a very different experience. There weren't as many opportunities to meet like English speakers, you know, there were. You know, not many like fellow like [00:27:00] Americans or even, you know, North Americans in general in my town. So that posed more challenges, but to towards meeting people. Um, but, but here there's like countless opportunities. So it also kind of depends on like where you decide you want to, to live.

Jenn: I think that's an important thing for people to consider before they choose a place to live. Like how important is it for me to have, uh, uh, more opportunities to meet people? I think that's something that. Uh, I maybe would've overlooked. So that's a good point.

Meggan: Yeah, definitely.

Jenn: Yeah.

Meggan: Um, so you've been traveling for quite some time. Where have you lived? I'd be interested to know. Sardinia and obviously Florence. So besides that.

Jen: Yeah, so those are my two most recent places. I also lived for, uh, a sh brief period of time [00:28:00] in Lisbon for, I guess in more extended slow travel, uh, kind of situation. Um, and also in Budapest. So I lived, those two places for like slower travel experiences, not quite anything like Sardina or Florence now these are like my very much like most longest term, living abroad, living situations. but you know, uh, I would say Lisbon and Budapest were also extended stays.

Jenn: Yeah. How did you, uh, choose Italy?

Jen: Oh, Italy. Um, well.

Meggan: choose you? Jen? How did it go?

Jen: That is such a good question. Yeah, I, I think that Italy is actually my first love, you [00:29:00] know, like, like I've fallen in love with a lot of places around the world, but I think, uh, it does help that I am part Italian. So there's a connection, um, through, you know some of the culture, although I have learned so much more about Italian culture by living here than I ever knew before. so yeah, I think I, I, you know, chose Italy because my heart just sang here and I did come originally, um, to pursue the have my dual citizenship or my Italian citizenship recognized. then I just decided, I made friends here. I built a community here and I said, well, I do have distant family and I have friends now here, so I think I'm gonna stay.

Meggan: Nice.

Jen: yeah.

Jenn: Yeah. Amazing. Uh, do you have any, uh, [00:30:00] travel plans coming up that, uh, you can tell us about?

Jen: Uh, yes, I am actually leaving for Spain tomorrow,

Jenn: Very exciting.

Jen: yeah, I still need to, uh, finish packing my suitcase, but you know, it'll happen. It'll get done.

Meggan: Oh, I've got the shivers. Just thinking

Jenn: I know.

Meggan: that you just said that.

Jenn: Must be, uh, it must be a Jen thing we pack at the last minute. It's just what it

Jen: It'll be fine.

Jenn: is.

Jen: I'm always on the run,

Jenn: Yeah.

Jen: It'll be fine.

Jenn: Do I have my phone and my passport? Yes. Everything else I can buy, it'll be fine.

Jen: Yeah,

Meggan: You

Jen: it's all gonna work out.

Meggan: I'm assuming. Are you, ma? Do you even need your passport to go there?

Jenn: Oh, at,

Jen: a carta di identità

Jenn: okay.

Jen: a di,

Jenn: Hmm.

Jen: I can travel through the EU with,

Jenn: Nice. Amazing. Yeah. Very [00:31:00] exciting. So if our listeners want to find you online, find out more about what you are up to, where can they find you?

Jen: Uh, they can find me on my Instagram. It's Jenontherunn with two Ns at the end, then my blog is Jen on the run.com.

Meggan: Excellent. Well that is it for this week's episode. Huge thank you to you, Jen, for joining us. We are sure this will be inspiring to our listeners and it's really great to sort of hear about people living their dreams and that's. That's amazing. As for us, you can find us online at Travel Mug Podcast or our website travel mug podcast.com. If you wanna support the show, you can always leave us a review or buy us a coffee at the link in our show notes. And until next time, save travels and bye everyone.

Jenn: Bye.

Jen: Bye. Thank you so much.

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