Freelancing while Travelling - Graphic Designer Jacob Cass

Aussie freelancer Jacob has spent the last few years as a digital nomad. Freelancing on the road. And the plane. And the boat...

Before packing his bags, he packed a lot into building his personal brand. Growing his professional blog from his days as a student. So wherever he is in the world he knows potential clients will find him online.

But how do digital nomads get paid? How do they plan for the future? How do they make sure they do justice to both the working and the travelling?

More from Jacob Cass

Jacob on Twitter

Jacob on Instagram

Jacob's Just Creative website

Jacob's Just Globetrotting digital nomad blog with Emily Cass

Who the hell is Steve Folland?

Steve's a freelancer helping businesses use and make video & audio content in much better ways. Find out more at, track him down on Twitter @sfolland or lay a trail of cake and he'll eventually catch you up.

In 2015 is decided to create the freelance podcast (well, there weren't any others doing this then) where freelancers could learn from each other via their stories.

Check out Steve's Being Freelance Vlog that documents his weekly wanderings and wonderings as a freelancer.

Transcription of Being Freelance podcast with Steve Folland chatting to Jacob Cass

Steve Folland:      First of all, let's find out how you got started being freelance.

Jacob Cass:         I started, actually, I've been freelance ever since I started learning about design and it wasn't 100% full time freelance, just kind of moonlighting and this was probably 2007-2009. The years when I was studying design. Since then I've worked for agencies, I've worked for myself, moonlighting, and the last three years I've been freelancing full time while traveling. So that's where it brings me up to now.

Steve Folland:      So you were freelancing from a base before you set off on your travels, was that?

Jacob Cass:         Yeah, so it's a longer story than that. I just kind of condensed it for you. To further what I was saying, I studied in Australia for three years in New Castle, and then after that I graduated and moved to New York, and I worked for a number of agencies there for about four years, and I was also freelancing during that time running my design blog, JUST Creative, while also working full time. After those four years there, actually five years, I had the choice to renew my visa or not, and we decided that we would go traveling instead, and we just decided to go full time freelance. It's worked out great, and continuing to travel now as well.

Steve Folland:      Wow. So you say we, so you headed out with somebody else?

Jacob Cass:         My wife, sorry.

Steve Folland:      Awesome. Was she self employed as well? Is she freelance?

Jacob Cass:         She was working in New York as a teacher and a nanny, and on the road she's my PA, and keeps me organized, and works under me as well.

Steve Folland:      So you sort of packed up on your job, but you packed your bags and set sail at the same time, or got on a plane or whatever. How did that feel as you headed out? Did you have a load of clients ready? Or did you think, "I have no idea where I'm going, and I have no idea who I'm working for, but I'm out of here."

Jacob Cass:         Yeah. I wouldn't recommend just going out. You do have to plan. I had the foundation of my website and blog, and I have a steady stream of traffic to my website, which helps getting leads, and consistent work, which I'm very fortunate for. That has come through many years of content marketing, blogging, social media, and all of that. That's allowed me to do that. I've always had this travel bug in me and I've always wanted to travel the world for a long time. I kind of had to convince my wife to do that, which eventually she agreed to, and we haven't looked back since. It's actually much more affordable to live on the road and work than to live in a place like London or New York, which is very expensive. Even Sydney is terrible. Advice I do give to people is if they do want to do that, you don't have to go out to the bit European countries, or the rich places. You can start in Asia, it's much more affordable there. Southeast Asia would be the perfect spot and you can start building yourself up. That's actually quite, I say easy, but easy in comparison to doing something at home where you have overhead and many expenses.

Steve Folland:      So your blog, JUST Creative, was kind of key to a lot of this? So you started that when you were full time employed?

Jacob Cass:         Actually I started it when I was studying. Originally it was called JUST Creative Design, and I started as a place to document my design process and my learning and my studies, and when I was doing that it was just for fun, and I learned about blogging. This was before it turned into the word content marketing. It was real close knit communities, and I learned about blogging as a tool to promote myself and from there it turned to something bigger, and I now use it for affiliate marketing, promoting my work, and so forth.

Steve Folland:      So you started out documenting your process. So how did that change?

Jacob Cass:         Originally it was documenting my studies, and me doing design projects, what I learned, and translating that into articles for others to comment on and give advice to. So it was kind of a learning curve and sharing my knowledge as I learned it. Obviously I was still a student then, but it was still valid. A lot of the articles that I wrote during those years are still some of the most popular articles on my side today. It's kind of interesting.

Steve Folland:      How do you go about growing an audience for that? How did you do that?

Jacob Cass:         Back in the early days, it was much smaller communities, so even commenting on other people's blogs, doing guest articles, you still do that today, but there's so much more noise out there. It's a little harder to grow. It's all the things that people are using today. Social media, Facebook, Twitter, content marketing, writing articles that will get traffic to your site. That's how people find me. For example, I specialize in logo design, and branding, so a lot of my articles are tailored around that topic so potential clients can find me as well as other designers wanting to learn about the topic too.

Steve Folland:      Do you find that as well as people Googling graphic design, or logo, or whatever, people might follow you for a while before they contact you for work?

Jacob Cass:         I do know of people who have done that. Generally people looking, they're looking for something at that moment, but I have had people contact me four or five years down the track saying, "I've been following you this whole time. I loved your work. I finally have a project for you." Kind of thing. It's a long game. Yeah.

Steve Folland:      So you headed out with that, and clients came to you via your blog. How did you find working on the road?

Jacob Cass:         As long as you have the consistent work coming in, which as I said before, I'm fortunate enough to have through people contacting me through email, or referral, word of mouth, or through social, but the biggest is Google, as I say all those things. Working on the road is great. The technology is all there. Everyone is working digitally now, and I hardly ever meet people in person. It's 99% of my clients, I just do via email, or phone, or Skype.

Steve Folland:      What does a day or a week look like to you? When you're permanently on vacation, do you take time out? This week is a work week. Do weekends exist? How do you get the work done and the travel done?

Jacob Cass:         Yeah, it's interesting. The best answer is, it's a lifestyle. It's a different kind of lifestyle. I generally have a pattern of working in the mornings, like three or four hours in the mornings just cause I'm super productive during that time, and then the rest of the time, you can site see or go about other things. That's how I've found to work, and it does change. You have to be flexible, because in some places ... like, when I first started traveling it was a little bit quicker. You had visa restrictions, for example, it's expensive to live. So you kind of move a little bit quicker, and as an Australian, you can only have three months in Europe. You kind of want to see a lot, but still take it at a mid pace. These days, I'm going a little bit slower. Taking it easier, and getting more in depth into the country. That's allowed me more time to work on the business as well, and I'm enjoying it more. That's kind of where I'm at. There's no secret to work/life balance. It's different for everyone. I have a very organized wife, who does all the travel organization, so the hotels and flights and things like that. Then I do the design work, which brings in the majority of the income as well as the blogging.

Steve Folland:      How about dealing with getting paid? Do you have an American bank account? Or an Australian bank account?

Jacob Cass:         Yeah, I have a US bank account, Australian bank account, and PayPal. My business is registered in Australia, always has been. I pay tax in Australia. Paid US tax when I lived in the states. Mostly US clients to be honest. So it's usually US dollar, which it works well right now in this economy.

Steve Folland:      I see. Then when you're on the road, do you have to worry about the conversions and-

Jacob Cass:         Well, US dollar ... I go whatever is strongest. A little trick I do use is to get paid into PayPal and then I get paid in US dollars, and I keep it in my PayPal account, wait for the dollar to go up, and I change it to Australian dollars, and that way I can earn more money on that. You have to have enough cash flow to be able to do that, but I found that as a little hack to earn a little bit of money. Obviously there's risk to that, because it could go the other way, but most of the time it bounces back, and you can earn a good 5% to 7% extra.

Steve Folland:      Even though you're not living in Australia, and haven't done for ages, you continue to pay tax in Australia, that's how it works, is it?

Jacob Cass:         You have to be a resident somewhere. Tax is a very boring subject, and it is interesting, because when I lived in the states, I was a resident in the US, so I didn't pay Australian taxes. Then I would have to go through the books in the US taxes. There's different legalities of it and I had an account in Australia, and an account in the US, and that specialized in dual citizen, not citizens, but dual residency, and he helped me a lot. It was difficult at first, tax is always a little bit tricky, but he got me where I had to be.

Steve Folland:      As far as actually getting the work done, how do you stay on top of that?

Jacob Cass:         Everything thing is ... I can be on buses, trains, if I'm sitting down going somewhere, I'm often working, because it's downtime to me and I'm productive in the mornings, as I said earlier. That's when I focus to work on and there's no set place. I'm just flexible now. I can be anywhere.

Steve Folland:      Are you permanently backing stuff up in the fear of sand gets in your laptop, or-

Jacob Cass:         I have three backups, and thankfully I did have a backup, cause I was in a pretty remote island in Thailand, and my SD card broke. So I couldn't access anything, but I did have a back up from a week ago. I had to get an SSD card shipped in from Hong Kong to this tiny island, which they did. Paid a fortune for it, but it worked. Backup is very important. I have physical backups, and I have cloud backups as well. So, very important.

Steve Folland:      What has been the biggest challenge of living that lifestyle?

Jacob Cass:         Good question. It is the balance thing. You get to a place, you're like, "Oh, I'm here. I have to go out exploring. I have to feel what it's like." But you have to earn an income as well. So that's pretty tough, as well as spending enough time with the significant others, or friends as well as working. This goes anywhere. It's not just about working on the road, because everything is done digitally. Online services, software tools, I have are with me. There hasn't been any limitations, really.

Steve Folland:      How long do you spend in each place? How often are you on the move?

Jacob Cass:         Good question. It does depend entirely, because we generally plan in three to six month segments. The countries, and whatnot, just because of airfares, and logistics, and all of that, and planning with other people we're going to meet up with. I wasn't even going to be over in Europe, but my dad sprung on me that he was getting remarried in Italy and he gave us a month notice. And weirdly enough, we moved to Italy, and now we're in Italy for three months that we can be in Europe, and we just put an itinerary around three months at places we'd like to go, and we missed last time, and went from there. There's no set structure. We're just nomads really, but we always call Australia home, and eventually we're going to go back there. We have a kid on the way in about six months, in November, we'll have a kid and we'll probably nest there for a while and then who know? Might pick up and go somewhere again.

Steve Folland:      Wow. Congratulations. So you've had success with your graphic design blog, and you didn't perhaps realize what it would turn into, at the time. How useful it would be to you. I noticed you have a travel blog as well. Is that also a revenue stream?

Jacob Cass:         Yeah. It's a little bit of revenue stream with advertising, but nothing to write home about. A few hundred a month tops, in terms of ad revenue, which is nothing in terms of the big scheme of things. In terms of country deals and things like that, that's where the money is at, because you can stay at luxury hotels, and have free tours and things like that in return for reviews. So we've had a four night stay in the Maldives for free, with everything included. The scuba diving, lobster buffets and everything like that, in return for some writing on our blog. We have a lot of traffic. We're not so big on social media. It hasn't really kicked off on there for us, but in terms of website traffic, it's going pretty well. It's been enough for us to have leverage to help other brands who want to work with us, because social media followers, they're just numbers really. Some people they don't have the engagement, and they don't have the SEO traffic, which is really important actually. That's our biggest leverage right now, is that we have the traffic online, and the articles are going to be there for a long time, and they're going to get long term effects, rather than just a post that's going to be buried within a week. That's what we're using.

Steve Folland:      Do you approach that from a business point of view? Is that something that your wife takes care of when she's planning?

Jacob Cass:         No, actually I help with the business side of things. She does the writing for all the articles, and I'll do the photography and the SEO, and then the social media marketing, and I'm teaching her how to do that as well. In terms of reaching out to people, they generally work with her, Emily is her name, and we collaborate together and work with the hotels. It's about a 50/50 split.

Steve Folland:      Do you present them with a media pack and show lots of stats? Does it come across as this is a business, when you approach those sort of people?

Jacob Cass:         Yeah. We have just a one pager, really. Then an intro email telling us about what we can do for ... Who we are, what we can do for them, and our target audience. Generally, probably 70% of the time, we won't get a response, but the other times people will reply, and we'll figure something out.

Steve Folland:      That's so cool. What's been the best thing of living this digital nomad lifestyle?

Jacob Cass:         The freedom is the biggest thing. You can explore new places, experience new things. We put our values in experiences. We're not big luxury travelers. We don't put value in fancy hotels. Occasionally we do reach out to them, because it's nice to have it, but we often go to places to explore and we're never in the hotel so that's why we don't value it, but sometimes you do want to just relax and chill out and use all the facilities and we will do that. That's the best thing is just freedom to explore and work when you want.

Steve Folland:      Is there a community of people like yourself that you're bumping into each other? I don't know-

Jacob Cass:         Yeah, there's a huge community, but the world is a big place. There's a lot of people doing it, I don't know the background of every one of them, but yeah, especially on Instagram, there's a lot of travelers, and influencers on there. I think the digital nomad scene of designers and developers is a little bit more ... they don't move around as much. They'll stay at a place that is more of a hub, and they'll work like a coworking place. So there's that kind of traveler, and then freelancers who just do lots of traveling if they like that, but I think that's a little bit smaller. You definitely don't run into them that often. Unless you're staying at hotels, and things like that, but where we're at right now is, we generally just enjoy our company together, and we're living more away from hotels.

Steve Folland:      Have you made work connections along the way with those sort of people?

Jacob Cass:         Only through social. It hasn't been in person.

Steve Folland:      So through following each other and chatting about what you're up to and stuff?

Jacob Cass:         Yeah. Exactly. Occasionally we'll meet up if we're in the same spot. It happened the other day in Malta. Someone messaged me on Instagram, cause I just posted a photo on Instagram of Malta, cause we're working with the Malta tourism board, and they were going there the following day, and I told them a place and then randomly enough, I ran into them, literally ran into them and that was a weird experience. Other times I had been following them, and then just started chatting with them, and said I'm in this place next week, are you going to be there? Then would meet up. That's happened a small handful of times, which is interesting.

Steve Folland:      This whole time that you've been doing this, so a few years now, are you also thinking about longer term? Obviously you're starting a family now. So you don't need perhaps much money in certain places to get by, but are you also conscious of thinking about the future and do you put money aside and think about when that day comes?

Jacob Cass:         Yeah. Absolutely. We do have the idea of settling back in Australia as I mentioned before. Yes, we're obviously saving for eventually a house and what not. So we do have that in the background lines. We can't travel forever, especially when the kids start going to school and things like that. Unless you want to home school, but I think there's more benefits to have some roots in the ground for once kids are in school. That's my opinion. I think we still have another five, six years before that happens. We've talked about it, yeah we are planning for the future and I think you have to.

Steve Folland:      As well as using the blog to build up your reputation early on in your career, I noticed from your website for example, you've entered awards, speaking, things like that. There's obviously been other ways to grow yourself. When did you get into speaking?

Jacob Cass:         I've only spoken a handful of times. I don't enjoy it, cause I haven't practiced enough to be a good speaker. I get nervous like everyone else. I had this opportunity to talk at TED X one year, and I couldn't deny that. That's when I started getting into it more. Speaking is a good way to get your name out there more, but personally I haven't done it much.

Steve Folland:      When you said you had the opportunity to speak at TED X, had you been floating the idea to people so that they thought to ask you in the first place?

Jacob Cass:         No. Not at all. It was a cold call really. Cold email.

Steve Folland:      Really? That's so cool. So, you know what you're talking about. You're a handsome chap. Let's get you on that stage.

Jacob Cass:         Exactly. That's how it happened. I regretted it for the next month, but then I finally got myself together. It worked out.

Steve Folland:      Why? Because you were constantly thinking about what the hell am I going to say?

Jacob Cass:         Yes, exactly.

Steve Folland:      It's funny. Did you find doing a talk took a lot of effort? Did it distract you from your work? How was that experience?

Jacob Cass:         It was just putting something together. I think it was a 20 minute talk, and just something to talk about for 20 minutes, and not bore people is key. It was the first time I'd done a presentation. I had to practice it many times. So you can definitely see my nerves in all of that. I think if you practice a talk well, or know the subject very well, it may come off easier. I ended up talking about how I overcome some visa issues in the states. I got kicked out of the states and had two weeks to leave, and get a job, and I talked about that, and how I used my blog and social media to find a job and come back to the states, and all of that. It was a personal topic, and with the underlying theme of personal branding.

Steve Folland:      How did you use your blog and social media to get you ... Were you actively approaching people when that happened?

Jacob Cass:         You'll have to watch the video.

Steve Folland:      Such a tease. You have awards listed as well. Was that something you actively go after?

Jacob Cass:         Yeah. In the early days I went after the awards more, and whether or not they work, I'm not sure. That sharing your experience, they do have some merit, but these days awards are given out so easily. There's an award for this. An award for that. I don't think they have as much merit these days, unless they're quite well known. They're generally just known in the industry. Not so much to other clients, cause you could make up any award and the clients probably wouldn't have heard of it. I have a weird stance on it. I use it, but I don't know how powerful it is. I don't really trust awards.

Steve Folland:      Did it make a difference to you at the time? Not perhaps to clients, but to yourself?

Jacob Cass:         Definitely. You need to give some merit to your work, and you have to promote yourself. It's all part of the package really. Having testimonials, and having some awards under your belt, or even whatever you can. If you've been on articles. Like a press page, more or less. All of this helps. I generally just put on my about page, because people go there to check you out to see what you're all about, and it's a good place to put it.

Steve Folland:      If you could tell your younger self one thing about being freelance, what would that be?

Jacob Cass:         I would say learn from others. That's a very broad thing, but I think the best way to learn is to see other designs, and I'm talking about the design freelancer here. If you want to become a designer, and learn design, to learn from others and see. You can emulate, and directly copy, but I use that word loosely. Whether or not it's a design you could copy that design and learn from that. I'm not saying post that in your portfolio, but it's a good way to do things yourself in a way that you can learn from.

Steve Folland:      One thing I meant to ask, because obviously you ... as part of being a digital nomad, all of your clients are remote, so do you have any tips on working, that remote relationship. So not actually logistically, but rather managing that client relationship when perhaps you're not speaking to them at all?

Jacob Cass:         I'm pretty adverse on asking about that, because I purposely don't have a mobile number that clients can contact me on. I use Skype pretty much exclusively with email, because I'm always in different time zones, and my clients are in different time zones, so we often have to figure out a time that works, and when I'm not out exploring, and it's in the morning, so it changes. I just have to stick to that, and that's worked very well. People mostly go by email these days and then just for the initial contact, you can line up a time to chat better. That has worked for me.

Steve Folland:      Is there a knack to managing that email relationship so that it runs smoothly?

Jacob Cass:         If there is, let me know. Yeah. Email is-

Steve Folland:      Awesome. Jacob, thank you so much for talking to us. All the best. Being Freelance.

Jacob Cass:         Cheers, thanks Steve.