Rob Anthony O’Rourke’s success story continues to inspire digital nomads worldwide. In this podcast, he takes us through his journey, beginning in Ireland, and continuing through Canada and Colombia, and shares his best advice for the aspiring nomads.

Born and grew up in Ireland, Rob comes from a family of old tradesmen. He studied construction engineering in university but by the time he graduated, Ireland faced a massive recession and he could not find any job in construction.

Rob moved to Canada, and started off as a landscaper, worked in an Irish bar until he found a job as a drilling engineer. But after another recession in the oil industry in Canada, Rob found himself again without a job, so he decided to move to Colombia: “I heard it was a pretty cool place and it was pretty cheap. Moved down there, met some people, got a girlfriend and I basically wanted to stay on in Colombia.”

After a short failed career as an English teacher, Rob finally came across web design:

“I can’t really remember the exact original thing that got me started, but I just figured that this was a way that I could possibly make money. So I started taking some really basic courses on Udemy, Code Academy and I learned just the basics of HTML and CSS and basically just started trying to get projects.”


Getting the First Web Design Job

Getting the first web design job wasn’t a profitable task but it helped Rob jumpstart his career: 

“So after I’d done this Udemy course I kind of knew how to build one website. So I approached my uncle back in Ireland. I gave him a call and I was like, ‘Look, can I build you a website? It’s going to help your business.’ So he was like, ‘Yeah, sure.’ He’s like, ‘You build the website first. If it gets any sales, I’ll pay you.’ So I was like, ‘Okay.’ So spent a couple of weeks I think, coding this thing from scratch, built him the website, we put it online and it didn’t get like any sales, it didn’t get any results, which looking back now I can really obviously see why that was but at the time I just expected if you threw a website online that it was going to work. So even though putting all this time, it didn’t get any sales and my uncle was basically like, ‘Okay look, thanks, but I’m not going to give you any money.’ So my first job was a complete wash.

I worked on Upwork for probably like three, four months doing all these small little jobs. I think everyone kind of knows how Upwork goes, you’re underbidding, basically begging for work. I was able to get some work, it was like $100, $150 jobs and it would take me like a week, or two weeks, or sometimes even more, which luckily at the time in Colombia I was living in this place that was so basic. Basically, there wasn’t even hot water or anything. So my cost of living was super low so I was able to survive in that for a while and eventually, I just got really burnt out with the Upwork stuff. People were pushing way too hard for how much money they’re paying. I had this one job with this kid, he had this app, he must have been like 14, basically asking for unlimited changes on this project. Eventually, I was like, ‘All right, I’m just quitting Upwork, I can’t do this.’

So I was looking around and I was thinking, okay, I can build an okay website, but the people I’ve been approaching are not paying me that much money. So I needed to find somebody who would pay more, that’s going to get more value from the website than in building it. So at the time I had been doing some stuff with my Canadian visa, looking at possibly coming back and my lawyer in Canada, she had a really bad website but a really good business and she was always talking about, ‘Oh, we’re getting so many people applying and right now Canada’s so busy.’ 

I was like, all right, here’s a woman who’s making a lot of money. What she sells is at a high price, visa service is like $2,000, $3,000. She needs booking systems, she needs a better sales system. She was my own lawyer so I already had a good relationship, which is definitely a good way to start off when you’re trying to get work with some real businesses. So, Roxanne is her name actually. So with Roxanne we already had been talking back and forth. We had a bit of a rapport between us. So one of the calls I just said, ‘Look Roxanne, I actually … I know on the visa stuff I’ve been talking about the fact that I’m an oil engineer, because you got to apply through a certain category. So I wasn’t putting down that I was an amateur web designer. I was putting down that I was an oil engineer but with Roxanne I just told her, “Look, I do a bit of web stuff. Would you be interested in me trying to fix the website and maybe I can help with these sort of things?’

She was like so onboard, highly enthusiastic, and she’s like, ‘Okay, how much would something like this cost?’. Because she was charging me I think like two and a half to three thousand for the visa, I said, look, ‘Would you be okay with $2,000 to pay for this?’ She’s like, ‘Yeah, definitely. That’s sounds like a bargain.’ I just couldn’t believe it for that. One sale had happened in a few minutes.”


A Full-Stack Web Creator

Rob’s stories made us realize he already had different skills he acquired over the years, which helped him get a job in web design:

“I think as time goes on it’s going to be easier. The act of building a website is going to become easier and you guys obviously, and other businesses are getting really, really good at making a great looking website. So I think it’s gone from looking back 10, 20 years, just the act of making a website was valuable in and of itself and there was not that much competition online for smaller niches. So if you could pay someone to just code something, there was a lot of value there, but I think going forwards, it’s much more about people using tools to build a great website, but then also understanding what a website is, what it’s there for and why business would pay for a website. So I know, and I remember this in the beginning, you’re like, ‘They should pay me because I’m spending a lot of hours coding this thing.’

But when a business looks back from their side, that doesn’t necessarily make sense to them, they want more out of it and they’re only gonna invest in something that’s going to bring in some sort of result that they highly valuable, it’s usually more projects, new clients or whatever. So I think along with learning web design, if you want to be in this game and get good results, you’ve got to start learning those other skills as well. Really good mindset, just personally for your own business, then things like sales, copywriting, persuasion, communication skills, all those different things and really understanding how a business works, how a website connects to your client’s business.”


Complete Freedom

Being a digital nomad requires a lot more than just digital skills. Having the right mindset for one. To us, it seems that even before Rob actually became a web designer, he had  the freedom to move from place to place and not be bogged down. He was able to build a wide range of skills and utilize them. Does he agree with our assumption?

“Yeah, 100% yes. So when I look back at the jobs that I’ve had before being a web designer, I had some jobs that are really fun but didn’t pay well. Then I had jobs that did pay okay, like in oil, but I had no control, no freedom and no say in anything. So when I got into web design and I started to make it work, I was like, here’s a really good opportunity to control the work that I do. I mean, of course, you still have to work, but I control who I work with, the sort of projects that I work on and I also can make a whole lot of money and I have the freedom to do different stuff. That was kind of my main motivation that kept me motivated with web designer, you know, I can basically travel wherever I want, and I have been, and I can live the life that I would want to live and it’s been really enjoyable.

I mean I still got to show up and work of course, but it’s really, really fun and I think that would be my main motivation for running. I’m in there pretty much everyday for the last two and a half years answering questions, to help other people with those sort of things. Because I do remember what it’s like to work in a job that sucks, or your boss tells you to do something and you’ve got to do it. Then you’re just looking … sure you might be making some money, but you’re like, ‘Okay, I’m losing a lot of time in my life and I’m not being creative, or I’m not really doing these bigger goals that I’d like to be doing in life.'”


Tips for the Digital Nomad

We asked Rob what kind of advice he has for the aspiring digital nomads, to start their journey and what kind of rules of thumb he would you give them:

“Okay, so in the beginning, it is a little tougher. I mean you can’t do that stuff straight away. People might tell you that you can, but you got to put in some amount of work so that you are valuable to a business. If you look at who’s hiring you, what matters to them, that’s where your focus should be.

So my advice would be, learn how to code to a certain stage, so you do know how to control a project, you know what good design is, what isn’t, and you’re able to build a website that you know does actually work, it’s responsive and the basic stuff that a website has to do. Definitely have always been promoting things like Elementor, using something that it’s good code and it works. What I’ve seen from a very early stage was businesses did not care that it wasn’t custom. So I know a lot of people online like to, ‘Oh, you know, custom coded this,’ which is fine for some projects, but a lot of businesses I was working with, would see the past websites that I’ve done and be, ‘I want that exact design and style.’ If I actually design it a different way, they’re like, ‘No, no, no. Like we love the way you did that last one.’ So they are actually preferring knowing what they’re getting on the design side and then focusing on the business side.

Advice on the other side is learning to think like a business owner, because that’s who you’re selling to and really start to look at everything as sales, and it really is. A website has got to sell something maybe it’s not literally selling on the website, but it’s selling a business or it’s selling an idea. It’s selling a service, or a product, or a way of doing things. So you’ve got to understand what it is that your website does and basically make it a sales machine. I mean the thing has to go online and find as many people as it can and get those people to take action and of course that means you’ve got to work with high-value businesses and have some ethics about it of course. Really, I think how I see myself as a web designer is I build a tool that gets the most results possible for my client and it promotes their product or their service in the best possible way and it gets people to take action to go ahead and to use that product or that service.”


Keeping an Organized Schedule

One of Rob’s constant challenges is to keep an organized schedule:

“That’s something I’m working on right now. I mean I’ve done pretty well and I think everyone knows this, when they go through a certain progression in anything, they look back at stuff and they’re like, ‘Oh, I could have been doing that much better.’ But then they also know that they could start right now and just keep improving. So even when you improve, you always want to improve even more. So I’ve come a long way, but I want my business to keep growing and everything that I do to keep growing. So that’s something that I still work on as well. That’s why I’m actually, I’m taking this to 75HARD challenge by this guy Andy Frisella. He’s got a business podcast, but basically all about developing discipline.

I would say in the beginning, and even now, just keep it pretty simple, have a few key things that you work on every day. Get those things done. Then if there’s time to do the rest of this stuff, fine but what I find with a lot of people starting an off with stuff, they’re a little bit maybe scared and they have a bit of fear and they don’t want to take the big steps and they feel like, ‘Maybe I’ll just do all the little things and then I’ll call that a day.’ So I you don’t know, organize their desk or, they blast off some really low quality emails or … they’re kind of cheating themselves in a way cause they’re not taking the big action that they know they have to do. I remember doing that as well. But if you want to make progress and keep yourself accountable, I think keep it really, really simple. Do three, four, five big things every day and that’s going to see you massive progress over a few months.”