How to Become a Digital Nomad with the Projects You Win on Upwork

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Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.

A lot of salaried employees are starting to buck the norm and learning how to become a digital nomad.

The truth is a lot of people spend their entire lives devoting most of their energy to their careers. But, something has happened recently.

Many are starting to ask, “Why am I adjusting my lifestyle for my career, rather than adjusting my career to live the kind of life I want to have?”

There have been huge improvements with global online connectivity and employers are increasingly more open to hiring remote workers OR augmenting staff with freelancers. As a result, more and more people are leaving their day job and choosing to contract themselves out for projects while traveling the globe.

Bali one week. Mexico the next. New Amersterdam for Christmas. Basically, if you’ve got a laptop and wifi, you’re all set.

Robert O’Kruk’s Path to Become a Digital Nomad

This week’s guest is Robert O’Kruk. Robert graduated college and quickly found himself working a normal day job at a company. But, he wasn’t satisfied.

He wanted to travel and see the world. And, most importantly, he didn’t want to spend the majority of his life feeling trapped in a routine he hated.

That’s when he started learning how to become a digital nomad.

He realized there were other options and he didn’t have to settle for a life that didn’t fit him personally.

So, he bought a one-way ticket to Bali.

Using Upwork to Become a Digital Nomad

Fairly soon, Robert realized that he needed to find more projects to work on, or his stint as a digital nomad would be short-lived. That’s when he turned to Upwork.

He’d heard mixed reviews about Upwork itself. Some people had good things to say while others trashed the platform.

He decided to find out for himself and found huge success. He was able to use the projects he found on Upwork to sustain his lifestyle and become a digital nomad for the long haul.

He found there are four pillars to success on Upwork:

1. Upwork Profile Optimization

You need to have a profile that helps you stand out and helps make the clients deciding to hire you a no-brainer. You don’t have to come up with everything on your own to do that. You can look at what other successful Upwork freelancers are doing in their own profiles and use that for inspiration.

2. Automate Notifications for Ideal Jobs

Upwork has some great tools to filter out jobs that aren’t best suited for you. Then you can create a custom feed that sends you notifications the instant a job is posted with those search filters using tools like Leap Frog Leads.

3. Creating Strong Proposals

The proposals you send to bid on projects play a huge part in winning jobs on Upwork. The key is you can’t just copy and paste. You have to be thoughtful about what you’re saying and do your best to connect to what the client is truly looking for. But, you should be able to send in a winning Upwork proposal in 3 to 5 minutes

4. Call Handling

How you handle the call with a potential client is a huge component of your success on Upwork. The key is to be strategic about the conversation. Have a list of things you’d like to chat through with the client and be systematic about it. As you get more experience doing calls with clients you can add or adjust what you’re saying and how you’re saying it to be more successful.

Skip the Learning Curve and Become a Digital Nomad

You can become a digital nomad, too. And, Upwork can be a powerful ally as you travel the globe. There might be a bit of learning curve BUT using advice from people like Robert will help you skip a lot of heartaches as a freelancer and digital nomad.

It’s your turn to chose a career that fits your lifestyle rather than the other way around.

In This Episode You’ll Learn

  • How to become a digital nomad
  • How to overcome your fear of becoming a digital nomad
  • How to use Upwork to find projects and live a digital nomad lifestyle
  • Upwork profile hacks to win clients
  • How to make a winning bid on Upwork
  • How to automate notifications for job postings on Upwork


Related Episodes

[00:00:00] Chris: This week's guest is teaching us how to become a digital nomad by using the projects you win on Upwork. Are you ready? Let's go. 

What is up self-maders and welcome to another episode of this. Self-made. Designer podcast. A lot of people spend their entire life devoting most of their energy to their careers, but something has happened recently. Many folks are starting to ask, why am I adjusting my lifestyle for my career rather than adjusting my career to live the kind of life I want to have. 

And with that logic, a new type of freelancer was born known as a digital nomad. A digital nomad is someone who spends their time perpetually traveling and they make money from the projects that they find on blind Bali. One week, Mexico, the next new Amsterdam for Christmas. Basically, if you've got a laptop and wifi, you're all set. 

And Robert O Kruk is talking all about his journey and becoming a digital nomad and how Upwork was a huge part of that journey. And the best part is he's going to teach you how you can do the same before we dive in. I want to tell you about a free course that I've got in over 2000 people and climbing have been through, and it's called the web design. 

Starter kit course in it. I talk about how I went from knowing absolutely nothing about development and barely anything about design to doubling my income with a freelance web design side hustle. So go to self-made web and sign up for this four video course that shows up right in your inbox. 

So you can start a successful side hustle as a freelance web designer. Maybe even a full time career. Alright. Are you ready to learn from Robert about how to become a successful digital nomad from the projects you win on Upwork? Okay. Let's do it. Well.

Hey, Robert, thanks so much for being on the self-made web designer podcast. 
Good to have you, man. 

[00:02:15] Robert: Hey, Chris. Likewise having beer. Thanks for having me.

[00:02:19] Chris: Yeah. So 
tell us a little bit about who you are, what you do and how you got to where you are today. 

[00:02:23] Robert: My name is Robert. I was born and raised in Canada. I'm 29. Now about five years ago, I started working remotely and traveling around the world.

I run a community on Facebook called the digital nomads forum. It's got, uh, more than 16,000 members of people who are looking to learn how to become digital nomads or how to do it better if they're already doing. I run an upward consulting. Business. And I teach people with digital skills, how to become successful freelancers on Upwork. 

And I am an avid downhill mountain biker. I love anything to do with bicycles.

[00:03:04] Chris: I love how you've kind of you've confined the idea of. You know, like freelancing and, and Upwork, but also using that to, to do what you're really passionate about and that's to, to travel and do things like mountain biking and, and helping other people learn how to do the same thing. 

And I think a lot of people, especially over the course of this last year, They've started to take some, some really hard looks about, you know, what it means to have a job that supports your life versus the other way around. So talk a little bit about that, you know, cause you said you started five years ago that talked about the decision that you came to, to go, you know what, I'm just gonna do what I do, but I'm going to do it where I want to do it. I'm going to become a digital nomad, so to speak. Was that something that was a hard decision or did it come kind of gently or one day did you wake up and you go, you know what, I'm just, um, I'm bucking the norm and I'm going for it. 

[00:04:02] Robert: Basically. What happened for me? I was working in a semi kind of corporate digital marketing job in London, Ontario, Canada, which is where I grew up. Place in my opinion. And, um, the, the company actually took us on a vacation to Mexico and that was like the first trip I'd ever gone on, on, uh, outside of the country as an adult. 

By myself without my parents kind of thing. And I realized, oh, I wasn't even thinking about traveling. I was like, oh, I can travel now. And I've got a bit of money so I can afford, you know, within reason some, some travel adventures. And then I discovered someone shared this thing, this buzzword, this keyword, digital nomad. 

And then I just got obsessed with learning all about. Oh, it's Friday wine. Who's not super familiar with it. It's just means traveling somewhat perpetually and working or volley on your computer to fund yourself as you go along. Um, and it, it took me personally. It was really a struggle actually to build up the courage, to quit the job and go on what ended up for me being a one-way flight. 

Bangkok Thailand. And the biggest reason I think I had a struggle was because I was surrounded by people who thought that was crazy, or maybe even a poor decision you're responsible. Um, I was surrounded by people which, uh, with respect to lot in Ontario, it's a place people end up in. It's not a place that people choose to live. 

And so what was calling me out of digital nomadism was this idea of, um, learning. And I understand that. What supports me in a place that. Living, and then actually going there and living, I 

[00:05:50] Chris: wonder if you can just talk about how you overcame some of those fears of just kind of going for it and what you're thinking and feeling when you bought that one way ticket, you know, to where you're like, I'm, I'm burning the bridges and we're not going back. 

Right? Like what were you thinking? What was the process and, and how did you get past some of those hurdles in your own mind?

[00:06:09] Robert: I had a fire in my belly. If that makes sense to anyone listening in, I also was experiencing. Discontent in my job. So, uh, I was young at the time. I'm still young, but I was 24. I was younger and, um, earning pretty good money. 

You know, I was following the, the north American dream kind of thing. And I just very quickly into that process was. Yeah, there's just no way I want to do this. Like what I'm doing now for the next 30 years. Like, I do not want to be old and this is like, the life I've led. So I had this discontent, but then I also had this curiosity and that was the fire in my belly. 

I was just like interest in, uh, the rest of the world and kind of exploring and traveling. And so I think basically the discontent reached a point. Where every day of work was kind of like, it didn't start like this, but eventually it became like this as dread it's like you drag it, getting up and going to work. 

And then you're stuck there in dread for like 8, 9, 10 hours a day. Uh, and that, that is, um, soul crushing. And so you can use that, I guess, as motivation then to. To act on things that scare you because you hope that you'll get unstuck, um, or you, you get, you stay stuck and you become depressed or anxious or whatever it is. 

So luckily just the way, I guess my brain chemistry and mental health was at the time, uh, the fear of the shitty life evolving over the next three years was great. And the fear of like the consequences of trying what I wanted.

[00:07:59] Chris: You come to a point and I've heard a lot of people say that they've reached this point. 

I reached this point for myself when I began freelancing of thinking, you know what, I'm about to step into theirs. There's absolutely no way it's worse than where I'm at currently. Right? Like, so, so what do I have to lose? You know, and that being the motivation to keep going. Cause I'm sure. A lot of challenges once you launched out into
becoming a digital nomad, like I know, especially in the beginning stages of anything, like it's, it's, it's tough and you're presented with things like, I never expected to have this issue, but here we are, and I've got to figure out what, what to do. 

And so that can kind of be the thing that, that keeps you pushing forward rather than going, you know, I'm just getting a plane ticket and I'm going home. Right. And, and I think that's applicable. Whether or not, you want to be a digital nomad, whether or not you want to stay where you're at and just learn how to make a better life for yourself through freelancing or side hustles or, or whatever it is that you're doing. 

But, but maybe talk a little bit about some of the challenges that you. In those early days, trying to figure out how to be a digital nomad, you know, like, did you go nights where you had to didn't have a bed to sleep on? Did you, you know, have flight cancellations and have to stay stuck at an airport for days on end? 

Like, I don't know. You tell me what kind of stuff you faced when you were figuring it out in those first few days.

[00:09:24] Robert: Personally, the biggest challenge at the beginning was, uh, all about actually earning the money remotely. Like how do I make my. Remotely, uh, and that matches the number one challenge at aspiring digital nomads have as well. 

That's what I see in my community as well as broader communities, um, for this world of digital nomads in general. Um, that's the hardest part was, oh, okay. I've only really had these traditional style jobs where I was living in the place that I was getting. And now I'm in, um, Bali and Indonesia and, oh, I don't really have any more work moly. 

Uh, how do I get more work? So that was the biggest challenge. Uh, I would say the secondary challenge would, I think the kind of things like logistics, like yeah. Dealing with the stresses of international travel, planes, trains, and boats, and taxis, trying to rip you off and all this logistics, which backpack to buy. 

Do I need a visa to enter this country, but, um, the good thing, there's a learning curve with that stuff. Uh, but the good thing about the logistics learning curve is that the ant the best answer for a lot of those questions and challenges is more or less the same for every. If you're a Canadian trying to enter Thailand, everybody's got the same rules. 

If you're a man, this is the best backpack. Um, what, which internet provider is the fastest, there's only one. So those answers are kind of, um, universal in some ways. So they're much easier to solve. The first part though is not universal. And that is how do I earn money remotely. Every person is so unique and different with Def different strengths and weaknesses skills or lack of skills. 

And so there is no one size fits all answer, and we see that in what people do to earn their living. There's so many different ways people do it. Um, and there is no one best job doesn't matter. Um, There's no one best option. I know that 

[00:11:33] Chris: Upwork has been a huge part of your journey. Um, and you're now helping people to learn kind of how to master the Upwork system for themselves. 

So where did that, where did that come into play in your own? Working environment and your own, you know, freelance stuff that you are doing. And, and what did that look like? Was it really tough for you to get started on Upwork? And then how long did it take for you to get going? Anything you want to share around? 

That would be awesome.

[00:12:03] Robert: I was in. In Bali and Indonesia. And I had so far been surviving on clients. I had known locally where I grew up, who didn't really care where the work was done. So I was able to do some of that remotely as I started traveling, but they, those clients dried up the work ended, the contract ended and I wasn't replacing it at the same rate I needed. 

Um, so I was basically in Bali and I was like, okay. Um, just kind of burning through savings. Now I do need to find a way to bring the money in our, I got to go home basically. I don't want to go home. And so I found Upwork and noticed, Hey, there's always people doing the same thing that I know how to do, which at the time was digital advertising and they're doing it the level they're doing it at. 

Oh, wow. They're getting paid a lot more than me, but I can do it at that same level. And so I just spent a lot of time. Understanding, what are the people who are successful on upward doing differently than the people who are not? Because one of the things that intrigued me about it was there was so many people saying that it sucks. 

It doesn't work. Um, but interestingly, the results are public. So you can go look at any freelance. And see how much we're making, um, even like quite accurately too. And so I could see with my own eyes, that's not the case, what some, the haters, which seem louder to me at the time that's not accurate. And so that kind of made me curious, oh, why is it not true? 

What are these guys doing different? And I found that. There is very much a repeatable process for how to use Upwork, how to set up your profile, how to message clients, how to handle a phone call with a potential client. All of these things were things that weren't really random or luck in terms of who was successful with them. 

Um, they were much more, uh, Related to skill and strategy and skill and strategy where things you could learn in an affect and change and control. Um, whereas of course, luck is luck. 

[00:14:15] Chris: So what were some of those repeatable things that you saw? Some of the more successful Upwork freelancers put into practice? 

[00:14:23] Robert: So to start kind of, cause I braked success in Upwork in four into 400. Um, the first pillar is profile optimization. So that's how you create your profile, how you present yourself. And at the simplest, like, quick answer I can give right now is based on competitor research. So don't create your profile until you have thoroughly reviewed it 20 to 30 people doing what you want to be doing. 

We're getting paid what you want to be earning or more who have success on. And again, they're doing the same kind of work. So look at people doing what you want me doing on Upwork. Look at 20 to 30 profiles. Take what you learned from those profiles and put effort, real effort into building your profile based on that. 

That is the super cool. Quick and dirty answer on how to do a profile. That's your first pillar for success. Second pillar is learn how to automate notifications for ideal jobs. Define what a good job looks like for you and use tools like mine, beat frog leads or others. There's some other ones you can learn. 

And these will enable you to make it. So when jobs on Upwork that match the criteria that is ideal for you pop up, you can be instantly notified, apply first or close to first, and you can just save a lot of time looking for them. So that's the second pillar automate notifications, bridal jobs. Third pillar is about proposals. 

So that is the message you send to connect with the class. Um, it comes down to read what they said they need help with and write a custom tailored, thoughtful response. Do not put a copy Patty's template at its core. Success of proposals comes to learning how to write a thoughtful, um, response. And with some effort and the right training as well in a time efficient way. 

How fast is fast? I don't know. Some people might eventually wanted us three to five minutes is what it takes my clients. Right. A good quality tailored custom proposal might take you longer at the beginning. That's fine. But that's where you should be aiming for last pillar for success on Upwork. It's call handling. 

Hard to describe in words, but basically instead of just winging it and showing up to a call, take a piece of paper, take an online app like Miro, M I R O N. Write out your process for how you go through the call. Introductions. First questions you want to ask her second. This is why I'm a good fit to help with that as third, this is what it's going to cost this fourth. 

Dealing with their questions, objections, concerns is fit. Write it out so that you've got those sections somewhere. And then as you keep getting on your calls and keep practicing, keep practicing in the same way and adjusting your structure as you get stumped on calls as you discover. Oh, if I reawakened to the way I kind of bring something up the calls go better. 

Just keep practicing consistently and update. Um, if people put effort into these four pillars on Upwork, this is what I find it, uh, makes it very, very controllable, repeatable, easy to get great clients on Upwork, get good results and ultimately earn money remotely. And then do what you want with that freedom that. 

[00:17:47] Chris: And I love that. And just very succinctly I think has given just a real good strategy for being successful on Upwork. And it's the same thing I've found with students who have gone through my course, you know, that it's theirs, it's not magic. You know, it's not like we're, we're taking something and doing something. 

Like sleight of hand, that's incredible that you get lucky. And every once in a while you get a really big client, there's something you can systematize and put into place over and over again. And you know, I I've even had students come back and say, I know you said it's not magic, but it feels like magic. 

It was like, no, this, like you knew you knew exactly what you were supposed to do every time. And you just did it, you know, like there's not much more to it than that. You mentioned leapfrog. And I I'd love it. If you could talk about that for a second. Cause I think this is something that a lot of freelancers don't know about Upwork and you've created a great product for folks to be able to utilize it. 

[00:18:45] Robert: Whenever you're on Upwork, you can do a search for jobs, right? So we can type in, let's say you build websites, let's say you built Shopify stores and you can do a search, uh, on upward and. Shopify web development, and then you can set your filters so that, uh, not only does the job need to contain that phrase of words, it needs to be a job where the client indicated they're looking for an expert. 

They're willing to pay whatever. Uh, let's say a hundred dollars an hour or $50 an hour. You can set that, or they have a budget of $2,000. You can set that as well. You can set the location you want the client to be in. So let's say you like working with the U S clients. Um, you've always filters, so you can configure all the filters to really, and the keywords you use to really dial in on a list of jobs that's appropriate for you to. 

Applied to. And so then what leapfrog leads does is it enables you to subscribe to that list. So basically what that means is anytime a new job pops up that matches that criteria. You set, you're going to receive an email notification. As soon as that job comes up. Now what an ideal set up looks like though, is a variation of searches. 

So you're going to have one search as looking for Shopify web development, Shopify store. Let's say you have personal interests. This is my favorite way to use it. Let's say like me, love mountain biking, yoga, vegan food, whatever the hell you care about. And you're passionate about, okay. Change up your words to be web developers. 

Uh, yoga well development, vegan, yo, well development and mountain biking. And you'll be notified about jobs that match or interests. So you can do your interest or you can do like things like professional criteria as well. Like when it's super technical and, you know, anytime they mentioned that phrase, you're like, oh, that's what I do.

Um, and so you can have this collection. Of types of jobs, basically that you're subscribed to. And together what you get is this place in your inbox that you can very quickly sift through faster than you can sift through on Upwork, to hone in on jobs that are appropriate for you to apply to. And then ultimately applied to that. 

So you save a ton of time and it makes it so much more likely that you're the first person to apply. And the first person you apply on. Are closer to first, um, we'll have a better response rate consistently. So the, the, the, there is a free version of the app. There's a 30 our plan, whatever version you're on though pays for itself on a times over when you use it properly. 

Uh, because if you land, you know, one additional client a month as a result of the tool, then you're laughing. But for many people they're easily, uh, getting a much better return than one additional client. So that's kind of how it works in a nutshell. 

[00:21:42] Chris: And I am a huge advocate of being the first to the punch on in any Upwork bed, you know? 

And so I think that is. A huge reason why a lot of people are successful is that they are one of the first five folks to actually bid on a project. And you've created something that makes it super easy for somebody to, to be able to do that. So highly encouraged everybody. To check that out. If somebody is wanting to figure out more about leapfrog leads, word, where they go?

[00:22:12] Robert:

[00:22:14] Chris: Well, I really appreciate you being on the show today. Robert, if somebody's wanting to connect with you more, uh, where, where would they go on the internet?

[00:22:21] Robert: We'll leave. I guess the link in the show. And check out my awkward profile on upward. We'll leave a link to my profile and the show notes. 

[00:22:31] Chris: We'll have to have you on again and see where you're at in the world. I know you're coming to us from Mexico right now, but who knows five months from now where you're going to be. So it'll be an adventure and we'll just do it again. 

[00:22:41] Robert: I don't know either. Thanks for having me, 

[00:22:43] Chris: You know, the main thing that I love about Robert's story is that he didn't settle. 

He was unhappy with what his life looked like, and he did something about it. And here's the deal. If you feel the same way, if you're not satisfied with where you're at, you can do something about it yourself. You don't have to be stuck in a job that you hate or barely earning enough to. For you and your family, you can change your story and the story of your family, but it all starts with a decision that you can make right now. 

You're not, you don't have to change everything overnight, right? It doesn't have to be immediate. It doesn't have to be dramatic or drastic, but you can start making small baby steps towards your goals. And here's the thing when it gets difficult and it will, you've just got to keep going, putting one foot in front of the other, do that. 

And you'll come out on the other side and your life is going to be completely different than what it looks like right now. All right. I hope you have enjoyed this episode with Robert. Make sure to visit leapfrog And don't forget to subscribe to this podcast, the self-made web designer podcast. 

So you don't miss episodes like this and many others from awesome guests that we get here every week until next week, when another episode drops at midnight. Make sure you keep going for it. And don't forget if you don't quit, you win.

A plane window view to symbolize how to become a digital nomad


Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.



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