Travel Job Interview: How To Become A Remote Employee Or Freelancer

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So I’ve started doing this thing where I interview an amazing digital nomad every a week, to share what they do to make money online while traveling and help you to start living your dream lifestyle!


Today I am joined by Kate Smith from the Remote Nomad, where she also gives a lot of tips and inspiration to help you to become location independent.

In this interview, Kate is going to share all about how to become a remote employee/freelancer while traveling and give lots of tips to help you get started.


Take note, there are a lot of great tips in this one!

** Before I forget I also recommend checking out these 15 awesome travel job courses that’ll teach you the exact skills you need for many kinds of remote jobs you can do from anywhere.


Travel Jobs Interview: How To Become A Remote Employee Or Freelancer While Traveling

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So helpful! | An in depth interview where I chat with remote nomad Kate Smith about how to become a remote employee or freelancer while traveling as a digital nomad. Click through to read now...


Welcome Kate it’s really good to have you here and I am so excited to talk to you all about this!

Can you tell us a little bit about yourself, where you are from and what you do?


Yeah, so my name’s Kate and I am from Canada, near Toronto, and I do online marketing.

I work remotely for a remote company and then I have my blog as well as a new program I’m launching which essentially shows people how to live this lifestyle – from earning an income remotely to navigating the logistics of living this nomadic lifestyle.



When I first got in contact with you through Facebook I was really inspired by what you do, especially when you mentioned this new program/retreat because I always thought about how cool it would be to do something like that!

So, when and how did you get started as a digital nomad and what inspired you to do it?


So in Canada, it’s pretty common to have very limited vacation time. It’s usually around ten days when you’re starting out, even if you’ve been to university.

I started in a corporate job, working in advertising. I did that for three years and then I started to get this feeling most people probably have…

You sort of feel like “I can’t keep doing this, something needs to change, is this my whole life?”

I was really passionate about traveling and I found that my career was really restricting that.

I really liked my career but it always seemed like I had to pick travel or work and there was never really any compromising.

So I went through this process of thinking… “OK, what’s my ideal job?”… and then listing down the criteria of what I wanted to look for in a job.

I was doing my research and exploring different avenues when I came across this article on Facebook about Remote Year…

Remote year is a program that takes a group of people to essentially work remotely while traveling the world.

So you’re making connections, you can keep your professional career, you’re earning an income but you’re also traveling.

It seemed like the best of both worlds finally together.

So I did my year with Remote Year and learnt the ins and outs of this lifestyle and the uniqueness of it.

So that’s how I got started.


When you were in the Remote Year, did you start doing something else career-wise or were you still working in advertising?


Yeah, so the evolution of that was…

I worked at an advertising agency as a project manager and it was very traditional. I was working with TV, print and billboards but I knew that everything was going online.

So I transitioned over to a shop that did web development and design and I was a project manager there.

When I joined Remote Year and became a “digital nomad”, I didn’t even have a remote job.

But it was actually in one of the co-working spaces where I found my remote job opportunity.

I was just connecting with people, explaining what I do and that I was looking to make the transition into online marketing instead of project management.

And when you’re in that environment, surrounded by people, working remotely, it’s easier to find a remote opportunity.

So I found a contact there who knew someone that was hiring remotely and then it sort of just worked out from there.


Cool! So you’re working as a remote employee for a company?


Yeah, it’s technically “freelance” but I’m mostly working with just them.


And where they based?


Several places… The company is based in Prague and we have employees in Prague, Canada and England. Then we have clients in Australia, the USA and all over the world really.


So what knowledge and skills did you start off with and what qualifications or experience would someone need to start doing what you do? 


So with what I’m doing in online marketing, I think my background definitely helped… The project management, going to school for business, etc but is by no means what someone needs to do.

There is so much information online, so many courses you can take online that are much more cost effective and will teach you the exact same things you need to know.

I’ve learned a lot of my stuff on HubSpot… They do free certifications and teach you a lot about online marketing.

There are definitely ways. I mean, I had a natural career progression into something that is pretty popular online…

So I think, looking at what’s popular online in terms of earning an income and what your opportunities are and then transitioning your skills.

There’s a lot of transferable skills that most people have that you can move over to a new role.

So you don’t necessarily have to make a huge career change. You can just make a transition.

I also think that everything is based online now, so the more you’re kind of dabbling around online, the better…

Whether it’s just playing around and trying to get your own website up and creating an email list, that sort of thing.

My blog has been a really great way for me to learn because I get to test new things and be within that online atmosphere… Digital nomad Facebook groups, Reddit, etc.

It’s about trying to get yourself more comfortable with the kinds of online tools that you’ll probably use.


You mentioned HubSpot… What is this platform and what kinds of free online courses do they offer?


HubSpot (see bottom of post for link) is a great tool and platform for doing online marketing…

So online marketing consists of capturing emails, sending automated responses, creating online offers, creating pages, managing your website, etc.

HubSpot is this tool that does all of that and they obviously want people to use their tool to the best of their ability and to make the most of it, so they offer this free training so you can get certified in online marketing.

Online marketing is really about attracting people instead of trying to sell to them so yeah, HubSpot offers a variety of free certifications that will teach you this.


Awesome, that sounds like it would be a really valuable resource for people just starting out, especially being free because a lot of these courses require significant investment.

So where exactly does your income come from?

How did you go from zero to now earning a location independent income that is able to support you while traveling or working from home?


I mean, I was earning my salary when I was working in an office and then when I transitioned into working for this new company, it’s now on a freelance basis.

So essentially, you’re transferring your salary to an hourly rate.

And then there’s also other considerations you need to think of when you’re freelancing because you’re responsible for your own equipment and stuff like that. Usually the employer would cover those costs but now you’re going to cover them.

So you just need to incorporate those things into your rate.

I mean, a very common way for people to earn an income is to freelance, and you have complete control over how much you’re earning when you’re freelancing.

I think there’s this misconception that people are taking pay cuts in order to do this but I’ve had friends that have received promotions and raises.

And when employers see how well it works for them, they become more receptive of this lifestyle.


I also think once you start gaining your client base and getting recommended to other people, you can start increasing your price as well.

Obviously, the work that you’re doing is of high quality, so don’t undersell yourself.


Absolutely. And I think that’s a big and very important thing. Just because you’re working online does not mean you’re delivering any sort of poor quality or different quality of work.

You’re delivering the exact same as you did before.

If your rate or value was something before, there is no reason why that should be lowered just because you are working remotely.


I mean if you think about it…

If you’re working in a traditional job and your employer pays you an hourly rate, don’t go below that for your freelance work.

That’s what you are worth and people will pay if they know that you’ll do a good job and you’ll actually help to grow their business and be of value to them.


I also think people need to keep in mind that when you’re offering such great low prices, usually people associate those low prices with the quality you’re going to deliver.


How long did it take to start earning a comfortable enough income to be location independent?

I know you started out in the Remote Year but what was it like to transition?


It’s a lot of work and that’s the thing… It’s not easy and it’s easy to give up. For some people it happens really fast and for some it won’t.

I had been applying for remote jobs for a good three months.

This was because I was applying to work for someone else when it reality it was probably a better avenue to start freelancing.

In my head I thought I’d have to start a business or work for someone, but I didn’t consider the fact that freelancing is a good in between.

It’s going to take some networking and effort and even if you’re this awesome person, you need to build your online presence and build your clientele.

So you just have to be persistent.

At the end of the day, someone’s going to hire you and you’re going to be able to work remotely.

It’s just toughing through that.

For some people it’s faster, for other’s it takes a lot longer.

It is just about being persistent and taking action steps towards making it happen.


When you were in the process of applying for these jobs, was that when you started your own blog and retreat? Or did that come later?


So when I started this journey on remote year, I knew I wanted to blog about it.

I had no idea what my niche was, I didn’t know anything about blogging at all. I just started writing and I just started doing it.

And it was sort of an evolution, like I learned…

I’m not much of a very descriptive storytelling writer, I am very to the facts, here’s how you do something. I guess that’s sort of my business background coming in.

And it was with my blog I realised the various pain points that people have. One is how you actually get started earning an income and how you take that first step…

Like what country do you go to?

How do you know you’re going to have internet?

So it sort of went from Remote Year and evolved into creating this blog, which then evolved into this new program/retreat as a way to fill the need that I was seeing.


So do you work on your job in online marketing and the blog/retreat simultaneously? What is your schedule?


Yeah, so half my time is focused on my online marketing work and the other half is focused on developing the the program.

I feel it’s hard with the blog, there’s always so much that I want to put out there…

And I always feel like I’m just so short for time, there’s always something going on and it’s hard to put out there.

But I do know that in creating the course material for the retreat and putting that together, it’s going to provide more value.

I do still try to blog more frequently, especially not being on the Remote Year program anymore.

That was very fast paced, this is giving me an opportunity to focus more on the blog. So yeah, I’m trying to get a post out every week or so.


How was your experience with this group of people traveling to all sorts of places in the world?


When people ask that, it’s the hardest thing to put into words. It was a life changing experience for me.

You know, I never knew this lifestyle even existed and I learned so much about it. And it’s the most unique situation you can be in…

Traveling with seventy-five essentially strangers for a year.

It makes you grow as a person, I was in a really great headspace and it really makes you really self-reflect.

You become very self-aware, just given all the situations and always having to adapt.

I really didn’t get a chance to process it all until I came home because it’s just like Boom! Boom! Like, you’re working full-time, then you’re hopping to one country after the next.

It’s a lot to take in but it was definitely an experience of a lifetime.


I think the Remote Year and other similar programs are really amazing ways to get support.

So if you’re just starting out or you’ve got an idea and you don’t know how to get it started, having seventy-five like-minded people surrounding you, who are all in online business, is such great support.


Yeah, I think the biggest thing is that the community was the most important part of the program and any of these programs you go on.

Living this lifestyle and finding your sense of community is really important… To have people that get you.

Because you’re essentially a big group of black sheep that really don’t fit in at home and everyone gets each other when you’re together.


Definitely, because I think a lot of people start out on this journey of becoming a digital nomad and they don’t know how to find the community and it feels lonely.

Some people end up just giving it up and going home to have that sense of community again.

There are a lot of communities out there. Even when you go to specific countries.

There are groups of people who come together that live this kind of lifestyle in cities around the world. You can always find your community.


Yeah, you’re never alone. I remember when I was in Bali, my mom was all nervous because I was alone in Bali. And I was like, no, I’m not a lonely… My community is everywhere, it’s very easy to not feel alone when you know they’re everywhere.


Speaking of like traveling and visiting all these countries, where has your digital nomad journey taken you so far?


So we did a lot of Europe, Asia, South America…

Places like Turkey, Croatia, Malaysia, Indonesia, Japan, Argentina, Peru and Chile.

I think I’ve been to thirteen now so far.


So the idea of working and traveling at same time sounds amazing to most people….

But how do you stay productive while you’re trying to work or build an income and travel at the same time?

What kind of process do you have to stay focused and productive?


Sometimes it can be really hard.

I think you need to be clear on what your goals are.

By doing slow travel it’s less overwhelming because that way you know you have the time to do your work.

Then when you’re done working, you can go do whatever it is you want to do in the country.

And once you’ve had opportunities do all those things, then you can move on to the next one.

I did a month at a time and it was just way too fast.

I would suggest at least 3 months, that way you don’t feel rushed.

I knew going into this that I was going to be in all these amazing countries and be very tempted to go everywhere else and do all these side trips. So I set the expectations for myself.

I thought, this is a great experience, I’m going to really embrace the city I’m in and make the most of it whilst focusing on my work.

I mean when you’re meeting travelers and they all want to go out and have fun it can be very tempting.

But you know at the end of the day they’re there for two weeks and then they’re back home for a year. You’re doing this forever.

It really is a lifestyle, it’s not a vacation.

When you recognise that you have the opportunity to continue staying in each country for as long as you want, and the thing that’s going to fuel that is by working, you’re going to prioritise your work.


When you’re running a business or developing your career online, it’s always important to invest back into what you’re doing…

So what kinds of things do you invest in?


There’s a lot.

I’ve always really believed in investing in yourself and I feel like a business is almost a piece of yourself.

So I have a life coach that I work with and she also helps in terms of not just life but in a business perspective as well.

Also, online courses, I love learning online. In fact, I’ve just purchased an online course.

Then there’s the actual investment into the company…

You’re paying for your website. There’s deposits you have to put down in terms of getting things started. There’s a lot of online tools that I use to run the business.


And that’s what helps you to grow as well. That’s what helps a business to grow.

You can’t just start something and expect the money to come. You have to put it back in again.


I think that’s what people don’t understand, they see all these people making money online or starting businesses but there is a good year or two of struggle that people don’t see.

But then there’s the breaking point and that’s what people see.

You need to be aware that it does take time. Things don’t happen overnight.

You’re going to have to build and work towards it. But if you want it enough, you’ll be patient enough to go through all that.


And similar to what you said earlier, a lot of people don’t have the savings to be able to just start working on their own business for two years and not see results.

But if you start getting into something like freelancing at the same time, you can start bringing some of that income in while working on the project on the side to eventually build your business or career online.


When I started this lifestyle, I didn’t have savings to pull from. You can save a lot of money by living in different countries. So it really is cost effective to be somewhere else.


So my final question…

Do you have any tips or strategies for people who are wanting to start out on the digital nomad lifestyle?


Yeah I mean, the best thing you can do is to find a remote job first.

That’s sort of two fold because when you’re in the environment surrounded by digital nomads and you just take that leap, it presents networking opportunities and more opportunity to find remote work.

But try to start with some savings… By no means do you have to, I didn’t have any savings, but it helps to give you that bit of comfort and breathing room, especially if you’re trying to bring on new clients, it just gives you that security.

Just saving up a little bit, even a couple thousand is good. Two thousand, it doesn’t have to be crazy.

Start trying to think about taking those action steps towards how you’re going to transition to a remote job.

If you want to start freelancing then start getting your website up…

Start trying to take on freelance clients after work, after your corporate job and build up that portfolio.

I think that people really need to be persistent.

I never thought I’d be living this lifestyle in my wildest dreams and if I can do it, I know that anyone can.

Set a timeline, create your actions steps.

If it’s just this vague goal you’re working towards, you’re not going to achieve it well.

List out what kinds of remote jobs you want. Write down the steps for how you’re going to get there. Figure out your backup plan. Set a goal date for when this is this going to be achieved by.

Following that timeline and making sure you are taking those action steps action is probably the biggest and most powerful thing.

Don’t over think it, there is a lot to learn, yes, but if you’re taking action, that’s the best thing you can do.


Definitely, having that set goal and working towards it.

I think this is a mistake a lot of us make… Not having a strong goal and kind of just working towards something, not really knowing where we are going.

So it is really important to have that desire and strong goal and taking those action steps like you said.

It doesn’t have to be perfect, just get it done.

And once you’ve done it, you’ll find it much easier to do it again and again and then improve from there.


If I started my blog when I was ready, I would be starting it maybe this month.

So you just have to put it out there and sort of lose a bit of that perfectionism.


It’s hard to do that, especially when you’re a perfectionist, but it’s necessary because otherwise you’ll just be focusing on the small things and not actually focusing on the big picture, which is getting an income into your bank account.




Kate, thank you so much for sharing all of your tips and strategies about how to become a remote employee/freelancer.

It’s been really helpful and really inspiring at same time.

It’s always nice to learn other people’s stories because everyone has a different background… Everyone does different things to achieve his lifestyle.

And it’s really interesting to find out what you’re doing!


Thank you!

Important resources about how to become a remote employee/freelancer

Before you go, I highly recommend checking out the links below.

All of these will take you to places which will help you to become a remote employee or freelancer and live the digital nomad lifestyle!

Over to you! Leave your thoughts in the comments section below…

1 – Are you looking to become a digital nomad and interested in more details about how to become a remote employee or freelancer? Leave your questions below…

2 – Are you already living the digital nomad lifestyle and have some more tips about how to become a remote employee or freelancer? Please share!