Dom Wells
Let me introduce you to a very good friend of mine, and you might recognise his name from another guest post on That Marketing Dude… It’s Dom Wells.

Dom Wells is the founder of Human Proof Designs and a fellow digital nomad. Dom is originally from the UK, spent several years living in Asia and is currently in Canada. Here’s how Dom describes Human Proof Designs:

” This site exists to make starting a niche website that much easier. With the training on the blog, the ready-made sites we’ll sell, and the custom projects we’ll do, you will find that getting started doesn’t have to be as confusing as you first thought. ” 

If niche websites are you thing, you should check out his Facebook group Tested On Humans where he drops more knowledge bombs on turning those into little money machines.

Dom has created a beast of a post here… And as always, it’s awesome.

I’ll now leave you in Dom’s very capable hands…


Becoming a digital nomad is a fantastic dream for many people, and a lot of those people go on to achieve it as a reality. For me, I’m more of a semi-nomad. I work from my laptop, but I prefer to stay in one place for several months so that I can actually get work done.

One thing I want to talk to you about today is, how to ease into life as a digital nomad. How to gradually build up your business and free up your time, before taking the leap and going full-time nomad.

There are generally two paths to the digital nomad lifestyle. The first is the more gung-ho approach; sell your stuff, jump on a plane, live off your savings until you can build up an income. In this path, you might not even be sure what you are going to do for your business, you just know that you won’t get started unless you go out there and do it.

I know a few people who have succeeded with this path, and I also know a few reasons why I’m not keen on it. Before I go into this, though, let’s look at the other, more conservative approach.

The second path is to build up your business before you go. How much your income reaches before you do finally pull the trigger is up to you. Do you wait until you can fully support your nomad life and build up an income of say, $1,000-$2,000 per month, or do you get yourself started, get some income coming in, and then go abroad to commit to the full-time approach?

I think ultimately the answer to the above depends on your own goals, the place(s) you want to visit first, and the level of savings that you have in your bank account. The most important thing here though is that regardless of income level, you have at least started before you take up roots and leave.

Which path you take depends on you, but let’s take a look at some of the pros and cons of either.

Pros of leaving before growing anything:

This is definitely the more “Screw it, let’s go!” approach, and it can be effective. Assuming you’ve got enough savings to support yourself for the first few months, there are a few reasons why I like this model.

First of all, it forces you to take action and get started. There can be no paralysis by analysis when you’re living off savings in a new country. If you want to stay there, you’ve GOT to start earning sooner or later.

Secondly, you have more time. Sure, you’re going to be doing some travelling and exploring, but you no longer have the restrictions of a 9 to 5 job keeping you from working on your site in your spare time.

Thirdly, if you head to the right place, there will be a bunch of other digital nomads around to get experience from, and it can be easier to convert to the right mindset. A lot of people who jump in the deep-end like this end up heading to Chiang Mai, and there are plenty of coffee shops for you to work in and adapt to the lifestyle.

How To Ease Into Life As A Digital Nomad - Or How To Not Jump In The Deep End

Finally, heading somewhere where the cost of living is significantly cheaper can help you hit your targets sooner. If you only need $500-$1,000 per month to live, it can be a lot easier to just go there first, start saving on everything right away, and let your money creep up. It actually buys you more time than if you were trying to build up your business in the more expensive west, that’s for sure.

You can check out for more places to go.

Cons of leaving before growing anything

Of course, there are plenty of cons in this method too. The first is the risk. What happens if your savings run out before your income catches up to your lifestyle? What happens if you end up dealing with culture shock or homesickness while also trying to bootstrap a business?

What happens if you lose your passport/laptop/whatever else and your trip becomes a complete nightmare? Having a business and income to fall back on, in this case, would make your life a lot easier.

Another con to consider is that it might be hard for you to actually focus on building a business while travelling the world. You’re travelling! You’re seeing new sights! Do you really want to spend 10 hours in front of the laptop every day?

The dream of “working from the beach” is a bit different from the reality of it. Besides, growing a business and maintaining one are two very different things.

A lot of people who do head to Chiang Mai or elsewhere before their businesses are in full swing end up living on a couple of thousand dollars only and don’t really have well-structured businesses, though. A lot of them end up doing freelance work or constantly hustling to get something new off the ground.

It works for them, but it’s not the kind of business I’d want to run myself.

There may be some other pros and cons depending on your own personal situation and goals, but these are the main ones for me.

Pros of building something first

It’s a lot easier to hit the ground running if you already have something to land on, and know the direction you’re going. Even if this just means you’ve chosen your niche, set up your website, and got something to work on, you’ll find life easier abroad.

Of course, if you play an even longer game and get an entire business set up and some income flowing in before you go, then that’s a huge pro. Imagine if your income level is at four or five thousand dollars per month before you start your travels? You’ll be able to just focus on maintaining that level, and enjoy the rest of your time travelling.

Building something first also does wonders for your mindset. I can still remember the self-doubt I had when building my business that first year and to some extent the second year. I feared so much that I might never succeed, might never reach a good income level, or that it might all come crashing down on me.

Now I live abroad, and my business is stable enough to support me here. There’s always the “Well I can always go home” exit strategy, but I don’t have to give it much thought since my business is thriving.

Now, I say this because if things were different, and I was trying to start a new nomad life while dealing with this doubt and fear, I think that first year would have been even more stressful.

You can’t put a price on the mindset benefits you get from having something established before you go, the benefits really are intangible.

Cons of building something first

The cons of this are that you might end up becoming a slave to your business. In my case, I wasn’t planning on becoming a digital nomad, so while my business grew to the point I was making five figures per month, it meant that when I travelled, I would be inclined to spend 4 or 5 hours per day in front of a laptop. I would be driving to a hotel thinking “I hope their WiFi doesn’t suck”.

Not bad, but not exactly a passive income either.

Still, it paid for my travels and then some.

More cons of building something first are that you may very well never get started, or you may not take the plunge into a full-time income. Sometimes it’s easier to dream than to actually take action.

If you’re living in the west, where your income requirements are much higher, and you’re stuck in a 9-5 job, while also trying to maintain a social life and all the other things, it can be hard to actually dedicate the time to getting started, and even harder to maintain momentum.

The amount of people I know who haven’t started yet because they’re “waiting for the right time” is crazy. It’s like smokers who talk about quitting and never try. It took me about 5 or 10 failed attempts to quit, but I got there because I kept trying dammit.

Sacrifices can be made in the name of achieving your dream, so you’ll need to consider how badly you want to grow that income to the point where you can quit your job and head off around the world.

The rest of this article is going to focus on the practicalities of achieving the second path. How to ease into life as a digital nomad, and get started before you set off on your adventures. This comes directly from my own experiences, and there are definitely some things I would have done differently.

I’ll lay it all out for you, and you’ll be much better off than I was.

How To Ease Into Life As A Digital Nomad - Or How To Not Jump In The Deep End

Step One: Define The Lifestyle You Want

Not every digital nomad is equal in their goals. Some people want to travel as much as possible and work as little as possible, while others don’t mind working as long as they can do it anywhere.

Still, some people are happy being glorified backpackers, who occasionally stay in hotels and have a bit more money than the average gap-year student, while others want to have a life of luxury.

Do you know exactly what you want, or do you just know that you want to get the hell out of where you currently are?

The better you can define what you want, the easier it will be for you to make a plan and hit those goals. Of course, it’s fine for you to have a rough idea and tweak and pivot it later. My goals have changed over the past few years, and I’m sure yours will too.

What Are The Options?

Believe it or not, there’s not a one-size-fits-all solution, and the joy of lifestyle design is that you get to design it how you want!

Do you want to make just enough to support yourself, while having as much time as possible to enjoy yourself?

Or would you prefer to be able to put some money away every month, at the expense of putting more effort in?

Would you like to work in batches, doing solid work for a week every month, then letting things sit for three weeks?

Or maybe you’d like to earn as much as you can, work as much as you can, but move on to a new location every few weeks/months.

There really are a good number of options for you, but as you may have guessed, each of the above requires a slightly different strategy.

For example, those who like to work once a month and then let things sit would be better suited to affiliate sites, where you can do a lot of your work in bulk then wait for results to come in.

For people who want to work a bit here and there, freelancing may be a better option.

For those who want to follow more solid working hours but get a higher payoff, running a service business may be better. Service businesses (such as SEO, PPC etc) can pay very well, but they are more time intensive and far from passive, at least until you earn enough to be able to build a team.

Step Two: Picking Your Niche or Business Model

Following on from my last point, it’s time to determine what kind of income you want, and what kind of model would suit that.

Here are the most popular income models for digital nomads:

1.) Affiliate Websites

This is where you own one or more niche websites which make money from affiliate commissions. Usually, your traffic would come from Google search, which can take several months to build up.

If you’re going with this model, you really do want to ensure that you get things rolling before you leave. It can take a while to find out if a site is going to be a winner or not, and the feedback loop is long with affiliate sites, especially if you’re new.

Now, assuming you do go with this model, you still have a couple of options. Do you go for a portfolio of sites earning anywhere from a few hundred to a few thousand each, or do you build out one authority site?

I’ve gone into the pros and cons of each in this post, but to give a quick summary, an authority site is much easier to scale once it gets going, whereas a portfolio is more passive later on. It also increases your chances of finding a winning niche.

This kind of model is suited to people who want to do bulk work once or twice a month (make the updates to your sites all at once, then schedule them to have new links or posts go live throughout the rest of the month), or someone who wants to earn a decent income but doesn’t mind doing a fair amount of work either (authority site model).

2.) Services

The most common services are SEO, PPC, Web-Design, or another service aimed at helping other digital marketers. The reason why the best services target digital marketers are simple, if they too are based online, they won’t expect you to help them from any one place. You get to travel and work from anywhere.

Services can pay well, but are more time intensive. SEO and PPC services need a few decent or high paying clients to really make sure your income is high (and diversified), and this can be quite time-consuming.

It’s essential that you have a bit of a funnel or customer acquisition model in place before you go abroad because you don’t want to be in the feast-famine cycle while travelling. This is essentially where you have a lot of clients at once (feast), which means you have no time to get new ones, which leads to famine. If you have a constant supply of new customers, though, you’re all good.

Ultimately this kind of business can scale up to the point where you can build your own team working below you. This means that your business model can evolve over time. You start off with a more “I want to work longer hours in exchange for higher payout” model but get to move to a more passive model.

This is essentially the path I followed. I built a business to $20k per month by myself, then started hiring a team. My income dipped slightly as my expenses went up, but I have much more free time to enjoy the money now.

3.) Freelancing

Now when it comes to freelancing, there really are a number of options for you. Anything from writing, to web design, to working for a service or authority site, you are only limited by what you learn how to get paid for.

However, let’s look at some of the cons of freelancing. Financial security, and finding clients.

I’ve hired a lot of freelancers, and one thing I’ve noticed is that they are always looking for new clients. This means that when I first hire one, they work well, but as time goes by, I can tell I’m slipping down their list of priorities, which ultimately leads to me looking for someone else.

Of course, I do have freelancers who work for me almost full-time, putting in 10 or 20 hours per week. This is the type of freelancer you want to be. If you’re a writer, you need to work your way up to getting a few high paying writing gigs for a few businesses that aren’t going anywhere fast.

Somewhere like nichehacks is a good example; Stuart has hired a few good freelancers in his time and the ones who work for him have a security. Your aim should be to grow your reputation to the point where you can find this kind of client.

The same applies whatever form of freelancing you do, not just writing.

Now one massive pro of freelancing is that you can, for the most part, set your own hours. If you’re a highly skilled freelancer, you can work a few hours a day/week and still make enough to pay your way around the world. As long as you have clients, you can find a good balance between going to the beach, and making bank.

If security is your thing, you definitely want to build up a list of clients and testimonials before you go abroad though.

If money is your thing, you might want to use freelancing as a stepping stone towards building your own service instead.

In fact, freelancing is a great transitional model, as it gives you the option to strike out on your own later on.

Step Three: Getting The Necessary Skills

This brings me nicely to the next section, developing skills.

No matter what option you go for, spending the time to develop skills is essential before you go abroad. If you want to hit the ground running, you don’t want to have to deal with a six-month learning curve.

Here are some tips for learning the skills:

1.) Practice

Let’s say you want to own a bunch of affiliate sites while you travel. The more sites you build and develop before you go, the better you’ll be. You’ll also have a basic income to work with as well.

The same is true for freelancing, and offering a service.

2.) Work Experience

Why not make your full-time job related to what you want to do? Quite a few people who want to build an SEO or PPC service start out by working for a big SEO or PPC agency. It makes sense, and it means you get a solid income while learning the ropes. You can probably utilise some of their tools to start building up your own portfolio on the side as well (more on this later).

3.) Read and Network

The more blogs and content related to your business model you read, and the more people you can network with, the better things will be.

See if there is a digital nomad or online entrepreneur community in your local area and see who you can find!

Luke’s Dude Brood is a good example.

How To Ease Into Life As A Digital Nomad - Or How To Not Jump In The Deep End

Step Four: Transitioning Into The Move Abroad

Now for the nitty-gritty part, when and how do you take the plunge?

First of all, I’m going to assume that you have a full-time job when you start building your business and preparing to move abroad. If you don’t, and you’re building this up from scratch, then go as soon as you can afford it and feel that your income is stable.

For those of you with a job, it’s not much different. I would suggest though that you transition from a full-time job to a part-time one first. This could be a good opportunity to move out of your main job and into a job that complements your own business. Freelancing for a digital marketing company, serving a few clients, helping someone else with theirs, that kind of thing.

The real benefit though is that you’ll have the extra free-time to focus on your business, while your part-time job pays your rent.

In my case, I had been hoping to quit my job for some time. However, after a year and a half of building my business, I was still only earning $500 per month. It was frustrating, because I felt like I couldn’t scale it higher unless I had more time to dedicate to it, yet I couldn’t afford to go full-time on just $500 per month.

In the end, I was able to move into a position where I could do a part-time job earning me just about enough to pay my rent and bills, but giving me double the free time I had to work on my business.

Sure enough, a few months later I was making $1,000 per month, then $2,000, then pushing $3,000.

I didn’t go fully full-time until about a year later, but this was because I was a little bit superstitious about quitting my job as soon as I had passed my income goals. I didn’t want to suddenly have to go back again if my new internet income didn’t last.

In your case, I recommend this kind of one-two step transition, but it’s not the only way to go about it. Some people can build up their business while working full-time, so I suggest at least trying this first. The more money you have to play with, the better.

You can also consider investing some of that money into outsourcing various tasks that you need to perform for your business, but don’t have the time to do. It depends on your own time:money balance. Everything can be done with enough time or money.

How To Ease Into Life As A Digital Nomad - Or How To Not Jump In The Deep End

Final Thoughts

As I’ve tried to make it clear in this post, there is more than one way to become a digital nomad. I know people who’ve done well with pretty much every method mentioned in this post, and there must be many more journeys I’m not even aware of as well.

That said, the main path outlined above is one very similar to the path I ended up taking. I never really had a huge desire to be a nomad, I just wanted to be free to work where I wanted, when I wanted. Once I was in that position, though, how could I NOT travel?

For you, whatever path you take, and whatever work:life ratio you want, my advice is to do as much preparation as you can, but not at the expense of actually taking action. Look at Luke as an example; he spent two or three years before he finally started getting traction, and most of that was down to procrastination.

Being well prepared is great, but a lot of this online business stuff needs to be adapted as you go, and you never really know how well things will go until they happen.

Keep trying, and you’ll get there, and that’s all there is to it.


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