How to Build a Career While Travelling the World

In my last post I discussed how realistic it is for someone with a marketable skillset to work remotely and travel the world indefinitely (in a sentence: very realistic).

Now I’m going to get more specific. I’m going to talk about the actionable first steps someone could take towards building themselves a career that enables them to work remotely.

Avoiding False-starts

If you’re sold on building a location independent career, there’s some important advice I’d like to give you before you jump in with both feet.

Firstly, I don’t recommend following your passion. If you want to start earning enough money to support yourself as a location independent entrepreneur, you need to focus on creating value, and creating value early - and passion is not the right path to value creation.

Secondly, don’t become a “blogger”… at least not with the intention of making it your primary source of income. While blogging is an important strategy for the long-term development of your business and career, most people aren’t going to be able to earn a sustainable income from blogging alone.

The Starting-point: Marketable Skills

Instead of starting a business based on one of your passions or trying to blog your way to profit, my advice is simple.

Focus on building a demonstrable, marketable skill that people are willing to pay you money for.

And what do I mean by “demonstrable” and “marketable?” I mean that you can:

  1. Tell me what you do.
  2. Show me examples of your work.
  3. Tell me how much it will cost for you to do the same thing for me.

And I believe the quickest, easiest and least risky way for people to get started making money from a marketable skillset is to freelance.

Think Strategically

A quick disclaimer. It’s imperative that you pick a freelancing career path with a long-term vision in mind. You don’t want to wake up after 12 months and discover that the portfolio and skillset you’ve put so much work into building is useless, because you don’t want to continue doing the work and it doesn’t help you to achieve some broader, more ambitious goal.

So think about this question: in 12-24 months time, what do you want to be doing?

  • Do you want to employ other freelancers and build a small agency?
  • Do you want to build a business selling products (physical, informational or software)?
  • Or perhaps you’re happy freelancing long-term, but want to work with clients in a specific industry and charge a certain amount?

I suggest picturing a long-term vision for your career, and then stepping back and considering what the first step in that career progression looks like.

Choosing the Right Skillset

With a long-term strategic vision for the trajectory of your career in place, the first and potentially most important decision you now need to make is what skillset you’re going to focus on building. This will depend on your personality, background and long-term career goals.


If you want to be a writer, I’d suggest copywriting as your first port of call. Copywriting might not sound as sexy as professional blogger or novelist, but it makes money for people, and making money for people IS a marketable skillset. Writing about your weekend beach trip or how much beer you drank at Octoberfest is NOT.


Perhaps writing doesn’t do it for you, but you are interested in the broader industry of digital marketing. In that case, I’d suggest becoming a SEO or PPC consultant. While it can be tough getting started in digital marketing as there are so many people claiming they have the skillset, I believe this can actually work in your favour. If you can act in a professional manner and demonstrate results, this places you in the top 0.01% of  candidates, making it very easy for you to build a sustainable consulting business based on referrals and word of mouth alone.


On the other hand, writing and marketing may not be your forte. If you’re technically minded, becoming a web developer is a great way to break into freelancing. This is the route that made sense for me (I majored in Software Engineering), and if you’re interested in the nitty-gritty details of the web it may be a good fit for you.


Finally if you’re an aesthete, consider becoming a designer. I recommend focusing on learning skills that are directly monetisable. For example, designing banner ads or landing pages for websites is a good idea. Creating 3D renderings of your favourite video game characters is not.

Getting Started: Client #1

Once you’ve decided on the right path for you, you need to develop your skills to the point where you can start charging money for them. This step is obviously outside the scope of this article, but there are plenty of resources on the Internet to set you on the right path.

When you’re ready to start charging, we hit our first roadblock. You need to have demonstrated your abilities in some way to convince clients you do work worth paying for… but how do you demonstrate those abilities without actually having a client in the first place?

There are plenty of potential solutions here, and you’re only really limited by your own creativity.

One way is to work on your own projects, and use those as portfolio pieces. This isn’t a bad way to start, but I’d use it as a last resort.

A better way is to reach out to people in your network (friends, family members, previous colleagues) and let them know that you’re getting started freelancing, and looking for your first few clients. On the topic of remuneration, I have a rule with projects for friends or family members: full-price or free. Either charge them what you would if they were a real client (and treat them as such), or do it free of charge as a favour. Don’t discount. It usually gets ugly.

While these are two good tactics to build your first portfolio pieces, there’s an even better way… simply ask. In more detail: identify your ideal client, contact them with a personally targeted cold email and offer to collaborate with them on a project for free. I recommend seeking out thought-leaders, or those with a strong personal brand in the industry you want to target.

An important point: make sure your first client knows upfront that you’ll be using the project as a showcase piece. This is one of the biggest mistakes I made early on. I worked on projects that didn’t enable me to publicly acknowledge my contributions, so while I did a great job and left the clients very happy, I couldn’t blog about the projects or post them as public portfolio items.

Levelling up

After you’ve secured your first handful of clients, it’s time to go prime-time. You should create a portfolio website for your freelancing business that clearly identifies what it is that you do, and makes it easy for potential clients to get in contact with you.

It’s then a case of levelling up. This phase involves cycles of:

  • Refining your definition of an “ideal” client.
  • Refining your service offering.
  • Applying for jobs slightly outside of your comfort zone (in terms of technical skills and budget).
  • Always charging more for each new project.
  • Updating your portfolio with your best and most high-profile work.
  • Rinsing, repeating.

Onwards and Upwards

As the quality of your clients improves and you start charging more, you’ll eventually cross an inflection point. Suddenly, things we start to get easier.

You’ll start receiving referrals from previous clients. It will get easier to win projects as the quality of your portfolio and ability to execute improve. You’ll be earning more, so you won’t have to work as much. The power dynamic will shift; you’ll be the one turning back work instead of being rejected.

And it’s at this point that you should do something that sounds counterintuitive: scale back on freelancing. Scaling back will afford you the mental breathing room and spare time to start working towards your long-term career vision.


  1. Sofie Couwenbergh April 27, 2014 at 8:03 am #

    Hey Corey,

    I found your site thanks to Nomadic Notes’ newsletter. Love this post (and the previous one).
    A lot of freelancers write about this “getting started” stuff, but a lot of them put too many flowers and colors around it, if you know what I mean.
    Appreciate the brevity!

    Just one thing: there’s a small typo in the first paragraph of the last section: “things we start to get easier”

    • Corey McMahon April 29, 2014 at 1:37 pm #

      Thanks for the feedback Sofie. Like most good things in life this stuff is “simple but not easy.”

      • Sofie Couwenbergh April 29, 2014 at 4:40 pm #

        I completely agree!
        I also think perseverance is important. A lot of things you have to do to get somewhere (or you read that you should do to get somewhere) only have some effect if you keep doing them.

  2. Chris Sapp May 29, 2014 at 9:00 pm #

    Dropshipping !!!

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