How To Land Your First Gig As A Digital Nomad

Following on from the Buckets Guide To Digital Nomad Success, we realized that many people are still pretty stumped on the ins and outs of actually pitching for work as a digital nomad. In this blog, you’ll learn more about the digital nomad movement, find out how actually land your first gig as a digital nomad, and learn about what’s involved in sourcing and pitching to prospective clients.

You can’t really escape the term digital nomad in 2016; it’s everywhere, just like the new breed of professionals who have adopted the term as they work and travel the globe.

At the start, the idea seemed a bit ‘out there’ and it had a hippy, backpacking vibe to it more than anything else; but digital nomadism is fast becoming a recognized way of life for professionals worldwide. And it’s not just for tech peeps either. Once you have a career that allows you to work online, the digital nomad world is your oyster — and that includes entrepreneurs, remote workers, CEOs, and freelancers alike.

Many digital nomads actually participate in ‘slow travel’, which is a great way of having some stability in terms of getting your work done whilst having time to experience the culture of each destination you travel to; rather than hopping from one place to the next whilst trying to navigate your workload at the same time. Some digital nomads even stay put for months on end; but the term arguably still applies, as they always have the ‘option’ to travel elsewhere if they wish.

That ‘option’ is the holy grail when it comes to escaping the 9–5, white picket fence scenario that’s pushed upon most of us as we progress in our careers. Why live in a cubicle when you can live in a….campervan? (okay maybe not the best analogy)

Before writing this blog, I spoke to Yulia Safutdinova — an adventure travel blogger at Yulia has been a digital nomad for a few years now and she was keen to dispel the myths about ‘leisurely’ digital nomadism that circulate the web;

“Let’s face it, we all have this picture of paradise in mind when we think about digital nomads: a half naked person on a hammock with a Macbook and a beach in the background. Don’t worry, I had the same image in mind before starting out my nomadic life.
The truth is, digital nomads work the same much like regular 9 to 5 workers (or probably more). And you know what? If you want to make things done, you cannot really do it from a hammock. Have you ever tried to work from the beach? The sun reflects everything and you won’t see anything anyway!” [Yulia Safutdinova]

I always did wonder how those sun, sea, and Macbook situations worked out… (mine can’t actually swim).

So, now that you know that the whole digital nomad thing is just as much about work as it is about play; how do you actually get a gig in the first place?

Getting Started

The real problem when it comes to kicking off your digital nomad career, is the ambiguity around how to actually get started.

  • Where do you find a job that will allow you to travel?
  • Should you freelance or find a remote work position as an employee?
  • Do you want to work part-time or full-time?
  • Can you convince your current boss to cut the reins and let you work from a beach hut in Thailand instead of your dreary cubicle back home?

What if you do all of that, and then you lose your job halfway through; get stuck in the middle of Cambodia or something, and wind up teaching English to 4 year old children for 5 bucks an hour, to pay rent on the fancy Airbnb you booked because slumming it just isn’t your thing?! ! Disclaimer: ESL is actually a pretty ok gig!

There are a few routes you can take if you want to work and travel the world, and freelancing is one of the best ways to get the ball rolling.

Establishing Yourself As A Freelancer

Work With What You Know

I often get people asking me for advice about freelancing and I always say the same thing; work with what you know. I genuinely think that the best freelancers are those who have honed their skills to the level where they can work autonomously and provide the best possible results for their clients. Your clients aren’t there to babysit you; they’re paying you to advise them. These are the freelancers who have built up ‘hands on’ experience in-house, and then use that experience to become reputable consultants in their chosen field.

Look, you can freelance in all kinds of ways. But the gigs that are going to actually give you the means to work and travel without hitting the poverty line are the gigs that allow you to excel in the area that you’re most experienced in. This is how you build a brand, a business, and a life that you love waking up to each day, rather than one that’s imposed upon you by societal norms.

I only started freelancing full-time after I had worked my way up the ladder for almost 10 years and actually earned the right to charge people for access to what I know. No-one was digital-nomading when I finished Uni and my first writing gig was for a magazine based in the UK. It wasn’t great money but it was great experience, and that was pretty much the norm for all of the freelance gigs I picked up around that time.

Was it worth it? Yes. Would it have sustained a digital nomad adventure for me back then? No way. Hence why I was also working in a call centre to pay the bills, which isn’t actually the tough slog that you’d think. I made great commission, met some awesome people, and learned a lot about the real art of selling which basically boils down to one thing — connecting with people.

Now, I’m absolutely not saying that you need 10 years of experience behind you — I definitely took the scenic route — but you do need to spend a year or so working with other people within your industry, learning from them, and developing your own working style and portfolio so that you have the confidence to successfully launch your freelance career.

Pitching For Gigs

If you want to get a gig as a freelancer, you have to go and get it (tiger). The work isn’t going to come knocking at your door (as much as many people seem to think so!). It’s obviously important to have your social media set up and start putting yourself out there as an authority in your chosen niche(s). In fact, the aim of this is to eventually have clients coming to you now and then on the back of your expertise. But, when you’re starting out, it’s imperative that you actively go and look for the clients that will give you a stepping stone into the freelance world.

Many companies will have already advertised the gig that you’re looking for, and you’ll find tons of digital nomad friendly listings on sites such as Problogger and We Work Remotely. I ran through most of these in our previous blog post if you want to check them out.

Because of my sales background, I probably found the cold pitching aspect of freelancing easier than most. But the thing is, it is easy once you have a bit of confidence in yourself. A lot of people I’ve spoken to seem to have a mental block over it, which is understandable — it’s tough to place yourself in the face of rejection! But nothing will happen either way until you stop talking about it and start to take action. And one of the best ways to do this is with an email pitch.

These are the steps I recommend to get started;

  • Figure out what kind of companies you want to work with
  • Compile a list of those companies and the person in charge of hiring
  • Find their contact details
  • Draft your pitch email (more on that in a minute)
  • Tailor the email to each company
  • Send the email
  • Schedule follow ups (and, you know, follow up!)

Here’s an example of how you could manage this process using Buckets;

This allows you to easily track your prospects according to what stage they’re at in the sales cycle, and it also makes sure that you don’t lose track of any pitches when you’re sending 20+ a week. Once the prospect has moved over to the ‘agreed terms’ list, you can then start up a new project to manage that client’s workload and even invite them on board.

To add a new member to a Project, just click on the Project Options dropdown menu and click on ‘Members’. You will then see the option to invite members to the Project.

How To Draft Your Email Pitch

There are a few fundamental functions that your email pitch needs to fulfil if you want to see a return on the time you spend drafting it.

  • Icebreaker: explain who you are what you do
  • Touch on what they do (i.e. show them that you actually looked them up and didn’t just google search a list of names)
  • Identify the client’s need/problem
  • Explain how you can fulfil that need(s)
  • Solve their problem — in detail — no wishy washy malarky.
  • Don’t overprice or underprice yourself. It’s a fine line. Some clients are worth reducing your rates for, so don’t ignore any potential extra advantages to a lower paying gig such as extra exposure or the chance to build up a strong portfolio.
  • Unleash your ‘human’. Close off with a friendly note or reference to something non-work related. People like to work with people and it’s important that you break down those initial barriers and work on developing a warm relationship with your client from Day 1.

Just Do It

When it comes to getting first gig as a digital nomad, the only person stopping you is you, because you’re not doing anything about it yet! Remember, you don’t have to go globe trotting every second week to be a digital nomad, that’s not what it’s about; it’s about fuelling your passion for travel with a job that allows you the flexibility to work from wherever you please. Ultimately, it’s about freedom. You’re basically a freelancer with wings.

If you don’t have the confidence or experience to pitch your services full-time yet, then why not start up a side hustle and take it from there? It might not be an easy ride, but it’ll be a million times worth it once you get there.

You can do all of this using Buckets to guide you. So don’t forget to set up your prospective client list today and get cracking on nabbing your first digital nomad gig.

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