How To Travel And Make Money As A Digital Nomad

Hands up who fancies the freedom of living anywhere in the world and working to your own rhythm?

I mean, only crazy nutheads would say no to learning how to travel and make money as a digital nomad, right? Don’t be a crazy nuthead.

At the time of writing this, I’m sitting in the Selina Hostel in Manuel Antonio in Costa Rica having just got back from a hike at the National Park. My trusty Salomon hiking boots that have seen me through a trek in the Himalayas are well and truly kicked off whilst my feet are taking a dip in the pool. Life’s pretty good as a digital nomad, hey?  

I’ve been a fully-fledged digital nomad for 6 months through only using Upwork. I wanted to write this guide because THIS LIFE IS SO BLOODY FANTASTIC I want everyone to do this too!

Nothing would make me happier than travelling the world and meeting more and more people doing the same as me. This hostel even has it’s own co-working space especially for digital nomads, how cool is that?!

I want to say to my friends “Hey, fancy living in Bali for a couple of months?” and at least one of them has the flexibility to do it.

So in the interest of building a bigger tribe of guys and gals equipped with surf board under one arm and laptop in the other, this guide will literally propel you into the digital nomad world, giving you the tools to secure your first job on Upwork, kick ass and earn some serious money.

Who’s with me?

I Honed in on a Skill

61% of freelancers on Upwork are specialists in 2 to 3 skill-sets.

Upwork provides companies with over 5,000 different skills across a whopping 70 industry/work categories. You, my friend, have one of those skills (probably even 2, 3 or 4).

The first step is to get really, really, reeaallllyyyy good at a select few skills.

Have you heard the phrase “Jack of all trades, master of none?” 

Basically, you don’t want to be Jack. Poor old Jack didn’t create a niche for himself. But you want to. Be known for a particular skill-set rather than having broad knowledge of many skills.

If a particular skill doesn’t spring to mind straight away, that’s okay. Here’s what you do:

  • Think about your current employment and breakdown all the tasks and responsibilities you have within it then pick out your strongest e.g. if you’re a PA then you have diary management, travel booking, planning itineraries etc.
  • Still stuck? Ask your friends, relatives, colleagues and your boss what they think you’re good at. By asking this question to people close to you, you benefit from a different perspective. This is super helpful and can be a real eye-opener to aspects of your personality that you had never really even considered or simply took for granted.
    • CAVEAT: If you’re asking your boss, be careful! You don’t want to give the impression you’re considering quitting your job just yet!
  • Failing that, there are a plenty of free online tests that you can take to identify your personality strengths. Try High 5 or if you are happy to pay for an in-depth analysis then Gallup’s CliftonStrengths online assessment is a reputable company to use.

TIP – If asking friends, family and colleagues about your strengths, I’d recommend sending them an email or text. That way, it gives them time to formulate an answer rather than being put on the spot.

I Set Myself up on Payoneer

Whether you’re using Upwork, Fiverr, People Per Hour, Guru or any other freelancer online platform, all of their exchange rates are shitty and most tag on additional withdrawal fees as well. That’s how they make money.

To get ahead of the game, set up a Payoneer account. I’ve found this the best payment method to avoid those pesky fees. It transfers from Upwork USD to USD and then once it’s in your Payoneer account, you decide which day you want to transfer it to your local bank so you get the best exchange rate.

Want to earn $25USD simply for signing up? Use my referral link here!

Yes, hands up this is an affiliate link guys, but this is honestly the best payment method to use, even better than Paypal. Here’s a look at all your options to show you why:

Withdrawal TypeDeposit LocationTransfer TimeUpwork Charges
Wire transferTo US or International Bank AccountSame day$30 flat fee for each wire transfer
Direct deposit to local bank accountUS bank account3 – 4 daysNo fee (USD to USD deposit)
Direct deposit to local bank accountInternational bank account (non-US)3 – 4 days$0.99 plus the currency conversion rate (Upwork provide poor exchange rates)
PaypalPaypal account2 – 3 daysNo fee
PayoneerPayoneer accountSame dayNo fee PLUS higher exchange rate compared to Paypal and Local Bank Account Deposit

I’d advise setting this up right away, because for security reasons it takes 3 working days for this payment method to become active on Upwork. Then you’ll need to go back into Upwork and make sure this is your preferred payment method.

When I joined Upwork I did all the legwork but forgot to go back in and select Payoneer as my preferred payment method. When it came to my monthly withdrawal date on Upwork they sent it direct to my bank account so I got suckered with the fee and the bad exchange rate. Dammit!

Sign up to Payoneer here and receive $25 USD

I Designed a Badass Portfolio

Upwork allows you to upload a PDF portfolio that attaches to your profile page for prospective clients to view.  

I personally have one in-depth PDF portfolio containing lots of imagery examples of my work and a few separate shorter portfolios that each showcase a relevant job I’ve recently completed. These shorter ones are particularly useful when your work is featured on a website because you can simply point the reader to a URL link or add a video link.


  • Keep it visual – Add images of your work to break up the text. This could mean taking screenshots of a website you’ve designed or pulling a brand’s logo if you’ve collaborated with them in some way.
  • Make it skimmable – avoid big chunks of text which are off putting to clients. Bullet points work well, for example:
    • Your client’s goal for the project
    • Details about your contribution to the project – what were your tasks
    • Summary of the project’s success
  • Keep it relevant – No one’s interested in your first Saturday job at the local dry cleaners (yep, that’s me!) or the work experience you did when you were 18 years old (unless you’re 21, of course). Include jobs that you’ve spent a considerable amount of time at and are highlight those that are directly relevant to the jobs you want to be applying for.
  • Explain gaps – If you have gaps in your CV, explain them. It pays to be upfront and honest before a client comes to their own conclusions.

I Added Personality to My Profile

Now that you’re clear on the brilliant strengths and skills you have that will wow your potential employers, you need to create a profile that makes you shine like a brand new penny. 

Here are some tips:

Keep it concise

You want to grab people’s attention in short snappy paragraphs. There are separate sections for your work history and qualifications so no need to repeat these in your personal statement.

Show some personality

The beauty of Upwork is that it brings people together for their skills rather than location. Your client might be living in Australia whilst you’re in Paris so it’s unlikely that you’ll ever meet face-to-face.

The downside of this is that it removes the opportunity to impress an employer in a physical interview where you can build rapport and interpret body language. Instead, clients are making hiring decisions based on how well you portray yourself in your profile. It’s a colder, cut throat process.

A client is not only seeking someone with A* experience and skills but also someone who is open, communicative and friendly.

Your profile needs a strike a balance between professionalism and personality.  Give them a flavour of what your passions are, but leave out the smiley faces. 🙂

Create specialised profiles

If you have more two or more skill-sets that are distinct from each other then Upwork now allows you to create specialised profiles. For example, you could have one profile as a Content Creator and another as a French Translator.

Each profile allows you to get specific so you can cherry pick the best examples from your portfolio and work history.

Benefits of a specialised profile:

  • You’ll show up better on search results
  • According to Upwork specialised profiles have led to 30% more job invitations from clients
  • You can tailor your rates accordingly
  • You can create a separate, more concise portfolio.
Take the Upwork tests

Upwork currently has 303 online tests ranging from spelling to bookkeeping to WordPress web development. Successfully taking some of these that apply to your niche not only provides additional assurance to prospective clients of your capabilities, but also gives the impression you’re committed to freelancing and finding work on Upwork.

TIP: If you rank below average on a test, hide it from your profile. Just because you fail a test doesn’t mean you’re not qualified or good enough in that area. We all know that some people can’t apply their knowledge effectively in a test environment so don’t fret!

I Wrote a Killer Cover Letter

You absolutely shouldn’t send out blanket cover letters to every job you apply for on Upwork. Client’s can smell this a mile off and will delete your proposal immediately.

Having said that, there is nothing wrong with formulating templates and then tweaking them slightly to suit each job specification.

I have 4 different cover letters adapted for slightly different job types because it means I can get specific and highlight only the skills that are applicable to that job.

A prospective client asking you to design a newsletter is not interested in your diary management skills.

Tips for writing a killer covering letter:
  • Talk about how you can help them rather than using a cover letter to demonstrate all your achievements.
  • Work through the job specification and pick out the skills or responsibilities they’re looking for in the perfect candidate. Provide examples of times you have done said task/skill.
  • Write a brief paragraph on your digital nomad situation e.g. where do you currently live? Why did you leave home? How will you being a digital nomad help them? E.g. competitive rates compared to London rates, adaptability, and flexibility.
  • If there’s quite a big time difference between yourself and your client, flag this and quash their worries. Say you can be adaptable for calls. Obviously there are limits and you’re not going to get up at 3am for a call! But be prepared to accept a 7am call or 10pm. It’s a sacrifice you sometimes have to make for this lifestyle!

I Hunted for Jobs Every Single Day

Upwork moves quickly. Freelancers apply fast and jobs are often secured in a matter of days. I rarely even bother looking at the jobs that are older than 7 days.

So if you want to be on the top of the pile, you need to be looking twice a day every day.

Remember clients on Upwork are from all over the world so there will always be someone awake and posting a job.

I Was Smart & Selective When Applying for Jobs

How To Use Upwork Connects

Upwork used to give freelancers 60 Connects for free every month with the option to purchase more. This meant you could submit 30 job proposals free of charge.

However, starting in May / June 2019, Upwork are throwing a spanner in the works and planning to roll out a new fee structure. Basically they’re doing away with the free Connects altogether. Booooo!!!!

Why? Apparently it’s to help us freelancers (hmmmm?!) because we’ll submit fewer job proposals which will make it easier for clients to identify high-quality talent from a smaller pool of job proposals (and Upwork will just happen to make lots of money in the process. That’s business I guess!)

Anyway, enough of my sniping.

From May 2019, there will be 2 ways of applying for a job on Upwork:

  1. Find a job and apply – this will cost you between 1 – 6 Connects depending on the job.
  2. Be invited to apply for a job by the client – this will cost you zero Connects.

TIP: At the bottom of each job posting, it tells you the number of proposals submitted. If it’s over 50 proposals, then the client is swamped with offers so I won’t add to the pile unless I absolutely 100% fit their criteria.

I Played Detective on My Clients

Before you apply, remember to look at the client’s reviews and work history on their profile. This is CRUCIAL for two reasons:

  1. To see how much they’ve paid other freelancers. If you’re charging $40 per hour and the most they’ve ever paid a freelancer is $5 per hour, then it’s unlikely they’ll stretch to your rate.
  2. To check if they’re a nightmare client. If other freelancers have badly rated the client for not giving clear instructions, being argumentative or uncommunicative then proceed with caution.  Even if you’re desperate to land your first job, one bad review from a client can put you completely out of the game.

I Sucked It up and Took the Small Jobs

Competition is fierce on Upwork and even if you have bags of experience it’s unlikely you’ll land a highly paid job straight off.

*hands thrown up in the air and laptops slammed closed*

But wait, guys! It’s just to start with, I swear!

All you’re missing is one major thing – Upwork trust.

When you’re starting out, you have zero ratings on Upwork so no one knows if you’re a decent human being or a crazy nuthead (and remember, you don’t want to be one of those).

So at the beginning, be prepared to take some of the smaller jobs. Not only will it build your ratings up nicely (client’s are going to love high quality work for low fees and will sing your praises), but it’ll also nicely rock you into the rhythm of how the Upwork process works.

I understand there’s nothing worse than feeling undervalued but this is a short-term strategy only to becoming an Upwork Rockstar, which brings me to my next point….

I Landed a Few Jobs Before I Went Travelling

Upwork works on a ratings system so the more jobs you have done (and provided you do them well), the higher score you’ll have, which means the more jobs you’ll land, and so on and so forth. It becomes a compound effect, you see?

Before I went travelling, I crammed in as many smaller jobs in my evenings and weekends as possible in order to boost my Upwork rating and act as a nice stream of pocket money alongside my full-time job. When you’re starting out, the last thing you want is the pressure of freelancing being your sole income.

Some prospective clients set an application criteria of a set minimum number of worked hours on Upwork. So trust me, there’s nothing worse than missing out on a job you know you’ll be perfect for, as well as paying the big bucks, because you’ve only got 2 hours worth of work recorded on Upwork.

I wish I was kidding when I say I’ve heard of so many people beginning their digital nomad lifestyle without actually having put in any ground work before they’ve left home.

I hate to crush dreams here but a digital nomad life doesn’t start simply because you’ve landed in Bali! It takes preparation to build momentum but once you’re there, you’re golden.

Read: How Backpacking in my Thirties Changed my Life for the Better

I Scouted out the Long Term Clients

For me, a dream client is one who is looking for a long term working relationship. If you do one job well, and they like you, then you’ve potentially set yourself up for a guaranteed monthly income. This is music to any digital nomad’s ears.

I have a client who I have worked with from when I started out and even though we’ve never spoken on the phone, we’ve built up a rapport and level of trust that I now get paid directly to my Payoneer account. Goodbye 20% Upwork fees!


Provided you’ve done the work and can prove it, Upwork guarantees that a freelancer gets paid. Going rogue will save you money but only do this if you really trust the client. Never, ever do this for the first job and always negotiate half the money upfront and the other half on completion so if they do pull a fast one, at least you’ve only bared half the risk.

I Avoided the Fake Clients

There are clients on Upwork who are just trying to scam you for free work.

No matter how desperate you are for money and no matter how persuasive they are that this is just a “trial”, don’t work for free.

It’s understandable that a client will ask you for a trial to test your capabilities, especially if they are offering a large sum of money for the job, however, this must be a paid trial.

Any respectable client will either suggest this or agree to your suggestion. End of.

If a client kicks up a fuss, politely decline and say you do not work for free. They are a scam shark and will swiftly move on.

For example, proofreading one paragraph may not seem like a big deal and will only take you 5 minutes. But that client is asking every candidate to proofread a different paragraph and voila, before you know it, they’ve had their entire 10 page document proofread for free! If the trial is super duper easy then charge a nominal fee like $5, but make sure you charge something.

enjoying digital nomad life in Merida Mexico

I Increased My Fees

Obviously not straight away but as you would in full time employment, you expect a pay rise for the more work you’ve taken on, the better your expertise and the greater your experience.

Value your worth and don’t be scared to increase your fees.

After all, working fewer hours for the same income means you’ve nailed the work/life balance and have officially joined the club of smug digital nomads.


Blimey, that was a lot of information I’ve just thrown at you! If you’ve skim read this whole article then of course you can PIN IT for later and be sure to do the following things before embarking on the digital nomad life:

  • Figure out what skill makes you a badass or whilst you’ve got the time, go off and learn a new skill
  • Take time over your Upwork profile and portfolio
  • Sign up to Payoneer
  • Take a few of the Upwork skills tests
  • Get a few jobs under your belt before you go travelling.

Looking for some support? Speak to other digital nomads! Ask me any questions in the comment box below, I’ll be happy to help.

I also joined a Facebook group that I dip in and out of. I can’t tell you how reassuring it is to know there’s a group of like-minded people available all over the world who can give advice, listen to your grumblings and generally keep you on the right path.

Want to keep it for later? Pin it to your Pinterest.

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