Eternal Arrival
Travel Advice

How I Work From Anywhere and Travel Indefinitely Using Upwork

It’s the dream, right? Find a job that’ll let you work from anywhere and travel as much as you want. However, one of the most difficult things about becoming a freelancer is finding work. Luckily, there are digital freelance agencies out there who will make that a little easier for you. I’ve been using Upwork since May 2016, and I’ve had great success with it. I’d estimate that on average,

I’d estimate that on average, I earn around $800 per month between my three steady clients. I only work about 10 or 15 hours per week as I want to spend the rest of my time traveling and working on this blog.

Some months are better than others, but in general, this makes it possible for me to finance long-term travel around the world and only withdraw minimal savings. I worked as a teacher for five years and lived frugally, so I have money stashed away to spend as well. My average monthly budget is $1000, though I do allow myself to have above-budget months. 

There are so many cheap destinations around the world to live or travel in that are perfect for the digital nomad. It’s quite possible to live or in many parts of the world off of an average of $30 a day, or $900 a month. In some parts you can live on even half of that!

RELATED: 40 Cheapest Countries to Travel to on $30 a Day or Less

So, how much do I work? On average, I work about 10 hours per week from anywhere in the world I want. I no longer seek new clients, as this is definitely a big time investment. Since I love my current clients and my workload is really manageable, I haven’t felt the need to scale up, especially since this blog still takes a lot of time. One day, my goal is to be able to monetize this travel blog, but this keeps me covered in the meantime. I also have savings which supplement my earnings, so in the event I don’t cover all my costs through freelancing, I have a cushion.

RELATED: How I Saved $50,000 to Travel the World Full-Time

As I’ve traveled and mentioned that I work from anywhere by doing freelance writing and editing online, many people have asked for more information. I’m a huge fan of the Upwork platform and want to spread the knowledge to bring travel a little closer to all. Maybe you won’t quit your job and become a full-throttle digital nomad. That’s okay. Maybe picking up a little extra work on Upwork will bring you closer to taking a longer or more luxurious vacation. That’s great too!

OK, OK, I guess Corfu's not that bad.

Watching the nightly sunset show in Corfu, where I stayed and worked online for a week

How to Work From Anywhere – Even While You Travel – Using Upwork

#1 Determine your skill set

What are you good at? Make a list of all the things you think you have some special skill in. Perhaps you speak a second language, you have a fantastic eye for catching grammatical mistakes, you love to write fiction, you’re a WordPress genius, you can Tweet and Pin like a pro… there is a job out for every skill and niche! Whether you want to ghostwrite erotic fiction (literal job I’ve seen on more than one occasion), edit calculus textbooks (literal job I’ve had), or translate, Upwork probably has work for you.

Terrible at grammar and editing? Can’t speak another language? Don’t think you have any special skills? English-language audio transcription work is fairly straightforward and plentiful on Upwork. Data entry is available but it often pays so little it’s not worth doing.

#2 Eliminate anything you absolutely can’t stand doing

When you set up with the goal to work from anywhere, keep this in mind: you don’t want to hate your freelance job or it’ll just be painful. I learned that I hate editing calculus textbooks, and it’s totally not worth $20 an hour to have my eyes feel like they’re dripping from my skull. So I no longer accept that work and I’ve made time for work I enjoy more, like copywriting and editing marketing materials. Sure, it’s not totally fascinating, but it’s challenging enough to be interesting without making me crazy. Score!

Best beaches in Spain - read more inside!

You’ll never want to work, but you’ll want to work even less when views like this are beckoning you – so choose projects wisely.

#3 Create a kickass profile

Don’t worry about tooting your own horn too much. This is the Internet, damnit! Shout into the abyss about just how awesome you are. Use strong words to describe yourself.

Example from my profile: “Experienced, meticulous, professional proofreader and editor available for academic and research papers, essays, articles, marketing campaigns, and more.”

Here’s a list of strong adjectives you can borrow for your page: experienced, efficient, effective, professional, meticulous, tested, deliberate, detail-oriented, focused, results-oriented, driven, motivated, methodical, ambitious, determined, careful, disciplined. If you work in a more creative field, you’ll probably want to throw in some words that are more artsy-fartsy.

Mention your school background, relevant work experience, and give your profile a bit of personality. Be specific about the kind of work that you’re seeking, as people will see your profile and invite you to apply for their jobs.

#4 Do some shitty grunt work to get started

You won’t start making the big bucks right away. When I first started on Upwork, I took the first jobs I could find, which basically meant that I took someone’s 4th-grade level college paper and turned it into a fucking prose masterpiece for $10. To me, that $10 is a terrible trade for what amounted to about 2 hours of work. But I leveraged that by mentioning that I was new to Upwork and was willing to do work for a lower price in order to bolster my job success rating. I delivered for the client, got a 5 star rating and a glowing review, was $10 richer, and it made it so much easier to score the next job. Just think of it as the unpaid internship you’re doing to get your dream job where you can work from anywhere.

Do this for a while until you’ve built up what they call a “Job Success Score.” This score is, honestly, bullshit. Mine is only 83% even though I’ve finished every job successfully, most with 5/5 stars, and my lowest rating being a 3.8/5 with a comment saying “highly recommend” (then why didn’t you give me 5 stars? COMMENCE EYE ROLL SEQUENCE.) I don’t know how 83% gets derived, but whatever. The comments and the stars system will matter even more to your clients, so focus on that. When you email potential clients, be sure to emphasize people’s reviews of you. Mention your 5 star reviews, quote satisfied clients, really sell it!

Sahara desert in Morocco

While I say you can work from anywhere, I definitely didn’t get any work done in the wifi-free Sahara Desert

#5 Develop your pitch

When you email potential clients, don’t send out a mass email! I have a section that I copy and paste that includes a bit of background information, but in general, I try to write at least 70% of the email as a personalized pitch, and the rest as a copy-and-paste job. Get really detailed with respect to the job at hand. Mention something specific from the post and tailor your message around that. Make sure you write at least one clear sentence showing that your specific prior experience connects to the job they’ve posted.

For example, if you were applying to a job in social media marketing, you could say “Having personally grown a Twitter account from 30 followers to 3,000 followers within one month, I understand the power of Twitter as a social media medium.”

This formula is useful for a variety of pitches. Basically, it boils down to: “Having [done this], I [can do that].” Of course, you don’t have to use that exact language, but showing a direct causal link between your experience and the results you can bring will improve your chance of being hired dramatically.

#6 Overdeliver and wow your clients

I don’t mean that you necessarily should do more work than asked for, but make sure that the quality is beyond what they expected or that you finish before the deadline. I usually aim to underpromise and overdeliver. If I know I can do something in 48 hours, I’ll tell them that, and then try to deliver within 24.

Sorgue River

Frolicking in the Sorgue in Provence by day, fixing people’s grammar by night

#7 Ensure clients leave feedback

I learned the hard way that if you move to end the contract, it’s possible for clients to never leave you feedback, which can end up tanking your job rating. When you’ve successfully overdelivered (or at least delivered) for the client, send them a friendly email in which you do all of the following:

  • confirm that the job met all of their required specifications
  • ask if there’s any additional way you could improve upon the work to ensure their satisfaction
  • write that if they are satisfied with the work you’ve completed, to please end the contract and give you feedback

 

#8 Capitalize on prior successes

Make sure you emphasize on your profile the work that you’ve successfully completed. With client permission, add it to your Upwork portfolio so that others can see you have a record of success. When you send out pitches to future clients, be sure to emphasize any relevant experience on Upwork, including quoting clients’ compliments of your work.

Provence Villages - abbaye de senanque

Provence: beautiful place to travel, terrible place to be a digital nomad thanks to awful wifi

#9 Aim for steady clients

The most frustrating thing about Upwork is investing the time to actually find decent clients. There are a lot of qualified people on the platform, so don’t be discouraged if you don’t get the response rate you desire. The key is to actually find those high quality, easy-to-work-with clients who have consistent and predictable work for you. The ultimate goal, for me at least, was not to make as much money as I possibly could, but to have a reliable source of income without a constant headache of finding new work and learning how to make new clients happy.

RELATED: 101 Simple Ways to Save Money for Travel

Determine your income goal and try to find the right amount of work to sustain that. When you search for jobs, try to seek out jobs that say specifically in the description that there is a potential for ongoing work. Also, look at the job duration. The potential choices you can select range from less than 1 week, to over 6 months. Once you’ve paid your dues and gotten some ratings under your belt, I would only aim for anything saying 3-6 months or 6 months.

I tend to privilege fixed price jobs over hourly as well; I find I make more money that way. However, hourly jobs use Upwork’s app to ensure you get paid for each hour you’ve worked, which is great payment protection. As a side note, I’ve never had trouble chasing down a client for pay, and I’ve worked with over 30 different people on the platform.

Remember, Upwork’s sliding scale fee system privileges repeat clients over one-off clients. They will take 20% of the first $500 of your earnings with a client, which will drop by half to 10% for the next $500 to $10,000 and then again by half to 5% for everything over $10,000. All of my clients that I have now, I started working with when the 10% flat fee was still in place. Regardless, I’ve definitely billed way over $500 with each of them now, so I’d be earning the same.

Any questions on how to work from anywhere in the world using this platform? Please comment below and I’ll do my best to answer your question!

Work from anywhere using Upwork to find high-paying freelance jobs while you travel the world. How to get started, create your profile, and find consistent work that pays well and funds the life of your dreams!

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46 Comments

  • Reply
    Sarah Stierch
    November 4, 2016 at 11:48 pm

    Awesome and helpful post. I’m slowly transitioning out of my day job into freelance 100% and this has been great to read. I’m extremely qualified (almost over qualified) for many of the jobs, but, without any previous experience, I’m having no luck. Going to suck it up and slog through a few junky jobs and do my best to build that credibility. Thanks for the tips!

    • Reply
      Allison Green
      November 5, 2016 at 10:55 am

      That’s awesome to hear, Sarah! Congrats on your transition! Yeah, unfortunately, it’s the same for me. I have a degree in English from a top university and a master’s degree in Education but I wasn’t able to land a single job at first because no one wants to hire someone who’s unproven, especially since you don’t really validate your credentials. The only way I was able to get work from the start was to start low and just think of it as a trial run to build credibility. The nice thing is that when your job success score is high (which should only take a few jobs), a lot of people will actually start to find YOU via searches and email you with interview offers. I got one of my gigs that way. Anyway, if you need any other tips or advice, please feel free to get in touch. You can comment back here or send me an email via the contact box on my website. Good luck!!

  • Reply
    Naomi Liz | Roaming the Americas
    November 5, 2016 at 12:21 am

    This is so helpful, Allison! I’ve heard of Upwork and seen people mention it in Facebook groups, but I haven’t really ventured into trying it yet. This has definitely put it on my radar as a potential income stream for me. Thank you!

    • Reply
      Allison Green
      November 5, 2016 at 10:52 am

      That’s great Naomi! I first learned about it from Facebook groups as well. It’s definitely a good potential stream of income, especially if you’re comfortable doing English editing and proofreading πŸ™‚ Please let me know any time if you have questions – send me an email via the contact box or comment back here and I’ll do my best to help out!

  • Reply
    Meg
    November 5, 2016 at 5:06 am

    This is brilliant advice. I’ve never read a blog about using Upwork before, so thank you for sharing your experience and tips with us!

    • Reply
      Allison Green
      November 5, 2016 at 10:51 am

      Awesome! I’m so glad you found this useful. Please let me know any time if you have questions – send me an email via the contact box or comment back here and I’ll do my best to help out!

  • Reply
    Katie @ The Katie Show Blog
    November 5, 2016 at 10:49 am

    WOW this is so interesting and I had no idea it existed. I’m off to look into it now – thank you so much for sharing!

    • Reply
      Allison Green
      November 5, 2016 at 10:58 am

      Thanks so much! I’m so glad it was a helpful read for you. It’s really revolutionized the way I earn and spend money when traveling… it’s a great resource. Please feel free to contact me whenever with any questions – you can comment here or send me an email via the contact box on my site (in the menu at the top)

  • Reply
    Laryssa Gobets
    November 5, 2016 at 10:52 am

    Thanks for the info I’ve joined up work but haven’t done any work yet. Glad to see it does work

    • Reply
      Allison Green
      November 5, 2016 at 10:57 am

      Awesome! Good luck! Feel free to contact me with any questions (comment here or use the contact box on my website!)

  • Reply
    Matt
    November 5, 2016 at 1:13 pm

    This is such a cool summary, especially #6! When you wow your clients, they will get back to you with more work! This is easier than trying to get new clients on board!

    Well done, Allison!!

    • Reply
      Allison Green
      November 5, 2016 at 1:23 pm

      Yes exactly! You’ve already done the hard work getting them to hire you – if you overdeliver, they’re more likely to come back again and again πŸ™‚ Thanks for your comment!

  • Reply
    Leah
    November 5, 2016 at 1:48 pm

    What a great resource! I had considered using upwork in the past because I work as a translator, but I had been frustrated by the idea of having to pitch. Looks like it really works in the end though!

    • Reply
      Allison Green
      November 5, 2016 at 6:00 pm

      The pitch can definitely be a bit annoying for sure! That’s why once I settled into my groove with my clients I stopped looking for new work. Sure, I could be earning a lot more, but I’m a bit lazy. There’s soooo much translation work out there though on Upwork! I considered doing it but my Spanish isn’t close enough to native level yet so it takes me forever to translate. BTW, they also have “tests” on Upwork you can take to prove your translating skills, which would help with your pitch.

  • Reply
    Katie
    November 5, 2016 at 6:24 pm

    Thanks for the tips! I have used Upwork before but found the ‘bidding’ system so much effort and I never had any jobs from it! I have only had jobs when people approach me but I will deffo follow your advise!

    • Reply
      Allison Green
      November 5, 2016 at 6:42 pm

      The pitch system is a pain, for sure! But once you get those clients who keep coming back to you for repeat work, you’ve got it made πŸ™‚

  • Reply
    Christie @ ckanani.com
    November 5, 2016 at 6:44 pm

    This is really great info! I’ve looked into USING Upwork but never thought about being on the other side of it… What a great idea for full time travelers. Gonna pin this for the future in case I ever take the leap πŸ™‚

    • Reply
      Allison Green
      November 5, 2016 at 6:46 pm

      It is really a great resource, Christie! If you ever decide to use it, feel free to contact me with any questions – just comment here or use the contact form on my site πŸ™‚

  • Reply
    Juergen | dare2go.com
    November 5, 2016 at 7:28 pm

    My biggest question: how do you manage to get internet good enough to search and bid for jobs? Or is all your work from invitations to submit a bid? I used to work on Elance, Odesk (I believe both were swallow by Upwork) and Freelancer. But since we’re travelling full-time I haven’t looked a single time at any one of these sites. Not that I couldn’t use the income! It’s just that I hardly find enough online time to publish on our blog and social media…

    Question: I read you do mostly ‘editing’. Can you handle text in British English? We are planning (for almost a year, but [reasons see above] haven’t quite finished) some eBooks to go with our blog. A good and not too pricey editor might be a godsend.

    • Reply
      Allison Green
      November 16, 2016 at 3:11 am

      Sorry this got caught in my spam queue! Honestly, I did most of my bidding and job searching before I left to travel full-time… I spent about a month building up my client base while I was living in NYC and working full-time and now I do all my work from the road. πŸ™‚ It does take some time though, but I think it pays off! It did for me, at least πŸ™‚

  • Reply
    Goni
    November 5, 2016 at 9:42 pm

    Brilliant resource! I was thinking about using Upwork for a while, maybe this article will motivate me to do so. Will definitely follow your advice when doing so.

    • Reply
      Allison Green
      November 5, 2016 at 10:22 pm

      I hope it does! Feel free to ask me any questions along the way πŸ™‚

  • Reply
    Charles McCool
    November 5, 2016 at 10:15 pm

    Love your attitude about being location independent. Once you make the decision to do so there are many resources to support your dream and lifestyle.

    • Reply
      Allison Green
      November 5, 2016 at 10:22 pm

      I totally agree. It’s a bit corny to say, but when there’s a will, there’s a way if you’re willing to put in the work

  • Reply
    Luda
    November 6, 2016 at 8:06 am

    I recently got into the Upwork game before I head off to Europe next year (you’re basically living my dream!), and all of these points are spot on. I’m a bit bummed about Upwork’s new 20% policy, but it’s good motivation to retain clients. Awesome post and photos btw!

    • Reply
      Allison Green
      November 6, 2016 at 8:12 am

      Yeah the new 20% policy sucks when you’re getting started but if you focus on building true and lasting
      relationships with clients then you’ll be down to a 10 or even 5 percent fee soon enough. I’ve billed at least 5k with one client so when it goes down to 5% I’ll be thrilled! Let me know if I can help you out with anything along the way. Comment here any time (I always get notified of new comment ah or email me via the contact form on this website. Good luck! You can do it! Just make sure you have a safety net for those lower-earning months πŸ™‚

  • Reply
    Karin
    November 9, 2016 at 3:56 pm

    Great post! Wanted to pin it, but it didnΒ΄t let me :-/

  • Reply
    Dalal
    December 14, 2016 at 5:12 pm

    Great and honest article. I am currently at stage #4 (Do some shitty grunt work to get started). I was feeling guilty (and maybe unworthy) about it, as I took jobs for a low rate, but I honestly didn’t see any other way to make a start. I will continue later, it becomes more difficult to freelance as I still have my day job. I plan to travel the world for few months, and make a little income on Upwork meanwhile πŸ™‚

    • Reply
      Allison Green
      December 14, 2016 at 10:00 pm

      It is true, I really don’t think there’s another way to start out. I took maybe 3-5 crappy jobs before I started rejecting jobs that weren’t worth my time. But every field may be a little different…. luckily, English language editing pays pretty well.

  • Reply
    Brittany
    December 15, 2016 at 3:24 pm

    This is great advice! I recently started using Upwork, and definitely found that completing a few not-so-awesome jobs was a great way to boost my profile. I like your tips on how to sell yourself, I’m going to update my profile today πŸ™‚

    • Reply
      Allison Green
      December 15, 2016 at 9:42 pm

      I’m glad you agree! It seems counterintuitive to tell people to work for less than they’re worth… but as a temporary measure just to get your rating up and prove you’re legit, I found it was so so helpful! Glad you found the tips helpful – feel free to get in touch if you have any other questions πŸ™‚

  • Reply
    Helena
    December 19, 2016 at 11:56 pm

    This is really interesting. I have always wondered about these sort of things. I work full time and blog part time but I just don’t think I could justify leaving my job for a gamble. But with your tips, I could definitely do some work on the side!

    • Reply
      Allison Green
      December 20, 2016 at 8:11 am

      Yeah, I definitely wouldn’t advise leaving your job hoping to strike it big as a blogger. I like that I earn money on Upwork because my hope is that I can eventually monetize blogging in a way that feels organic and not have to grab at every opportunity just to support myself. If you want to transition away from a full-time job, I think the key is to save up some backup funds in case you have a lean month and get yourself going on Upwork. It’s a great way to stretch those funds! Let me know if you ever have any questions.

  • Reply
    Bina
    December 22, 2016 at 5:42 pm

    HI Allison,

    Oh goodness I can’t tell you happy I am to have found this post! I have been wondering for some time how I could work remotely to complement my travel plans, this sounds a potential perfect match. Even though my current role in the UK is IT Project Manager, I often end up proof reading or copy writing for my company anyway.

    Did you see many IT or corporate type jobs on Upwork? Do you think being a languages (French, Spanish, Linguistics) graduate helps?

    Thanks,
    Bina

    • Reply
      Allison Green
      December 22, 2016 at 6:38 pm

      Hi Bina! I think there’s a lot of IT jobs on Upwork, though with developing and IT jobs you often have to compete with people from lower-wage countries who are willing to work for much less due to the lower cost of living… that’s not to say you can’t market your experience and charge appropriately, though, I just think it could potentially be a bit difficult. Just my two cents from observing – I don’t have skills in that market to have firsthand knowledge.

      Where I think the money is in language-specific things like editing and proofreading and translating. I think you could definitely gain a lot of work through English-Spanish and English-French translation (and vice versa) as well as English proofreading and copywriting. Copywriting is where I make more money.

      I’d definitely say that Upwork work can come and go – I’ve had busy months where I make well over $1,000 and quieter months where it’s more like $500. So I’d recommend having a nice safety net saved up if you want to quit to work remotely πŸ™‚ I have a post on 101 Ways to Save Money you might find useful as well!

      Best of luck and feel free to ask any more questions πŸ™‚

      Thanks,
      Allison

      • Reply
        Bina
        December 29, 2016 at 11:35 am

        Thanks a lot for the advice Allison. I’ve had a little look around on Upwork and agree, there is far more media / marketing / copywriting work than there are IT PM jobs (well, ones that suit my skillset). I’m now looking in to building myself up as a copywriter – a resolution for 2017.

        I hope you had a great Christmas, and a happy new year!

        • Reply
          Allison Green
          December 29, 2016 at 11:05 pm

          Yeah, that’s what I’ve seen as well, and the rates are much higher to boot. I definitely think you could do it — like I said, do a few smaller jobs to start off, then work your way up towards bigger and better stuff and use your Upwork work as your copywriting portfolio πŸ™‚ You may not earn a lot at first, but it’s a good learning opportunity and then it helps you get bigger and better things. Just my experience at least.

          Happy holidays to you as well!!

  • Reply
    Carolyn V. Hamilton
    January 5, 2017 at 1:50 pm

    Great information, Allison, and well-written in an easy-to-understand style. I’m living in a beautiful home in Ecuador and love working online from home, as there are days when I just don’t want to leave my house. I’ve been an Upwork client, but never a service provider. You have inspired me to explore this.

    • Reply
      Allison Green
      January 5, 2017 at 11:38 pm

      Oh wow you are truly living the dream! Glad this post inspired you – it’s definitely a great way to make some extra income!

  • Reply
    Meg
    January 16, 2017 at 4:45 pm

    Thank you, thank you for this post. I am an English teacher who has had it with education. I’ve decided to call it quits at the end of the school year and embark on a solo RV travel adventure to begin. I have been taking post-grad classes at UC Berkely with editing and professional writing to gain more experience outside of the classroom and a certificate to compliment my English BA and M.Ed. This post is JUST what I needed. Thank you for posting. I look forward to following your blog and social media accounts! Meg

    • Reply
      Allison Green
      January 16, 2017 at 9:15 pm

      Girl, PREACH! I worked in special ed for five years. The amount of bureaucracy and lack of care for the actual living conditions of the kids we teach (we bussed in kids from all over the inner city of Queens, rough parts like Jamaica, Far Rockaway, etc.) from the people up on high is so infuriating. And with Betsy DeVos entering into the equation you’re getting out at exactly the right time, that woman is going to burn up what remains of public education in our country…. *SIGH* Anyway, Upwork is really great for that, and you’ll be sure to find tons of work with your qualifications. You can also teach English online, especially to kids in China — that’s a major way people fund mobile lifestyles. With your qualifications I bet you can earn like $20-25 an hour. Don’t know any exact companies but I bet you could look around…. Anyway, any questions about Upwork, hit me up here or my Facebook – that’s where I’m most active πŸ™‚ facebook.com/eternalarrival and GOOD LUCK! πŸ™‚

  • Reply
    Liz
    May 21, 2017 at 2:45 am

    Hi, I love your blog, it is very informative and inspirational. I have been thinking in using UPWORK for translator jobs since I speak Spanish also. I already have an account with them but because I don’t have any experience nor certificate I get very intimidated by and I have not been able to apply for a job yet. Now, after reading your tips I think I will take the chance and see what happen since my husband and I want to star next year to travel full time.

    • Reply
      Allison Green
      May 22, 2017 at 4:21 pm

      Thanks Liz! So great to hear that πŸ™‚ Upwork has tons of translator jobs available so that’d be a great place to start. I’ve thought of doing translator work as I also speak Spanish but editing English writing is definitely easier for me so that’s what I’ve stuck with. Definitely give it a chance! It’s a great way to work from the road.

  • Reply
    Taylor
    June 19, 2017 at 1:13 am

    Great tips girl! I’m currently working my ass off applying for jobs on Upwork and find I get so discouraged by seeing some of the low rates for the amount of work they want done. Luckily I have one steady client who’s amazing but I’d definitely like to pick up some more! Thanks for sharing, I’ll be putting some of your tips into practice tomorrow!

    • Reply
      Allison Green
      June 19, 2017 at 1:29 am

      Thank you, Taylor! It definitely takes some sifting through to find good work. I find that I have the best luck with stuff that requires native English level proficiency like proofreading, editing, etc. But once you have those steady clients, you’re golden! Hope you have some better luck after taking these tips into account πŸ™‚

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