FastCompany's article, titled The Digital Nomad’s Guide To Working From Anywhere On Earth, states that "Still, the majority of digital nomads are freelancers or small business owners, and a disproportionate number of them are developers or content creators of some kind."
We have managed to start earning income within only a few months of traveling by starting a blog. Jenny has taught English in Japan as well (and I have a friend that teaches English in South Korea as well). You could start a blog or teach English abroad as well, or you can try an alternate option. Here are a few ways that we think will work best.
Teaching English Abroad
Most of the best travel bloggers started by teaching English Abroad. Drew Binsky started out by teaching English in South Korea. Nomadic Matt started out by teaching English in Thailand. The couple from Goats on the Road (Nick and Dariece) started out by teaching English in China. Even Jenny (from our site) started out by teaching English in Japan. This is the most proven, hands down, easiest way to start out - there’s no real competition. The pay is fair, you work around 35 hours per week, the cost of living is usually quite low, and thus you’ll be able to save a decent amount of money. They are mostly located in Asia: Japan, South Korea, China, Hong Kong, Taiwan, Vietnam, and Thailand - which all have great expat communities and amazing cultures.
Here’s what you’ll need: A Bachelors Degree - any type - and usually also a certification, such as the TEFL - Teaching English as a Foreign Language, a TESOL - Teaching English to Speakers of Other Languages, or a CELTA - Certificate in English Language Teaching to Adults. Generally, contracts are 1-year and renewable. We recommend MyTEFL.net if you want to start out this way too. Make sure you check the country/program you are interested in to see which language test they require. If they require anything other than TEFL, check GoOverseas to find alternate programs.
Additionally, if you are not a Native English Speaker, you may still be able to choose this option; however, it does depend on the country and the type of visa you are applying for - but you will generally also require a TOEFL in that case. See the free TOEFL prep below from edX.
You may have heard of "remote-work", but have you ever tried to find a job that allows you to do it 100% of the time and from anywhere that you go? Most remote work is temporary, for a few weeks or maybe even a few months at a time and permitted as part of your regular job (if it is allowed). Some remote jobs will allow you to work remotely 100% of the time but require you to be situated in a specific region or country. When we looked into remote work for ourselves, it appeared that the ones that were available were also mostly within a handful of categories, such as developer or content creators, that we didn't really fit into at that time. However, training at places like Kaplan IT Training can help get you the skills. Additionally, if you have the skills, you can sign up with Fiverr and start showcasing your work for some quick cash.
A few other sites would recommend remote work boards - but most are focused only on technical jobs. Here are a few of the Remote Work Boards that might be worth checking out: Working Nomads, Jobbatical, Flex Jobs, Remote OK, The Remote Working Company, We Work Remotely, Remote.co, Jobspresso, and Skip The Drive.
Starting a Business
What seems to work the most often in real, non-hypothetical, life is launching and growing a small business. Starting a business may seem more difficult than the other options to many people, but it really doesn't have to be super complex. It could be as simple as a Blog. Also, in the end it will allow for the greatest flexibility in location as well as the greatest flexibility in working hours and income generation. You just have to have the drive and dedication to actually put it together and make it work. Many businesses can be set up with little or no initial costs, but if you believe you have a breakthrough idea and will require some money to be raised to get it started, try looking at seedrs.com. Need some pointers? Check out Y-Travel for a step-by-step!
Freelancing & Consulting
Freelancing and consulting are both ways to use your current skills to earn income. This is similar to working at a regular company, but you are not an employee of any particular company. Instead, you are self-employed and you'll work on a contract basis with a number of different companies that you come across. The trick with this method of income is to learn how to attract companies that will hire you in many different countries. Speaking their language is typically a requirement. Check out Fiverr or Design Crowd to put your design skills to work, or check out upwork to start Freelancing. Interested in gaining a few skills that would qualify you for most freelancing jobs? Check out “4 digital nomad skills that you can learn online for free (or less than $10)” by Elise Darma or “How To Learn The Top 5 Freelance Skills With Online Courses” by FreelancingHacks. Additionally, there is a good walk-through on how to market yourself successfully as a freelancer at The Hard Refresh: “How to Earn More Money Freelancing”. If you are very serious about working as a freelancer or consultant while you travel and don’t just want to pick up the little jobs, consider our FREE Nomad MBA.
Volunteering / Work Exchange
This method may offer you a free place to stay and usually even free meals, but they don't typically pay you any more than that. So, you could look at this as a really great way to save the money that you currently have instead of doing actual work - but it really is work that essentially pays you in room and board, so you may not see any actual cash. You may be doing some good deeds around the world, though! You can get started by looking up workaway.info, wwoof.net, or helpx.net to see if there is a place that fits your volunteering desires. For more advice on WWOOFing, check out this page.
Cruise Ship Work
Have you considered working on a cruise ship? Wandering Earl shows that you can explore many different destinations: from Alaska to the Caribbean, Europe to South America, the South Pacific to Southeast Asia. Pay of USD$2000-$3000 per month to start (up to $6000 depending on position), very few expenses (room and meals are provided), access to crew bars, crew lounges, internet cafes, hot tubs, swimming pools, a crew gym, crew-only sunbathing decks, crew parties, discounted tours in each port, international friendships, and 2-4 months of vacation per year. Interested in this type of lifestyle? Check out Wandering Earl - the authority on cruise ship jobs.
This is usually the fall back plan - and/or staple job - for many endless travelers. The pay is widely variable as you will likely make most of your money on tips. Tips are dependent on the popularity of the place you are bar tending at and the tipping custom in that part of the world. This type of work is usually seasonal if you’re in a tourist area, or it could be year-round if you are hired by hostels. It is also one of the easiest types of work to find while you are traveling.
Also see “Working around the World: 28 Awesome Jobs you need to do” at UNRAVELLING TRAVELLING
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