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How to Become a Digital Nomad

In today’s world, more and more people emphasize the life aspect of work-life balance. They want flexibility, and they want to see the world. These aren’t impossible goals, and we want to help you achieve them! So, we’ll use this article to explain how to become a digital nomad. 


In addition to writing about his and Jenna’s travel and work adventures, Chipp is a CPA and founder of Walutes Capital, a real estate development and accounting firm. Wearing this “other hat,” Chipp offers real estate investment and development consulting services to clients. If you’d like help with your own real estate investing journey, contact Chipp here to set up an appointment! 

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What is a Digital Nomad? 


While there may be a number of variations on the lifestyle, there are two features all digital nomads share. Namely, they: 1) find a way to make money with their laptops and a wifi connection, while 2) not having one designated home base (or office). Basically, people work remotely in some capacity while traveling


On the more formal side of the equation, this situation may involve a full-time, remote employee renting an apartment in Cape Town, joining a coworking space, and working their normal job hours - albeit with a shifted timezone. In this scenario, you reap the benefits of foreign travel with the stability of a steady paycheck and your own apartment.  


On the less formal side, someone may decide to hitchhike around Southeast Asia, staying at hostels for a couple of weeks at a time, and sneak in some freelance work online here and there to pay the bills. With this approach, you sacrifice the stability of a reliable paycheck and your own apartment, but you gain the freedom to travel wherever and whenever you want. 


Regardless of which approach you take, becoming a digital nomad lets you see the world while continuing to earn money.

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Freelancing Abroad vs Remote Work 


Before asking how to become a digital nomad, you need to ask what type of digital nomad you actually want to be. 


Related to the above examples, broadly speaking, two types of digital nomad exist: 1) freelancers (i.e. self-employed independent contractors), or 2) full-time employees working remotely. Do you want to assume the risks and (potential) rewards of “going out on your own,” or retain the financial security of full-time employment? More specifically, how will you answer these three questions about work as a digital nomad:


  • Who will pay me while working remotely - an employer or clients?  

  • How much can I expect to get paid for my remote work?

  • What limitations on my time will remote work impose while traveling?  


How you answer these questions naturally defines which of the below options will make the most sense for you: 


Option 1: Conduct freelance / self-employed work. You may want to head out on your own, operating as a self-employed freelancer. This option gives you significantly more travel flexibility, as you’ll define your own hours and responsibilities. But, the inherent risk here is that, what you gain in travel flexibility, you lose in financial peace of mind. As your own boss, you only make money when you earn it - no more guaranteed, bi-weekly direct deposits. 

Option 2: Continue in your “traditional” remote work capacity. If you have a 9-to-5, W-2 job that allows you to work remotely, you have significant financial flexibility to travel. That is, you know that every two weeks, you’ll get a paycheck deposited, meaning you won’t have to stress about making money while traveling. But, the inherent downside to this approach is that you’ll still be working 40-hour weeks tied to your employer’s timelines and other job requirements. 

Digital nomad life in South Africa

Digital nomad life in South Africa

How to Get on UpWork with No Experience


Let’s say you opt for Option 1, choosing a digital nomad lifestyle of freelance work. The next question becomes, okay, so how do I actually find clients? Chipp had significant success on UpWork, so we’re huge proponents of marketing your freelance services on that platform. 


UpWork serves as an online platform (app and website) for 1) clients to hire freelancers, and 2) freelancers to market their services to potential clients and apply for specific contract jobs. For digital nomads, UpWork essentially provides one-stop-shopping for securing freelance work. 


But, what if you don’t already have any freelance experience? Can you still get on UpWork with no experience? Absolutely! Just follow the below steps, ideally six months to a year before you plan on going full-time digital nomad, as that will give you some time to ramp up your client base:


  • Step 1 - Conduct a Professional Skill-Set Inventory and Grouping: Consider this your professional skills inventory. Identify your professional skills (e.g. SEO writing, accounting, digital marketing, financial analysis, etc.), then group these skills into related categories. These categories become your potential freelance service offerings. 

  • Step 2 - Familiarize Yourself with the UpWork Platform: Create an account and explore the platform. Honestly, UpWork’s pretty intuitive. But, if you need extra help navigating the platform, UpWork offers interactive help options and a community forum for asking other freelancers for help. 

  • Step 3 - Conduct an UpWork Market Analysis: Next, analyze the listed jobs (i.e. the contracts potential clients have posted). You need to confirm that one of your skills categories aligns with a market for potential jobs. Otherwise, you’ll struggle to find people to pay you for your freelance services. 

  • Step 4 - Create Your UpWork Profile(s): After confirming your skills align with a market of potential clients, create an UpWork profile 1) highlighting those skills, and 2) tailored towards attracting the client type identified in your market analysis. 

  • Step 5 - Create Your UpWork Client Onboarding Processes: You don’t want to reinvent the wheel every time you lock on a new client. Yes, UpWork handles all of your client messaging and payment processing requirements, but you still want a professional set of processes for onboarding new clients and confirming you have what you need to complete a contract. 

  • Step 6 - Apply for UpWork Jobs: Finally! You can now start actually applying for jobs on UpWork. The platform uses a system of “Connects” that you can buy (very reasonably priced), with each job requiring some number of Connects to apply. As a new freelancer (i.e. without any client feedback on your UpWork profile), your hardest contract to secure will be your first one. Bid at a lower price point than you normally would, and apply, apply, apply. Once you complete that first contract, ask your client, if he or she was satisfied with your work, to leave you a positive rating. This helps you become a “known entity” on the platform. 

  • Step 7 - Conduct Regular Freelance Work and Gradually Increase Your Rates: After your first contract, continue securing new clients. Gradually, as your number of positive reviews and experience grow, you can increase the rate you charge for your services. That’s why we recommend starting well before you actually start living as a digital nomad - to have the time to build a high enough hourly rate and client base to pay for your travels. 


Other Digital Nomad Considerations  


Unfortunately, there’s more to the digital nomad lifestyle than just making money while seeing the world. You need to consider a number of ancillary admin and logistics factors. Though not an exhaustive list, here are some additional considerations successful digital nomads must account for: 


  • Time zones: How will different local times affect any required remote work coordination?  

  • Wifi / power reliability: Do the places you plan on traveling have reliable wifi and power sources? If not, do you have a back-up battery and wifi hotspot?

  • Log-ins / IP addresses: Do the remote work websites and software you use require log-ins from a specific IP address location? Will these work without a VPN while overseas? 

  • Virtual personal network (VPN): Do you already have a VPN for overseas travel? Signing up for one is critical for 1) digitally protecting yourself on unsecured wifi networks, and 2) allowing you to change the location of your IP address (e.g. use a US-based IP address while traveling in Southeast Asia).

  • Laptop portable monitor: Does the work you do require a second screen? If so, you’ll likely need a portable monitor for your laptop

  • Do you need any additional computer equipment for your remote work? 

  • Office / coworking requirements: Will your work require you to spend any time in a physical office or coworking space? If so, have you identified some potential options in your different travel destinations? (NOTE: Chipp absolutely loved overseas coworking spaces. In addition to being more productive in an office-type setting, he met tons of interesting people in these spots). 

  • Visas: Do the countries you’re visiting have visa requirements? If so, have you completed any associated tasks before leaving home? 

  • Medical / vaccine requirements: Some countries also have medical and vaccine requirements prior to arrival (e.g. having your yellow fever passport). Have you completed these items? 

  • Mail processing: How will you handle your “snail mail” processing back home? Do you have a friend or family collecting items, or will you use a professional mail processing service? 


Hope this article helps guide you on your path, and best of luck becoming a digital nomad!

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Affiliate Disclosure


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