Working Remotely, Insight from a Digital Nomad Newbie

Working Remotely, Insight from a Digital Nomad Newbie

This post is meant to share with you some insight I have gained from my job search as a newbie digital nomad. It is my hope that it will help you to explore your motivations for working remotely, while also providing some lessons to guide you along your job search.

The Decision

We have all seen them…the Van Lifer photos of tailgates open to show off the views of the Colorado Rockies in the background; the travel blogger “point of view” pictures with toes hanging out in a hammock overlooking the beach; the digital nomad images of a laptop set up inside a tiki bar in Hawaii. These individuals all quit their typical office jobs to travel the world.

Digital Nomad
Digital nomad photgrapher and filmmaker @Mitch.cox

Well if they all did it, then why can’t I? So here I am. I quit my full time desk job in Washington DC in order to convert a van into an RV, and travel the continental US for one year with my hubby. We have spent the past 6 months downsizing, selling all of our belongings except the few essentials which will fit within the 150 sq ft of space. By living out of a van, we will eliminate a few substantial expenses, mainly rent, utilities and home maintenance. In its place will be the costs of converting a van into an RV, gas, and car maintenance.

Ok, those are still nominal costs in comparison to paying DC rent. We could easily afford to take a few years off from work on this great adventure, however, we do not plan to simply sit behind a wheel for 365 days. We want to LIVE, explore, and experience all this country has to offer. The cost of tours, excursions, national parks and historic landmarks will add up.

Rather than quitting our jobs entirely, we decided the “digital nomad” lifestyle was more appropriate for three reasons: 1.) Having an income would open up the doors to experiences which are more expensive (e.g. hiking half-dome; spending the night in Americas’s only under water hotel, etc.) 2.) It’s always good to have some kind of financial inflow if you know you will be spending 3.) Because we plan to return to a “normal” job after our trip (as of now), we will be avoiding a significant gap in employment which may be seen as a cause for concern among some employers.

Sounds great, but how do you become a “Digital nomad”?

I have just gone through the process of finding a remote job, and while it is still fresh in my brain, I would like to share what I have learned along the way.

My Top 11 Tips and Lessons for working remotely

Lesson #1: Think long and hard if remote work is for you. Identify your goals, your motivation for working remotely, and also weigh the pros and cons.

Common Pros:

No commute – There is no need to waste 2 hours each morning and afternoon sitting in traffic or a crowded subway. Furthermore, there is no need to spend mucho money on the toll roads, gas and metro cards.

Flexibility in schedule – Remote may mean full time tele-work, or 20 hours a week working as a virtual assistant, or it may also mean 15 minutes per day as a freelancer completing independent tasks.

Work from anywhere – Whether you want to work from home, or travel the world working out of café’s and hotel wifi, remote work gives you that option.

More family time and more “me” time – Not having to commute allows for more time in the day. This means more time to spend on hobbies, and more energy to play with the kids…and significant other.

No office stress – Working from home means no suit and tie! That is, unless you have a Skype meeting that day.  It also means that you are free from distractions and drama tied to an office environment. No micro-manager popping their head into your cubicle every 5 minutes (although this could potentially be replaced with emails every 5 minutes), no chatty co-worker distracting you from work, and significantly less gossip.


Isolation – You no longer have those “water cooler” moments of bonding with the co-workers. After work Happy-Hours are likely to become less prevalent. You may feel detached from the organization’s culture, and in some cases left out of the loop.

Fewer resources – Working in an office, you can always drop by your friend’s cubicle to ask them a quick question. If you are having computer trouble, you can just submit a ticket to the IT guy and it will be taken care of. Need to make a photo copy or fax an important document? All of the equipment you could need is there in the office. Although it is possible that some of these challenges can still be addressed virtually, it may not always be as quick or convenient.

No face time – If you work virtually, you do not have the same face time with higher up managers and directors. Networking is very important when seeking a new job, contract or promotion. Without this precious face time, it can be difficult to distinguish yourself from just a number on a piece of paper.

Related Content: “Remote Job Search, Resources For The Aspiring Digital Nomad”

Lesson #2: Decide if you want a full-time job or freelancing work. You may need to be flexible if time is a constraint.

Are you looking for a part-time to a full-time career where you can grow within the organization? Do you need benefits? If so you will want to search primarily in job search engines like Idealist and Flexjobs.

Are you wanting just a few paid tasks here and there so that you will have more time and flexibility given back to you? Are you ok with handling your own taxes as a contractor? Then you will want to search on a freelancing site like Upwork.

Lesson #3: Know that remote jobs can be very difficult to come by, depending on your industry.

Digital nomads conduct their work using telecommunications and technology, so naturally, the majority of remote roles will be in technology. If you are a web or app developer, graphic designer, or tech support specialist, you will have a much easier time finding positions to apply for. Other popular jobs held by digital nomads include copywriting, content creation (blogging and photography), online coaching, online English teaching, and translation. This is not to say that other positions cannot be performed remotely, however, it may be more difficult to find a remote job outside of these industries. Don’t become disheartened if you do not find a position in your field right away, just stay persistent, think creatively, and explore your resources.

Lesson #4: Search for specific keywords.

After you decide to work remotely, no doubt the first thing you will do is type into our friend Google “How to find a remote job”. Lexicon is actually pretty important here. Companies refer to this type of work under a large number of different words and terms. If you search for “remote work” it may give you one set of results, however, if you search for “virtual company” it will produce a whole new set of search results. Some helpful keywords to guide you along your search are:

  • “Virtual company”
  • “100% distributed”
  • “Completely distributed”
  • “Remote company”
  • “Telework”
  • “Flexible”
  • “Work from home”
  • “Virtual”

Lesson #5: Explore your resources.

There is an abundance of resources for finding a remote job. These include blogs with helpful lessons and tips, job listing sites, virtual placement agencies, and freelancing databases. In my article Remote Job Search, Resources for the Aspiring Digital Nomad, I list a few of the top resources I have come across, some of which helped me to land my current virtual job.

Lesson #6: Not all job search sites are created equally.

Don’t waste your time on sites that are not conducive to what you want. Indeed, and Monster are all reputable sources for finding career leads, however, they are not designed with the virtual job seeker in mind. On occasion, you can find a remote job posting, but some are still location specific and others are with unknown companies. On Indeed and Monster, you may also run across several “easy money” schemes like taking surveys, posting ads and getting paid to surf the web. It can become overwhelming and frustrating searching these job listing sites, trying to weed out the good opportunities from the bad.

Lesson #7: Create job alerts for job listing sites, and create a bookmark folder for companies you want to frequently check their job listing page.

An easy way to stay on top of new job postings is to create a job alert with one of the listing sites, such as Flexjobs. New opportunities will be emailed to you daily or weekly. However, several companies do not actually post their openings on these job listing sites. It may be helpful for you to identify the companies you are interested in, visit their careers pages, then create your own spreadsheet with hyperlinks. This makes it much easier to quickly track and reference companies you are interested in while keeping a lookout for potential openings.

Remote Job Search Excel Sheet
Example of a Remote Job Search Spreadsheet in Sheet

Lesson #8: Learn to play up your soft skills.

Communication and compatibility are always important skills when applying for a job, however, virtual companies view them as vital to the success of telework. Be prepared to discuss your communication style, how you manage conflict, and how you handle feedback. Also be prepared to talk a bit about yourself including your work ethic, motivations, interests, goals, pet peeves, etc. These questions are meant to provide a glimpse into your personality type and to make sure you are a compatible fit.

Lesson #9: Be willing to learn new skills.

Depending on the role for which you are applying, familiarity with multiple platforms and technologies may be desirable or even required. For example, virtual assistants may be asked to use task management tools (e.g. Asana, Trello, or Evernote); if you are working in sales you may need to learn CRM platforms (e.g. Hubspot or Salesforce); social media managers may need scheduler and analytic tools (e.g. Hootsuite), and so on. Get training if you need it, to buff up your resume.

There are a few free resources to brush up your training in these areas including: Hootsuite academy, Hubspot Academy, Udemy.comSkillshare, and Coursera .

Lesson #10: Ask if the job can be performed remotely.

If you are already employed with a company you enjoy and find that your work is performed mainly through technology (for example research, analysis, writing, bookkeeping, etc), ask if you can transition to a work-from-home basis. If you have developed a high level of trust with your employer where they are confident in your work ethic and quality of output, it is possible they would rather make accommodations for you rather than lose you. Similarly, if you are applying for a new job that is listed under a specific location, but you believe it can be performed remotely, just ask. The worst that can happen is that the potential employer says “No.” If you are well qualified and can prove that you are the best candidate during the application process, certain employers will be willing to accommodate your request for telecommuting.

Lesson #11: If you can, do not quit your desk job before you have secured an offer for working remotely.

Last but not least, don’t be in a rush to quit your current job. I know there is that whole idea of burning bridges so that you have no option but to move forward with your goals. The problem is, as mentioned previously, finding a remote job can be easy or incredibly difficult depending on your field, experience, and flexibility requirements. You never know how long it will take to find the teleworking opportunity you are looking for, so if possible, you want to try to avoid a crisis of long-term unemployment. Take your time, and make smart decisions. Start your remote job search on weeknights. When you have your offer for the remote job you want, THAT is the time to flip over the table and throw up the “peace out” sign.

Cecilia is a bubbly Filipino-American with an affinity for constant change...that or a 10 second attention span. Refusing to sit still, she travels the world, in pursuit of adventure, excitement and meaningful experiences. She holds a Masters degree in International Development and Public Policy, and a BA in Business Management.

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