Digital Nomads! Should I...Get a job?

Often when you read the experiences of digital nomads, normally the people telling their stories are inherent risk takers, a quality which goes hand in hand with setting up your own business. Most people who end up doing their own thing, do so on the promise that one day they’ll have far more control over their schedules, their lives, the size of their bank balance and their ability (hopefully) to positively impact the world around them. But setting up a business is hard work and not for everybody, and whilst it’s held up as the gold standard of Digital Nomad life and many of you will progress into this way of earning an income, we’re here to tell you that there are other options should you choose to explore them, especially if you are just starting out. Here at Wifi Tribe we have had the pleasure of doing life with lots of different people, who are doing amazing things independently and also as employees, and they’ve been gracious enough to bestow a gold mine of information so that you can get to the end of this two part article series confident in your decision either way. So to start, we’re gonna tackle the pros and cons of getting a job!



One of the things that working for a company offers is a stable level of work AND income for the forseeable future. Now across the board for all working folks both employed and self employed there are super busy times and then quieter times but as an employee with a salary, that doesn’t affect your paycheck every month because what you get paid is set. Your tax is already sorted out so you don’t have to worry about the extra accounting side of things, you know exactly how much you can spend on things like accommodation, fun, food, experiences etc and you can plan in advance. In a lot of ways it takes the worrying out of the Digital Nomad life and if you decide to set up a business on the side and test out different models that may work for you, you can still test out those things and keep yourself afloat in the meantime. It’s a lot of work if you do this but it means you can have your cake AND eat it…(that’s a British expression right there, basically means you can have the best of both! )

Refine your skillset

One thing that gets offered by most employers is training and development. When you’re self employed, YOU are responsible for paying for any extra information that will help, whereas if you’re employed by a company, they are obligated to keep you trained to the highest standard in order to do your job to the best of your ability. Depending on how you work this, you could end up being paid by another employer to become an expert software developer for example and then when you’re ready to go can charge expert prices and be in a great position to earn a good living from training you didn’t necessarily have to pay for’s more complicated than that in a lot of cases but check it out and think long term; see if there are ways to practice your craft and get somebody else to pay for it.

Employee Benefits

Aaaaah the world of employee benefits. Not to be overlooked my friends; I used to work in Human Resources so I have seen a plethora of employee benefits, some SIGNIFICANTLY better than others. In Fast Company’s article about employee benefits they listed the following benefits as the Top 5 (you can see if you agree with these as the top ones - I am baffled as to why food has not been mentioned but there you go)…

  1. Health Insurance - (Medical, TRAVEL, Dental (if you’re based in the UK we all know how much we love our Private Dental care. If you don’t care it’s probably because you are either fortunate enough to have an AMAZING NHS dentist already, OR you’ve never experienced a drilling session with a fool NHS dentist. Just sayin’...))

  2. PAID time off - we’ll discuss this in just a sec

  3. Performance bonuses

  4. PAID sick days - this is one to keep an eye on - I didn’t appreciate this until I worked for a pretty large company that did not offer paid sick leave. This will come in handy if you’ve moved to a different place and as you get used to the new climate you catch a virus, have stomach issues etc. Sick Leave is normally finite of course, so generally it is not advised to take the peanut BUT it does give you a bit of a safety buffer if you do fall ill. Its purpose is to give you adequate time to recover from any ailments without the impending doom of financial ruin as an added pressure. Anything can happen anywhere it’s true, but when you’re a beginner nomad and you’re abroad away from all the things you took for granted, getting sick and then not being able to recover properly is not the one.

  5. Pension Plan! (again if you’re in the UK you know there is a good chance we will all die before EVER seeing our pension so...make what you will of that employee “benefit” mwahaha)

Other benefits from different companies include discounts on things like electrical equipment, discounts on holidays, free kindles and a monthly allowances for books so that one's mind can be fed (Twillo do that apparently just in case you were wondering), allowances for equipment needed to do your job; basically employees potentially have access to a whole host of benefits that actually go a long way to making life a bit more comfortable for you. It's already organised and thought out, all you need to do is take advantage. I'd say its worth thinking about.

Annual Leave

Paid time off is the bomb and I don’t care what anyone says. Yes in some cases it comes with its restrictions but they aren't always that bad and if running your own business is not an option right now, there are worse things that could happen. For fully established entrepreneurs that have businesses generating reliable income, hold your fire! Of course you are now in a situation where everyday is a holiday and you pride yourself on working 4 hours a day and having fun for the rest of the time, but tell the truth! It took a little while for you to get to that place. I’m sure at a few points you would have known the pain of wanting a break and not being able to truly let go simply because you’re worried about money or clients etc. When working as an employee, this particular stressor is somewhat alleviated because you get paid holiday and a support network to help cover your work so that you can truly relax! What’s not to love right?

Team Spirit!

One thing that people love, is being part of a small close knit team who support each other through thick and thin. For a lot of people who are remote employees, their teams are some of the best teams ever because if anything you stay in constant communication rather than taking their physical presence for granted and not communicating as effectively. Remote working as an employee is a much sweeter pill to swallow when your team is awesome and our Wifi Tribers who worked for larger companies will certainly tell you that the team they worked in had a massive impact on how much they enjoyed their roles. As a remote employee some of your most brilliant ideas will come out of the interactions you have with people. In short, that team dynamic has the potential to maximise your strengths and support you in your weaknesses which is why we love it!


Okay so we've had a look at some of the advantages; let us now remove the rose-tinted glasses and turn our scrutiny to some of the potential challenges faced by remote employees near and far.

Time-zone restrictions

So imagine this, you are working for a company in England and you are based in Australia for example. You are a whole 11 hours (or 10 hours depending on daylight saving) ahead of your colleagues and clients which means if your role relies and you being able to respond to your team and your customers in a timely fashion or you’re on a tight deadline and you need your colleagues to respond to you quickly, you working for certain companies and being abroad might start to get a little tricky. It’s not by any means always going to be a deal breaker as an international friendly set up makes allowances for this, but there comes a point when for certain jobs, particularly client facing one’s like being an online teacher, or some kind of a salesperson, a vastly different timezone could end up becoming a disadvantage for you because when you’re preparing to be asleep, your client base is waking up and getting ready to make business decisions. So unless you change your entire routine and work at night, there are going to be timezones that won’t suit certain roles. If you work for yourself then it’s far more likely that you can choose to be in whatever timezone you like, whereas if you work for an employer you will want to be thinking about the needs of the business and your job role when considering the time zone you will be in on your nomadic adventures. There’s no point travelling to somewhere new and exciting, if you don’t actually get to enjoy it because you’re working like a maniac at night to service your clients and then recuperating during the day. Just food for thought.

Progression Opportunities

So progression opportunities, let’s talk about those. A lot of people who progress in their companies are around and based in the office with senior management...hmmm. They obviously work hard, I am in no way trivialising the amount of work people put in to get their promotions but the difference between them and you is that they get SEEN, whereas you could end up doing amazing work and because you are out of sight and out of mind, you run the risk of being overlooked. In 2013, Yahoo had a massive restructure and the new CEO Marissa Mayer banned remote working in a bid to increase worker productivity. Her view was that people are more creative and more motivated when they aren’t isolated as much and that so many more ideas are birthed when collaborating with others.

So what’s this got to do with progression opportunities? Well it stands to reason that if you are working for a company, particularly those larger ones, those collaborative conversations where problem solving, promotion generating ideas are thought of are less likely to happen for you because you aren't physically present. Now then, if everyone in your company is remote then cool, but if you are the exception rather than the rule, BEWARE. It's not all doom and gloom, I appreciate that, and the world is waking up and workplaces are now putting in infrastructure that allows nomads to feed that desire to travel the world, but we’re not there yet and the reality is that a lot of people’s promotions are wrapped in conversations had at the right time and at the right place i.e. the office, and of course, in some cases, not all but certainly some, you’ve got to be in it to win it.

Smaller pool of appropriate jobs

When we were talking about timezones earlier on, I hinted that not all jobs are digital nomad friendly. As the world becomes more digitally integrated and the ability to communicate and work together across the countries becomes more advanced than ever before, the opportunities to find jobs that support our sort of lifestyle will become more widespread. Having said this, there will always be those jobs where face to face human interaction is non-negotiable simply because for some companies, that’s just how they do things, or you’re a surgeon and actually you need to be y’know...present in the hospital...I’m kidding but you catch my drift. So the kind of jobs you’ll be looking at are things like Software Developers, Writers (see our How To: Be a Remote Copywriter article here), Travel Consultants perhaps...there’ll be an article coming up about the Top remote working jobs out there so look out for that.

The ability to contribute to the bigger picture

If you’re an entrepreneur you have the responsibility of directing the overall vision of your business. A lot of our nomads said that one of the main things that got on their nerves is not being able to contribute to the bigger picture and actually for a lot of people, being able to have an impact is a real motivator for them, so simply following orders as it were but not actually being able to influence top level decision making became a real frustration. If you work for a big company this may grate on your nerves a bit more but if you work somewhere a bit smaller where your input doesn’t get lost in the corporate machine then this con won’t necessarily put you off working as an employee - maybe look at working for a startup where its all hands on deck. Either way it is definitely worth some careful thought as you map out your own journey.

So that’s it for part 1! Look out for Part 2 where we have an in depth look at the pros and cons of starting your own business. Whilst there are plenty of articles that discuss that, we wanted to give you a side by side comparison that’s more balanced in its outlook and empower our nomadic compadres with the tools to make the choice that’s right for them. Let us know of anything we've missed in the comments please as well.

Until next time...stay cool and stay free!