Remote Work Guide

Just a short 15 years ago, the very idea of working remotely and traveling would sound like science fiction. Internet was slow, telecommunication applications were making baby steps (Skype was introduced in 2003), and laptops cost more than a used car. If you worked an office job, you had to go through the same ordeal every day: wake up, commute, work, rinse repeat.

How to negotiate a remote work position

Nowadays it is possible to negotiate a remote working position with a company, whether you are a new or existing employee. Most modern office jobs can be done through a PC and work communications take place in chat programs anyway. Whatever your reasons are for wanting to work remotely (from avoiding long commute times to traveling the world), achieving it is very doable as long as you have a plan. In this article, we are going to see how you can convince your boss to let you work remotely, and which steps to take to make it work for you.

The case for remote working

According to research conducted by the Harvard Business Review, people working from home reported higher levels of productivity, efficiency, and engagement. And that doesn’t always happen because commute times are eliminated. The reasons are many and not always easy to see:

  • Proximity means very little when it comes to effective communication. Just because a team is located in the same building, it doesn’t mean they will communicate more. That is a logical fallacy. In most cases, face to face time in office environments is kept to a minimum. Usually, communications go through emails and private messages, even when employees are in the same room.
  • Remote employees will make the extra effort to connect with co-workers. When you work remotely, no one can see you working. Therefore, remote workers tend to be more attentive to meetings and much more thorough in their reporting.
  • People feeling more valued. A company that lets you work from anywhere in the world trusts that you are a responsible professional. More often than not, people appreciate this and are more likely to be more committed to their job.

Although it may initially sound counterintuitive, not being in a loud office all day can help you be more focused on getting work done. The Harvard study also revealed that people who weren’t in the same location as their superiors were more productive than their on-site colleagues.

Why people are still skeptical about remote working

Even though remote work and digital nomadism are becoming increasingly popular all over the world, this lifestyle is still viewed with suspicion. Nicholas Bloom, a Stanford University professor, claims that some employers and HR departments are still “deeply skeptical” about it: “They refer to it as ‘shirking from home’ or ‘working remotely, remotely working. They think it means goofing off and watching cartoons,” he added. Besides productivity issues, employers might also be apprehensive for security reasons. Data theft and risk of classified information leaking is multiplied when working on your personal computer.

The truth is that it can be quite hard for a company to justify letting you work from home (or become a digital nomad), especially if they’ve never done it before. Here are some things you can do to alleviate their fears:

  • Send weekly and monthly reports on your progress to your manager. Set up an easy to read template and be thorough.
  • Be consistent and dependable. If you go AWOL without permission, you’ve pretty much ruined your chances.
  • Make sure to clarify that you will be working from company-issued laptops that can be tracked and are vetted for security. If that’s not possible, schedule an appointment with IT to prep your device.

Find out if remote working is really for you

Working remotely while traveling the world sounds like a dream come true. Who wouldn’t want that? Digital nomadism and telecommuting have a lot of obvious benefits, but it also has a hidden dark side. That’s why you must think long and hard about your motivations and ask yourself the following questions:

  • Can my job be done remotely? If you’re a doctor, technician, plumber, etc., remote working is not for you. At least not without significant sacrifices in quality.
  • Am I disciplined enough to be productive without direct supervision? You have to be a grownup about this. If you can’t work unless somebody is looking, you’ll be recalled to the office in a heartbeat.
  • Do I have the communication skills necessary to keep my colleagues updated? You need to be super familiar with productivity tools and communication software to make life easier for those who are at the office. Chat, email and project management tools must be second nature.
  • Can I maintain my mental health while being isolated from the office? You must accept that life will go on without you. Your colleagues will form stronger bonds and probably tell inside jokes that you’ll never understand. If you think that you’ll miss office banter while you’re away, think about this again.
  • Can I deal with distractions? Your kid or your cat couldn’t care less that you’re supposed to be working. They want your attention, and they want it RIGHT NOW (or right meow, depending on the situation). It’s your job to deal with it and still be great at your post.
  • Is my remote working environment/home reliable/ergonomic? Fast WiFi is the Alpha and the Omega of remote working. Without it, there is no way to do anything. Make sure you maintain a correct posture (since you’ll be working from a computer) and that you have all the devices necessary to stay connected.

The dark side of remote working

If the answer to any of the above questions was “no,” then you might want to rethink that meeting with HR. Especially if you plan to travel and work full time, you must realize that you will still have to clock in eight hours of work every day. Sightseeing and fun should always come second, and that takes an enormous amount of willpower.

Despite what you might see on travel blogs and motivational posts on social media, you will never actually work from a hammock or a beach. On the contrary, you will find yourself looking for a good WiFi connection, air conditioning, and comfortable desks. You know, like an actual office.

Things will be more comfortable if you decide to work from home, but you will still have to deal with isolation, self-discipline, and distractions. That’s why it’s a good idea to dress up and go work from a suitable public space (like a library or a cafe), even if you could just spend the day in your pajamas.

How to ask your employer for a remote position

A growing number of employees are getting tired of the burden that our daily commutes have become. On the other hand, traveling long distance has gotten more comfortable, and the community of those who want to work while exploring the world is growing.

Thanks to the development of Internet technologies, it is now possible to work from home, or from anywhere in the world while keeping your job with a remote position. But how do you ask your employer for one? What is a good strategy to get a yes out of your boss? Let’s dig in.

Formulate a proposal

The first step is to formulate a clear and concise plan. Unless you are interviewing for a remote position, your employer will never come to you with an offer to work from home. Instead of chatting about it with colleagues and managers, take your time to write a thoughtful proposal for your boss.

There are two reasons why this should be your first step. First of all, it will show you are serious about this, and you are not just doing it to get up later in the morning. Then, if the matter needs to be taken to higher-ups for approval, it will be much easier for them to deal with a well crafted and professional proposal.

Your proposal should be short and to the point. If it takes up more than one page, you are doing it wrong. Your plan should (at the very least) include the following information:

  • Your reasons for wanting to work remotely;
  • The hours per week you wish to work remotely;
  • A plan of your daily schedule;
  • A communication plan;
  • What’s in it for your boss.

If your company does not have a remote work policy, it is advisable to start small. Chances of your employer letting you work off-site full time are slim, even if you are an experienced member of the team. That being said, don’t be afraid to use your stellar track record (if you have one) to your advantage. Your supervisor’s support is vital in your employer’s decision and if you have that, be sure to use it as leverage.

Communication is everything

Be prepared to discuss your proposal in person after you file your request. In all likelihood, your employers will have questions, concerns, and might want to ask for adjustments. The key here is to remain open to communication and discussion. Concerns may revolve around your productivity while being at home, or the transportation of sensitive information and IT devices outside of the office space.

Be willing to make compromises, and to take the time to ease your boss into the situation. If your performance exceeds expectations, then they might be more willing to let you work long-distance full time.

Provide value

Your proposal to work remotely should not be only about you. After you have answered the essential questions above, outline two or three reasons why your employer will benefit from your remote work. The truth is, nobody cares if you want to stay home with your kid. But what if they stand to benefit from this arrangement?

For example, if you have a long and exhausting commute in the morning, avoiding it could help you start working earlier and be less tired – and thus more productive. If your company promotes green policies, this could be a great argument as well. Staying at home even just one or two days each week can significantly reduce the carbon footprint of the company. Additionally, having remote employees could help your company downsize their office space and as such save money on rent and electricity.

Increased productivity, reduced costs, and higher employee retention are enough to get your boss thinking about it. Even a part-time arrangement is a win at this point. From then on, your performance is the decisive factor.


Productivity is often a concern employers have when employees ask for a remote position. And it is easy to understand them: at home, all sorts of distractions are present, from children to pets, from TV to a nice hot bath.

Thankfully, several actions can be taken to reassure your employer you will not stop being a good worker if you stop physically coming to the office. Being a great employee at the office helps a lot. Do not brag, but let your actions and results speak for themselves. Become an invaluable member of the company. You may not like it, but those guys get what they want more easily.

Once you have been granted permission to work from home, even if it is just for one day per week, exceed expectations and crush your goals. No need to announce you’ll do that beforehand; it will spoil the surprise. In other words, underpromise and overdeliver. This will solidify the trust between you and your employer.

If you are a new hire, things are quite more complicated. If a remote position wasn’t promised to you, then you don’t have a whole lot of leverage to support your request. Take some time to establish yourself in the company before coming forward with a request. After all, if remote work is what you wanted, you should have been upfront with it right from the start!

Take it step-by-step

If all goes well, your employer may want to start with a part-time remote position. That way, they have the time to evaluate how this new situation works out and how it differs from you being physically present at the office. This is more likely to happen if you are among the first employees in your company to ask for a remote position. Congrats on being a pioneer! Don’t feel pressured, but the future of remote work lies on your shoulders.

Do not feel discouraged if that is what they offer you. Instead, be thankful your proposal had at least some effect. Whatever your end goal is (work and travel, spend more time with your cat, avoiding a 4-hour commute) always keep it in mind and work towards it. Ultimately, being an excellent remote employee boils down to three basic pointers:

  • Always be available for communication
  • Master the art of reporting
  • Be extra productive with your time

How to deal with rejection

Like we mentioned above, your employer has the final word. If your work wasn’t remote to begin with, you have no right to be upset. And even if you are, keep it to yourself. Politely ask them why they didn’t let you do it, what are their motives and take some time to reflect on their reasoning. This will help you realize what you could do better the next time around. Being negative around your colleagues will not help one bit. On the contrary, it might cost you your job.

If you feel that getting a remote position is something that will elevate the quality of your life, consider your options. For example, trying to work from home to avoid your coworkers is downright stupid. On the other hand, if you truly are better at what you do in solitude, it is worth chasing an actual remote job.

How to find a remote job

Nowadays, telecommuting isn’t remotely unusual (pun intended). There are entire companies with employees scattered all over the world that only meet up occasionally for team-building trips. Some of the most notable ones are:

You can either pursue a full-time/part-time job remote work opportunity or, if you want absolute control over your hours, start freelancing. The latter is a bit harder to get into, but once you build a solid clientele, you can earn a respectable amount of money and work as much as you want.

Here are some of the best-known websites for finding telecommuting positions.


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