Signs Telecommuting Jobs Market Is Increasing

The ‘gig economy’, and ‘digital nomad’ are two new and trending buzzwords that indicate the telecommuting jobs market is healthy and expanding. Interest in telecommuting jobs is high. Decent paying telecommuting positions, some that even pay benefits, are readily available. Computer savvy people with tech and programming skills are doing best in this new economy, but there is work available for people with various interests and skill sets. New, function-rich telecommuting job search sites like this one are popping up to service employers and job seekers.

How the telecommuting jobs market is expanding

Google has recently created an ad markup category specific to telecommuting in its job postings that allow employers to indicate that the listing is for a telecommuting position.

Google Adds Markup For Telecommuting Positions in Job Postings

Google Adds Markup For Telecommuting Positions in Job PostingsGoogle has added a new type of markup to its job postings guidelines, which will let publishers indicate that they have a telecommuting jo…

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Technological innovation seems to be driving the creation of many, hitherto unheard of types of work that can be done remotely.

115% Increase in Telecommuting since 2005, Says Report

The 2017 State of Telecommuting in the U.S. Employee Workforce report has been released by FlexJobs and Global Workplace Analytics. This report is the most up-to-date and comprehensive data analysis a…

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Technology drives work…

The Futurist: automation and telecommuting will be as common as Wi-Fi in 2026

Sapna Saxena, country HR manager, APAC, Telstra predicts that the move towards greater automation and telecommuting will push the HR community to completely rethink its approach to work.In 2026, I pre…

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A nice example of how technology is creating new types of jobs in the telecommuting jobs market that can be done remotely…

Telepresence Robots: The New Look of Telecommuting

A telepresence robot could change the way people telecommute. Here are a few reasons for the increase in popularity.

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the Telecommuting jobs market future looks exciting indeed.

Advantages and Disadvantages of Telecommuting


With the power of connectivity and internet access today, a new form of work arrangement called telecommuting has emerged. In fact, telecommuting has allowed employees to work from any preferred location like at home or a café rather than at traditional-workplaces (offices). Additionally, with telecommuting employees can easily communicate with people from the office and even accomplish their tasks while at home. However, although telecommuting is gaining popularity, there are also some disadvantages about it and below are some of the advantages and disadvantages of telecommuting:


  1. It eliminates commuting to the workplace: If your job requires commuting every day, then telecommuting will eliminate the commuting and help you save a lot of time daily so that you can spend that time on doing other productive things you enjoy like spending more time with kids or spouse, exercising, sleeping or other activities of interest.
  1. Greater Flexibility: most work-from-home jobs allow for a flexible work schedule. So, in case you want to do something else in the middle of the day like laundry or shopping, then you will be able to achieve this with telecommuting.
  1. Increased Independence: Work-from-home jobs will allow you to complete your work without constant reminders which most people absolutely love. In fact, with telecommuting there is no office politics, no boss orders and no distracting coworkers. However, there are distracting factors with telecommuting like television, laundry, a comfy bed for napping but these can actually be eliminated with a high degree of self-control and self-discipline in-order to make you a more productive telecommuter.
  1. : People who telecommute have very little need for professional clothing and this actually helps them save a lot of money every year. On top of that, telecommuting doesn’t require public-transit or fuel for your private car, lunches-out, dry-cleaning and child-care while saving on taxes each year because of the tax-deductible expenses associated with working from home.
  1. Suitable for Vulnerable/Disabled People: Telecommuting actually offers a great work-alternative for the disabled, physically handicapped or mothers who may find it difficult to cope-up with traditional-modes of working. In fact, telecommuting allows vulnerable people to opt into gainful employment and even live a great life than never before.
  1. Greater Fulfillment: With telecommuting, employees will feel happier and more fulfilled than those who work under a traditional working arrangement. This is actually brought about by factors like flexible work schedules, minimal supervisions and the lack of commuting to and from work.
  1. Increased Employee Satisfaction: Telecommuting allows employees to work from a remote location thus giving them the freedom to get away from a work-routine and make them feel like the company is looking out for them. This actually makes employees more satisfied and happy with their jobs which can result into increased production.
  1. Increased retention of employees: with telecommuting, an employee will be able to work from home while moving from an old house to the new one that is far-away from the workplace. So, this will help companies to retain competent and loyal employees by simply allowing them to work remotely.

Disadvantages of Telecommuting:

  • Less human interaction: if you’re a kind of person who loves interacting with other people, then working from home will make you feel isolated. However, you can solve isolation by chatting with friends through e-mail, phone calls, instant messaging, and video conferencing but still it’s not a greater substitute to face-to-face interactions. Additionally, some telecommuters consider working from a coffee shop or library in-order to satisfy interaction-habits. On top of that, a co-working space might solve this problem by allowing you to telecommute while working from an office setting.
  • : Working under a home environment actually comes with plenty of people or things that can easily distract you like; Radio, Television, Kids, etc. This will negatively impact you productivity levels.
  • It requires high self-motivation: With telecommuting, an employee must be highly self-motivated in-order to be more productive. This is mainly because there are many things that can distract you while working from home ranging from kids, friends to electronics.
  • It Mixes Work and Personal Life: With telecommuting, you can’t always shut-out your personal life while you’re working or turn-off your work-life while you’re “off the clock”. However, having a separate work space from your home can help solve this but some people find it difficult to stop working when they know it’s only a few feet away from home.
  • Lack of the ability to Brainstorm: Telecommuting is totally different from working in a traditional office environment where you can easily brainstorm with peers when encountering problems. In fact, with telecommuting there is no one to consult in-case you get a problem and this greatly affects your performance and productivity-levels.
  • It Hinders Career Growth and Development: Telecommuting actually makes it almost impossible to evaluate and supervise your performance. For example, it’s very hard for a company to a telecommuting employer for promotions thus greatly affecting your career growth and development.
  • Breach of Security: With telecommuting, employees can be provided with pass-codes to get connected to company network but this actually increases on security risks like hacking and unwanted intruders who might gain access to pass-codes thus putting an entire company at risk.
  • Affects Employee Morale: incase a company allows top-employees to telecommute like supervisors and managers who are looked up to by other employees, Then this will greatly affect the morale of members of the team that is left behind. In fact, it will affect the decisions needed to be made since it’s very difficult to decide without people brainstorming for solutions to a problem.
  • Difficult to Demonstrate Workload: If you are a telecommuter working for a company with a traditional office setup, other office-bound coworkers might perceive you as doing less-work simply because you’re at home. So, it’s very important to showcase your workload to demonstrate to managers and coworkers that you are accomplishing as much or more in-case your telecommuting.

Remote Work And Burnout

Over the past several months, we’ve published a number of lifestyle posts encouraging people to try working remotely, or even to embrace a nomadic lifestyle. We are a distributed team, and our day-to-day operations involve a lot of online communication between people in different time zones, working from home offices, co-working spaces, or holiday spots. We’re living proof that remote work, for lack of a better word, works.

Rather than being less productive, researchers have found that most remote workers are more productive than their office counterparts. Remote workers have to deal with fewer distractions, have flexible working hours, waste less time commuting and getting ready for work. No traffic jams, no office dramas, and on the face of it, not a lot of stress. However, they are still prone to burnout.

Years ago, I saw a clever ad for a savings scheme for young families. It showed toddlers playing at home, with a simple (and true) caption that went something like this: The job they will be doing when they grow up hasn’t been invented yet. At the time, I was dabbling in 3D graphics, a concept I didn’t even bother trying to explain to my parents, born in the 1940s. I was born at a time when computers were already showing up in homes and offices, and when space flight was looked upon as routine (until the Challenger disaster). My dad, on the other hand, was born before the advent of the first digital computer, when the only objects piercing our stratosphere were V2s raining down on London and Antwerp.

But here’s the thing: The world around us was not created by our generation; it was created by their generation. That’s why remote work felt a bit odd when I first gave it a go in 2007. A lot of things were missing, and a lot of people thought I was weird for not taking an office job, suit and tie included. It can still feel weird from time to time, but that has nothing to do with the infrastructure, or the work itself. It has more to do with the way I organise my time and go about my daily routine, and it has a lot to do with the human psyche.

Remote jobs can be good for you, but depending on your character, they can also have some unpleasant side-effects. This is what I intend to discuss today: stress, burnout, anxiety, caffeine, alcohol, nicotine, and more: the dark side of remote working.

I have no medical training, so I can only offer a few words of advice based on my personal experience. If you feel like you could use some proper help, you should get in touch with colleagues, friends, and your doctor.

Let’s start by taking a look at what makes remote workers prone to burnout, and why it matters.

Home Is Where The Broadband Is

Remote workers can turn just about any spot into an office. Whether it’s taking conference calls in a parked car or from a beach café, we can make it work. Our office is in the cloud, not in our dad’s office building.

This is, of course, the most attractive thing about working remotely. You can work while traveling the world, visiting your folks, skiing, island-hopping in the Aegean and Adriatic, or just get up in the morning and start working in your pyjamas at home. Sounds stress-free, right?

Remote jobs coupled with a nomadic lifestyle can be just as stressful as 9-to-5 office jobs.

If you’re nomadic, bear in mind that travel can be stressful without the added burden of having to think about work at airport terminals, or break out your laptop on a train. Seeing some nice scenery and touring picturesque cities might be fun, but it’s also a distraction. Besides, the human mind is wired to adapt to just about anything. As you keep moving, the buzz you get from travelling to a new place starts to fade, but travel-induced stress does not. You can experience burnout on the road as well.

It is also important to distinguish between hard-core nomads and people who just like to extend their holidays by a few weeks. The latter still have a home to come back to. If you spend a few years on the road, sooner or later you’ll start to detach from old friends and lose the familiarity and certainty of home. Basically, you can turn any place into your home, but at some point you won’t feel at home anywhere.

Being able to rely on a social safety net, trusted friends and family, is important. Things go wrong, and when they do, it’s good to have someone around. Being on your own can be relaxing, as long as you don’t overdo it. Eventually, people tend to settle down, start a family, and play with their offspring; you know, those little bundles of joy that will apply for the jobs we are inventing today.

So, where does this leave us? Wait a minute, wasn’t remote work supposed to be good for you? What could possibly go wrong?

Burned Out And Bummed Out

Remember that detail about remote workers being more productive than their office counterparts? There is a price to pay for that extra productivity. Remote workers don’t get a chance to spend time chatting with their co-workers at the watercooler, or grab a sandwich at the local café. They don’t go out to lunch with their colleagues, either, and they don’t head out for a beer or glass of wine after work.

Workplace bonding is good, and I must note that I met many of my closest friends through work, which is next to impossible on a remote gig. That seemingly useless office chitchat is good for you; you are forced to take a break and interact with other people. However, if you are a remote workaholic, you can get up in the morning, start working, and utter your first words of the day when you go out for lunch, or worse, order takeout.

So, there is no commute, no office gossip, no coffee or lunch breaks with your teammates, and next to no human interaction. This could be a disastrous combination if you are prone to burnout. You’ll end up pushing yourself harder than you should, and since there’s nobody around to notice that you could use a break, chances are you won’t figure it out until it’s too late. It happened to me and, it could happen to you. If you think it can’t, if you think you’re tough, consider this: I spent three years of my life in a warzone, only to experience burnout in my cosy home office.

You see, collaboration technology is making remote teams more efficient and productive, but the human body is the weakest link in a distributed workforce infrastructure. Routers, servers, fiber-optic cables, processors and RAM don’t experience burnout, but people do.

90-hour weeks aren’t just a part of 1980s tech folklore. They are very real for many developers.

Ambitious freelancers, which I like to think most Toptal members are, can be too dedicated. They want to prove themselves, they stride to be more productive than the next guy, and they aim for excellence. They can stack up man-hours like there’s no tomorrow. To some extent, the industry culture encourages such behaviour. Pulling an all-nighter to hit a hard deadline, sipping energy drinks to stay awake, then unwinding with a booze binge: anything goes in our fast-paced industry. I’ve witnessed cool-headed and experienced professionals break down halfway through a project because they pushed themselves too hard, develop a range of health problems, ranging from weight gain to substance abuse. Burnout can break almost anyone.

Remember, if you mess up your professional or private life, you can bounce back. If you mess up your health, it’s much harder, and sometimes impossible. Plus, if you don’t care about health, you also run the risk of destroying your career and personal life in a single blow.

A close friend of mine, for instance, ditched his job three years ago and decided to start a healthy lifestyle. At the time he was a consultant for a major tech firm, but being a workaholic, the six-figure job took a toll on his health. He gained a lot of weight, stopped exercising, and started smoking (again).

One day, I ditched work so we could hit the slopes for some morning skiing, just like the good old days. Glancing at the cloudless winter sky, crisscrossed by shimmering contrails, he said, “There’s gotta be a consultant like me on one of those planes, heading to a new job. Boy, am I glad I’m not that poor bastard!”

Over the next two years, he managed to lose loads of weight (about 35kg/70lbs), drop a number of unhealthy habits, and brush up on his professional skills. Earlier this year, he got an even better gig, so the two-year hiatus obviously worked for him. Not only did he get his health back, but he is better off from a professional and financial perspective.

Burnout Symptoms

That may be a drastic example, and I hope it will not encourage any Toptalers to take a two-year leave of absence if they experience their first case of burnout. However, even two weeks can make a big difference, provided you catch the symptoms of burnout early.

Burnout affects your whole body. Remote workers can easily overlook many early symptoms.

Here are some of the most common burnout symptoms:

  • Anxiety and depression
  • Chronic fatigue
  • Insomnia
  • Anger and irritability
  • Wide range of physical symptoms, such as indigestion, headaches, heart palpitations
  • Lack of motivation, degraded job performance
  • Cognitive issues, inability to focus, forgetfulness

Remember, this is not a checklist. You don’t have to exhibit all these symptoms if you are burned out. For example, my burnout symptoms included anxiety, fatigue, heart palpitations, and inability to focus. I am not sure about anger and irritability, because I’ve always been an irritable person.

I am not a doctor, so if you suspect you might be suffering from burnout, I suggest you do some research of your own, maybe take an interactive test or two, and consult your family physician. After all, this is a tech blog, not a health blog.

Burnout affects people in all walks of life and in all industries, so what makes remote workers different? Well, if an athlete starts cracking under pressure, the team and the coach will notice something is wrong. The same goes for office workers; their co-workers will likely spot symptoms of burnout early on. This isn’t possible with remote workers.

Recognising burnout symptoms early on is of vital importance and I cannot stress this enough.

The deeper you sink into it, the longer it will take to recover, it’s as simple as that. The obvious problem with remote workers, myself included, is that most of us work alone, so we fail to notice something is wrong, and if we do, we still keep going for longer than office workers. For example, I became anxious about driving months before I figured out what was wrong, which would have been a much bigger problem if I was supposed to commute to work. I might have caught the symptoms earlier, and consequently, addressed them sooner. My failure to act on these early symptoms made things worse.

Remote workers are more prone to burnout than their office counterparts for a number of reasons.

Another potential burnout issue for freelancers is that they can jump from project to project, client to client, in a matter of months. In that case, most of their communication will involve people who are unfamiliar with their personality. If you spent the last five years sharing an office with a couple of people, they’ll probably spot your burnout symptoms before you do. If your work involves a dozen remote clients each year, they will simply not get to know you well enough. Digital nomads and many on-site consultants have it even worse because they are not surrounded by friends and family who could help spot the problems.

There is not a lot of research on remote burnout, but I suspect people like us are exposed to more risk than office workers due to the fact that we may overlook many early symptoms.

So What Can Remote Workers Do?

I will not turn this into a blog post on how to tackle burnout. The Internet is already full of them; some are good, some aren’t, so if you need more information, feel free to Google them. Basically, they all boil down to this: take a break, work less, exercise more, and eat healthily.

The idea behind this post is to help fellow remote workers do the following:

  • Be aware of burnout risks
  • Spot the symptoms early on
  • Take steps to avoid burnout

Burnout is real, and just because you haven’t experienced it yet, doesn’t mean you won’t. Sure, you can do 12- to 14-hour days, and you can work weekends, I did too, but you can’t do it forever. That’s how burnout got its name to begin with.

If however, you are aware of the risks, you need to be on the lookout for burnout symptoms. I already explained why this can be a lot more challenging for remote workers than office folk. That’s why I keep emphasising this vital step, so please forgive me if you think I am overdoing it.

In my opinion, prevention is the best course of action, and I really wish I read something like this post a few years ago, it would have saved me a lot of trouble and unnecessary visits to the doctor’s office, including one to the emergency room. My hubris landed me there, and I hope my experience keeps some of you out.

The best way of combatting burnout? Be informed and take steps to prevent it altogether.

Here is what all of us can and should do to avoid burnout:

  • Don’t put your social life on the backburner
  • Take breaks and put them to good use
  • Try to exercise more
  • Create a routine that works for you
  • Prioritise your work and your life
  • Make sure you get quality time off
  • Don’t be cocky and overconfident
  • Be careful with caffeine, sugar, booze

Our social lives are the obvious starting point. We’re people, not lone wolves, it’s innate nature. Make sure your work does not get in the way of your social activities. No excuses, just don’t do it. Ever.

We spend hours glued to our computers every day, so it’s important to remind ourselves to get up and engage in some activities every now and then. A sedentary lifestyle is very bad for you. Go out for breakfast or coffee, go for short walks a few times a day, do some housekeeping. Do anything. On that note, I am off to fold my laundry.

Use your free time to exercise. You don’t have to hit the gym every other day, but you do have to walk around a lot to compensate for your sedentary lifestyle. Exercise also helps keep stress and anxiety at bay.

None of this is possible without a good routine. Find one that works for you and stick to it. Restrict most, if not all, your work to certain hours when you feel productive (for most people, it’s the morning). As odd as it may sound, consider some less efficient habits. When you head out to lunch, for example, don’t restrict yourself to places minutes away from your home or office; take the long route, create errands that will compel you to spend more time outdoors and get your mind off work.

Quality time means that you need to set clear boundaries. For some people, it’s no work after a certain time of day, while others may refuse to do any work over the weekend. Our office is anywhere we want it to be, but that doesn’t mean we have to be in it all the time.

Being overconfident and biting off more than you can chew is never a good idea. Like I said, my hubris was responsible for by burnout. I thought I could handle everything right until the moment I ended up in hospital. Be reasonable and take it easy.

Eating healthily is one thing we should all do, regardless of stress and burnout yet many of us don’t. An often overlooked problem involves stimulants, ranging from your morning coffee to your nightcap. A lot of stressed-out freelancers are hooked on caffeine, alcohol, and over the counter medications.

This brings me to the next point.

Things You Should Avoid

Caffeine is not harmless. It can cause problems if you overdo it. I am not suggesting you stop drinking your morning coffee, but if you drink a lot of caffeinated soft drinks, or energy drinks, it might be a time to slow down. They’re burnout fuel.

Caffeine, stress, and sugar are a bad mix; caffeine can make anxiety worse, mess up your digestive system, lead to more sweating, urination, and so on. Energy drinks are the worst offenders, although many of us enjoy them. They often contain loads of caffeine and loads of sugar, both of which can have nasty side-effects when combined with stress. And I won’t even waste time explaining why spicing up your morning coffee with a cigarette is bad. Remember folks, for every cigarette you smoke, God takes a minute of your life and gives it to Keith Richards.

What about a beer or two after work? There is nothing wrong with having a couple of beers or glasses of wine, especially if you get good stuff and enjoy this guilty pleasure over a nice meal. In fact, many medical experts find that moderate alcohol intake is good for you. However, if you are stressing out and on the verge of burnout, it’s not. Alcohol masks some of your burnout symptoms and lulls you into a sense of well-being.

A lot of things can help you prevent and overcome burnout, but even more things can make it worse.

For the same reason, over-the-counter medications are not to be messed with either. These meds aren’t necessarily bad for you, but you should not self-medicate. Always consult an expert, just in case you have some underlying conditions, or if you are using happy pills as a crutch for something else.

Of course, the worst thing you can do when you are stressed is to abuse alcohol or prescription medications, which will just make things much worse in the long run. If you happen to live in Colorado, and you’re considering getting some recently legalised herbs, think again. In this situation, that’s bad for you too, and can cause nasty withdrawal symptoms if you are suffering from burnout, anxiety, depression, and a range of other conditions.

There are a lot of things to keep in mind, but in my opinion, the takeaway is simple: Be aware of the risks and take immediate action if you notice signs of burnout. Notify your superiors, your clients, consult your doctor, reach out to your friends, and take some quality time off.

That is what I intend to do next week, and that was one of the reasons I decided to cover this issue. Now I have a good excuse to head down to the beach.


Telecommute General Transcription with Transcription Express

~Post may contain affiliate links. I only share opportunities I feel will benefit my readers.

Transcription Express is seeking telecommute general transcriptionists to work on an independent contractor basis. The company currently employs over 190 home-based contractors. These work at home positions are available nationwide!

You will be paid a per-page rate.  Telecommute contractors can expect to make anywhere from $600 to $1,600-plus per month, depending on hours worked and speed.


From the company:


Requirements (from work-at-home job listing):

  • Type at least 60 words per minute with 90% or better accuracy. Previous transcription experience, particularly with verbatim style transcription, a plus.
  • Be able to show proficiency in spelling and homonyms.
  • Be a native English speaker and located in the United States.
  • Have a computer with the Windows 7Pro or 8 Pro  or newer operating system and reliable high-speed internet.
  • Have or be willing to acquire digital foot pedal.
  • Must live in the U.S. and have reliable high-speed Internet.

Be aware: this company does require its telecommute subcontractors to pay a licensing fee to access its system. They do have an A+ listing with the Better Business Bureau.

If interested in learning more about this telecommute opportunity, please see the telecommute job listing.  Good luck!

If you’d like to learn more about general transcription as a work at home career, you can read My Work at Home General Transcription Story.

If you’re interested in training for a work at home transcription career, and you want in-depth, step-by-step training, I highly recommend Transcribe Anywhere!

Want to See More Work at Home Jobs? Check Out FlexJobs! Every Job Hand-Screened, Legitimate, and 100% Guaranteed!


Transcription Express is seeking telecommute general transcriptionists to work on an independent contractor basis. The company currently employs over 130 home-based contractors. These work at home positions are available nationwide! #workathome #workfromhome #makemoneyonline #workathomemoms

4 Tips That Guarantee You an Interview For a Remote Work Role

Showcasing Remote Work on Your Resume

In today’s age of increased technology, employers are realizing that telecommuting and remote work is becoming more acceptable. However, not all candidates are qualified to work in such an independent manner, so showcasing a track record of success and remote work experience will significantly increase your employment prospects for remote positions.

They are a few ways to best highlight your remote work experience and talents. In your employment history section, instead of listing your home city and state next to the company name you worked for, it is recommended that you use the term “Remote” where the city and state would go. Lavie Margolin, author of Mastering the Job Interview, suggests using one of these three ways:


List the organization’s corporate location when using a city/state format but note that the work is performed remotely in the first sentence.

Skip city/state in the formatting and note that it is work that is performed remotely in the first sentence.

List “Remote Work” in place of city/state.


Another option would be to separate out home-office jobs into their own “Remote Work Experience” category. Directly seeing a list of other companies that have trusted you to telecommute builds a hiring manager’s confidence.

You should also include your remote work experiences in the descriptions of your job. Good resumes show rather than tell. As you discuss your past job responsibilities, detail how they were performed off-site. For example, an effective presentation of a customer service position might read something like, “Responded to 75+ client inquiries daily through the company’s website while stationed at a home-based office with a high-speed Internet connection.” For a sales role, you can include a bullet point such as, “Recognized by leadership as the top performer for the 2018 fiscal year for converting more cold calls into billable accounts than any other remote worker.”


Another good idea for highlighting your remote work could be to include it in the Skills Section. Being a self-starter, an excellent communicator, or an outstanding time manager are all good skills to present for an array of jobs. However, when work is being performed remotely, displaying your expertise in certain areas can make the difference between your resume landing an interview.

When discussing your skills, look at how they particularly fit into the remote environment. Exemplary communicators, for instance, may want to mention their comfort using video conferencing, chat platforms, and instant messaging to stay in touch with others on the team. Solid collaborators could discuss using shared documents and daily check-ins to accomplish company goals while working offsite.


Remember, your resume is the starting point for presenting yourself as a solid candidate for a telecommuting role. Continue to reinforce your background through a tailored cover letter and a stellar interview that lets employers know you will be a valuable addition to the team from any location.



How to Negotiate for Remote Work (at work)

If you’ve already got a job you love, there’s no need to quit. Instead, negotiating for remote work will allow you to keep your job, and according to this FlexJobs survey, it might make you more productive as well. 

Here’s how to start turning your job into a remote one. 

1. Establish whether you really want to work remotely.

Is it so you can travel? If so, have you travelled extensively before? Is it so you can spend more time with family – or maybe it’s so that you can focus on your health? Have you ever worked alone, outside of the social comfort of an office? 

Working online is not for everyone. It can be very isolating, and not all personalities are suited to solitude. 

Thinking about why you want to work remotely will really usher out any anxieties or naivetes you have about it. If it’s because you don’t currently enjoy doing your work, it may not be your location flexibility that you should change. Establish the real reason why you’d like to be remote, and whether you think you’re cut out for it (our Humans of Outsite videos might help you think about this!). 

2. Formulate a debate. 

Ok, so you’d definitely like to be remote for a legitimate reason. Now you have to consider whether this is reasonable with your role. If you’re a team manager, with on-site contact hours daily, it might not work so well for you. The same goes for any role where the job includes face-to-face client meetings, in one city. You should also check out whether you already have flexible hours, but you don’t know about them.

However, if you’re already spending the majority of your hours on a computer, you’re chatting to your colleagues on Slack and your meetings could be condensed to a Monday (and done via Skype/Zoom/Google Hangouts), you’re already remote. 

Chances are, your boss might be totally cool with it, see eye to eye with you, and there will be no debate. If there is, back up your argument with statistics about remote work, why you’re not necessarily more productive in office, and how the future of work is already changing. It may help them attract new talent, too. 

3. Write the email (and wait on it). 

If you’d prefer to ask in person, go ahead, however this is a conversation best left for email – it allows both parties to wait, and formulate their answer. There are a few elements that deserve mentions: 

– Propose a trial period (for example, working from home every Friday for 1 month to see the effects/potential issues) 

– Outline the following period (if the trial period goes well, how does the policy continue?)

– Outline how you intend to communicate with the team whilst ‘away’, on that day. 

– Potential benefits to your company, and your team! You could be networking with a community whilst you all work, in a beautiful place. That’s definitely a benefit.

Lifewire have an excellent outline of what you should be sending in your proposal.

4. Send it. 

Press the button, wait for it!

5. Enjoy, or re-negotiate.

If the first email hasn’t been received ‘well’, there’s room for negotiation. Establish why your company isn’t comfortable with remote work – if it’s because the profession does not translate well to a remote job, it may be time to seek out a new opportunity. However, if it’s the first request your manager has received for remote work, the proposal may need further reinforcement, and testing. 

Alternatively, it may have gone well, and you might be signing up for your first stay in Hawaii, Bali or Portugal. 

Ready to start your own adventure? Become a Member of Outsite, or suggest the Outsite Business Membership to your team – that way you can all kick back in your new Bali, Hawaii or Lisbon headquarters. 

Words: Tibor Lovas

Photographs: Tibor Lovas


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