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With remote work and freelancing become more and more mainstream, travel doesn’t just have to be limited to budget backpackers or week long trips for holiday makers taking a break from full-time jobs.

I recently wrote a guest post for Money Mini Blog on how to travel without sacrificing your job  and it’s a subject that’s really stuck with me.

The digital nomad trend has been growing from just an idea, to a way of life, for years, and that’s become so much more clear to me here in Chiang Mai, Thailand, which provides a hub for nomads around the globe. Digital nomad life certainly isn’t perfect, but it’s a huge step up to office life.

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Remote Work From Anywhere - How to Negotiate with Your Employer

In my guest post, I suggested that a remote work policy could help forge the gap between achieving your dreams of travelling the world without having to quit your job. No need to pay for scammy digital nomad programmes because you’ll already have a job.

As a slight disclaimer: I asked for a remote work policy, and my job said no. 

So, this isn’t a success story. But, it is a story.

It took making this proposal, and being rejected, to force me to get out there and land my first freelance client, and several more after that.

I’m one of those people that will read every single article on a subject before doing it – whether that’s launching a blog, trying a recipe, a visiting a new coffee shop, I can’t get enough of information. So when I decided to approach my boss and ask them to consider a remote work policy, I did a lot of research.

The thing is?

There’s bits and pieces out there, but there was no single resource that told me exactly what I should be doing, asking, and saying. So, I’ve created that resource, right here.

If you’re thinking about asking for a remote work policy with your current employer, I’ve discussed everything you need to prepare for – and some of the mistakes I made – to boost your chances of success.

How to successfully negotiate a remote working agreement with your current employer.

What actually is a remote work policy?

Remote worker’s are still employed by a company, but they don’t work in an office. They can work from home, in a coffee shop, or on the other side of the world if they need to.

What’s the difference between remote work and freelancers?

Remote worker’s are an employee with a company, they simply don’t work from a traditional office. Freelancers, on the other hand, work for themselves. If you’re a freelancer, you’re not employed by anyone. It’s your own business. You handle your taxes, holidays, sick-pay, everything.

Remote work from anywhere - How to Negotiate a Remote Work Policy with Your Employer

Why would anyone work remotely?

This is a good question to be prepared for when negotiating a remote work policy for yourself.

There are actually many reasons it can be extremely beneficial for both employees and employers to work remotely.

A few reasons I included when approaching my own work are:

    • Retention – Employers don’t need to lose valuable employees simply due to a change in location, inevitably losing money by having to rehire and re-train a new member of staff. More freedom and flexibility to work where one pleases also reduces the chance of an employee getting itchy feet and moving on to pastures new.
    • Productivity – Studies have shown an overwhelming 91% of people feel more productive when working remotely. This is huge. If employees are getting more work done and in a shorter amount of time while away from the office, there’s not many arguments employers can find against that one.
    • Growing the business – Being away from the office allows employees to network with people outside the business. It helps create new potential business contacts at best, and at the very least, spreading some positive brand awareness.
    • Innovation – Did you know that 54% of employees in the UK alone are currently able to work remotely in some form? Remote work is no longer a foreign concept for wacky companies. It’s very quickly becoming the next big thing, and has been revealed to be one of the biggest causes for growth and innovation in digital companies with increased happiness and productivity reported across the board. Examples of successful remote working in action include: Buffer, GitHub, inVision, and many more.
    • Give the people what they want – A FlexJobs report found that 82% of millenials rate work flexibility when evaluating a job. The same percentage saying they would be more loyal to their employer if they provided more flexible working options. The fact is, the 9-to-5 office job is archaic and unrealistic. More and more people are unwilling to settle for the old way of life – if an employer sees this and offers remote working as part of a contract, they’ll be rewarded with more applicants, and far more loyalty.

Outlining Your Remote Working Proposal

So, you’ve decided to ask your job to let you work remotely.

What is there to lose?

They say no, and you either accept your lot and go back to work. Or you realise you’re better than that old fashioned way of thinking and move on to something new.

Or, they say yes, and you’ve scored yourself your ideal working arrangement.

Remote Work Policy

You need a plan of attack when discussing your proposal with your boss – going in unprepared to answer any concerns or with no plan of how everything will work is a sure-fire way to get turned down.

Here’s what to include when putting your proposal together:

Your Proposed Remote Work Plan

Are you going to suggest you go from 5 days in the office, to 0 days in the office? Will you ask to work just Fridays and Mondays from home? To shorten your working hours from 5 eight-hour work days, to 4 ten-hour days?

Your remote work plan is entirely up to you. How you want to adjust the current way to work, but make sure whatever your proposal if, you’ve got it clearly outlined.


Be honest with your employers. If you want to work remotely from home to save money on childcare, tell them. If you want the opportunity to see more of the world while working from your laptop, tell them. Employers are still just people, and they want their employees to be happy.

If you explain why you’re suggesting a remote work agreement, they may be more willing to work with you to come to some sort of arrangement.

How will it work

If remote work isn’t the done thing in your office, you’ll need to quickly become an expert on the subject to alleviate any of your employer’s doubts. Outline exactly how you will be able to manage your workload and responsibilities when out of the office. This includes:

– Staying in contact with colleagues and clients
– Being readily available when needed (for example, will you work the same core hours, or will you agree on set hours where you’ll always be available each day to answer phone calls and IMs, such as 12 – 3?
– How will you keep others updated on your workload
– Do you need to show your progress to any superiors? If so, how will you send this across?
– What equipment will you use? Do you have a home office that is suitable for remote working, or access to a laptop when not in the office?
– Any resources you will use to make your remote work seamless with other employees and with your own workload, such as Trello, Google Hangouts and Slack.

Concerns You’ll Encounter

Your remote work plan has worked if your employer has zero concerns at the end of your pitch. That’s what you should aim for. Your proposal should so thoroughly cover ever single base, there’s no room for argument from your boss.

Remote work from anywhere - How to Negotiate a Remote Work Policy with Your Employer

However, it can be hard to make your proposal that water-tight. If remote working agreements aren’t the norm in your office, it’s likely that your boss will have some concerns.

A few I’ve encountered, and a could response to ease those concerns include:

How will we contact you when you’re not here

Simple – you’ll agree fixed working hours where you will be available by phone, IM or email every single day.

If any of your colleagues need to contact you, they will know the hours you are guaranteed to be available. If you will be out the country, these core hours may only be a few hours where two different time zones overlap, so agreeing other forms of contact is a good idea.

Set up Slack to communicate with colleagues. Use Google Hangouts for meetings. Pay the cheap price for a Skype number so making and receiving calls is much easier. If you think contact and communication may be a big issue with your employer, put together a solid plan of how these channels will allow you to work just as, or more, efficiently as when you are in the office.

How will we know you’re working

This wasn’t a concern with my employer. Honestly, if you like your boss well enough to think about asking to negotiate a remote work policy, it’s unlikely they’re so strict that they need constant updates of you’re workload. However, you must make sure you will be getting the work done when out of the office.

Apps like Trello are extremely useful for this, providing a clear project management tool that multiple employees can view and update as they work. If a member of your team need an update on your workload, they simply need to consult Trello to see how you’re getting on.

What if other employees want to follow suit

This was the reason my remote work policy proposal was ultimately rejected. My director worried that it would set a precedent in the company that would allow other employees to also request remote contracts, and that isn’t something they were willing to negotiate with employees. Fair enough.

My suggested response would be to show the many, many statistics that document not only how many successful businesses have remote teams, but also how much more productive and happy people working in those teams are. If one person working remotely sets a precedent for a clearly positive, innovative way of working, is that such a bad thing?

I can’t guarantee that your employee will grant your request if you follow these steps. However, I can guarantee that you’ll be taken far more seriously for doing your research and building a plan that could actually work.

Regardless, you’ll be far more educated on how a remote work policy can actually, well, work! Sounds like the perfect base to start building your freelance career to me..!

If you’re looking to launch into remote working, starting my own blog was one of the best decisions I could ever have made for focusing my mind on the goals I truly want to achieve.

If you’re interested in starting a blog of your own, I strongly recommend using BlueHost for a quality hosting provider at low prices (it’s the only provider I use!). Check out my exclusive link for a free domain and hosting packages as low as $3.95/month.

Alternatively, check out my free guide to starting your own blog from scratch in less than 10 minutes!

Find out how to negotiate a remote work agreement with your current employer. Work remotely and become location independent without quitting your job by getting a remote work policy with your current job. This guide will take you through the action points you need to successfully propose a remote work contract.

Remote work from anywhere - How to Negotiate a Remote Work Contract with Your Employer