Remote Working

Interested in remote working?

Perhaps you’re an employee seeking greater freedom or a startup CEO hoping to incentivise employees.

Either way, ever since the emergence of the four-hour workweek, destination hopping from one exotic beach to another, mojito in hand, is like cultural pornography.

Combine that with passive income and you have the supposed holy grail of existence.

But is working remotely all it’s cracked up to be, and if so, what are the caveats?

Let’s take a look. But first, a quick look at my credentials…

My story

I’ve been working remotely now, on and off, for a few years, now as a digital marketer.

I’ve had the opportunity to live in various places around the world and experience the delight of foreign lands.

As with anything, there are both good and bad sides to the deal, so I’ll try to provide a balanced analysis, before presenting my final verdict.

Who’s this digital ramble for?

If you’re reading this article, you’re likely a knowledge worker or aspire to be one.

After all, it’s almost impossible to work remotely in some traditional professions (although we are seeing the emergence of online doctors).

However, this article is more aimed at laptop monkeys like myself, where all that’s really required for work is an Internet connection and solitude.

Benefits of remote working

Firstly, let’s talk about the benefits of working remotely, of which there are certainly many. There have to be really, to have spawned such a cultural zeitgeist.

Location independence

Probably to biggest draw to remote working is, unsurprisingly, location independence:

  • If your target company is in an undesirable location, no problemo – you can work from anywhere you want.
  • If you want to keep your family settled, stay close to friends etc, there’s no need to relocate for work.
  • Want to go travelling and working simultaneously? You can (technically) do this, and digital nomadism is a phenomenon in its own right, although it definitely comes with its own set of drawbacks, as we’ll discover later in the article.

More autonomy

Working remotely simply provides more autonomy and the flexibility to choose how and where you work.

You can generally tweak your schedule and hours to suit without the usual grind of a daily commute.

Rather than traipsing into a dreary office, you can select your most productive hours to get work done.

If you fancy a change of scenery, you can always head to a local coffee shop or different coworking space.

This autonomy is, according to Simon Sinek in Leaders Eat Last, one of the essential factors of employee wellbeing.

More money

This is a big one with remote working.

Rather than living in a potentially expensive city and paying a prohibitive cost of living, you can choose somewhere cheaper and save on travel and rent.

That means more dinero at the end of the month.

It’s a great feeling when you realise how little you need in some parts of the world to live the good life.

More time

Time, the non-renewable resource that’s slipping away like a thief in the night. Oh, you slippery beast.

By working remotely, you instantly reclaim a large portion of your life. This is perhaps one of the biggest advantages of this work setup.

No more boring commute shoved on a train with smelly people. You get to walk across the hallway to your study, or bicycle, Netherlands-style, to your local coffee shop.

If you need to take a little break in the day to run a personal errand, you can flash your remote working ID with a cheeky smile and make up your hours elsewhere.

You also save significant time in pointless meetings – as Jeff Bezos says, most meetings are wasted time.

As a remote worker, you’re more action-orientated, distilling instructions and eeking out efficiency wherever you can.

Increased output

As you save time in meetings to reinvest in meaningful action, you can naturally create more.

Where water cooler gossip is interesting, being out of the office and away from the drama allows you to pick a project and get to work.

You’re somewhat removed from office politics and work more objectively on your tasks.

There’s generally less infighting when you’re remote, or if there is, you’re not there to see it.

Instead, you bask in your remote bubble of joy, like a silent disco, rocking out to the track of deep focussed work. Oh yeah.

Increased quality of work

When you’re remote, you tend to take increased ownership of your craft, sometimes, to a fault.

Perhaps because you don’t have the instant feedback you receive in an office, you tend to overcompensate and put your all into each project.

The result? Excellent work that pleases your overlords.

It’s rather similar to the notable study in which a professor stopped giving grades to his class and they started producing better work (out of sheer panic!)

Better Environment

One of the main benefits of working remotely must be the fact that we can create our immediate environment to be conducive for effective output.

Do you work perfectly with a particular ambient temperature? Like to organise your pencils and colour coordinate your post-it notes? Fed up of people stealing your food from the communal fridge?

You can play music all you want and you don’t have employees chewing gum or cutting their fingernails next to you.

This means you’re free to express yourself.

Preferred equipment/setup

Similar to your environmental factors, you get to choose your equipment.

This might not be a huge departure from the office, but working remotely, you may be offered a budget to invest in your preferred tools – dual monitors I hear ye cry?!

You can retrofit your home office with all the bling you want and organise it just so.

A sophisticated leather-bound chair? Go on then. Walnut desk with leather writing top? Yes please.

As long as you work for yourself or persuade your superiors, that is.

Either way, entering an office which is already set up doesn’t provide nearly as much flexibility as your bespoke home setup.

As you can see there are many reasons to consider working remotely.

Obviously, the benefits will vary depending on whether you’re a freelancer or permanent company employee.

This too, might require some experimentation, as there are benefits and drawbacks to both.

Let’s take a look.

Drawbacks to the deal

While location independence is amazing in many respects, there are also downsides that remote working advocates gloss over.


Depending on your role, taking holidays in a remote role is tough, mainly because you feel more attached to your work.

Part of this involves the feeling that because you’re not working on-site, your colleagues are more productive (spoiler: they’re not!), or curry more favour with the company.

Indeed, there’s some research stating that remote workers take 30% less holiday than their office-bound colleagues.

It’s vital, therefore, when working from home, to book holidays in ahead of time and claim your full quota.

Such decompression and escape from work is essential for sustainable health and wellness.


When working from home, it can be hard to separate our work and home life.

Time bleeds from one area into the next and you never quite know when you should be working or relaxing.

This can result in perpetual low-grade anxiety, where you never fully switch off and enjoy your downtime.

It’s vital to delineate the two and maintain these boundaries, otherwise, it’s easy to feel overworked and overstressed.


Perhaps one of the main dangers of working remotely is the lack of collaboration with teammates, making you feel like the unpopular child in school.

While applications like Slack allow you to communicate with colleagues in real-time, in some respects, it’s not the same as getting face time with your work buddies.

This may have an impact on teamwork, creativity and speed of execution.

The solution?

You need to be extra communicative with colleagues and learn the lost art of succinct and clear email/messenger conversations.


One big danger of working remotely is loneliness.

Perhaps in conjunction with the modern social isolation epidemic, it’s no wonder that working alone in a cold, dark house-dungeon might exacerbate such feelings of disconnection.

It’s funny, but when working from home I intermittently forget how to talk to people.

It’s like one of those prison movies when a cellmate emerges from solitary confinement as a raving lunatic or complete mute.

Engaging in idle coffee shop chit chat after working alone for one or two days, I stumble over my words like a drunkard.

digital nomad

Types of remote workers

There are three main buckets of people who work remotely. One type isn’t really a focus for this article, so let’s cover them first.

Business owners

The whole Internet thang has spawned a generation of digital nomads determined to live the high life, climbing mountains in the morning and scuba diving at sunset.

And why not?

If you can make a living from your laptop, you likely want a nice place to do it from.

This type of work is remote by nature and is a primary ambition for many creating online businesses.


This group are obviously still business owners, but are less into the whole dropshipping and vlogging and instead work with other humans/organisations one-on-one.

Freelancers constitute a large percentage of remote workers, and although some companies specify that freelancers work on-site, a large proportion are location independent, especially when serving different clients around the country/world.

Being a freelancer definitely has it’s own pros and cons:


  • Working with multiple clients means diluted risk – if one stops paying, you have other gigs to fall back on.
  • As a freelancer, you really are removed from team politics. Whatever internal strife they face, you’re distant enough to simply do your job and leave the drama to the full-timers. This can be a blessing.
  • Also, physical removal from the client location provides more freedom to engage in projects on your own terms. They hire you to solve specific problems in the most efficient way possible.
  • Freelancing provides the opportunity to apply your skills to a range of exciting projects in distinct industries.
  • It can also be a wonderful networking medium as you hobnob with various business owners.


  • It’s not all fairies and rainbows however, with many freelancers feeling the pressure of looming deadlines and work excess. As work can’t be guaranteed, you take what’s offered, in a typical feast and famine cycle.
  • With simultaneous deliverables and tight deadlines, stress and burnout are common.
  • With greater freedom comes greater choice and indecision. What project do you focus on? What service will you deliver? Do you focus on a specific industry?
  • Repeatedly pitching new companies to maintain your work pipeline proves tiring.

Full-time employees

Okay, onto the final group; the full-time employee.


  • In some senses, being a full-time employee is much easier than freelancing – you get to work with the security of a monthly paycheck.
  • You build deeper, more stable relationships with your colleagues and boss, and don’t have to be constantly thinking about sourcing the next client or contract.
  • You’re unburdened from all the annoying admin of running your own freelance business; chasing invoices, sorting out insurance, and tracking tax expenses.
  • This liberates much mental energy to invest in the work and makes you more productive.


  • There are also downsides to full-time employee life. Unlike freelancing, where you can hop, skip and jump between different industries, a permanent role doesn’t offer equal freedom.
  • Sometimes, if you simply don’t like your work, going remote won’t help you assuage your annoyances.
  • It can be frustrating to work with a team over long distances, with those who are used to office life experiencing a feeling of disconnection.
  • Depending on your area of work, absence of physical contact might impede project development and progress.


It’s worth highlighting that some of the aforementioned drawbacks can be partially remedied through coworking.

Perhaps the main benefit is that you spend time with other human beings, rather than talking to yourself at home.

It can be great to build relationships professionally in your local area and collaborate with those in related fields.

Speaking to people to doing interesting things with intersecting expertise areas can spawn new ideas and boost creativity.

In this way, co-working provides important access to an extended community of creatives for psychological support.

Personally, I’ve tried working in various shared spaces, with mixed results.

In some senses, I get more done when I’m distraction-free at home without loud conference calls blaring away next to me (who woulda thought?!)

Depending on your personality type, you may prefer the home office over the shared environment.

However, the great thing about hot desking is that you can dip in and out as it tickles your fancy.

As you can see, there are muchos pros and cons of working remotely, but if you’re currently an office monkey, how can you finally hit the road and work from afar?

Obviously this varies wildly depending on your situation. Let’s take a look.

How to make the transition

For employees

If you’re an employee currently, is there any way you can ask your boss about the possibility of going remote?

If you’re adding value to the company and they don’t want to lose you, they might be willing.

Perhaps this could be an exercise in graded exposure, where they allow you to work from home for half the week before going full-time remote.

You may need some bargaining power before suggesting this, and it might help if the company’s already set a precedent for previous employees.

Applying for jobs

Obviously, if you’re currently searching for a full-time job, you can be pickier about what you apply for.

The whole remote working culture has grown pretty mainstream now, so more companies are adopting an agile approach.

A few good places to look are We Work Remotely, AngelList or, and even if you find positions on normal job boards, you can ask about remote options before you apply.

Going freelance

As we’ve already mentioned, the other option you could explore is freelancing, which can provide greater flexibility if full-time options aren’t working out.

What’s nice is that you might be able to test the waters in the freelance world before leaving your full-time job, to see if it’s a good fit.

Just be careful when quitting your job to go full time if you haven’t pinned down any clients first.

The final verdict

surfing girl laptop

As you can see, remote working isn’t all Thai beaches and Pina Coladas, but it can be a pretty satisfying way of working, providing a healthier work-life balance with everything up correctly.

I’ve thoroughly enjoyed my time remote working and will likely continue to do so.

It provides all the flexibility I want, greater life autonomy and improved engagement in deep, focussed work.

And whatever makes employees/freelancers happier, should also be better for the companies that hire them.

Hopefully, you found this mini-guide useful and feel free to hit me up with any comments or questions.