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The challenges of remote working

Prior to writing this post, I had just read two of Scott Hanselman's blog posts, Being a Remote Worker Sucks - Long Live the Remote Worker and Tragedies of the Remote Worker: "Looks like you're the only one on the call".  I totally identify with the concerns raised regarding the aspects of remote working. 

Remote working certainly does have its challenges but at the same time, it has its rewards. I thought I would take to opportunity to add my own perspective on the issues raised.

Over the past few years, I have worked 100% remotely for a number of organisations throughout Europe and Northern America. I predominantly work from purpose-built home-office. After having been inspired to make the leap after reading Rework and 4 Hour Work Week books which have had dramatic effect on my approach to work and life.


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Essentially over the years, I have converted my double garage and created an office environment which has become a bunker, with enough computing power and resources to take over the world.

This is not my only experience of working from home though, back in the 90's I had my own business which I ran 100% from my home in South Africa. I had over 70 people working for me, granted not all of them in the house, as that just would've been weird and a bit cramped. The nature of the business was that everybody worked on construction sites across the country.

I spent most of my days, driving from site to site monitoring and managing progress and attending site meetings.

The only reason why I closed the business, was due to the fact I wanted to fulfil life long ambition of travelling the world.

Before boarding a plane and leaving an extremely comfortable lifestyle behind, I thought long and hard about which career path I would pursue. A  large portion of that thought pattern and the decision comprised how much potential there would be to work from home.

I have always had a dislike of Corporatism, I guess this can only be attributed to my love of Punk and Heavy Metal music and for a large part of my youth played drums & guitars in various garage bands. I've always had a healthy disdain for authority and conventionalism.

I have also spent the vast majority of my working life, as self-employed. In total I think I have only ever had, what some people would call real jobs. Independence and self-reliance are huge aspects of my personality.

Jumping on an aeroplane with the intention of arriving someplace and having to make money somehow, can be daunting because in reality, you have no idea what you're walking into. I needed to pick a trade that was somehow universal.

Software development seemed the most likely choice, due to the fact that during the '90s there was a lot of hype about how Information Technology would soon enable everyone to not only work in a paperless office but also enable anyone to work anywhere.

In fact, I remember as being a child who was educated in the '80s, there were actually serious educational concerns and programmes that were going to be introduced to actually help educate people on how to make use of the free time that computers would enable us to have. Governments were actively contemplating that the reality that most people were only going to be working 2-3 days a week, primarily because computers and robots were going to do all the work for us.

It seemed a no brainer at the time, not only was it an of working within the industry that was transforming the world, but it would enable many to work in a transformed manner. Fortunately, like many kids of my era, I already some of the basic skills required due to my part-time interest in developing games and learning about this new fangled thing at the time called the internet.

It was only when I started working in the IT industry did I notice how hypocritical its attitude was towards remote work.  It seemed like an industry that was focused on delivering the concepts of delivering efficiency, productivity and flexibility to organisations, was not by its own standards particularly efficient, productive and flexible.  

A vast majority of the management thinking was still very much based on the conventional thinking of the '60s and '70s, and the concept of people working in centralised location i.e. Offices. Apparently, this was the only way to foster effective collaboration, comradeship and supervision.

It was this, conventional wisdom dictated that because people were sat at their desks in the office with management oversight therefore, they had to be busy.

It also apparently dictated that because people were sat in a room together it will enable collaboration.  Unfortunately, I have worked in many organisations that prove the complete antithesis, of these conventional wisdom nuggets.

The primary problem with conventional wisdom is that by its very nature requires conventional thinking which unfortunately also stifles innovation.

Remote working is not for everyone

Even though I love working remotely and I will do everything in my power to continue to do so. I have to admit, it's not for everyone. I appreciate that some people need to have the structure and conformity of the office.

Personally, structure and conformity is everything I detest about the world work. I don't need an environment, dress code or a pre-defined set of hours to get me into work mode. I'm a self-starter, self-motivated and self-disciplined enough to do this for myself, I also have a strong desire and free will to want to let myself make these decision.

I want to be able to choose how to fit work into my life rather than to fit life into my work.

I have done more than my fair share of crazy commutes, pre-defined hours, uncomfortable office furniture. I've had to endure really de-motivating office environments, stupid dress codes and weird office cultures. I much prefer having zero commuting time, working my own hours, choosing my own office furniture, creating my own comfortable environment, wearing what I want and enjoying my own eclectic culture.

Occasionally I like to mix it up a little and change my work location a bit. For instance, both my parents and in-laws live a fair distance away from us, so taking the kids to spend sometime with the grandparents, I can easily take my laptop and set up in another room and work. Sometimes, I might just fancy a change of routine or scenery and will setup in a coffee shop or something. I sometimes find working in these areas offers unique innovative inspiration or alternate perspective to problem solving.

Working remotely is not for the reclusive

Many people have misconceptions regarding remote workers, considering them to be reclusive loners working in their underpants. I can honestly say that the vast majority of remote workers I know, are on the complete opposite end of this scale.

The typical stereotype of the remote worker is one of somebody who is socially awkward and reclusive, working on their sofa still in their pyjama's all day.

Like all stereotypes, this is totally inaccurate and in reality, is far from the truth.

The very nature of remote work requires you to be more sociable, engaging, self-assured and sociable. If you're any other way, you will not survive. You need to possess the ability to engage with people on any level and your ability to be able to communicate effectively and to be understood clearly needs to be second to none.

The converse needs to apply too, you need to be able to clearly understand instructions and not be afraid to labour the point to ensure all instructions provided to you are clear and concise and free of ambiguity.

Once you're detached from an office environment, you'll quickly come to realise how dysfunctional most corporate communication is and why there is a need for so many meetings.

Meetings are never an avenue for decisions, they are simply a convenient excuse for people to start understanding what a problem is. When people are co-located it becomes very easy for them to justify unnecessary meetings and ad-hoc meet-ups. These are primarily just a mechanism to help people to decide that they will need to meet again later to further discuss the same problem.

There is a natural tendency for people to think, that in order to quickly solve a problem or facilitate a discussion they need to "get everyone in the same room".

Similar to Scott's post, I've lost count of the number of times people have emailed me to ask me when I am next in the office, or when do I plan to be in the office, or if I could make a special trip to the office to discuss a matter. The matter apparently requires Face to Face time to be discussed.

When I video conference, Skype, Slack, Lync, Phone or use any one of the numerous other communication platforms solutions we have available we have available these days, with quite literally more arriving every day. We're able to discuss and come to a positive resolution of the issue pretty easily, without the need to undertake an onerous journey and incur totally unnecessary expenditure

Be your own IT Department

To be successful as a remote worker, you need to be able to be able to work effectively with technology. Your home will effectively become a satellite office, and you will become your own one-man support and operations unit.

I can assure you that most IT departments are barely well enough equipped to deal with on-site issues, let alone technical difficulties experienced by someone working a few hundred miles away.  It will be a lot easier and less frustrating to be able to sort your issues out on your own.

You also need the ability to use your own devices. I for one can't believe that companies still think it's necessary that everyone in the organisation needs to have a "standard build" or "standard device", in my opinion, this is absolute bovine dollop.

Inevitably this will lead to at least 70% of the organisation will have the complete incorrect configuration for their needs.  

As a remote worker, you really don't want to be confined to a completely underpowered VPN and an inadequate computer.    You also need to have administrative rights on your laptop with the ability to securely connect your device to your local sub-network.

A few years ago, I ran into a truly bizarre situation, when I actually needed to take a whole load of marketing paraphernalia and such like to a local printers to be printed for a trade show in my area,  but due to security restrictions I was not permitted to connect my laptop to my home network to enable me to use my home printer, burn CD's or download the documents to a thumb drive .

The corporate laptop I was issued with, had most of the great usability features disabled. i.e. DVD drive, USB ports etc. I had to connect to the corporate VPN in order to use it.

The documents, and the group of files that were in the same bundle.  Were too big to be able to send to my home email address in one zip file. There was a corporate restriction on external file size on attachments,  the company also had a no file sharing application policy i.e. DropBox etc.  

It was such a hassle that the only way I could get the files was to get a colleague to snail mail a DVD.   Which I duly took the printers, who in turn copied the files to their system etc.

I couldn't believe there were so many security restrictions in place to protect information I was going to give away for free anyway!

For a remote worker to be truly successful, they need the ability and be empowered to make their own technology choices and organisations need to be able to adapt to a hybrid cloud model.  Of course, security is a concern and it certainly must be front of mind when considering technology solutions, but it doesn't have to be a barrier.

Networking is essential

You will inevitably run into to situations where you need assistance outside of your immediate circle. I've had situations, even when I have worked on site, that a quick phone call to an ex-colleague or acquaintance helped solve an issue.  When you're working remotely this is even more vital because you can't always rely on your immediate colleagues to be of assistance due to Timezone restrictions etc.

Having the ability to network is essential. I have built up an extensive network of other remote workers and other business acquaintances, that I can quickly call on for assistance.  I have all the communication details for these people available. Most trade is carried out on a per favour basis, and no hard currency ever changes hands.  It's like having an office water cooler, but on a global scale.  We all catch up from time to time, have chats, exchange ideas and sometimes just generally shoot the breeze but seldom are able to meet in person due to geographical constraints.

We all have one thing in common, we all share to same passion and enjoyment of working remotely and wouldn't change it for the world.

A passion for what you do

In my opinion, probably the most fundamental component to becoming a successful remote worker, you have to seriously love and enjoy what you do for a living. I enjoy programming so much, I would do it in my spare time too. That being said, you also have to be versatile and adaptable.

In fact, even before I became a professional programmer, I did do programming in my spare time, admittedly I wasn't very good at it, but I found it interesting and compelling.

Even when I had my previous business I would often find myself tinkering around with computers and technology for fun.  I managed to turn my hobby into a career and because of that, I feel I don't work a day in my life, I'm just having fun and make money while doing it.

I read in the comments section of Scotts post that a few people complained about not being able to focus at home and being easily distracted.  I would have to say that without coming across as too judgemental, these people probably don't really enjoy what they do for a living, and that's ok. I know not everyone is fortunate to do what they really want to do, but if you want to be successful at being a remote worker, you really do need to love what you do, and want to be the best at it.

I don't have any aspirations or dreams of climbing a corporate ladder.  There is no job, I would really want to be doing other than writing code to solve problems.  I also know what I don't want in life, and I don't want to sit in traffic jams, over-crammed public transport,  poorly ventilated offices with people who would rather be somewhere else or at home and wearing some "corporate uniform".

I shun the idea of the conventional working day and trying to fit life around some set of hours in a day, watching the clock as it gets to some pre-defined intervals.  

I love and appreciate having the ability to define and work my own hours, location, choice of clothing and enjoying my time at work.


I totally appreciate that the concept of remote working is not for everyone or even will be suitable for every conceivable work environment or type of work. There are still very many types of jobs that will require a physical or co-located presence.

Gary Woodfine
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