The challenges of remote working

I 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.  It certainly does have it’s challenges but at the same time it has it’s rewards.

Over the past few years I have worked 100% remotely for a number of organisations throughout Europe and Northern America. I work from my own purpose built home office . 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. The only reason why I closed that business, was due to the fact I wanted to fulfil a life long ambition of emigrating. In this post I will share some of my experiences gained from work from home.

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. Software development seemed the most likely choice, due to fact that during the 90’s 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. It seemed a no brain-er at the time, not only was it an of working within the industry that was transforming the world and  enable me to work in a transformed manner, but I also had skills and a part-time interest.

It was only when I started working in the IT industry did I notice how hypocritical it’s attitude was towards remote work.  It seemed like the industry that was focused on delivering the concept of delivery efficiency, productivity and flexibility to organisations was not efficient, productive and flexible.  A vast majority of the management thinking was still very much based in the 60’s and 70’s.

The conventional wisdom dictates that because people are sat at their desks in the office therefore they must be busy. It also dictates that because people are sat in a room together it will enable collaboration.  I have worked in organisations that prove the antithesis.

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 that is everything I detest about 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 choose to fit work into my life, 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 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 posses the ability to engage with people on any level, your ability to be able to communicate 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.

Once you’re detached from an office environment, you’ll quickly come to realise how dysfunctional most corporate communication is and 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, just 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. When I video conference, Skype, Lync, Phone or use anyone of the numerous other solutions we have to communicate these days. 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 unnecessary expenditure

Be your own IT Department

To be successful as a remote worker, you need to be able to be able to work with technology. You’re effectively going to be a satellite office, a one man support and operation 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 ox manure.  What this inevitably leads to is that 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 under powered VPN and an inadequate computer.    You also need to have administrative rights on your laptop with the ability of being able 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 a 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 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 to me, was  to get a colleague  to snail mail me a DVD.   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 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 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

This is probably the most fundamental part to being 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.  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 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 don’t work a day in my life.

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 a life around some set of hours in a day, watching the clock as it gets to some pre-defined intervals.  I love been able to choose my own hours, my own locations of work, my own choice of clothing and enjoying my time at work.

Gary Woodfine

Freelance Full Stack Developer at
Helps businesses by improving their technical proficiencies and eliminating waste from the software development pipelines.

A unique background as business owner, marketing, software development and business development ensures that he can offer the optimum business consultancy services across a wide spectrum of business challenges.

Published by Gary Woodfine

Helps businesses by improving their technical proficiencies and eliminating waste from the software development pipelines. A unique background as business owner, marketing, software development and business development ensures that he can offer the optimum business consultancy services across a wide spectrum of business challenges.