Making A Living On The Roads- An Update

Posted on Posted in Journal, Journal & Musings, OptingOut!

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So here I am again with another update fresh from the back roads of the Wild West of Ireland. I need to first of all apologise to all my followers for the long delay since my last blog post; it has been more than a month. The reason for my being so quiet was simply that I have worked very hard at trying to solve one of my chief problems right now – the issue of how to earn a living, while retaining the freedom of being a nomadic van dweller. This is somewhat of the “holy grail” of us digital nomads, so I dedicated myself to it fully.

To make a long story short, there’s no free lunch to be had. It is hard, and it takes time, but it can be done. And oh boy, is it a learning curve.

Right from the beginning the point for me was to be able to earn a living while on the road, not by hopping from one traditional “casual” job to another. I wanted to retain my freedom as much as possible, and not tie myself down, and be it only for a few weeks at a time. So, for me the chosen approach was freelancing.

This is of course not a new concept. There are a number of services on the internet which are build specifically to connect freelancers with clients, most notably sites like and These platforms are huge, with hundreds of thousands of people being registered on them, so there can be little doubt that the concept itself works pretty well ( otherwise no one would bother ). The question is just – can you actually make a living doing this ?

Obviously, the answer to this depends very much on what your needs are. If you have a family to feed, a motor loan to service, a huge mortgage, and an expensive hobby, then it is fairly safe to say that you shouldn’t even bother. Freelancing is no magic recipe to make big money with little effort. If it was, people would have long since stopped doing their 9-5 office job thing. The reality of the situation is that getting yourself established in the freelancing world isn’t easy, and requires patience, effort and perseverance.

The upshot is that everything is based on reputation. The basic template upon which services like Upwork and Freelancer are built is simple – clients publish jobs they need done, and freelancers can submit proposals ( i.e. “bid” ) on these jobs. A proposal is just simply a statement of the form “I can do this job for $xxx within xxx hours. My qualifications are xxx, and I am a suitable candidate because of xxx”. You get the idea. The client will then choose a freelancer whose proposal hit the sweet spot, and award the contract. Once the final work has been received, the client will give feedback to a freelancer and vice versa. This feedback shows up as a star rating, or something similar.

The thing is this – every single job will attract a large number of proposals, just as every job ad in the real world will result in a large number of applications received. And just like in the real world, clients want to hire the best people. When you start out with a fresh, blank profile on a freelancing site, without no ( or very little ) existing feedback, it is extremely difficult to get any kind of work at all. This is no different to work in the real world – when you first start out with an essentially empty CV, it is very hard to find your first few jobs. Likewise, it is very hard to find work if your feedback score is bad – so don’t take on jobs you can’t do, and take the ones you do accept seriously, like you would a job in the real world. Any mistakes here will come back to haunt you.

The kind of work that is available on these sites is pretty much everything and anything that can possibly be done remotely on a computer – popular examples are translations, transcriptions, developing websites, content creation, design work, editorial work, email handling and customer support, “virtual assistance” ( like a PA/secretary, but remotely on a computer ), tutoring in various subjects, ghostwriting, data entry etc etc etc. The list goes on. Some of these are one-time projects, others are regular work for a number of hours each week.

The advantage of this type of work is probably obvious – you are your own boss, and generally speaking you will be able to work when, where and for how long you want, so long as you meet your deadlines and deliver whatever it is your client is looking for. No being stuck in commuter traffic. No boss breathing down your neck. No obnoxious coworkers. What’s needed is only a computer with a decent Internet connection. In my case, this is an iPad Pro ( which I got as a display model, at a huge discount ) with Internet connection via 4G mobile network, on an unlimited data plan at a fixed monthly price.

A month ago, when I first started out as a new freelancer, I was a complete greenhorn and rookie – I didn’t have a clue what I was doing. I didn’t even have a proper idea what I actually can do, and – more importantly – what I cannot do, or what the skills I have are actually worth in the freelancing world. The very first thing that I learned was that there are plenty of unscrupulous clients out there who will try to take advantage of new freelancers to save themselves big bucks. To give you just one example among many – I received an offer once to translate a 20,000 word document ( ~ 40 pages ) for $20. To put this into perspective, this would have taken me at least 8 days of solid work, and if you went to a professional translation agency, they will be charging you in the region of $2500 for a job of this magnitude. You get silly offers like this all the time. The danger is that things aren’t always obvious – sometimes jobs are described in ways that make them seem easy, whereas in reality they require huge amounts of time and effort, for very little money. So one has to check very carefully before accepting anything – once you accept, you are stuck with it, because cancelling a contract will almost certainly lead to bad feedback.

With this being said, the opposite is also true – every once in a while you come across jobs that are geniunely quick and easy, and pay good money. I once did a job for someone that took me less than 10 minutes to complete, and paid $25. That’s pretty good, considering that I can spend the rest of the day hunting for more work ! The vast majority of once-off freelancing jobs are in the $5-$200 bracket, so one has to be smart about it and apply for those that fit your skill set, take the least amount of time and effort, and are posted by genuine and trustworthy clients. There is no point labouring away for days, in exchange for just a few dollars; time is money, and that time you could have used to find more lucrative assignments.

The next thing I had to learn was that the true winner in these deals is neither the client nor the freelancer, but the website. Places like Upwork and Freelancer take a chunk of your pay as commission, and that cut can be as high as 20% of the contract value. Not only that, but placing bids on open job offers will require you to spend tokens – you can join these sites for free, but the basic free membership plan usually gives you only a very small amount of tokens, so you are basically forced to upgrade to paid membership plans in order to be able to bid on lots of jobs. And placing lots of bids is needed, because, just like in the real world, you will hardly ever get the first job you apply for. And it doesn’t stop there – after the transaction is complete, and you get paid, you need to somehow withdraw those funds. This usually works through services like PayPal and Payoneer, who will themselves level fees for the privilege of handling your funds. So, by the time your hard earned funds hit your bank account, you might find yourself having lost a good portion of it in various fees. And of course that’s before you declare it for the purposes of income tax !

So the lesson is – in order to make any real money at all on freelancing sites, you need to be smart about it. Don’t just willy-nilly bid on all and any jobs; only bid on quality jobs ( = paying decent money commensurate with the required time and effort ), which you can actually do within the deadlines given ( = good feedback ). Also, look carefully at how many competitors you have – if there are already 50+ proposals from other freelancers for a given job, chances are your own bid will not even be noticed by the client, unless your profile really stands out in some way. It is better to bid on jobs where you have little competition – something that requires a unique talent you have, otherwise you are just wasting both your time, and your limited tokens. Specialise, and stand out that way. In my case for example, I speak both English and German to native level, which sets me apart from most of the pack so far as translation jobs are concerned. In addition, be smart about how you put together your proposals – for example, if you see a job where the client states a budget of $100, go in at $95 – the missing $5 won’t make a huge difference to you, but they will immediately set you apart from other applicants, because most people are greedy and will go for the full $100. If a client sees a freelancer with excellent feedback scores, who offers a slightly better rate, then that’s who they will go for.

So where do I stand now ? I have begun my freelancing career on, for the primary reason that the site works well on my iPad ( which is something that can’t be taken for granted, because many sites don’t ). I have initially dabbled in a number of things, but now, after my first month, I find myself specialising in translation work and being a Virtual Assistant. I work a number of hours each week on a permanent contract handling emails for an education provider in Australia, and outside of that I do once-off translation and transcription jobs ( translating websites, letters, academic papers etc ). I also have some regular students whom I tutor in German and English via Skype, and I do a very small amount of ghostwriting. All up, I probably average about 20 hours of work per week at present. In monetary terms, over the past month I have been able to almost – but not quite – been able to break even from freelancing. The means I have been able to almost cover all my groceries, fuel, gas, and miscellaneous expenses. This being said, it has been a month without any unforeseen expenses – had anything unexpected happened, things would have looked different.

Now, that may not sound particularly impressive or encouraging; but I actually consider it somewhat of a success. True, it may seem that I have spent 20 hours per week for very little return. But it has to be remembered that I started off with absolutely nothing – a blank page, so things were very slow in the beginning, and I had to find my feet. I now have a profile with a five star feedback rating, some documented work experience, a regular contract as Virtual Assistant, as well as regular students whom I tutor. I am now beginning to receive invitations to apply for jobs that are not publicly visible, meaning clients are actually finding me, instead of the other way around. That is a good sign, and I am hopeful that in the long run I may be able to not only cover my expenses via freelancing, but earn a real living, with money left over at the end of the month, without having to break my back or stress myself out in the process. So, the verdict is that it is still a struggle, but I am hopeful that things will improve as time goes by, and I have not given up. The jackpot would be a regular contract that pays a good hourly rate, and gives me guaranteed hours per week; I am on the lookout for that. These opportunities are there, I just haven’t been successful in applying for them yet. I will now also branch out to other sites, such as, so as not have all my eggs in one basket.

I am not going to lie to you – psychologically it is a challenge too. Everything is uncertain, you never know where or when your next contract comes along, and how much it will earn you. One day you might receive so many offers that you actually have to turn down clients, and on other days you might not get anything at all. You are free to plan your own time, but you are also fully responsible for finding sources of income – you are fully responsible for yourself, for making a living. It is much harder than just showing up at the office at 9am, and going home with a guaranteed amount of pay.

But some things cannot be measured in terms of money, and so my dream lives on – I see the beginnings of earning a living while being free out on the roads. So I leave you with the promise of more regular updates from now on, and once again a view on what my “office” now looks like; stay tuned 🙂


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