September is a month of beginnings. A little like January, when we commit to a set of resolutions for the new year, September inherits from the school tradition the promise of reinvention, of this year I will be better or that something will change. From the motivation that the holidays provide – more time for ourselves, for our loved ones or for what we really like to do – or from the Sunday blues felt in the last days before returning to work, September may lead to (the will of) change – namely regarding the working life.

It’s not news that the working life translates itself, to a large majority, into a greyer daily life than the one imagined. There are more documents, Excel spreadsheets and e-mails than the exciting and challenging work envisioned. There are a lot of hours – the vast majority of the day while awake – in a placesometimes unfamiliar, with colleagues with whom we have no empathy, with concessions, with extra hours and in a job in which we do not see ourselves. How many people reach the end of the day with the feeling what the hell am I doing? Is this where I will be in ten years? Nooooo.

Some have an epiphany and some reach their limit after months and years of disappointment and a total lack of career development prospects. I guess it’s increasingly common. Although the labour market is more and more saturated, in almost all areas, the digital and the internet have opened many doors for entrepreneurs, individually or not, and freelancers. Statuses covered of a certain romanticism that becomes attractive when we find ourselves in our gray cubicle, from nine to five (or six, eight…) and imagine a different life.

There are many inspiring and successfulstories, probably increasingly as the world moves in this direction. I have no data but I suspect that the vast majority that reach the freelance life do not want to leave it, at least after a while (there are a lot of pieces on the consultant with a six figure annual salary that left everything to create the bar of his dreams and not the other way around, right?) but the reality is that it’s not all a bed of roses. Is the freelance life a solution (to you)? It doesn’t have to be. It doesn’t have to be for everyone. And there’s nothing wrong with it.


Freelance, a (small and light) reality check:
  1. Working hours [flexibility yes, constant availability… Hmm…]. The freelance life is immediately associated with flexible working hours. It’s a fact: you work when you want, where you want. However, the reality is that it’s not always something entirely controlled by you, especially at the beginning when you seek to create a portfolio of clients and are willing to accept work at improper hours to improper hours. Another feature related with the working hours: the vast majority of your friends continue to work from 9 to 5. Unless you start spending time with other freelancers, no, you won’t have anyone available to go to the beach with you, in the middle of the week, in the middle of the afternoon. Not even for a midmorning coffee in the park. Everyone is busy. On the other hand, it’s good to attend some services at less crowded hours. Nevertheless the reality will always be the following: more hours outside during the day, more working hours later in the day (when probably the rest of the world is free and available).
  2. Working at home [do the neighbours really spend all day at home?]. When we’re home on the weekend, or even on holidays, it seems like the best place on earth. After all, it’s our home, warm and comfortable, that we miss during the day. It’s easy to think that we could be happier working from home, without facing the traffic, public transportation and pollution but… There are a lot of sounds only noticeable when we spend more time at home [the upstairs neighbour spends all day wearing high heels at home?] or there are things that start happening when you work alone or your work does not involve oral communication: you realise that you don’t speak. Your mum calls you around 6 pm and you hear your voice for the first time in the day. Yes, there are more and more coworking spaces but the truth is that the rates are not tailored to the freelancer reality in the beginning of his/her career. On the other side, because there’s always a bright side, it’s really nice to not have to go out in the winter, when it’s raining outside.
  3. People don’t answer [and when they answer, they answer all at once]. This happens in any professional situation but when you’re a freelancer it can be more complex (you depend on answers, answers are a sign of work). As a freelancer you’re probably even more dependent on others, on their answers, contrary to what people may think: on their interest in your product, on their willingness to cooperate, their financial availability to invest in your work. There are answers without which we do not move forward and then there are answers that come up all at the same time and require a great capacity to answer all – because we want to answer all, we want to do as much as possible, how to say no? And by no, there are also a lot of noes and one must be prepared for it. You need a plan B and C, to be proactive and to go after it. And none of that, still, ensures a client.
  4. Weekends and holidays [I have to work this weekend, I promise I won’t miss the next one!]. There is one thing that ends when you start working as a freelancer. The Friday’s taste. That sense of freedom leaving the office at the end of the day, after a week of work, with the promise of the weekend ahead… Is lost. You don’t have defined working hours, remember? Every moment is useful to work, to go a bit further – at night during the week, on weekends or on a supposed vacation time. One should not overstate, of course, for the sake of sanity but in a freelancer reality time is really money and once light decisions (like weekends and holidays that involve being completely off) become a little heavier. Having so much work that you even question the possibility of a weekend or holiday abroad is a very good sign but there is no creativity – or simple reasoning – that resists.
  5. Instability – Anxiety [yes, your service is exactly what we need but we cannot pay / anyone is able to do some translations, create contentor manage social media / oh you’re asking too much]. It will always depend on the area and demand of the product or service but generally the freelance life is more unstable – and not necessarily just in the early days, it may be constant and is required ability to adapt to this (permanent) reality. You may earn well for each product or service, even more than when working for others, but months may be all different and full of ups and downs. It becomes more difficult to plan long-term (will I have work?) and there’s the need for an extra amount of responsibility and financial management capacity. There are taxes, insurances, months that have to make up for other months and no paid holidays. There is a lot of anxiety involved.


Positive psychology invades our smartphones daily, through social media, blogs and lives that seem perfect. We are chased by the need to leave the comfort zone (because there is where magic happens), of taking the lead of our own (personal and professional) life, of designing our own days, of learning something new every day, of reinventing ourselves… And it’s everything right. It’s true and it’s inspiration. I really think we should try to be better and we must seek the best for us – and I think that is something that is in our hands, is not responsibility of anyone else and we can not get cranky if we don’t try. However, the solutions are not the same for all and there are steps that should be well considered before taken, namely in terms of a professional career.

But after all who am I to talk about all this? I have already experienced different professional statuses over time: I have worked as employee for an organisation, as a freelancer by my own initiative and I currently work for a company again, as employee, remotely – so far probably the best option (still under review). I think the future will be brighter for freelance workers – that will be the trend, there will be even more – but I believe countries (I just know the Portuguese example) are not yet prepared: taxes are too heavy for freelancers, companies don’t consider freelancers as a viable option (they see them as a solution when they come as more affordable) and there is widespread unawareness around the freelance reality – oh, he is a freelancer, he has a lot of free time.

However, if we are moving towards this trend the world will, gradually, adapt. Let’s hope so.


This post was also written in Portuguese. Click here to read the Portuguese version.