Lessons Learned from Freelancing
And why it’s not for everyone

Freelancing seems to be the Holy Grail of countless individuals eager to make a living independently from corporations and without any physical constraints. It is also the most frequent path for newly converted Digital Nomads.
Eighteen months ago, I decided to quit my job out of boredom and with the will to discover new horizons, both professional and geographical. Due to very bad timing and planning from my part, I ended up with no plan, no job, no fixed address. I had some savings I did not want to burn up while waiting to figure out what to do with my life. So I started freelancing. I registered on a few online market places, and Upwork appeared to be the one working best for me.
Without having planned it, I eventually found myself living a kind of digital nomad life, working online with a few different clients and free to roam wherever I wanted. At first, I enjoyed it very much. I could wake up at 8:45 am to start working at 9 in my pajamas, sipping my coffee in no hurry. I could stop working in the middle of the day to go for a swim when nobody else is in the pool. I could take my Tuesday and Wednesday off to go on a road trip and work on the weekend instead. I could work 60 hours one week, then 10 hours the next week. And I could spend as much time I wanted to in beautiful places I would explore outside of my working hours, without dreading the end of the holidays. All in all, I was making less money than in my previous job. But I also spent much less on clothing, I ate much more homecooked meals, and I managed to live on much less than before.
After a few months, however, I started experiencing all the downsides of such life and work styles.
What hit me first is the loneliness of it.
What hit me first is the loneliness of it. At first, my partner in life was also working remotely from our flat, so we were spending the day together and socializing with other people in the evenings. But when we moved back to the city where his company has their office, he stopped working from home to commute to work every day. I could spend several days in a row without having to get out of the flat and without orally speaking to anyone but my partner. Now I make sure I go out everyday, be it for a run, a beer or a movie screening, and I regularly work from coworking centers of cafes. However, working remotely as a freelance not only means that you miss all the socializing aspect of a classic workplace, but also that you receive much less feedback on your work. Most of my work consists of completing tasks ordered by my clients. There is hardly any group brainstorming and basically no confrontation of ideas. I miss that terribly. And it is much harder to replace than the chats with colleagues at the coffee machine.
The freedom in freelancing can as easily lock you up in anxiety than a corporate job can.
Another downside of freelancing is that you are basically selling your time for money. When you work, you make money. When you don’t work, you don’t. That may seem obvious, but it is actually quite different from the way it works when you are a classic employee, at least in most European countries I know. Having no certainty on your future income, you as a freelancer want to work as much as possible while it is possible. Your clients may bail out anytime, or even just temporarily suspend your work for various reasons. There is nothing you can do about it. So you keep searching for more work and working all you can for weeks on, and then you realize you didn’t take a proper break for more than a year. You also have this constant anxiety and stress. Am I doing enough hours? Did I reach out to a sufficient number of prospects today? My client suspended my work for one week, what the f… am I going to do now and where do I get the money from? The freedom in freelancing can as easily lock you up in anxiety than a corporate job can.
it can get extremely hard to keep a firm stand on what your time is worth
As a remote freelancer, you also end up competing with people from all over the world. Literally. This means that no matter how much you lower your rates, there will always be someone cheaper than you who can do an equivalent job. The worst you can do when freelancing from a rather opulent part of the world is trying to compete on price. But when you haven’t landed a new contract for weeks, it can get extremely hard to keep a firm stand on what your time is worth. The temptation to lower your fee is huge. It takes time to learn how to sell yourself properly on these online market places. What is at stake is not only to get well-paid contracts, but also to work with decent and respectful clients. I read a lot of posts from clients complaining about the unreliability and low work quality of freelancers on the marketplaces. Believe me, the same is true when it comes to clients. You don’t want to end up fighting over ten dollars of extra time if you have any self-esteem.
nobody will push you up any ladder if you don’t do it for yourself
Finally, freelancing may not be the best way to improve your skills and scale up in your field. I reckon it varies a lot from one type of work to another. But the fact that you are working mainly alone, on dispersed and temporary contracts, makes it hard to get really better at what you are doing. Of course, you will be gaining experience. But you there is hardly room for any kind of mentoring, and nobody will push you up any ladder if you don’t do it for yourself.
I am sure that freelancing can be an excellent work choice for some people. The most interesting lesson I learned about freelancing, is that it just may not be for me — but I wouldn’t know I had not tried. So if this way of working appeals to you, go ahead! Just be warned.
Tell me, what is your experience of freelancing?