On Freedom and Freelancing – Some Thoughts

Freedom, one of mankind’s biggest dreams. From abolishing slavery to the freedom from Earth’s gravity, man has always sought out to escape whatever tied him without his will to a certain situation or place in this world. Across the ages, the constraints that mankind faced have changed dramatically. Today, most of us live in a relatively free society, therefore the desire to escape has shifted towards finer concepts like work, travel or creativity. Freedom and freelancing is now a big goal of many people around the world, especially millennials.

More and more people today want to get rid from the routine of traditional work and life. They want to get away from the offices, from the 9 to 5 life, from the tight schedule that keeps them on the hamster wheel Monday to Friday, sometimes even Monday to Sunday. People want the freedom to choose where to work from, what to work on, to pursuit something bigger than what a traditional work environment offers. They desire a flexible schedule and diverse projects.

But when most people think about freedom and freelancing, they don’t get to see the bigger picture. At least not in the beginning.

The Dream of Freedom and Freelancing

My journey in chasing freedom and freelancing was somewhat the same. Several years ago I was only dreaming about this alluring ideal. Tied in a system that didn’t value personal freedom too much, I was dreaming of a life lived without too many rules to comply to and without the feeling that I always had to come back somewhere.

Being in the military meant that my freedom was limited. Well, I did love to play with big boys’ toys but on the other hand, I was always counting how many days my freedom lasted. When I went somewhere, there was always a specific day and hour when I had to be back to my unit, a day and hour when my freedom would end. And that was always painful.

Somehow I felt that pain throughout my entire life almost every time I had to be somewhere at a specific point in time. I still have that feeling today in some situations. It’s like somebody steals this freedom from me, the ability to do whatever I want whenever I want to.

freelancing hub

The Freelancing

So what is freelancing? The term comes from the mercenary soldiers of the Middle Ages who were called ‘free lances’, further referring to the fact that they were independent soldiers – equipped with lances – available for hire to anyone who needed them or to those who paid more.

Nowadays, the term freelancing is used to categorize those people or specialists who sell their services to other individuals or companies by the hour, day or even by project. They’re free to choose their clients, their work time, days off or vacations.

Sometimes, the grass is greener on this side, but other times it’s not. On some occasions, too much greener grass means that you’re only wasting your time having fun and being free rather that hustling and building your future. And that’s not a very productive way to live your life.

The Freedom

When i started down this path, I was thinking that I wasn’t free. I was thinking that freedom was something else than what I already had. I was thinking that I’ll be free when I’ll have the life I live today. Today though, I’m tied to the insecurities of this freelancing dream turned reality.

But that’s the irony of our society today. We think we’re free, when in fact we’re tied to psychological concepts we may not even understand. Sure, today we’re not slaves anymore. At least not in the historical way our ancestors have been. But we’re surely not entirely free, with all the messages with shady consumerist or political purposes bombarding us every day through every medium.

Freedom is such a diluted concept today. We’re free to watch TV, we’re free to be afraid of the world we live in and then we’re free to buy products we don’t need in order to make that fear disappear. There’s a lot of debate going on today on this matter and nothing is clear. Today, freedom is a gray shady area, accentuated by technology and by those who control that technology.

But this is only one reality. Across the years, I learned that freedom can also be a state of mind, no matter your external circumstances. The truth is that there are all kinds of freedoms, so make sure you think for yourself and find out which ones you’re striving towards, because each of these freedoms comes with a price to pay and some consequences. You have to make sure you’re willing to trade some important things for that chosen freedom.

The Why

Before starting on this path of freedom and freelancing, make sure you give an honest answer as to why you want it. Make sure it’s your dream and not something that sounds cool because some hot chick posted a picture on Instagram with herself looking sexy while working on her laptop on a mesmerizing beach somewhere in the Philippines.

Think about what you have right now. Make a list with all the pro’s and con’s of what you have and balance that against what you want from being a freelancer. Go beyond that and start a side hustle before you decide to quit everything and go deep diving into freelancing. Learn about the why’s of your dream. You might be surprised by the results. You might not even need or want to go freelancing.

The Reality Check

girl wearing virtual reality set

From the outside, everything looks amazing. It’s a given. No matter the field, everything is so alluring when you’re only dreaming about it and not doing the actual work to get there and keep yourself in the game. But once you get behind the curtains, everything changes.

Behind the scenes of this freedom and freelancing dream, there are a lot of details that you can’t think of in the beginning. And the most important fact is that most of them depend a lot on the type of person you are. Some individuals are better off with a regular 9 to 5 job while others thrive under chaos and uncertainty. You’d have to know yourself really well to know if freedom and freelancing are for you.

The Upside

It’s true that some will see advantages where others see drawbacks, so learn to understand yourself and get to know what fits you like a glove and what’s not for you.

The Flexibility

The main advantage of being a freelancer is that you’ve got a lot of flexibility. Work days, schedule, wake up time, everything is yours to decide. You choose when you go to the gym and when you get to work. And it feels amazing, as it gives you the space and time that you don’t have on a normal job.

The Office

office with a view

The work space is another nice advantage of being a freelancer. You get to choose your office. Tired or bored of the view you have right now? Pack your shit and move to that bohemian cafe across the street for some inspiration. Or to the park. Maybe try the library or a hub for people who work remotely. Or don’t even leave home and keep your pajamas on. The whole world can be your office, depending on what field you’re in and the limitations it sets.

The Vacations

Vacations. Or workations. Say goodbye to the 20 or so days of vacation per year. Get more. Get 3 months. Or a year. In some cases, you can even take the work with you, become a – digital – nomad and travel around the world in a big workation – work + vacation. You can do anything. If you have the means, that is.

packing bag for vacation

Mornings Off

Have a morning off. That was one of my hopes in the past. To have mornings for myself. Especially Mondays. And I bet I’m not the only one. It’s amazing to be able to take a morning off if you don’t feel like working at that moment. Just make sure you don’t abuse that option, otherwise you’ll get nowhere.


Diversity is another plus for freelancing. By choosing your clients and projects, you can diversify your work so you don’t get bored doing the same old things all the time.

The Paychecks

When they come, paychecks are another good side of being a freelancer, because you’ve got more control over when you get paid. And at least in my case, being paid smaller amounts a couple of times per month feels a lot better than waiting for the full paycheck next month.

Constant Learning

When you’re a freelancer, you’re constantly learning, always improving yourself, and that in many aspects. It can be a lot at first, but after awhile, you’ll see that what you do gets better and better and that’s a good and motivating feeling.

The Downside

punch in the face

Now to the downsides of being a freelancer. As I’ve mentioned earlier, everything has a price to pay, and freelancing certainly has a lot of them.

The Routine


The first and biggest downside that hit me hard after a few months was routine. Routine was probably the thing I ran away from in the past and here I was again. Free but doing routine work nonetheless. So get this straight before you decide to take on this path. Routine is everywhere, even in freelancing. Sure, you can have more diversity by being a freelancer but you won’t be completely free from routine work and meaningless tasks.

The Discipline

Then there’s discipline. Yeah, you got it, the discipline you need to get through that routine work when nobody is forcing you to. When all those motivational quotes stop working right before you start what you have to do and your willpower gets depleted, you’re all alone and have to deal with it.

In theory it’s simple.

You only need to take that first step, but often times that first step is the hardest thing to do, especially in a world of distractions and with so many opportunities to do something else, something a lot more appealing and interesting than the job you set out to do.

So make sure you’re disciplined. And then get even more disciplined. Otherwise, you’ll soon find yourself looking for a job where somebody else will make you do your work. Being your own boss isn’t easy at all.

The Hustling

hustle mug

While at the end of the workday on a regular job you get home, switch off your work mode and do something else, things are not that simple anymore in the freelancer world. You need to hustle to make sure you’ve got something to work on, to find new clients, to make ends meet, to build a clientele. You need to make sure you’re up to date with the newest trends. You need to always get better at your craft to stay on top of the game. You need to be hustling and you also have to know when to stop.

The Uncertainty

While being free to do anything you want whenever you want is an amazing feeling, it’s counterbalanced by the uncertainty of it all. Freedom and freelancing come with a high cost of not knowing if at the end of the month you’ll have enough money or if the clients will keep coming back to you and many other unknowns. This is probably the biggest setback you’ll face as a freelancer.

It’s not easy to live with uncertainty, but you can get used to and even thrive in the midst of it all if you learn how to deal with it. After all, nothing in this world is certain. So you might as well learn to cope with this feeling.


Since most of the time the income will be variable, you’ll need to have the financial department in good order to cover for the fluctuations in your field of work.

The Loneliness

Another important disadvantage I’ve noticed is the loneliness of being a freelancer. Depending on what your chosen field of work is, you might or might not have colleagues. I don’t. And after awhile you will feel that.

Taking a break and going for a talk with a fellow worker is a nice and very useful break. Also, sharing ideas with others while working can also be more productive than working alone, but as a freelancer you don’t always have that option, so take this into consideration as well.

The irony is that all the advantages you’re looking for when thinking of freedom and freelancing come disguised as drawbacks when diving deeper into the matter. That’s why it’s very important to know yourself and to know what works for you and what doesn’t.

freedom underwater

The End Result

Are we all going to be freelancers?

What do you do with all that freedom once you get it? What comes after? Are you going to do something meaningful with it or just want freedom for the sake of freedom?

Think of the latter as of a cookie. It’s delicious, but you can’t have cookies all day long, every single day. Eventually, you’ll get tired of eating them all the time. Cookies are a lot more delicious when they’re scarce and you have them as a treat than as your daily menu.

It’s the same with freedom.

Is freedom your end goal? Or is it the way through which you can achieve your end goal? Start making the difference, because it’s an important one.

P.S.: I might have missed some important points on the matter, so if you’re in the game, feel free to share them in the comments, so we can all learn together.

Photo Source: Unsplash


  1. Marius
    September 21, 2018

    To be totally free means, that you loose everything. That includes belongings, social bounds, friends and so on. So everybody has to choose its own level of freedom. I think you could write an article of the advantages to not be free, have routine, be needed, have a set day and so on.

    Everybody seems to see freedom as a great thing, but when you have it, its hard to handle.

    • Vlad C.
      September 21, 2018

      Well, yeah. Complete freedom is what our ancestors had tens of thousands of years ago when they were roaming on Earth hunting mammoths and picking fruits and vegetables without being tied to anything. That would be a nightmare for most people today.

      And yeah, freedom comes with great responsibility, which makes it so hard to handle.
      Thanks for the idea with the advantages of routine and a stable life. I’ll think about it. 😉

  2. Kennedy
    May 31, 2020

    This really helps puts everything into perspective! Thank you for making this post. What I especially like about this one is that it doesnt just give off a sugar-coated, rose-colored image about what freelancing is like and saying stuff like, “Totally do it!!! You wont regret it!!” Its totally fine to be passionate about what you do and to want to encourage others to consider the path you’re on, however I feel that it’s unwise to recommend that same kind of path to EVERYONE. Because like you said, it’s not for everyone. Everyone has their own limits to the things we can handle. You really have to be realistic and truthful with yourself when it comes to these things.

    Take me for example. I’m quite risk-averse when it comes to certain things. I know that doing things like dealing with/investing in really volatile stocks isnt for me because the level of uncertainty would be too much for me. Less invigorating and more so anxiety-inducing. I definitely wouldnt last long doing that and also dont think I would last very long doing only freelancing and nothing else. I personally would much rather have a main job while also having the option to work on other projects on the side. That I feel is the best solution for me.

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