Freelancing Vs Employment – Honest Long Term Review

For most of my working life, I’ve been freelancing. Not so much by choice as by luck, convenience, and in some sense, family tradition. Growing up, my parents were always self employed. Both journalists, they quit their full-time jobs in Stockholm to move out to the countryside when I was two years old. As far back as I can remember, I never saw them going to work, at least not in the same way as the other kids’ parents.

That is not to say they were not working, they definitely were, it just wasn’t very clear where work started and private life ended. They divided their time between running a bed & breakfast in the summers, and doing freelance writing and voiceover work during the winter. So it’s no surprise that the idea of “work” that I brought with me from my childhood was basically this:

  1. Sit in front of a computer for a couple of hours in the morning
  2. Get up and do something completely unrelated for part of the afternoon
  3. Take some phone calls while doing odd jobs around the house
  4. Skip work Wednesday because Saturday is busy
  5. Do gardening for two weeks straight because you’re in-between projects
  6. Then work 200% for the coming month to meet a deadline
My mom always seemed to be doing three things at once.

“It felt less like a leap of faith and more like a homecoming, a return to the flexible, unpredictable rhythm of work that I had grown up with.”

After graduating, I got a full time job as an in house video producer. I was very excited; this was what we had all been working so hard for. Pretty soon though, I got restless. I was already running a small business on the side with my brother (who, surprise, has always been self-employed), and doing some design gigs in my free time. And though there was no secure future in any of these things, the most natural thing to me seemed to be to quit my job and give them all of my attention. It was a move that felt less like a leap of faith and more like a homecoming, a return to the flexible, unpredictable rhythm of work that I had grown up with.

And I was lucky. As the years went on, work kept coming in, and me and my brother kept growing our business. But at some point, I started feeling like I wasn’t learning anymore. I felt like I was doing the same thing over and over again. And no wonder – I was doing all of my freelance gigs solo, and my brother and I were not sharing many responsibilities in the company – I had no one but myself to bounce ideas off of, no one to challenge me or inspire me to be better. That’s when I realized it was time for a change.

Time for a Change

So, armed with a lot of questions in my head and a dash of fear in my heart, I began my quest for an honest to god job.One that would allow me to learn, to be challenged and to be inspired. From the onset, I had doubts. “What if I don’t like being employed and want to quit?”, “If I decide to go back to freelancing, will I lose all of my clients?” was another big one, and of course “What if I’m not good enough?”.

Floating amongst job listings and applications

I was hesitant, afraid even, of stepping out of the comfortable cocoon of freelancing that I had built around myself. But somewhere I knew I had to take the leap. So, I waded through job postings, sent out applications and attended interviews.

And even though I considered my resume quite decent, looking for employment when all you’ve been doing is freelancing and running your own business is not all that easy. With most job listings requiring you to have “3+ years of experience working in a studio environment”, many people deciding who to hire get confused by the CV of a freelancer. It’s too broad, too nonlinear and importantly, too lacking in titles. But yet again, I was lucky. In applying to Block Zero, I found an employer who could see past these things and instead see the value in the experience I had.

It’s been almost six months since I started, long enough that I now feel that I can now make a somewhat fair evaluation of life as an employee, in contrast to life as a freelancer. This is, of course, highly subjective, and if you’re reading this trying to decide whether to go one way or the other – your mileage may vary.

The Dream of Endless Flexibility

The classic case for freelancing goes something like this: Forget all your worries – wake up at noon in a bungalow, take a quick video call with a high paying client in California, work for three hours and invoice for the full day, quit early and go surfing with the other happy and good looking digital nomads. For a lucky few this might be close to reality, but more often than not it’s not as simple as that. Yes, freelancing offers a lot of flexibility, something that I exploited many times over the years, traveling for months at a time to escape the cold and wet winter in Sweden.

How employees view freelancing

However, you know what I was doing most of the time I was away? Working. Going up early to secure a spot at that one cafe that I knew had good internet and decent tables. Or wandering around for hours trying to find one. Or answering emails on my phone in the middle of dinner. And when I wasn’t working? Well, then I was mostly by myself. Sure I would go to co-working spaces and meetups and what not and hang out, but it’ll never be the same as traveling with your close friends (who can’t come with you, because, you know, they have a normal job), with the focus being completely on the traveling. The point is, it can easily get a bit lonely.

“If a client approaches you and asks you to do something you have never done before in your life, you quickly learn to smile and say ‘That’s completely doable’, then dig into a thousand tutorials to get it done.”

The Joys of Freelancing

Another case that’s often made for freelancing is that “you get to choose the projects you take on”, and again, this might be true for some. But the reality is, as a freelancer, you may not always have the luxury to decline projects. Especially when you’re starting out, there is really no choosing involved –- you will take on whatever project comes along in order to stay afloat.

As for the variation of the work, this will of course be dependent on your skillset and your connections. I have been privileged enough to get to do a range of things from visual design and website development, to filming and editing videos, doing product photography and making music for skateboarding videos. But for many, they find a niche which they get known for, and when word spreads; that’s who you are and what you’ll be doing for most of your gigs.

I know, I know I’m making freelancing sound like a terrible idea. It’s really not, in general I’ve enjoyed it. There are also many things you learn from running your own shop that’s hard to pick up otherwise. Some of the biggest ones being:

Feeling comfortable being the person in the driver seat
Not having anyone else to lean on when making decisions, both business wise and design wise, naturally develops your ability to trust yourself and move forward even in unknown territory.

Learning whatever skill is necessary for the task.
Like I said before, most freelancers can’t be choosy, so if a client approaches you and asks you to do something you have never done before in your life, you quickly learn to smile, say “That’s completely doable”, and dig into a thousand video tutorials to get it done.

Developing a sense for business
Starting out freelancing, what freaks most people out (it definitely freaked me out) is talking about money. But as with anything, practice makes perfect, and pretty soon you learn how to maneuver lots of different situations and adapt your offers and the way you communicate for a range of different clients.

These things took me many years to figure out, and nowadays as an employee, I still benefit greatly from all of them.

The Joys of Employment

Over on this side, there are also some classic stereotypes: being employed squanders creativity, it’s repetitive and boring, you’re never paid what you deserve and sooner or later you’ll burn out.

And again, there are of course some jobs that fit this bill, but I have learned that employment has its upsides:

Team and social context.
This is not to be underestimated. Even though I saw my friends, family and partner in the evenings a lot when I was freelancing, during the days I was mostly by myself. But having an office to go to in the morning, where you feel safe and needed I think fulfills some kind of deep yearning for belonging.

Being challenged and inspired
When you have people around you that are very skilled and at the same time have very different experiences and styles than you, that’s when you’re really pushed to keep developing your own craft and not settle for “what works” as can easily happen when freelancing.

Collaboration and shared success
Creating something together with other people will often make you feel more motivated. You are no longer just making something in your bubble with no one to hold you accountable, now you have people relying on you, supporting you and asking for your support. And an often overlooked benefit is when you’re finished, you have someone to celebrate with.

As for that last point, I’m still learning how to collaborate efficiently. Being so used to working on my own, it’s a big shift, but one that I’m committed to stick with.

How freelancers view employment

And while it is true that employment will never be as flexible as freelancing, you’ve got to ask yourself what you’re looking for with all that flexibility. I’ve seen friends go years freelancing and traveling the world, living by the mantra “I will never be tied down!”, only to realize much later that their biggest challenge wasn’t getting on a plane, but sticking around long enough to build something for the future.

The Verdict

As you might have gathered, I’m not really set on either or, and the short and unsatisfactory answer is – it depends. It depends on where you are professionally, mentally and socially, what you want from your work and your life at this moment and where you want to go in the future. Right now, I’m enjoying being part of a team and learning to work in new ways, and don’t mind the sacrifice in flexibility. But for you and anyone else it might be different. What I will say is that if you’ve been doing one thing for a long time and are considering taking the plunge in either direction, go for it. At worst you’ll learn that you were already doing what you wanted and come back feeling more motivated, and at best you’ll discover a completely new side to yourself and a new way of working and living.

Keep reflecting, try to be open to many different directions, and when you feel either a spark of excitement or a sense of friction, keep tugging on that thread and see where it takes you.

BZ™ 2015-now

Independent consultancy specialized in Design and communication. Current and past clients include: