Should I Get A Job Header

Should I Get A Job? 13 Pros & Cons Of Freelancing

Should I get a job?

A question that’s been on my mind since I started working on this blog. Constantly. Not exactly a common question, right? I mean, what else are you supposed to do to pay the bills?

How about…


Along with habit coaching, freelancing has been my major source of income for the past 1.5 years. While the path for most people is mapped out very clearly – go to school, eventually college, get a job, and start working – for me that hasn’t been the case.

Whether you’re a freelancer or working a full time job, if you’re an avid reader of this blog, you probably have many side projects, goals and things you’re passionate about. For the past few weeks, I’ve been thinking a lot about the quickest way to making your passion your paycheck.

Again and again, I find myself left with the question: Should I get a job?

That’s why today we’ll dig into some pros and cons of freelancing, in order to find out what’s best. Even if you’ve already found your earning habit of choice, the medium of creation you think might make you rich, you can’t possibly know how long you have to play that game before you win.

It might be just a year.

Or two.

Or ten.

Or 25.

In fact, it might never happen, no matter how much you work for it. So even if job vs freelance is only your secondary career choice, it’s an important one.

Today’s article will help you choose well. With each pro and con I’ll include a self-awareness tip, to help you figure out whether it’s something you can benefit from.

Now, without further ado…

Should I Get A Job Ted

Let’s start with the pros of being a freelancer!

Pro: You can make your own hours.

This is probably the biggest argument for anyone who dreads their full time job. “If only I could make my own hours, I’m just not a morning person.”

Yes, making your own hours is great. You get to decide when and how much you work. There’s no need to kill time when you’re done early, you can get up whenever you like and can work out or get groceries in the middle of the day.

However, making your own hours also indicates actually making them. With a freelance job it’s very easy to slack an entire day and after 5 hours of snacking and 2 back to back movies you find yourself scrambling together the last bits of the day to get some work done.

Self-awareness tip: Ask yourself, if you’re disciplined enough to work the hours you’ll need to put in. A good indicator is how you spend your afternoons and weekends. Does using free time well and productively come easy to you? If so, you’ll probably do great making your own hours!

Pro: No boss.

Whether it helps us or not, nobody likes being told what to do. As a freelancer, you are your own boss. You are the one who’s responsible for figuring out what’s important, what’s urgent and what’s both.

If you have the budget, you can delegate things to virtual assistants or even hire someone part-time, if you work in an office space, for example.

Not having to answer to anyone feels great, but it is also a weight on your shoulders you’ll have to learn to carry. This pro eliminates all the fear of being fired every time a potential boss might call you into his office and it’s a much higher level of freedom any job could ever offer.

Self-awareness tip: Are you good at prioritizing? Or do you struggle with pinpointing what matters most? If you’ve organized an event before or coordinated a bigger project and found things went well, you’ll really be able to reap the full benefits of this pro.

Pro: Several sources of income.

A common practice in computer technology is to never have have a single point of failure. What does that mean?

Take your wifi setup at home, for example. You probably only have one device, which connects you to the internet, and then spreads the connection to all your devices, right? Well, if that device blows up or breaks down, you’re offline, whether you like it or not. Until it’s replaced, it’s back to 1950 for you.

That’s a single point of failure and you’d best avoid systems like that whenever you can, because a single external event, which you can’t influence, might break the entire thing.

An extreme scenario would be a domino chain, where basically every point is a potential point of failure, which makes it so difficult to set them up.

Should I Get A Job Dominos


As a freelancer, you’re automatically avoiding this, because you always work with multiple clients (otherwise, why be a freelancer?), which means no single client can ruin you financially, in case they fire you. This is very comforting, and can alleviate your worries about money.

If you’re working a full time job, you only have one employer, and depending on how much your boss likes you, screwing up once or twice might get you fired fast, which is of course a huge source of stress.

Self-awareness tip: Look at your income. Does it have a single point of failure? If you’re in a job right now, it’s really time to get those side projects of yours up and running to make some cash that doesn’t come from your steady paycheck. If you’re a freelancer, check if your clients and what they pay you is balanced well. For example, having 4 clients who each pay you $500/month is a lot better than having 1 client at $1500/month and another 3 at just $200/month.

Pro: You get to decide which projects you work on.

How cool is that? Not only do you get to pick when to work, you also get to decide what to work on – in part at least.

As a freelancer, you can apply to projects via job boards, try to score ongoing work with bigger clients and of course, get referrals from previous clients to new ones. Work will come to you in ways you could never imagine, which is why nurturing your network and your reputation is important.

For example, writing for Lifehack isn’t just helpful for spreading the word about this blog, but might also draw someone’s attention to my work as a freelancer. Your side projects and work projects will often mix and positively affect one another.

The better you do this, the more work you’ll have coming in, and once it gets to a place where you’re requested for more work than you can handle, it gets interesting. You’ll have the freedom to decline work you don’t like, only work with people you think are a good personal fit and pick projects that really make you go “HELL YES!”.

Self-awareness tip: I found above all, this requires people skills. Are you good at guessing whether you’ll get along with someone right from the bat? If yes, then this will really work out well for you. If you find yourself often picking the wrong people, you might not benefit from this as much.

Pro: You can pivot at any time.

Here’s a short excerpt of things I’ve done as a freelancer:

  • Write articles
  • SEO
  • Pitch companies and individuals via email
  • Outsource design work for logos, stationary and business cards
  • Build websites
  • Translate highly technical texts
  • Act as an interpreter (German-English)
  • Edit other people’s content

Try to find a job that offers that kind of variety. I dare you. Being able to pivot at any time is a huge advantage of freelancing, because in tough times you can go back to doing things you might not like as much, but which pay the bills for the time being.

A word of advice though: This doesn’t mean you should pivot all the time. You don’t want to seem like you’re a jack of all trades (you’ll see why in one of the cons) and cater to everyone’s needs.

Should I Get A Job Dominos

It’s a measure for tough times or when you find out you really don’t like what you’re doing, but it’s sure better than realizing you’re stuck in a job you can’t easily get out of without major education first.

Self-awareness tip: If you already know what you’re good at and want to freelance in, that’s great, but if not, jumping around initially will help you pinpoint what your unique skill set is. Once you know that, double down and set yourself apart from the crowd as a specialist!

Pro: You can work from anywhere.

Alright. That’s it. In addition to determining the when AND the what, you can also decide where you work? Wow. That’s nuts!

London, Brazil, the Bahamas, Tokyo, the sky’s the limit, right? Technically, yes, but most of the time your bank account will be. Chances are you won’t want to drop $4,000/month on living costs in New York when you’re just starting out, nor even be able to, but the world has many places and plenty of them are quite cheap.

Unless you’re absolutely crazy about travel and want to jetset around the world, where this pro really shines is in your daily life. Even if you’re firmly planted in your hometown somewhere in the middle of nowhere, you can still change your office.

This not only helps with focusing, but also keeps you motivated. It can be refreshing to work at a coffee shop, outside on the patio, or even at the local library or your couch at home for once. Depending on your industry, most freelance careers only require a laptop and a good wifi connection, so the world really becomes your oyster!

Self-awareness tip: Are you a traveler? A restless soul? Or have you always been happy going to football practice in your hometown on Wednesdays? Knowing whether you’ll spend shorter amounts of time in various locations or stay in one place will help map out your finances and projects well in advance.

Okay, getting closer to the answer. Remember, should I get a job, that’s the question here. That wraps up the pro side, time for some cons!

Con: You’re not just a freelancer. You’re also a CEO, CFO, COO…

Being a freelancer won’t just get you one job. It’ll get you at least 5. Let’s say you want to be a developer, because you love coding. If really all you want to do is code for several hours a day, a job will probably be a much better fit for you.

In a full time job you can focus on practicing one particular skill, all the time. But when you go for a freelance career, you’ll also be responsible for marketing, pitching, closing sales, managing and communicating with clients, organizing yourself, doing your own accounting, and a million other things.

That means you’ll probably end up spending less time doing the actual thing you’re freelancing in, than when just working a job where you’re assigned specific tasks and project and can get started instantly.

This can be frustrating if you’ve gotten into freelancing for the love of coding, writing, or designing and only gets worse when you eventually start your own agency or company.

Self-awareness tip: It’s impossible to know whether you can live up to all these tasks in advance, but think about how you handle your own finances, how you organize your day and how you present yourself to the world. If you happen to be a complete mess in any of these, for example because you keep spending money you don’t have or are never on time, then you can expect this to directly translate into your business. After all, a freelancing career is just that, and if you don’t have what it takes to run it like a pro (yet), there’s no shame in starting small and doing what you love with someone else carrying the responsibility.

Con: People will expect you to be available. Always.

Nobody ever thinks of calling a freelancer at an unfortunate time. People won’t expect you to be busy. Ever. Don’t be surprised when you get requests from people to finish something over night or a project request with set deadlines, price and an expected yes, as if availability isn’t even a question.

This is mostly due to the public image of a freelancer as someone who’s always struggling to make ends meet and is permanently on the lookout for new work. Seriously. Just try it. Turn someone down and watch the look on their face.

Should I Get A Job Joey

This means people’s tolerance for you declining a part of their requests, but not all of them, is generally not high. You can turn down a few things here and there, but often people get upset quite fast and might go with someone else. Not the biggest lost, since high quality clients will understand the value of your time, but still a frustrating experience – a feeling that always comes with being “available on demand.”

Self-awareness tip: Do you panic when someone comes to you with a short-term request? Or do you handle those situations well? If you’ve ever scrambled to submit a document for an unexpected deadline, you know what I’m talking about. Not all of your work will be like this, but if you break at the slightest stress spike, chances are freelancing isn’t for you.

Con: You’re considered a cheap source of work. Deal with it.

As in any industry ever, there’s a huge amount of low price, low quality work available. But if you really want to thrive as a freelancer, you can’t fall into that category. There are too many people competing with you, who are willing to work for wages where you can’t even earn a living, so trying to compete with others based on price is useless.

Should I Get A Job Pricing

However, most people will assume that’s what you’re trying to do. You’ll be seen as a cheap source of work, until proven otherwise. Communicating that is up to you, but it’ll take a while to find your voice and positioning. Meanwhile, you can expect to justify your prices more than once, or never hear again from a lot of people.

Self-awareness tip: Are you concerned what others think of you? If you’re rather insecure about things like your appearance or how others see you, this might be a problem. Get some thick skin and believe in the value you can bring to the table. A job has more respect included, but obviously offers no way for you to make your own pricing.

Con: Freelancing is more stressful than a job.

That might sound obvious, but it’s really not. It’s easy to forget that you have all these other jobs and responsibilities on top of doing all the freelance work and they can become a crushing burden if you’re not prepared for them.

What’s more, it’s super easy to overestimate how much you can handle, and you’ll end up sick in bed (which is a whole other problem, as you’ll see later).

With a normal job you clock out, go home and are done for the day. The borders between work and your personal life are a lot clearer, which isn’t always a good sign, but might help you build something on the side a lot faster, if that’s what you’re trying to do (yes, you should).

Self-awareness tip: This is very much related to how well you handle your workflows, processes and organize yourself. Freelancing can be a breeze from an administrative standpoint, but only if you’re a master of productivity. Nothing you can’t learn, but not starting at zero will help you stay sane and healthy.

Con: Your pay won’t be steady.

There is a lot of comfort in going to bed, knowing your bank account will show the same number on the first of the next month it did for the last one. Financial security is the biggest driving force behind people getting a job. “Should I get a job?” “Yes dear, it’s the safe way to go.” is a conversation that’s probably had thousands of times around the globe every day.

Not knowing how much you’ll earn next month is scary. As a freelancer, your pay will never be steady, and even though you’ll get a lot better at dealing with it over time, seeing your income drop from one month to the next, even if it’s a planned drop, is tough to swallow.

Should I Get A Job Income

This is all good and fun if you’re young, single, and have nothing to lose, but consider feeding a family and potentially buying a house – the older you get, the more serious your financial commitments tend to become. Keep that in mind.

Self-awareness tip: Are you good with money? Do you like saving? Having a few months of emergency savings back in the bank makes this con a lot less threatening and gives you peace of mind even when income is down in any given months. If that graphs causes you to have a panic attack already, you should probably err on the safe side and stick with a job for now.

Con: It’s harder to build a side hustle.

I’m not 100% sure about this one, but from my own experience, this feels true. It was a lot easier to spend a weekend building a cool website, just for fun, and see what comes of it, when I knew I had to go back to work on Monday and didn’t have anything else to do.

With a freelance business, work is never done. There’s always something you could be doing, and chances are a lot of it will fill your weekends. Sometimes it’ll even be client work. Walking out the door with nothing to do until the next day not only makes it easier to spend guilt-free time on your passion projects, it actually boosts your creativity.

When you’re worried about paying bills, undone work and where your next project comes from, it’s really hard to write without getting writer’s block or paint something that isn’t influenced by those emotions.

Even though a job is probably less total work than a freelance business, it still limits the amount of free time you have available and thus still provides a solid motivation to get cracking on your projects once you get out of work.

Self-awareness tip: How important is your passion to you? That’s the question you have to answer. If writing books means the world to you and you’re 100% sure that that’s what you want to build your life around, getting a job will probably give you the most time to work on it. Don’t waste it.

Con: When you’re sick, you won’t get paid.

This depends on how you set yourself up, but if most of the work you do is based on an hourly rate, well then if you don’t put in any hours, you won’t get paid. This is something I witnessed first hand last month, and I’ll be the first to admit that it’s very disturbing.

You lie in bed, too sick to do anything, and when you eventually need the money the most to pay the medical bills, you might’ve just run out.

Should I Get A Job Sick

Retainers are a good way to avoid this. These are contracts where your clients pay you a set amount each month on autopilot for you to do a pre-defined set of tasks and projects. It works well for maintenance, for example, and can be a good way to secure your income in cases like mine.

Self-awareness tip: Similar to the general income problem, this is up to your saving habits and how well you deal with these types of situations mentally. There’s a solution for this, it just might take some time to get yourself set up well, and you have to know whether you can pull it off or not. It helps if you rarely get sick, but that’s nothing you can predict for sure.

So…should I get a job?

What do you think? Would you be a kickass freelancer, or are you better off trucking along in a job, while minding your own business on the side?

More importantly, cast your vote! Should I get a job? Or keep freelancing? I’d love to hear your thoughts.

If you liked this article, sign up for more!

Share in the comments: Which side of the fence are you on currently? What’s your true passion and how much time are you dedicating towards it on the side?