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Freelancing Pros and Cons: The Good, The Bad, and The Ugly

Freelancers decide to veer off the beaten path of Corporate America for many reasons. Maybe your free spirit doesn’t want to be held down by the parameters of a 9 to 5. Maybe you are tired of working at the same place, with the same people, five days a week. Maybe freelancing is just a temporary solution until you secure a full-time job.

Before you take the plunge, you should take a cold, hard look at the pros and cons of freelancing.

Here are some of the benefits of going freelance:

You’re your own boss.

You’re in the driver’s seat, and you’ll never be late for work again – because you call the shots.

You can take advantage of tax deductions.

You can write off things like your home office, work-related travel expenses, insurance premium, internet, phone and any other cost of running a business.

Monday can be whatever day of the week you want.

Think Mondays are a crappy way to start the week? Start work on Sunday or Tuesday.

Are you a night owl? You can get your work done between 7:00 pm and 4:00 am if you want. Why work 9:00 am-5:00 pm if your most productive self works from 3:00 pm-9:00pm? When you make your own hours, you can do whatever you want. And that includes scribbling ideas on a bar napkin over some cocktails.

As long as you do the work, you can decide how and when you want to do it. (With the exception of communicating with your clients.)

Going freelance can feel, well…freeing.

When you create your own hours, you can schedule your time around important events you may have otherwise missed. Need to visit an old friend during the week? No problem, you can just work odd hours that day.

Another great thing about this type of flexibility is that you will no longer have to schedule all your DMV and dentist appointments during lunchtime. Making your appointments when everyone else is working will change your life.

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You pick your projects.

When you work for a firm, you are always hoping to snag the best clients and projects– but you have no control over which ones you’re going to get. You just get assignments.

If you’re a freelancer, you pick which projects you want to work on.

*And unlike working at a firm, if you get stuck with an awful client, you can actually make the choice to fire them or not.

You pick your workplace.

You can work wherever you want because the internet has made the world a smaller place. As long as you’ve got your equipment and some fast fiber-optic Wi-Fi, you should be good to go. That also means you can simply work from home if you don’t feel like commuting in traffic.

If you’re adventurous, you can work at a different coffee shop each day or travel around the world working at different coffee shops. You could even work somewhere off the coast of Bali, as long as you’re down with scheduling your meetings in the middle of the night.

Yeah, freedom.

You can make more money.

When you work for someone else, there is a limit to how much money you can make.

But when you work for yourself, your income isn’t capped by a salaried rate. If you have the ambition, raw talent and willingness to outthink, outwork and outsell your competition, the sky is your limit.

If you’re really good at what you do, this is a big one. Many freelancers with the drive and passion can easily make more than they would in a salaried position.

The more effort you put forth, the more money you can earn.

Save the political banter for your newsfeed.

Sick of your annoying cubicle neighbor or weird co-worker who always “bumps into you” by the vending machine?

The only person you have to interact with when it comes to working at your apartment is your pizza delivery guy.

On the flip side…some of the cons of freelancing:

There are no guarantees.

Choosing which coffee shop to work at isn’t the toughest part about freelancing. The number one stress factor when it comes to freelancing is money. Money is something that isn’t guaranteed when you work for yourself.

If you’re an employee, you’re in good shape unless the company goes out of business or they fire you. If you aren’t self-motivated (or you’re lazy), you could make less freelancing than you did with a salaried position.

When you’re working for yourself, everything is up to you.

You’re responsible for everything.

You’re on stage, and the only one underneath the spotlight is you. Don’t feel like dealing with an issue? Well, you can’t pass it off to someone else like you could as an employee. If something goes wrong or needs to be done, it’s all on you.

You’ll have to handle everything from calming down a raging client to following up on invoices and going to Apple to fix your laptop (yeah, no IT team). You also have to build your client list, portfolio and reputation.

The point is that you’ll have to deal with things you don’t want to do.

You need to earn more than your current salary.

You’ll have to calculate your rate to estimate an annual income that includes the benefits you had, sick days, vacation time, 401(k), personal and business insurance, and any expenses you incur from running a business. You might need to make anywhere from two-three times your current base salary.

There’s no structure.

Flexibility is amazing. But the flip-side is that you’ve got to make sure you’re on a somewhat strict schedule (or routine) so that you can stay focused.


As an employee, you get a regular paycheck and you know exactly what to expect. As a freelancer, you might feel like you’re on a rollercoaster when it comes to that very important thing we like to call income.

This won’t be the case (unless you have a few regular clients). Some months you’ll barely be able to manage your workload (if you’re lucky), and other months will be filled with dry spells. That means you could make four times as much as you did one month – and zero the next month.

You have to be the type of person who is comfortable with uncertainty and who can set some money aside to get through the dry spells.

There’s no community.

You won’t work with the same people every day or have employee Christmas parties. If you’re an introvert, that’s awesome.

But if you like hanging out with people and playing ping-pong during your breaks, you can always consider a coworking space.

You have to find your own work.

Unlike working at a firm, there will be no one handing you assignments each day. You’re the one who has to go out and bid on work. You’ve constantly got to market yourself and your abilities to bring in work. Freelance job boards like Upwork will be your best friend until you start to build a reputation through word-of-mouth.

But if you just like designing or writing or whatever it is you do, freelancing may not be for you.

You have to do all the administrative work.

Unless you get an assistant, no one is going to help you with all the monotonous nitty-gritty that comes with owning your own business. That means doing things like taxes, invoicing and accounting.

These things are non-billable activities, and you’ll need to count on spending five-ten hours a week doing them. Luckily, there are a lot of tools out there that help with that.

You will fail if you aren’t highly motivated.

When you work for someone else, you’re motivated by not getting fired. That’s why you show up to work on time and do what you’re told.

When you work for yourself, there is no one telling you what to do or how to be. No one is going to tell you to stop watching Netflix and get a jumpstart on working each day.

The consequence for being lazy or unmotivated is failure.

Should you go freelance?

If you’re a self-starter, yes.

The pros of freelancing can far outweigh the cons if you’re willing to put in the blood, sweat and tears that it takes. Just sit down and evaluate the pros and cons objectively before you make the leap.

Sometimes freelancing on the side is a good idea to get your feet wet and see if it’s right for you. If you go through a rough patch, stick it out, because doing what you love is exactly what you should be doing. Indulge in your passion. And when you need a break, there’s always Netflix and a bowl of ice cream, whenever you want. Because, after all, you make your own schedule.

If you’re not a risk-taker, it’s probably not the right gig for you.

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Recap: The pros and cons of freelance work


  • Choose what you work on
  • Control over when you work
  • Choose where you work
  • You have more income potential
  • Take advantage of tax deductions
  • No office politics
  • You’re the boss
  • No commute
  • Pursue passion projects
  • It’s always casual Friday
  • Control over variety of work


  • Work not guaranteed
  • Unpredictable income
  • You could make less money
  • Hustling to find work
  • You have to do administrative tasks
  • No employee benefits
  • No community
  • No structure
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