Pros and Cons of Being a Freelancer, From a Freelancer

Jessa weird have to go to work every day

Credit: Girls, HBO

It’s surprising to me when I think about it, but I have now been successfully running my own freelance writing business for a full six months.

Though everyone in my life was very supportive when I told them I was leaving my full-time reporter job to write on a per-assignment basis for various tech companies, I have since learned that pretty much all of those people secretly thought I was acting like a crazy person.

After all, why would anyone want to part ways with a steady paycheck and health benefits from a known entity? Were there really enough companies that would pay me to write for them? And, as many concerned people have asked me, what would I do if things didn’t work out?

It’s true that all of these questions have been difficult for me to answer at different times over the past half year, but on the whole, I’m extremely pleased with my decision to make the leap. While it might not be for everyone, the benefits of freelance life have far outweighed the drawbacks for me thus far.

If you’re thinking about taking the plunge yourself, here are some pros and cons I’ve discovered in my time without a full-time gig:

Con: Freelancing is extremely expensive.

Having a full-time job comes with a lot of benefits — some of which you never even think about.

While the Affordable Care Act has made it easier for individuals to purchase health care, most of the plans available through the state and federal exchanges will likely wind up being significantly more expensive than what you’d be paying to buy healthcare through your old employer with no help from employers that pick up part of the cost. Employers also pay a portion of their workers’ social security and Medicare taxes, meaning that going freelance will require you to pay an additional significant percentage of your income in taxes each year.

On top of all that, there’s the double whammy of the fact that most employers withhold your taxes and health insurance payments from each paycheck, so usually the money you get from them is yours to keep, and all you have to submit to the IRS at the end of the year is your W2 form. As a freelancer, you’re constantly reminded of just how much these things cost because it’s up to you to set aside money to pay for them. From experience, it’s always a bummer to go from the excitement of receiving a nice-sized check to the disappointment of remembering how much of it will go to the tax man after you’ve collected your 1099 forms at the end of the year.

Another thing to think about is that if you have equipment you need to do your job, you’ll have to pay for that equipment — and any repairs — all by yourself. All of these added expenses should be factored into your calculations when you think about starting your freelance journey. You can, at least, deduct some of your expenses from your taxes assuming you’re keeping track of everything properly.

Pro: You don’t have a boss — mostly.

Having a boss is the absolute worst. Every time you take a full-time job, you give a virtual stranger the power to control an unreasonably significant portion of your personal happiness. If you don’t believe me, think about how much time you spend complaining to your friends and family. Then try to figure out what percentage of that time is devoted to complaining about your direct supervisor.

Often, your boss’ interests aren’t aligned with your own. Sometimes your boss leaves or gets replaced, leaving you at the mercy of someone you didn’t even choose to work for. And even if you have a “good” boss, you are required to manage an extremely important professional relationship from a position of subordination. I thank my lucky stars every day that goes by in which I’m not interrupted by an instant message asking what I’m working on or nudged to apologize for a mistake I didn’t make.

While I still need to maintain a good relationship with my clients in order to make a living, the power that was once concentrated in a singular boss is now distributed across about 10 different people. So if I decide I want to stop dealing with one of these mini-bosses, I can do so without agonizing over whether I want to undergo the highly unpleasant task of applying for a new full-time job. And rather than giving up my health benefits and livelihood by quitting a job, all I have to do when I drop a client is find another one to replace a small fraction of my income.

Even then, managing relationships with a client is a lot easier than with a boss because both sides are coming to the table on equal footing. This allows me to have more control over the relationship and set certain boundaries — for instance, I prefer to communicate via telephone or email rather than instant message.

Con: There’s no one else to motivate you.

While it’s nice not to have anyone nagging you to do your work, being a freelancer makes it very easy for you to let things slide.

In a way, my first few months of being a freelancer were a lot like my first semester of college in that both time periods contained a stunning realization that, for the foreseeable future, there were would be no immediate repercussions for shirking my responsibilities. But just as skipping class would ultimately come to haunt me when finals week rolled around, I soon learned that it was best not to spend my Monday mornings playing video games in my underwear.

Even during weeks where it appears that I don’t have much work to do, I’ve learned that I need to start taking care of my writing before I can relax. Invariably, the moment I put my feet up will be the moment I get three emails from clients asking for new pieces. If I haven’t started on the work that was already on the books, I either have to turn down the new jobs (and the money that comes with them) or make my clients wait (which isn’t good for anyone).

As someone who sometimes struggles to be a “self-starter,” I’ve learned that in the absence of a boss, I need to be disciplined about making sure I have had breakfast and am starting my work by 10 a.m. at the latest every morning.

A word of advice: even if you’re not planning to leave the house, make sure you put on pants and shoes to get yourself in the working mindset. Extra points if you’ve showered.

wearing a rob and jordans

Credit: Keeping Up With The Kardashians, E!

Pro: The amount of money you make is contingent on how much work you do.

Oftentimes in the world of full-time jobs, how much you get paid can be completely divorced from how much work you do. If you are on salary, you get paid the same whether you’re productive or not, and it can take years of great work to get a raise, if it ever comes at all.

One thing I love about freelancing is how much control I have over how hard I work and how much money I make. If I put in extra hours to finish a few additional projects this week, I’ll get paid more for completing them. And if I decide I’d rather have free time than the extra money, I can make that decision, as well.

Best of all, being a freelancer pretty much eliminates all of the time I used to have to spend looking busy. If I finish everything I need to by 3 p.m., I’m going to go for a run or kick back with a glass of wine instead of finding an additional task to work on so that my boss doesn’t think I’m slacking.

Con: Financial uncertainty and the crippling anxiety that comes with it.

Of course, not having a salary means you’re putting yourself at risk of not making enough money to pay your bills. Obviously, this is terrifying! I never forget that I am always two or three clients away from really having to scramble to make things work.

While things have gone incredibly smoothly for me thus far, a great deal of my success as a freelancer has been due to fortuitous circumstances outside of my control. At my last job, I sort of stumbled into learning how to write about advertising technology, an extremely niche skill that happens to have been deemed valuable by a number of venture-backed companies that have money to spend on content creation. Beyond that, I have parents who care enough about me and make enough money that they could afford to house and feed me for a while in the event that all of this blows up in my face.

All of this is to say that I have been extremely lucky to have made freelancing work for me, and there is no guarantee that other people will have similar success, or even that I will be able to sustain the roll I’ve been on.

With that said, there are things you can do to cut down on the financial uncertainty of making the freelance jump. If you can, you should try doing some freelance work while fully employed to gauge how much demand there is for your services. Another way to make things easier on yourself is to start reaching out to prospective clients to see if they would have regular work for you in the event you left your job.

Lastly, you’ll also want save up some money because you’re not always going to get paid on time as a freelancer. Having a few thousand dollars stashed away has allowed me to not sweat it when I’ve had to wait a couple months for a check to arrive or while sourcing new clients

Pro: That freelance lifestyle!

I “took off” one Monday in April because I wanted to watch Wrestlemania on Sunday night without having to worry about work cramping my style the following morning.

It’s possible I could have done this at a full-time job, but it certainly would have been difficult to explain my absence to a boss expecting me to be a go-getter and a team player. As a freelancer, though I’m out of sight and out of mind. So long as my work is in on time, no one needs to know or care how I spend my time.

There is nothing quite as freeing as going for a run in the park at 2 p.m. on a Tuesday with the knowledge that everyone else is at work. Or waking up and being at your desk immediately while your friends are pressed shoulder to shoulder on a crowded subway car. While this arrangement sometimes means I have to work late to get everything done, it’s a tradeoff I’m more than willing to make.

Con: Freelancing is lonely.

I don’t miss all of my co-workers, but I do miss some of them. As a bit of an extrovert, sitting by myself in my apartment all day can be a real drag. I also sort of miss the camaraderie of being part of a team.

In order to not go crazy, I try to make time to chat with my friends online and make sure to work from a coffee shop some days so that I can be around other human beings. I also have made friends with another freelance ad-tech writer, who I can call to commiserate with or to ask for advice when the time comes.

While everyone has a different experience, this list should give you a pretty good idea of  at least some of the things you should consider before leaving your job to make it as a freelancer.

Even with all of the negatives I just wrote about, I almost can’t imagine signing up for another full-time job. If you decide to go freelance, I hope you’ll wind up feeling similarly.

*Written by Aaron Taube on behalf of Benny*

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