The Downside of Working for Yourself


In 2008, I was laid off from my job as a paralegal. The economy was tanking and there were no future job prospects in sight. I moved back in with my parents and returned to my college gig: waiting tables. I worked at that restaurant for a year until I found my way into the tech industry, teaching lawyers how to blog. And then I was fired again when the company reorganized and eliminated my department.

That’s when I vowed to never work for someone else again.

The year was 2010, and I was officially freelancing full-time. At first, I had no idea what I was doing, but I quickly learned how to find gigs, why contracts are critical, and what happens when you don’t set aside a third of your income for taxes.

I’ve floated between being flat broke and raking in five figures a month. (Note to future self: Don’t spend that all at once.) Some days, I hate working for me. Here are six reasons why. Who’s with me?

1. It Can Be Lonely
As a freelance writer, I have no office. My commute consists of walking from my kitchen to my home office. The office overlooks a lake, and the view, combined with natural sunlight, helps inspire the two or three posts I write each day, plus several others I edit. I might hop on a Google Hangout with a client, but unless I have downtime to Skype with a friend, there isn’t much social interaction.

While those in an office might share funny stories or laugh at a meme, I have few people I can connect with. My days are rewarding — but lonely.

2. Income Is Irregular
One of the worst things about working for yourself is the irregular income stream. While I’ve been lucky enough to have several consistent clients, there have been months when a startup loses its funding or corporate clients “go in a different direction.”

While I have a monthly budget, I don’t always earn enough to pay my bills. Alternatively, some months I might make three or four times what I need — which means setting aside money in a separate savings account for those rainy days (or months) is critical.

While freelancers give up a consistent salary, we arguably have more control over our income — but it can still be tough when you don’t know how much will be in your bank account each month.

3. Workflow Is Inconsistent
Just like income, workflow is inconsistent. Some months I have only one client who needs me for 10 hours a week; the next month that same client might need 30 hours a week, and five pitches I sent weeks ago were all accepted — with the same deadline. (Yay!?)

As a freelancer, it’s nearly impossible to know how much work you’ll have, which makes it hard to decide whether to pitch another article, say yes to a new client — or worse yet, say no.

While office work can ebb and flow, at least you usually know you have a job. As a freelancer, half of your job is to ensure you have more jobs. It’s quite the balancing act.

4. Work-Life Balance Is a Struggle
When you work for yourself, you have to constantly hustle: hustle to find an expert to interview, to make the deadline, to get your next pitch in on time, to find more clients. Most companies have business development managers, sales teams, and marketing all devoted to reaching new customers. When you work for yourself, you do all of this — plus all the actual work.

Some freelancers are lucky enough to have a consistent client and income base that allows them the freedom to grab lunch with friends or go to yoga regularly. Most, though, can rarely shut down at a reasonable hour — even on weekends. Finding work-life balance is hard, if not impossible. And while your friends who work 9-to-5 leave their job in the cubicle, freelancers don’t ever have that luxury.

Oh yes, there’s more.

5. Taxes Are High
A great thing about working for yourself:  You get to keep all the money — and then give about a third of it to the IRS.

Salaried employees are federally taxed at around 15 percent, taken out of every paycheck. But not freelancers. I found out the hard way how much Uncle Sam taxes those who are self-employed after my first year of freelancing, when I was forced to go into debt to pay nearly five figures to the IRS.

Now I set aside a third of my income — and use accounting software to track expenses that could be deductible — so I’m not surprised when I file. I also raised my rates significantly to compensate for this hit to my income.

6. No Benefits Here
Alas, no perks. You have to pay for your own health insurance, set up your own retirement fund, set aside your savings for vacation days, work through sick days, and let’s not even start on “maternity leave.”

There are ways to receive some benefits through associations like the Freelancers Union, but it doesn’t come close to what your traditional employer offers — especially when you really need a vacation.

Why I Love It Anyway…
Despite all that, I still love freelancing and would never consider working for someone else again. I get to wake up every day and do what I love, on my own terms. If an article isn’t due for two weeks and I’m really not in the right mindset to start writing, I can lace up my sneakers and jog around the lake to clear my head and work out my priorities.

If I’m working with a client who keeps pushing my boundaries and asking for extra revisions despite our agreement, I can decide whether I want to keep working with them — or whether their lack of respect is too much of a drain on my energy and creativity.

But most of all, I can choose to work on what makes me happy.

Kelly Clay (@kellyhclay) is a freelance writing coach and blogger who contributes to The Write Life, a website that helps writers make a living from their craft. Sign up for their newsletter to receive actionable writing tips and advice in your inbox each week. (Bonus: You’ll also get a free ebook about how to land your first paying client!)

You Might Also Like:
Your Social Media Strategy — From Facebook to LinkedIn
7 Strategies To Work Successfully From Home
You Need to Give Yourself a Raise

Join the Discussion