Many people have dreams of working for themselves. And, as someone who is self-employed, I can agree that it isn’t a bad gig. For the most part, I set my own hours, and I can work in my pajamas from my home. Even if you work outside of the home as your own boss, it can be refreshing to be responsible only to you. However, being self-employed isn’t always sunshine and rainbows. I was reminded of this yesterday after reading J. Money’s post at Budgets are $exy on paying quarterly taxes.

I’m pretty used to paying quarterly taxes by now, since I’ve been self-employed for more than six years. However, when I first started, it was a little bit of a bummer. (Of course, paying taxes is never fun.) J. Money’s post got me thinking about some of the other items that constitute the dark side of being self-employed:

Paying Both Sides of the Payroll Tax

One of the biggest bummers related to being self-employed is that you have to pay both sides of the payroll tax. When you work for someone else, your employer pays half your payroll tax. However, when you work for yourself, you are both employer and employee. So you get socked with paying both portions. It can be a real eye-opener. Paying quarterly lessens the blow a bit, especially if you budget it in, but it’s still painful.

Vacations Aren’t What They Used To Be

When you are self-employed, you can’t always just take a vacation. I’m a freelance writer, so I can shift some of my assignments around, but I rarely go a day without doing something related to my business. The only exceptions are Sundays and my yearly three-day camping trip. Usually, even when I’m away from home, I’m on the laptop for at least two hours day. Sometimes that means getting up way before everyone else so that I can get my stuff done before the activities of the day.

And, even when I go camping, I usually have to put in extra work to get everything done ahead of time. Deadlines don’t go on vacation just because I want to take a break, although I am lucky to have flexible clients who let me skip when I am under the weather or have a family emergency. Of course, there is no paid vacation or paid leave when you work for yourself.

Sometimes You Have to Work Even More

Entrepreneurs, especially when starting out, sometimes have to work a lot more. Sometimes, your schedule really isn’t your own, and you don’t actually feel like your own boss. If something needs to be done right now, you’re the one who has to do it. Sometimes, being self-employed means working more than you did when you worked for someone else. And you never really leave the work at work. Many people with 9-5 jobs get done, go home, and forget about work until the next day. When you’re self-employed, this rarely happens. Drawing the line between work life and home life is especially hard if you work from home.

It’s All On You

When you’re self-employed, your success or failure is all on you. Was I stupid enough to take on a major project without half in advance? Sure was. Yeah, it’s the guy’s fault for not paying me. But I’m also partly to blame for doing $2,000 worth of work without first seeing some sort of guarantee in the form of cash money. Decisions about your business can’t be blamed on someone else, and when things aren’t going well, you can’t blame your situation on being fired unfairly. And you can’t even collect unemployment if you hit a dry spot in your business.

I really do like being self-employed, and feeling as though I am in charge of my financial destiny. However, there are days when I think it would be nice to just clock out and go home — and maybe be paid for a vacation day or two.



Miranda is freelance journalist. She specializes in topics related to money, especially personal finance, small business, and investing. You can read more of my writing at Planting Money Seeds.