18 Everyday Struggles That Will Only Make Sense If You’re Self-Employed

4 min

7. People asking when you’re going to get a “real job.” 

You already have a “real job.” It’s the one (or ones) you do every damn day.

6. Having to sometimes work multiple jobs.

Speaking of a real job, you might have more than one. Especially when you’re just starting out, and you need a little extra income to make ends meet.

5. Setting boundaries and knowing when to say no.

It’s tempting to take all the work that comes your way, but it’s also important to know when to say “enough.”

4. Holidays and long weekends not always applying to you.

You might be able to schedule time off, but that doesn’t mean your clients are going to respect that. You get calls every day, at all hours of the day. You often have to check your email on holidays and force yourself to answer the phone even if you don’t recognize the number. Some clients will expect you to be available 24/7. And some jobs, like pet care, for example, are busiest during the holidays, so while everyone else is getting together to drink eggnog, you’re taking care of someone else’s dog.

3. The nightmare of filing your taxes.

You either deal with the nightmare of having to file your own taxes or pay a real accountant to do it and then there goes any refund you might have gotten. Although, with self-employment taxes, the idea of a refund is kind of a joke. You’re probably gonna owe a lot, is what I’m saying.

2. Having to deal with all your own invoicing.

Not only are you now in charge of your own billing department, you’ve also got to go after those people who are slow to pay you.

1. Never ever being able to switch into “off” mode.

This is especially difficult if you work from home. While most people have an actual workplace that they go to, if you work from home, it’s going to be hard to know when it’s okay to stop working.