Let's get a few things straight

When I tell people that I am a designer and work from home, they typically respond with envy and ecstasy as they imagine sleeping in, unlimited creativity, and the freedom to casually work from coffee shops every day. Even when I try to explain that it is, in fact, hard work, I think most people still tend to glamorize the late nights and deadline rushes. So, this is for everyone who has considered freelancing or going out on their own. Let's get a few things straight:

Yes, you can work in your pajamas.
You can work in sweatpants, or the jeans you've worn for three days and it never matters. Right now, it is almost 1:00 in the afternoon and I have yet to change. The catch: it's not always by choice. I've been working steadily since 6:30 this morning, coordinating with clients, preparing documents, and sending out proofs. Wearing sweatpants is comfortable and makes sense, but I personally miss getting ready for the day sometimes. And, it's awkward if anyone comes to the door.

Yes, you can sleep in as late as you want.
But you're still on a deadline. Your clients, for the most part, are still going to be working normal business hours. While I personally work better late at night, it isn't always the best option for my clients. If they need to contact me, or I have a question, it helps to be on similar schedules. If I ever sleep in, it is usually during a stage of the project that involves little client communication, or after working a 12 hour day. Sometimes you get up early and stay up late - for days at a time. This isn't the art school, "those were the days" late nights, either. These are the nights where your eyes and back hurt, your creativity has been zapped, and the deadline is getting closer and closer. Working as a freelancer involves serious commitment, discipline, and sometimes, sacrifice.

You work whenever you want.
Much like the previous statement, this can be completely true. And it can hurt your business. Clients want people that they can contact easily. That has occasionally meant taking phone calls earlier or later than normal business hours, or even on the weekends. I would definitely suggest setting up contact hours and enforcing them (holding both yourself and your client to them). If you want to work into the night, great, but it's also good to be available when your client has a question the next morning. My schedule is typically fairly flexible, so I enjoy grabbing coffee or running errands in the afternoon. I've had some really cool opportunities that I wouldn't have had with other jobs. One of the most important things you can learn is time management.

It is so fun.
Finally, I get to run projects. I get to concept them, meet with clients, research cool concepts, and learn new things every single day. I actually get to be creative! I have the freedom to try new things and experiment. That said, I have also had to learn about the financial aspect of owning a small business. I literally fell asleep reading about it all. I've had some amazing opportunities and met some great people, but I'm also the one who has to deal with the difficult clients and any problems that might come up. If there is a computer problem, file issue, difficult client, printing issue, or lack of creativity, I have to deal with it. I've had more fun in the past few months than I've had in years of working for other people, but, I've been through more stress, too.

You get to do whatever you want!
You have complete creative freedom over the projects that come your way. Until your client has an idea. As a designer, I feel like my most important responsibility is to create something that the client feels good about. That has meant that some of my favorite designs have never gone beyond the concept stage. As a designer, I have certain standards that I stick it to. I have a lot more freedom than I have previously had, but it doesn't mean that the clients aren't going to express their opinions and have requests as well. Some of the best advice I've received was to "Fall in love with your client". You have to know them, be their biggest supporter, and really want their brand to show through. That definitely doesn't mean that you can let a client walk all over you, but you have to remember who you're doing the work for.

I didn't write any of this trying to discourage someone from trying their hand at freelancing or going out on their own. My goal here was to be really honest about what it actually means to work on your own. It's one of the most educational and enjoyable things I've done thus far. It is also one of the toughest, most challenging, and most stressful. It isn't for the lazy, uninspired, shy, or weak. If you are considering going out on your own, there are tons of useful programs and sites out there to help. I'd be happy to answer any questions or send along any tips. One of the biggest favors you can do for yourself is to network - both offering and accepting help. Good luck!