The first thing to do is come up with an act. This can be very difficult. It's much harder than just arranging your tricks from easiest to hardest and then playing your favorite song in the background. Volumes have been written on the subject and rightly so since it's hard to come up with good material. Just like a writer can get writer's block, so too can jugglers have difficulty being creative and original. Sometimes I get the feeling that all of the good material was already written during Vaudeville and it's futile for me to even try. But if we didn't like a good challenge, we wouldn't be jugglers, would we?
Once you've put together something you feel is ready for an audience, you have to go out and sell yourself. Even if your juggling has won awards, you won't get a stage without some marketing effort. Business is an aggressive field and it's easy to be timid especially when you are asking for money for something you enjoy doing so much.
Starting out can really be a struggle since it's difficult to find work (there aren't a lot of venues in this field). Sometimes we have to accept less ideal work (such as kindergarten birthday parties) in order to make ends meet.
Most jugglers go into show business because we love to juggle, not because we want to be entrepreneurs (although it can be nice to be your own boss). Many of us are bad at the business aspects of being self-employed. It takes a lot of organizational skills whereas we'd rather spend our time improving our juggling skills.
Let's say that you overcame the hurdles of putting together an act and you even found a venue. Well, your troubles aren't over.
Once you get on stage there are a million potential problems, especially with the condition of the performance space: ceiling too low, stage doesn't bounce balls well, stage not level, stage too narrow, lights in eyes, audience too close or too far, etc. On top of that audiences can be difficult - either uninterested or filled with hecklers.
Then there are all the things that can go wrong with your routine (no matter how much you've practiced). Juggling is one of the highest risk performance arts there is. Dropping really puts you on the spot which can be embarrassing and sometimes even dangerous to you and/or members of the audience. There are just good days and bad ones in terms of skill. As much as you may practice, you will still have shows where you drop. Sometimes you may feel like you drop more than you catch.
Other things can also go wrong such as problems with: music or microphone, lighting (too bright or dark), tripping on stage, or knocking over your propstand. (see JAG's accidents.)
For me personally, the worst thing about performing is that I simply hate being in front of crowds. Many performers thrive off of the attention but I'm more of an introvert. I essentially hide behind the juggling when I'm on stage. Especially hard for me is being enthusiastic while delivering my same jokes show after show.
The challenge of doing a good job pushes me, though (especially since I love juggling and everyone should be so lucky as to get paid for their hobby!)
On a practical level it can be scary deciding to work for yourself. There is the lack of security money-wise since you can't always be sure you'll find work.
I've been performing over 200 shows per year for the last 5 years and have gotten used to show business. It's been an extraordinary challenge and I'm always thinking about how to improve my show.
The first step is to take the plunge. Start with informal shows so you can get experience. One of the most common places to go for experience is to the streets. There you will learn to juggle under unusual conditions and unpredictable circumstances. I also recommend doing freebies for children's wards at hospitals or for charitable organizations. Since you're not getting paid there isn't very much pressure.
Even when bad things happen to good jugglers, just remember the cardinal rule of Show Business - the show must go on. Bounce back with even more determination.
The most important thing I've learned from performing is simply to relax and have fun! (this took me a long time since I worried too much about all off the other things). Luckily audiences are there to enjoy themselves and they usually will. They want you to succeed since they want to be entertained.
So go for it and you will also have one of the most rewarding jobs possible!