I am of the belief that no matter what you do, you should set goals for yourself. That is really the only way to know if you are actually advancing. It is also a good way to stay on track. Everyone’s goals are different, and I am not the exception.
I think first starting out in comedy your goal should be to get on stage. You would be surprised at how many people can’t get past this step. It seems simple to those of us that are on stage weekly, but a lot of people are so afraid of that stage that it hinders them from ever progressing into show business. I think the reason for that is in performance art, you are exposing your thoughts to the world. A lot of things that we think about are not easily digestible to other people because what we think about and what we actually put out in the open are different. A lot of can’t handle that. A lot of people also have stage fright. Let me tell you something, I am probably the most socially awkward person you will ever meet. At some point I just went up and did it. That is how you have to do it. Just jump!
After just getting on stage you should be trying to get a certain amount of time. This is different depending on your writing style. If you are mostly an improv type guy, then you can just get up and try to do it. If you write heavily, then you should be trying to get more stuff written. I never really thought about time. I just always thought about getting enough jokes that I found funny. I was told that you should try to get 5 solid minutes at first and I think that is good. If you write more of course try to get more time, but the average person might not be writing every day to the point where they can get 20 minutes in their first couple of months doing comedy. Just focus on writing good stuff.
Your next goal should be getting stage time. If you live in a city like Spokane, with not to many stages in which to perform, you will have to be more conservative in this goal. If you live in or near a larger city then you should be trying to get out every night you have available. When I was first starting out I went to every place that had a stage and a mic (and sometimes not the mic). I was able to test out my 5-10 minutes in front of almost every type of crowd. I learned what worked where and what didn’t. This is an important goal because it get you comfortable in front of any crowd. I have seen people freak out because older people were in the audience. Well, if you play in front of everyone this will not be an issue.
After that this is where the goals can branch off. You can try to get paid after you have sufficient time under your belt or you can just keep it as a hobby. I wanted to see if I could get paid and where I could get paid. The comedy club in town was paying so I made it my goal to try to get paid to do stage time. Independent shows were paying me after about 4 months of doing comedy, but that isn’t going to happen for everyone. After just getting paid you may think of what you want to specialize in if you want to pursue this as a career. You could be just a road comic and drive all over and get paid that way. Or you could try to be a club comic and work the many clubs in the country (and Canada!). You could do cruise ships, or focus on corporate entertainment. You can even be a speaker and just go from school to school telling funny stories about why you shouldn’t smoke crack. There are many avenues to go. What I see though is a mix of things and someone just falls into one because they get booked there the most. Don’t put yourself into a corner unless that is what you want.
My goal right now is to do well in the Seattle International Comedy Competition. That is what I am focused on. After that I want to get booked more in clubs. Hell, I just want to get booked more! Right now I average about 2-3 paid shows a month. That is not really good enough for me. I want to be booked about 3 weeks out of the month. That is my goal. I am not worried about being a millionaire and buying a jet and a ocelot that I will name Jeffery. I am more looking to support myself with comedy. That means making about 900-1000 a month on just comedy (that is after all travel expenses are taking care of). I don’t focus on just clubs or casinos I try to get booked anywhere that will have me. I try to write jokes that I can do in more than one situation. That way I can perform in front of suits and ties and perform in front of a bar crowd. I would like to get into acting more, but that is just because I like it not because of the money (although the money is pretty good). So you should get your goals together and work toward them. Even if you don’t obtain them all at least you are working towards something.