Working on new material, writing jokes, trying them on stage, listening back to the recordings, it can fucking suck. But it's one of the aspects of comedy I've come to enjoy and respect the most.
At the beginning, it's not so bad. If only because you don't have a choice. You don't know what works, so you just write anything you can think of, and hope it sticks when you go on stage and throw it against the wall. Eventually (hopefully sooner than later!), something does. And now you have the premise for your first "bit". The goal then is to keep telling it, but a little differently each time, and shape it into something to be proud of. A polished bit that you can take up there and be confident that more often than not, it'll get a laugh.
I gained a TREMENDOUS amount of confidence once I came up with a bit that consistently got a positive reaction (my lazy eye stuff). I worked on (and still polish it now), that bit for months; adding a line here, taking something out. Listening back to recordings of it to see what got a laugh, what didn't. Maybe I approach it too seriously, but I time how long I go between laughs, and if it's more than 20 seconds, I work to come up with a way to either shorten what I'm saying, or find a way to make it funnier. One of the things I enjoy least when I watch a comedian is when there is just too much fluff between jokes. A punchline that misses the mark is excusable (especially when working on new stuff), but when it's just rambling for 30, 40, 50+ seconds, I have a tendency to tune out. By the time you get to the punchline, I've forgotten where you were going.
In my eyes, stand up comedy is an art. As a joke writer, we're artists. I love the freedom that comes with creating art. When you write a joke, you can write anything you want. One of the things I like thinking about is that every single killer bit that hasn't been written or told yet is just sitting out there in space, waiting for someone to come along, write it down, and make it their own. When I sit down to work on new material, I don't go into it with the mentality of, "if I don't come up with a new closer today, it was a waste of time". I just start letting the pen move, scribbling anything I can think of about a particular topic. I try not to get frustrated if nothing good comes of it. It's the thrill of the hunt. It's like fishing. You aren't going to catch a fish every single time you cast your line, (or rod, or whatever the term is. I don't know, I don't fish.) But you keep doing it, because you know eventually you'll get one. The thrill of the hunt.
I totally understand how comedians develop some jokes that work, and then just keep telling them. It's just easier to go up there and use the stuff you know is safe. I've been working on forcing myself to get out of that comfort zone. If I have a 5 minute spot, I use 60-90 seconds to tell an abbreviated version of a joke I know works, and then I try to experiment with the rest of my time. Either trying a new approach to an old joke, or a new premise altogether. Once I get bored of something, I struggle to keep any interest in it. Doing the same thing every night is boring. I want to hit a point where no matter how much time I'm expected to do that night, I have enough material that I can plug and play with my set list. Keep it fresh and exciting.
I don't have a lot of shows over the holiday season. Some open mic are shut down until January, and I just want to take a little time to hang out with family and friends, and focus on my writing. I can't wait to hit the stage in the new year with some new stuff. I told someone the other day; "I write for an hour, to come up with 5 minutes to take on stage, to find out 20 seconds of that 5 minutes of material is any good."
Louis CK once told a story about how he had a really strong closing joke. So when he would do an hour, he would coast on stuff that was OK at best for 15 minutes toward the end of his set, because he knew he had a bit that was so strong, he could end with it, and nobody would remember that the previous 15 minutes weren't that good. It wasn't making him a better comedian. So, he moved that really good joke to the FRONT of his set. He would start his hour with it, and it forced him to not only beef up that 15 minutes, but write an even better joke to close with. When he did it, he would move THAT joke to the front of his set. It constantly forced him to write more, and get better. That's the stuff that I find fascinating about the art of writing jokes.
I'm trying to employ that method of writing myself. Jokes I told in March, I look back on now, and think they're terrible. I'll never tell them again. If all goes to plan, I'll hit a point where I feel that way about every joke I have in my arsenal right now, too.
Force yourself to get better, and enjoy the thrill of the hunt.