Comedy is a Catch-22. You can’t learn to headline without experience headlining. But you can’t get experience headlining until you learn how. So what do you do? You take steps.
But how do you know when you’re ready to move up? The truth is, you never know for sure. But this may help.
1) You are not ready to move up until the level you’re already on seems easy. Being able to do well on a good show doesn’t matter. You move up when you can do well on a bad show. No one sitting on the bench in the minors gets called up to the majors. You have to be one of the best of your level before you go to the next level. Eeking by is not enough. Be honest with yourself. Are you killing night in and night out? No? Then learn how.
2) Ask yourself this: How much time do you have? Now that you have that answer in your head, ask yourself this instead: How much time do you have if the whole room hates you? THAT is the time that you really have. When you absolutely HAVE to fulfill a contract in a no-win situation, can you? I don’t mean crowd work or freaking out – I mean actual material that you can stick to no matter WHAT happens in front of you. Because no-win situations happen, and you need to be reliable.
3) Every comic has an off-night. But professionals don’t bomb. You can’t bomb if you’re comfortable. You can do poorly, sure. You can struggle. But you can’t bomb. If you still have more than one “what the hell was that?” night a year, you are NOT ready to move up. Professionals handle whatever situation they’re in, because professionals are comfortable in whatever situation they’re in.
4) There are plenty of terrible gigs that are thrilled to have any comedian take them. If you can’t headline one of those, what makes you think you can headline a real club? Cut your teeth in D rooms – then A rooms become easy. Not getting hired to feature at the Improv? Try to master featuring in a Sunday night bowling alley gig first. It’s a place where you can learn to do more time, and there’s very little at stake.
5) Moving up doesn’t simply mean doing more time. The pacing and the arc of a headlining set is very different from a feature. You have to learn how to handle check drops and drunker patrons, how to follow a feature that just killed for 20 minutes, etc, etc. Are you a great open mic-er? Well, maybe you’re not a host, as that’s a completely separate skill and requires likability. Each spot and each level is different. You need to learn to master the one you’re applying for.
6) Every next level in comedy pays about double the last one. So 40 weeks of feature work and 20 weeks of headline work pay about the same (that’s gross, not net – you’d actually make more net on the fewer weeks of work because you have fewer expenses). It’s scary to have an empty calendar. But saying no to people is the only way they start saying yes back.
7) Part of moving up is treating yourself how you deserve to be treated. Bosses give raises when they feel they have to. So if you’re getting steady feature work, stop taking MC work. If you’re a headliner now, why are you featuring? We’re conditioned to say “yes” to everything. But the only way to move up is to move yourself up.
8) Steve Martin said it best: “Be so good they can’t ignore you.” If you’re consistently killing at your level, people will notice. Keep your head down, do good work, and you may not know when you’re ready to move up, but the rest of the world will.