I've had a decent amount of success in the field of Internet comedy. Enough that I was able to quit my day job and just do this for a living, anyway. As a result, people ask me for career advice all the time. And if you're an Internet writer like I am, you know "all the time" means "it happened once."
That doesn't matter, though, because I don't really have that much advice to give. Anyone can write for Cracked, and I just did that a lot and now I work here. There's no reason you can't do that, too.
Well, almost no reason. There are some things about being funny that no one can teach you. If you decide to pursue comedy as a career, you'll inevitably encounter these things. If you don't figure out a way to overcome them, you probably won't have a ton of success. Things like ...
5How to Be Funny (If You Aren't)
I know it's going to be a bummer for some people to hear, but in my honest opinion, I don't think you can teach a person to be funny. It's just something you are or something you are not. There are a lot of books and classes out there about comedy, but if any of them claim they can take a person from "not funny" to "funny," they are talking snake-oil nonsense.
That's not to say books and classes aren't useful. I took a stand-up comedy class when I first moved to Los Angeles and it did great things for my confidence. But no one goes into a comedy class as an unfunny person and just magically learns how to identify the quality punchlines hiding in all of those depressing stories about natural disasters and dead people that we read every day. It's just not something everybody can do. To suggest otherwise is like implying that anyone with access to a basketball can play in the NBA, provided playing professional basketball took way less talent and paid fast food money.
Not even name brand fast food.
So that's the bad news. The good news is that being funny is something a lot of people can do. And you could very well be one of those people! The only way to find out is to try it. You can't wait for the right book or class to come along and explain how to be funny. You should already know if you are to some degree. Or at the very least, you should be delusional enough to think you are when you really aren't. Either way, there's only one way to find out for sure, and that's by giving it a shot. If you want to write Internet comedy, my personal suggestion would be to start here like I did. If you want to do stand-up, go to an open mic night and tell some jokes. See what happens from there. It's as easy as that, minus the easy part. That brings us to the next point.
4How to Build Up the Nerve to Find Out
Nobody wants to be rejected. It's that fear that keeps countless people from trying any number of different things every day, but it's an especially imposing threat when it comes to comedy, because the rejection is almost always going to be on a wider scale than usual. Getting rejected romantically, for example, is a personal thing that contains the humiliation mostly to you and the person you weirded out by leading with a story about your passion for taxidermy.
Comedic rejection, though, usually happens in front of a group. Granted, if you're at an open mic night, that group might be just a handful of people, but they will feel like the entire world if they all decide they don't like you.
Writing on the Internet isn't much better, because, unlike at a comedy club, patrons of Internet websites are encouraged to tell you what they think of your performance. Depending on where you're writing, that could mean millions of people with the potential to turn into impromptu critics if their dislike for your work is strong enough that it compels them to comment.
Unfortunately, every one of them is this guy.
If the fear of being rejected by a lot of people all at once is keeping you from trying your hand at writing or performing comedy, it's mandatory that you get over it somehow. Some people use alcohol. I can't recommend that, because this is a family show, but if you do go that route, take comfort in knowing that you can just blame the booze if your jokes turn out to be terrible.
And you never know, maybe they won't be. You might find out that you really are as funny as your friends, family, and inflated ego have all led you to believe. In that case, keep this next point in mind.