I've put up a few posts about freelancing, and freelancing really is a great way to go, especially when you're starting out. I do acknowledge, though, that some people are looking for, you know, actual jobs in entertainment, and that one's a little more tricky. The paths in aren't straight, which leads to this being called "the business with no front door." There are ways to do it--none of which are sure-fire, but just like with freelancing, you have to start somewhere.
I'm going to be upfront about this: personal connections help. They really, really help. Sad but true, the best way to get a job in entertainment is to know somebody who can get you one. Robert Gottlieb of the Trident Media Group, who spoke at Emerson a little while ago, called publishing "the easiest industry in New York to get an entry-level job in," and then revealed that he got his first publishing job through a personal connection. This is the best and quickest way to get a permanent position; anyone who tells you otherwise is planting insidious ideas in your head.
That said, one of the peculiarities of the entertainment industry is that more education will not get you a higher position right off the bat. This isn't because education is unvalued, it's because there just aren't many high positions available at any given time. And when they are available, they normally go to people who already work for the company.
If you want to manage a radio station, or direct movies, or edit books, you can start by working under people who do--in any capacity. Robert Gottlieb's first publishing job was in the mail room, and there are far less glamorous starting places than that. Things that, in other businesses, would be dead-end jobs are anything but that in entertainment. You may be taking out the radio station's garbage, but what's important is that you work for the radio station, which gives you inside knowledge--and which gives people on the inside knowledge of you. So when it comes time to find that new DJ, you've seen how the station operates, and everyone's familiar with your personality and tastes. You're at the head of the line, so to speak.
Getting in this way doesn't always mean at the same company. One of my professors, Beth Ineson, who works for Houghton Mifflin, first got into the publishing industry through work in a bookstore. She got in touch with the first publisher she worked for (MIT University Press) through a conference, and her bookstore work was a major point of interest that factored in her hire. The reason, again, was inside experience. Especially when it comes to sales and marketing, bookstore work gives you a close-up look at what appeals to people and what they buy. If you can't find an immediate opening in the business of your choice, it may be a good idea to look for work in a related field that's a little less parochial.
In essence, the best way to work for the entertainment industry is to work for the entertainment industry, and almost all of the jobs come "experience required," which is why it's hard. Some freelance positions lead to permanent hire, but they tend to be highly competitive, and even if you land one, permanent hire isn't guaranteed. The best policy is to take your opportunities as you find them. When you do get a job offer, it's probably best not to wait for a better one. If you want a better job, work at the ones you can find. They'll get you somewhere, though it may be along a slow and zig-zagging path.
But What if I Want an Actual Job?
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