Illustration by Nicholas Konrad; Source photographs from Alamy / Getty

My first job in media was as an assistant at The American Prospect, a small political magazine in Washington, D.C., that offered a promising foothold in journalism. I helped with the print order, mailed checks to writers—after receiving lots of e-mails asking, politely, Where is my money?—and ran the intern program. This last responsibility allowed me a small joy: every couple of weeks, a respected journalist would come into the office for a brown-bag lunch in our conference room, giving our most recent group of twentysomethings a chance to ask for practical advice about “making it.” One man told us to embrace a kind of youthful workaholism, before we became encumbered by kids and families. An investigative reporter implored us to file our taxes and to keep our personal lives in order—never give the rich and powerful a way to undercut your journalism. But perhaps the most memorable piece of advice was from a late-career writer who didn’t mince words. You want to make it in journalism, […]

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