It seems like these days the most sought after jobs are reserved for graduates of elite educational programs and/or well connected people. However in many depictions historical depictions such (eg Mad Men, How to Succeed in Business Without Really Trying), people are able to work their way up the food chain at large companies through grit, talent and determination. While I know this still happens occasionally at companies with cultures that encourage this (eg UPS), it is rare. Was this kind of thing actually more common in the past, or is this just fictional myth?
I can speak to this specifically for the entertainment industry, specifically talent agencies.
Talent agencies have typically followed the apprenticeship model, and hiring non-agents to come in and represent clients is a relatively recent phenomenon that was not very common before the 1990s.
Mailrooms as the system of funneling new talent into an agency was pioneered by the William Morris Agency, which originally represented vaudeville performers. Abe Lastfogel, who went on to found WMA's West Coast office and eventually ran the entire agency, began as an office boy for William Morris. In the 1940's, WMA rebranded their mailroom positions as the "William Morris Agent Training Program", where hires were expected to start in the mailroom, rotate through different departments, and then be promoted to assistant or coordinator. WMA ceased hiring assistants and coordinators, and its junior roles were then filled by graduates of the training program.
WMA, as the dominant agency in the mid-twentieth century, also had many agents eventually leave to found their own agencies and they followed a similar model of having people start in the mailroom. Creative Artists Agency, ICM, and UTA all adopted similar training programs and most new hires were funneled through the mailroom rather than beginning as an assistant for a specific executive. The mailroom was often seen as badge of honor and a way to weed out people who would not be able to succeed in such a cut-throat business as Hollywood, and the major talent agencies to this day often recruit employees specifically to their mailroom programs.
Source: The Mailroom: Hollywood History from the Bottom Up by David Rensin
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