Becoming a Lobbyist

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The usual progression goes like this:

Get some internships/crappy jobs
Go work on the Hill for a few years
Make connections with lobbyists
Get a job lobbying
Profit

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This is accuarate. Another option is to work in a Presidential Administration and lobby Federal Agencies like the FCC. To be successful you need to understand both the policy and the political implications of what you are advocating which is why working for a party committee or campaign could be good.