Obama went to college after which he worked for Business International Corporation (now part of The Economist). Obama then went to work as a community organizer (an actually really difficult and largely thankless job) first for NYPIRG and then for Developing Communities Project (DCP), a church-based community organization.
During his three years as the DCP's director, its staff grew from one to thirteen (I guess, he was a job creator after all!). He helped set up a job training program, a college preparatory tutoring program, and a tenants' rights organization in Altgeld Gardens. Obama also worked as a consultant and instructor for the Gamaliel Foundation, a community organizing institute.
In late 1988, Obama entered Harvard Law School. He was selected as an editor of the Harvard Law Review at the end of his first year, and president of the journal in his second year. During his summers, he returned to Chicago, where he worked as an associate at the law firms of Sidley Austin in 1989 and Hopkins & Sutter in 1990.
In 1991, Obama accepted a two-year position as Visiting Law and Government Fellow at the University of Chicago Law School to work on his first book. He then served as a professor at the University of Chicago Law School for twelve years—as a Lecturer from 1992 to 1996, and as a Senior Lecturer from 1996 to 2004—teaching constitutional law.
From April to October 1992, Obama directed Illinois's Project Vote, a voter registration drive with ten staffers and seven hundred volunteer registrars; it achieved its goal of registering 150,000 of 400,000 unregistered African Americans in the state, and led to Crain's Chicago Business naming Obama to its 1993 list of "40 under Forty" powers to be. In 1993 he joined Davis, Miner, Barnhill & Galland, a 13-attorney law firm specializing in civil rights litigation and neighborhood economic development, where he was an associate for three years from 1993 to 1996, then of counsel from 1996 to 2004.
He began his political career as state senator in Illinois while at Davis.
In other words, he's an extremely intelligent, hardworking and accomplishment self-made man.
What is it you do, again?