The very first thing Mayor Daley will miss is his driver.

Though Mayor Daley didn’t comment for this article, the Reader solicited advice and anecdotes from seven ex-pols to help shed light on Daley’s impending transition. They said Daley will need to acclimate himself to a wholly unfamiliar emotional, intellectual, social world—more comfortable, less stimulating, in many ways easier and yet demanding of new skills and real wisdom.

Another of the obvious perils of public life is the loss of privacy. Part of that involves the constant expectation that a politician be ready to discuss any and all constituents’ problems. Soon after U.S. senator Peter Fitzgerald took office in 1999, he realized that “You just want to go to the Jewel to get milk, and people want to tell you about problems they’re having with the post office or the IRS. So you end up avoiding going out on your own.” Fitzgerald hardly has to deal with such entreaties these days.

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Every day a joy, ‘even if it was not good’

Thompson loved campaigning so much he did it throughout each of his four terms, year-round.

She desperately tried and barely succeeded at keeping the city out of bankruptcy, and wasn’t thanked for it. “Solvency—that doesn’t sell, they just assume it.”