The phrase "working the street" has referred to many things, but the connotations have mostly all been negative: prostitution, selling drugs, policing dangerous neighborhoods. Even after ideas espoused by Jane Jacobs seem to have become unshakable doctrines like "street life," an intractably negative view of the street still remains.
Nonetheless, the first introduction most children have to work and business skills still takes place on the sidewalk. Think lemonade stand. It's great learning experience, exposing them to planning, patience, customer service, and math, among other lessons that will serve them well in life (especially in a capitalist society).
For adult observers, a lemonade stand can also be a lesson in how a neighborhood works. Pedestrian activity and community cohesiveness affect the relative success of these budding ventures. The sheer number of potential customers in denser urban neighborhoods is an obvious advantage. Having more neighbors with a view from their window helps as well, since people often stop by to show their support for kids. Walking speed and face-to-face contact break down the barriers to stopping at a stand that sometimes limit interactions with neighbors driving by in the suburbs, as well.
Kids can get a great start by working the street, and places where people are generally walking by and friendly to one another offer the ingredients for a sweet little sidewalk stand.