Baltimore has a problem. A squeegee problem. Teens and young adults, largely with little economic opportunity, rely on aggressive and often illegal harassment of drivers to make ends meet. While a few “squeegee boys” may make ends meet, it ultimately keeps people out of more productive work and abuses random motorists.

Some may see this as entrepreneurial, but the very aggressive tactics that squeegee boys use very often evolve into theft or conflict. This is not to over-dramatize their situation or make them seem evil. They’re not.

They are simply trying to get by.However, they cannot be allowed to be violent or hold people up in the middle of moving traffic for their own economic gain.The city has attempted to direct squeegee boys to job offers and training, but the scope of the issue is so great that this solution does not really scale.

I didn’t really believe the scope of the issue, or how Baltimore specific it is, until I had driven around the city at all hours of the night, but I think there are three ways that the city could begin to ameliorate the social issue and direct lives on a more productive path.


1. Telework 

Connect young people with jobs that pay more than they can make on the street, without having to leave home. Easy opportunities to do this are teaching English online, as well as other gig economy jobs. By the time squeegee boys split their take four or five different ways, English teaching might win on economics alone.

2. Socially Conscious Businesses

Young people need jobs to keep them from causing trouble in the street. Benefit Corporations and socially conscious business models may not always throw billions in revenue or have a 70% profit margin like a SaaS startup, but they are probably what is needed here. Even a low margin socially conscious enterprise that could employ a few hundred people downtown would provide a more fun and consistent alternative to squeeging.

3. Relax regulation

There are a myriad of ways that low importance regulation can limit job opportunities for limited gain in public safety. At home food businesses, license requirements, and cumbersome rules around using public space can all limit the growth of more entrepreneurial and less harmful ways to make spare cash for people with lower socioeconomic status. For example, a current squeegee boy could sell cookies or T-shirts at a popup shop or on a street corner and make a real business, rather than one based on bullying drivers.


None of these solutions are complete on their own, but they are high impact, low cost, and could actually bring “charm” back to the Charm City.

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