For years, Kahlil Nottingham washed windows for tips.

Squeegeeing was a means for Nottingham, 19, to earn money, take care of himself and develop independence, he said.

He’d started washing windows in 2017, after spending a night in a juvenile detention holding cell for trying to steal a woman’s purse. He decided to try making money a different way — first, by selling water bottles, then by squeegeeing. With an income, he’d be able to buy things he wanted on his own, without having to ask a parent for help.

As of a few months ago, he’d planned to continue squeegeeing. But then he found a program called From Squeegee To Success, and decided to give up his stick — for good.

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“Why would I keep running in place?” he thought.

The program, led by 19-year-old Gregory Simmons and 20-year-old Lamar Hill, ran from around February to April. It aimed to pull young people off squeegee corners and give them an opportunity to grow personally and professionally, and to help them achieve their version of success, according to Simmons. The program offered two-hour lessons on Mondays and Saturdays that discussed everything from mental health to elevator pitches. It also provided career opportunities and created a support network that felt like family. Young people were paid $25 an hour to attend.

From Squeegee To Success encourages squeegee workers to drop their sticks in a bucket when they are ready to give them up. Of the 28 squeegee workers who participated, not one has picked their squeegee back up, Simmons said.

When a young person puts their stick into the bucket, it shows that they are really dedicated to learning a new way of life, according to Hill.

“It shows you, ‘I’m really trying to see stuff from your perspective, I’m trying to fill those shoes,’” he said.

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It also creates a sense of integrity. They are making enough money to buy a new squeegee but are trusted to keep their word, he said.

The program’s effectiveness is significant in a city that has tried for decades to eliminate squeegeeing, a heated issue that came to a head in July 2022, following a fatal shooting in which a teenage squeegee worker was charged. The 16-year-old was convicted of voluntary manslaughter last week.

After the shooting, a group of city, business, and community leaders called the Squeegee Collaborative launched a new effort to reduce squeegeeing. The plan, which went into effect in January, emphasized connecting squeegee workers to jobs, education and other services, and enforcing bans at certain high-traffic intersections where squeegeeing is common. Nearly seven months in, city officials say there has been significant progress, but some work remains.

Kahlil Nottingham, 19, holds his squeegee, which he gave up from the start of his time with From Squeegee To Success. (Heather Diehl/The Baltimore Banner)

From Squeegee To Success is part of a nonprofit organization called HeartSmiles, which works to help young people from underserved communities succeed by developing their leadership skills and providing mentorship, career opportunities and other support. Joni Holifield, the organization’s founder, came up with the idea and asked Simmons and Hill, who both joined HeartSmiles in 2020, to design and manage it.

Four participants attended Simmons and Hall’s first session. In just a few months, the group grew to 30, as people brought their friends, siblings, spouses. There was so much interest that the program ran out of money. HeartSmiles received American Rescue Plan Act funds and, in the first year, allocated $16,415 to From Squeegee To Success. With no money left, the program had to fold in April. It will start up again after the organization’s funds are renewed, Holifield said.

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Hill and Simmons designed lesson plans on many different topics. They hoped to expose squeegee workers to a different way of making money.

One session, they assigned mock business ideas and tasked participants with designing each business from the ground up. At another, participants wrote down and shared their values. The group acted out scenarios focused on emotional maturity. In a situation where Nottingham and his partner pretended they’d bumped into each other on the street, the group discussed de-escalation.

Participants also practiced job interviews and writing a resume and a cover letter, Hill said.

The managers learned about each young person individually. “What is your version of success?” they’d ask.

HeartSmiles has connections with local businesses through the Goldman Sachs 10,000 Small Businesses program in partnership with Bloomberg Philanthropies. A man has given them access to a music studio in East Baltimore. The group is working on a culinary school, where young people can learn from a certified chef.

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“We have some musicians out there that want to make music. OK, we have a studio for you. You want to be an artist? We know people,” Simmons said. “Whatever you want to do, we can do our best to get you to your version of success.”

Nottingham, who has participated in other programs designed for young people, said this one is special.

“This was the only one that actually made me give up my stick and take a chance, step outside my box, outside my comfort zone, actually want to learn different opportunities,” he said.

At the start of the From Squeegee To Success program, participants can give up their squeegees to hold themselves accountable to no longer wash windows for tips. (Heather Diehl/The Baltimore Banner)

What made a difference was that young people were leading the program.

“That really spoke to me more,” he said. “I could actually learn things from people that’s in the same age range I’m in ... and we come from the same struggles and things, so I can relate to them more.”

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The program also created a sense of accountability, he said.

After Nottingham gave up his stick, he felt that continuing to squeegee would be like “not being honest with them,” he said. “You get a choice if you want to be here or not, so why would you choose to be here but actually going right back to being outside?”

And the program felt like family, Nottingham said. He gained a support system of people who cared for him, who he can now turn to for opportunities, for advice, or even to talk about things such as his mental health.

Cultivating that sense of family, Hill said, was a priority. When young people have others to lean on, “it makes them feel more inclined to actually try, regardless of the risk,” he said.

After each two-hour session, there was a third “personal hour.” Participants could be open during that time about anything they might be struggling with.

Outside of lesson hours, participants could call Simmons or Hill if they needed anything. Simmons has gotten calls about family, friends, food, housing. He once got a call at midnight from a young person who had no way to get home and needed money for a Lyft. When another participant couldn’t pay for transportation to prom, they offered to pay.

“We are there for the big moments, for the little moments, whatever, 24/7,” Simmons said. “This is a family, not just some program.”

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