For teenagers growing up on the city’s Eastside, it can be difficult to imagine a future as a CEO, an entrepreneur, or a trailblazer in an aspirational profession. It’s not that the path looks difficult, many of them are accustomed to overcoming difficulty. The missing piece of the puzzle is the possibility. The idea that dreams, even big ones, are worth having.

The Eastside Dreamers Academy, housed at the Eastside Boys & Girls Club, plans to change the conversation about dreams for underserved teens ages 13 to 17. Rather than portraying dreams as unlikely fantasies that magically come true – or more often do not – teens are encouraged to view dreams as life-shaping ambitions that can realistically be achieved.

Through mentoring and site visits with local leaders, students will get a taste of the many possibilities and pathways toward accomplishing their goals. 

“We’re going to be exposing them to those wonderful futures that are just sitting there waiting for them,” said Winslow Swart, program facilitator and CEO of Winslow Consulting.

Winslow Swart and Councilman Alan Warrick (D2) staffer Millie Ernestine at Eastside Boys and Girls Club. Photo courtesy of Winslow Consulting.
Winslow Swart and District 2 staffer Millie Ernestine at Eastside Boys & Girls Club. Photo courtesy of Winslow Consulting.

The program, a pilot with, helps students build confidence through “small wins.” It teaches them to develop small dreams – like personal success – into big dreams – like affecting change in the community and beyond. They are encouraged to think of goals as stepping stones toward something that is always growing.

“Even small dreams (are) not just a goal,” Swart said.

Swart engaged the Eastside Boys & Girls Club staff to help identify students who excel in school as well as those who might fly under the radar. For five weeks they will work toward identifying their dreams and meet with mentors to discuss strategies, pathways, and other possibilities they had not yet considered. One day per week they will visit local leaders in their workplaces.

This week the 30 students enrolled in the program will tour the Toyota Factory. They will discuss entry level jobs and how to progress in a company like Toyota. Later this summer they will visit the San Antonio Zoo to hear CEO and Executive Director Tim Morrow speak about the importance of civic and conservation organizations. They will visit VIA to learn about the role of public transportation, Rackspace to learn about the growing technology sector, and Geekdom as an introduction to the world of startups.

On a visit to University of Texas at San Antonio, the students will not only tour labs and discuss research, but talk to admissions officers to help “de-mystify higher (education),” Swart said.

With each visit, Swart hopes that students will understand that career paths are available at multiple entry levels, not just for straight-A students. Beyond that, he wants to attach those gateway goals to the dream of making the world better by leveraging their growing influence along the way.

“It’s not just careers, it’s also about finding your voice and influencing policy,” Swart said.

For many disadvantaged students, their environments demonstrate a particular ecosystem of influence and agency. Their basic needs and desires for self-determination, economic security, and relational capital can lead them to idolize people who have found those things in illegal or destructive avenues.

Swart said the futures students really want – ones that go beyond their human needs and inspire their imaginations in ways that also strengthen their communities – are not often the ones they are told they can achieve.

“A lot of their parents and teachers have stopped dreaming a long time ago,” Swart said.

The program will not only put the students in contact with staff members who are themselves participating in the Dreamers program, but also will help them create a peer network of support. While the students are in different classes at different schools, the hope is that they will remain in contact with one another. The program does not downplay the fact that many student will face significant obstacles. In fact, it addresses the fact that setbacks and occasional failure are part of almost any pathway to success, because at some point, constructive risk-taking is necessary.

Alan Warrick and Winslow Swart mentor their a staff member Christian during the Dare2Dream project.  Photo courtesy of Winslow Consulting.
Alan Warrick and Winslow Swart mentor their a staff member Christian during the Dare2Dream project. Photo courtesy of Winslow Consulting.

Swart credits City Councilman Alan Warrick (D2) for being “the catalyst” and spearheading the effort as well as the collaboration with the City of San Antonio Parks and Recreation Department. While businesses and social services play a large role, getting the City involved completes the picture, he said.

Warrick has adopted the Dreamers approach with his staff at City Hall and wants to see the mentality take root in areas ripe for change. Swart sees Warrick as a leader who can work within the realm of bureaucracy and yet challenge it to be better.

Swart also turned to Ramiro Cavazos, president and CEO of the San Antonio Hispanic Chamber of Commerce, to lead the program. Through the chamber’s Hispanic Leadership Development Program, Cavazos will provide accountability and oversight for the Dreamers program. His work as board chairman of the San Antonio Housing Authority under mayors Hardberger, Castro, and Taylor gave him years of experience as well as knowledge on public and private investment happening on the Eastside.

“I think it’s really the last piece of the puzzle,” Cavazos said. “Not just the capital investment and physical assets, but the brain power.”

For longtime advocates on the Eastside, accountability is a welcome asset. The partners are focused on building momentum and investing in leaders and ensuring that Dreamers doesn’t become a banner project.

“Hopefully it’s the first of many years we do this in District 2,” Cavazos said.

Swart and Cavazos both expressed their hopes that the program will extend beyond the initial Eastside chapter.

“As we build on the successes of this program, we can build on it for other districts,” Swart said.

Future scaling also is in the works for After this human pilot, the program hopes to expand to a digital social platform.

Following the announcement Photo Editor Scott Ball traveled with the Eastside Dreamers Academy along with District 2 Staff to the Toyota Motor Manufacturing facility and City Hall.

Top image: Councilman Alan Warrick (D2) talks with Eastside Dreamers about their future careers on the way to the Toyota Motor Manufacturing facility on the city’s Southside.  Photo by Scott Ball. 

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Bekah McNeel is a native San Antonian. You can also find her at her blog,, on Twitter @BekahMcneel, and on Instagram @wanderbekah.