Optimism Wins the Day

Chesapeake Charities, a community foundation located in Stevensville, is partnering with Attraction magazine to share the stories of individuals and organizations in our community who make a difference. We encourage you to look for the good in others.

Ever wonder how someone you admire developed the character and determination to remain positive and find the silver lining in a difficult situation? Nine times out of 10, they learned these skills by watching someone important to them model this behavior.

For Robert Woolley, the founder and owner of The Edge Training Academy in Stevensville, seeing the good in others and being good came from his grandmother. The love between grandparents and grandchildren is special, and it was during the summer months with his grandparents that Robert adjusted to the challenges of a divided family after a divorce. Although “Mom-Mom” suffered from health issues that challenged her mobility, she never let these limitations distract her from what she wanted to accomplish. It was a powerful lesson for a young boy, and it firmly anchored Robert’s positive outlook in place.

By the time he got to high school, Robert had leadership ability and an innate resiliency to the challenges he encountered. Some of these challenges came in the form of sports injuries caused by Robert’s aggressive style of play. His football coach at Kent Island High School appreciated Robert’s tenacity, but encouraged him to channel his efforts into lacrosse, as it was a better fit for him physically.

Today Robert realizes that this one decision, to move from football to lacrosse, changed the trajectory of his entire life for the better. Approaching lacrosse with the ruggedness of a football player gave Robert a winning edge. He began to notice how physical and mental preparation affected attitude and how attitude was often the key to winning a close game.

Realizing that many of his high school teammates who were gifted athletes failed to move into college sports, Robert’s mission became to build an environment that would foster the growth of local student athletes, helping them create opportunities for themselves past the high school playing level. In 2013, Robert opened The Edge Training Academy with the initial goal of sending just one athlete each year to college to pursue their sport at the NCAA level. True to form, Robert quickly exceeded that goal and, as a result, hundreds of high school athletes have successfully advanced to pursue their dreams of playing at the collegiate level and beyond.

Never one to settle for good when great is just around the corner, Robert realized that what worked for athletes could be applied to people from all walks of life. He moved to a larger facility with a full gym and court space where he is able to provide the resources, opportunities, and support to help people of all backgrounds pursue their dreams and reach their full potential, whatever that means for them.

Behind the scenes, Robert created the Giving The Edge Foundation, a component fund of Chesapeake Charities that has been a driving force for positive youth activities in the community. Kickstarted by a generous anonymous donation, the foundation’s focus is on empowering the next generation to be of service to the community. The Foundation is able to keep programs at The Edge financially accessible and scholarships are available for those who need them. Robert believes that providing kids with opportunities and support to grow will lead them to become successful, caring, responsible, and productive adults who will in turn carry on the mission of giving back and helping others.

Robert lives by the motto, “Win the Day.” A “win” is measured by how successful he is in creating the necessary resources so that others can grow and succeed.

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Allison Rogers



Attraction Magazine

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