Wolley previously worked with Outward Bound Adventures based in Pasadena, California, helping students get outdoors and backpacking with high school students from Los Angeles in the Mojave Desert in California. He also supervised crews and coordinated education of outdoor projects as part of the California Conservation Corps. After relocating to Oregon for his graduate degree, he returned to the Bay Area, did additional conservation corps work in career development, and worked for the Nature Conservancy as the organization's first Black Preserve Manager. Upon returning to Oregon, Wolley taught science and environmental education at the Oregon Museum of Science and Industry (OMSI). Wolley then served with the U.S. Forest Service at Mt. Hood National Forest as a Forest Planner and Conservation Education Manager (1989 – 1996). As a Forest Planner, he managed the planning timeline for an interdisciplinary team that published the Mt. Hood National Forest Final Environmental Impact Statement and Forest Plan, where he was the lead writer and editor. As the Conservation Education Manager in the Public Affairs Office, Wolley managed the regional natural resource education program serving the Portland Metro Region through collaborative partnerships and directed the Urban Rangers program, an eight-week summer program in partnership with Portland Public Schools.

Additionally, he co-directed the High School Conservation Leadership Conferences that ran for five years. In 1996, he joined the Metro Regional Government as a Regional Natural Resources Planner, where he managed natural areas in the Portland Metropolitan Region, developed natural area management plans, oversaw staff and contractors, coordinated restoration and permitting, and wrote grants. Wolley served in the role for five years before joining the Tri-County Metropolitan Transportation District of Oregon (TriMet) as the Community Affairs Coordinator (2001 –2003). His responsibilities in this role included coordinating outreach and communications, developing business survival strategies for those impacted by the construction of the Interstate MAX light rail, and collaborating with other partners.

Wolley joined the City of Portland as the Small Business Marketing Manager in 2004, where he drew on his expertise from previous roles to manage marketing and outreach programs, including, but not limited to, advertising, special events, and training. In this role, he collaborated with the Portland Community College Small Business Development Center and the SBA Service Corps of Retired Executives (SCORE) to deliver training and assistance to small businesses. Wolley was promoted to Training Manager in 2013, where he was responsible for city-wide professional training. This training included instructor recruitment and hiring, co-developing training, and delivering curriculum. Courses taught covered topics such as sustainability, small business management, and equity and inclusion. The curriculum included a wide range of work skills and safety training to improve employee competence. His responsibilities expanded when he was promoted again to Training and Workforce Development Manager in 2015, where he hired, trained, and managed a team of seven professional staff. He also developed an internship program for college students at Portland Clackamas Community College to learn hands-on about the operations of a building permitting agency. Wolley worked with the City of Portland for almost 13 years, from 2004 to 2017. While still in the City, Wolley was appointed as a State Commissioner for the Oregon Department of Fish and Wildlife, where he was the first African American to serve in the role (2012 – 2021). As Commissioner, he helped guide policy decisions to enhance the department's mission to preserve fish and wildlife and their habitats for the use and enjoyment of future generations. Additionally, he conducted performance reviews of the State Director and was part of the review and approval process of the biennial agency's 280 million dollar budget from 2021 to 2023.

Wolley is the Principal Consultant at Creating Tomorrow's Workforce, a consulting firm he founded in 2018. He brings his extensive background in planning, workforce development and training, and natural resources management to the role. Wolley is also the Co-Founder of the African American Outdoors Association (AAOA), an organization founded in 2005 that promotes outdoor recreation to improve mental and physical health among the African American community while fostering connection with one another and the environment. The Association conducted hikes, ranging from easy to more strenuous, and other recreational activities, including canoeing, cycling, snowshoeing, and cross-country skiing. The Association has received grants from REI, Enterprise Rent-A-Car Foundation, and the African American Chamber of Commerce Black United Fund to help support outings and ensure they are accessible to all. The AAOA has since transitioned its resources to People of Color Outdoors (POCO), which is also based in Portland. Wolley has served on numerous boards as director and advisor, including the Columbia Land Trust, Oregon State University Extension Service Outdoor School, and Zenger Farm. He received Southern Oregon University's Alumni of the Year Award in 2021 for outstanding dedication to service to the community and Southern Oregon University.

Wolley is most proud of mentoring young professionals of color in navigating their natural resources careers and exposing new audiences to the physical, health, and spiritual benefits of communicating with nature. A high point of his career was teaching environmental education in Swaziland as a Peace Corp In-service trainer. While the organization doesn't preach health during outings, these conversations naturally come up, which is one of the main reasons why he founded the organization – to improve health among the African American community. Moreover, he is proud to create and support sources of community.