When Dianne Morales graduated from college with a bachelor’s degree in psychology, her plan was to make a career of working directly with troubled teens. And at first, she did. Morales, who is now CEO of Phipps Community Development Programs in New York City, worked for a year as a case manager for the New York City child welfare system and then for a year as a special education teacher in a New York City public school. What bothered her in those two positions, however, was the clear message she got from her supervisors at both of those jobs: They really didn’t care what she did with the kids as long as she kept them quiet.

“When my assistant principal told me to keep the door closed and the kids quiet, I literally thought to myself, ‘I am going to come back here and be your boss,’” Morales said. She decided then and there to shift her career plan from direct service to a more macro approach where she could change the systems that affected at-risk children.

The best way to develop management and finance skills quickly was to attend graduate school, Morales felt, so she earned a master’s in social work administration from Columbia University. While there, she deliberately chose field service assignments that would bolster her business skills—like budgeting and administration—rather than more traditional clinical social work roles. Upon graduating, she landed a job as director of planning and policy at a community action organization, where she immersed herself in issues ranging from housing to early childhood education to substance abuse.

Not every career move she has made has been the right one, Morales reflects, but she has tried to learn something from every role. For example, after working at the community action organization, she joined a for-profit research consulting firm. While the content—conducting national studies of HIV in women—was right in line with her interests, she realized pretty early on that in that position, she felt too far removed from the people affected by the research. However, making the best of the situation, she stayed on long enough to learn some valuable skills, including finance management, administration, and budgeting.

All of which she needed for her next career move, becoming a founding member of the Jumpstart early education program, which reconnected her to her passion for improving the lives of children. At Jumpstart, Morales was in charge of building the systems that were required to get the organization off the ground and that would also allow the model to be replicated. She later worked as an executive director of East Harlem Block Schools, as part of Mayor Michael Bloomberg’s transition team for New York City public schools, and as the executive director of The Door. (Ironically, Morales had participated in The Door’s programming, on the receiving end, as a high-schooler).

Morales left The Door to join an anti-poverty start-up that was going national, but quickly realized she was once again too far removed from the people affected by the mission. “I guess I didn’t learn that lesson the first time,” she said. But the experience prompted her to develop a list of what was truly important to her and what was not okay in a job—an exercise that has served her well.

She knew that she needed to move into a position that would put her closer to the people and causes she was passionate about. But with her list in hand, she didn’t jump at the first opportunity that arose. When she interviewed at Phipps, which develops on-site and neighborhood-based social, education, and career services, she had as many questions for the interviewers as they had for her. “I came loaded for bear  and that made a difference,” she said. “I’ve been here for 10 months now and I’m totally convinced it’s the right place.”

The role at Phipps interested her because the organization was an established, healthy institution looking for a leader who could rebuild and strengthen its internal practices. “It very much feels like a start-up, and I’m getting to lead that process,” Morales said. “I’ve learned that I want to be able to lead and to be responsible if an organization succeeds or fails. This job is the best of all worlds, and it incorporates all the skills I’ve developed over time.”