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    « Excerpt from Chapter 18: Harvard | Main | Excerpt from Chapter 16: The White House »

    Excerpt from Chapter 17: City Year

    One day after lunch, I was walking back to the office and ran into one of my former Co-op advisors from Northeastern. Janice had recently left the university to work for an organization called City Year. Michael Brown and Alan Khazei, roommates at Harvard Law School in 1988, founded City Year because they felt strongly that young people in service could be a powerful resource for addressing America's most pressing issues. Together they built City Year with the conviction that one person can make a difference; and since its inception, City Year has promoted the vision of service as a common expectation—and a real opportunity—for citizens all around the world. City Year’s vision is that one day the most commonly asked question of a young person will be, “Where are you going to do your service year?” Currently, City Year is serving in 25 cities across the United States and in three international affiliate sites located in Johannesburg, South Africa, Birmingham, England, and London, England. They are known for their red jackets, sense of idealism, and strong organizational culture. Many times on my way to work, I saw over 50 energized and enthusiastic young people with bright red jackets, khaki pants, and boots doing morning military-like calisthenics called PT on Copley Plaza. Rain or shine, wind or snow, they were out there. I was inspired by their spirit, discipline, purpose, and pride for the work they did throughout the community and thought City Year might be a better fit for me. I liked the image of working in a corporation, but I also wanted to work within the community helping the poor and other kids who grew up the way I did.

    My former Co-op advisor introduced me to a woman named Nancy Routh, who was the Director of Human Resources at the time. Nancy was looking to grow her HR department, and my generalist position at John Hancock and my HR degree from Northeastern were a perfect match. Almost six months later, before my next formal review with Diane, I resigned from John Hancock and accepted a position with City Year. I would be working with Nancy in Human Resources, making more money working in a nonprofit than I was receiving at John Hancock. The pay surprised me, but Nancy shared that City Year was looking to recruit top talent and was willing to compete with the for-profit sector to get the right people on board. Without looking back, I walked away from John Hancock, leaving the start of my corporate insurance career and Diane’s iron fist of poor leadership behind.

    The move to City Year felt right; the staff I worked with appreciated the skills I contributed. Not long after being hired, Nancy offered me a lateral move to become a Team Leader, overseeing and managing six to eight corps members. “Doug, I have been watching you since you started here, and I’m impressed with your attention to detail and professional sense of urgency. I think the role we have you in is great but will not get the best out of you. I would like to provide you with an opportunity where you can utilize your leadership skills and work more directly with our young people in the community,” Nancy persisted. This would be my first formal supervisory role and would give me greater exposure in the company as a burgeoning leader. It was hard to believe that Diane had told me at John Hancock that I was a procrastinator and had poor time management, and now in my new job, I was being asked to play a greater role. If Diane only knew, I thought.

    Being a Team Leader was more challenging because I worked with young adults, ages seventeen to twenty-four, who were working on their GED, had a high school diploma, had some college experience, or were college graduates. The young adults had different maturity levels, work experiences, and intellectual capacities. With nervous enthusiasm, I spoke. “So, hi, everyone. My name is Doug, and I will be your new Team Leader for the rest of the year.” The team looked at me with blank stares plastered on their faces; it was clear that we did not all share the same excitement. On cue, the team looked toward Jonah—the pseudo- Team Leader.

    He recognized the attention, stood, stepped forward one foot, and spoke. “You are the third Team Leader we’ve had in the past four months. I guess we are glad to have you, but I’m compelled to ask: will you be with us for the remainder of the year?” His voice was steady and stoic, but he wore an apprehensive and nervous look on his face, as if to say he wasn’t convinced I was there to stay. “I can tell you that I just joined City Year, and I don’t plan on going anywhere, so I hope you guys will at least give me a chance.”

    The team looked up to Jonah and trusted him, so I knew very early on that in order to make progress with the team, I had to get Jonah on my side as quickly as possible. City Year was an organization that believed in order and structure and had strict policies regarding being on time, wearing a neat and clean uniform, and wearing your nametag on the top right side of your shirt. If corps members or staff showed up late, were out of uniform, or forgot their nametag, they were written up. After three write-ups, corps members and staff members would be put on probation and risk being released by the organization. The first week, I wrote down infractions but did not formalize them. It was my way of showing the team that I meant business but that I wanted to make sure we were all clear on the expectations before I upheld existing parameters.

    The second week was a different story. At physical training, or PT, that Monday, I noted two members who arrived after we started. Once the exercise was complete, I pulled the team aside and explained the rules, the process, and my detailed notes regarding the previous week. “Someone once told me that if you are 15 minutes early, you are on time. If you are on time, you are late. And if you are late, you are fired. After today, if you are going to be late you need to call me. If you don’t, I will mark you down as a no-show, no-call, and you will be written up.” Immediately, there was push-back by Jonah. “Written up? You just got here and already you are trying to be Mr. By-the-Book Team Leader? Give me a break . . . I’m out of here!” He turned on his heel, his chin in the air, and walked off. I called after him. “Fine, Jonah. If you walk away, I will have to write you up for insubordination and for leaving our team circle.” But Jonah kept walking.

    I turned my attention to the rest of the team. “Does anyone else want to leave?” To my surprise, no one else left, even though they acted like they wanted to by looking in Jonah’s direction; some rolled their eyes while others huffed with a sigh of frustration. It was then that I realized that their alliance was not as strong as I thought it was. Later on that evening, after I ate dinner and had some downtime, I decided to give Jonah a call. Not really wanting to deal with the confrontation, I sat at my kitchen table and slowly dialed each number, and then took a deep breath when I heard the call go through. “Hello, Jonah, this is Doug. I find it ironic that you questioned me about walking out on the team and then you walked off when you heard something you didn’t like.” “Well, you became our third Team Leader and then within a week, you went on a power trip. You don’t even know who we are,” Jonah fired back.

    I cleared my throat, careful about the words I would use. “Listen, I just started working here, and I’m following the rules set in place by the organization. Our team needs order, structure, and accountability, and it is my role to make sure that happens. You can either help me or you can leave the team, because there is only room for one Team Leader.” Jonah’s frustration was palpable through the phone. “Is that a threat?”“No, it is a promise. But . . . I hope you will work with me to lead the team, because I need your help, Jonah. Give me a chance and see what I can do by backing me, bro. Can you do that?” I protested as the seriousness of the conversation lifted me out of my chair to a standing position. The tone of my voice was firm yet hopeful that Jonah would join me. Dead silence paused our conversation for so long that I wasn’t sure if the phone had died. “Hello, Jonah. Are you still there?”

    His voice dropped, an unhappy reconciling with the reality of accountability confronting him. “Yeah, I’m still here, but I have a lot to think about tonight to see if I want to still do this.” I exhaled relief. “Okay, I can respect that and want you to have that time. If I see you tomorrow, I will consider that you are with me on this. Thank you for taking my call.” And with that, we hung up. When I set the phone down, a lump filled my throat. I wondered if Jonah would be willing to work with me. He was a leader, and I really wanted to work with him—growing our previously leaderless team and him. Even though I was on the verge of strong emotion, I was confident I could do it with the right people surrounding me. I went to bed that night dreading the worst—that Jonah had called the other team members after our call and that no one would show up for work the next day. Despite my confidence that I handled it the best possible way, I tossed and turned, questioning whether leaving John Hancock was a wise career move. I realized that being in a leadership position is one thing, but becoming a leader is another. I was starting to learn that being a leader might also mean being misunderstood.

    The next morning, there were no messages from him or any of the other members. Right away, I concluded the worst: that they had bailed and that I was down to a team of one: me. At work before the morning program, other teams huddled and stretched together, but I stood alone. I replayed the conversation I’d had with Jonah the night before until it was a broken record. Was I off target with what I shared with him? Was I wrong to push him so hard? I sat down on the cement staircase and questioned my leadership and fit with City Year, the lump from last night returning to my throat. I looked up and shaded my eyes to avoid the beam of sun on my face, and off in the distance, Jonah clipped his way towards me, each team member behind him in single file. I sat there motionless and smiled on the inside, but my pride would not allow me to show it. The image of him leading the team towards me was a sign of the changing of the guard. My words had impacted him, and he now seemed receptive to letting me lead. I stood up, and when he was within a few feet, I first extended my hand to him, looking him directly in the eyes, and and then pulled him to me to show gratitude for him trusting me.

    I said good morning to each team member and gave them each a hug, too. Then we circled up. “Thank you guys for coming this morning! It means a lot to me. Now let’s get to work!” The big smile covering my face from ear to ear made the team smile and laugh, too. Our team worked at two different sites each day. In the mornings, after we finished all organizational affairs, we headed to Boston City Hospital where we worked in various departments. In the afternoons, we worked at an afterschool program called The Shelburne Community Center, serving as tutors, mentors, and recreational aides. We ran a homework assistance program, and once homework was completed, we led various athletic activities such as basketball, dodge ball, kickball, volleyball, and capture the flag. We had a two-hour break to travel from one site to the next via public transportation and ate lunch along the way. During the travel time between both sites, I gained the best insights on each of my team members.

    City Year changed my life and helped me realize my purpose in life! To read more about my City Year experience go to Amazon and order your copy of Watch Me Rise: From the Streets of Despair to the Halls of the Ivy League today.


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