I didn’t know that ambition could be a dirty word until well into adulthood. I was further shocked to learn that it was a downright insult if said about a woman. On one hand, I want to put gender issues aside; on the other hand, we can never put gender issues aside. I reflect on the negative words used to describe ambition: headstrong, stubborn, opinionated, selfish. Then there are the more positive words: hungry, motivated, smart, goal-oriented. As I was growing up, I heard more of the negative words used to describe my ambition, and it’s not lost on me that the positive words were used to describe my brother and other boys and men in my environment.

Infuriating as it is, this kind of pushback didn’t stop me nor countless other women from forging their own path toward leadership. Now in the middle of my career, I claim the title ambitious. I want to be the best possible head of school, I want to make a meaningful impact, I want to take risks that move our community forward, I want to be at the very top of my game, and I am willing to work hard to do this. I am hungry, headstrong, opinionated, smart and motivated.

Where does ambition stand in the world of Jewish leadership?

A search in our Jewish texts results in negative responses such as this: “Rabbi Eliezer HaKappar said, ‘Envy, desire, and ambition drive a person from the world’” (Avot 4:21). I asked text-savvy scholars for their input. One explained, “The thrust of Jewish thought centers around values, which could be construed as opposite to notions of ambition.” Our tradition doesn’t seem to hold ambition in high regard and doesn’t speak of it directly very much.

I find it difficult to square this with notion of the Jewish community and its commitment to education. At least in a modern sense, the pursuit of knowledge can easily be understood as ambition, and certainly the history of Jews in the United States is marked by high academic distinction and upward mobility. Is it not ambition that drives a pursuit of education and good employment? I am at a loss in understanding the Jewish cultural response to ambition and its lack of visibility in Jewish thought. As I look for examples of ambition in the Torah, I think about Moshe who didn’t want to be a leader, Yosef who insisted that all success comes from God, and David, perhaps the most ambitious, who didn’t get to build the Beit HaMikdash. Yet again, ambition is not presented in a positive light. Moshe, possibly the least ambitious, is hailed in Jewish thought as the paradigmatic teacher, Moshe Rabbeinu.

Perhaps ambition is best conceived as neutral, objectively neither good nor bad. Rather, the worthiness of ambition is better determined by asking, For what are we striving? What are we ambitious for? For me, the primary question is, Am I ambitious solely for myself, or am I ambitious on behalf of my community? While this dichotomy may sound appealing, it is surely too simple; ambition should be both for oneself and for something larger. Instead, I see ambition falling on a continuum between the individual and community. While it seems clear to me that ambition for myself, alone, lacks moral and ethical grounding, and can lead to pain and suffering of others, it illuminates for me the question of whether one can be ambitious solely for the other, for the community without the self. I am drawn back to Hillel’s famous quote, “If I am not for myself, who will be for me? If I am only for myself, what am I?” This reminds me to reflect on balancing my personal and communal interests, so that I find the room to include myself in my community’s needs.

For me and my work, ambition has been the toggling back and forth between moments of certainty and humbling reflection, between knowing what is right and wondering if I am completely wrong. Ambition forces me to be disciplined and exacting with my own reasoning and goals. My ambition pushes me forward through this discomfort; it opens me up to further listening and collaboration in order to garner wisdom from others.

A recent, significant change engaged all of these aspects of my ambition. Our school just went through a major educational transformation: We remade ourselves into a progressive, multiage learning school. When I first presented this vision to the board of trustees, I took a particular approach, showing them the future of education, our need to respond to it and what I believed was an inspiring goal. I entered that room with high confidence in both the vision and the presentation. When I finished, there was silence, confusion, then nonstop questions. I had completely missed the mark.

Eventually, I went home as the board continued its conversation. This was the moment of ambition, right between certainty and doubt. The board had committed to coming together for a follow-up presentation. Over the next few days I spoke with several board members, the co-presidents, my coaches and family. I rethought my approach, what was needed from me as a leader and a better understanding of my audience. At the next meeting, I walked in with a new sense of clarity, knowing that I had the right data for the right audience, that my belief in the vision was steadfast, and that because I listened carefully, my chance of success had grown significantly. At the end of the meeting, the board voted, unanimously, for this bold and big change.

Labor organizer Cesar Chavez explained, “We cannot seek achievement for ourselves and forget about progress and prosperity for our community. ... Our ambitions must be broad enough to include the aspirations and needs of others, for their sakes and for our own.” In light of how ambition plays a role in my life and leadership, Chavez’s quote rings clear. My first presentation didn’t include the needs of my audience; in that moment that I call ambition (between certainty and doubt), I discovered those needs.

While this was a decisive moment, there have been countless such moments for me as a leader; they happen in daily conversations with faculty, administrators and parents. I have tried tempering going in strong, a vestige of emotion from being called opinionated, stubborn and headstrong. I value the process that brings me to that moment of ambition, when I take the strength of my conviction and grow it to expand and make room for others, so that I can work and fight harder for my students and my community.

I now understand that my ambition was and remains far greater than me. My ambition is to help Judaism evolve, it is to help guide students and families toward a kinder, more welcoming, more inclusive, low-barrier, high-creativity Judaism. I want to help build a school that graduates students who are ready to co-create the Judaism that will be through a lens of progressive, innovative and inquiry-based education. Those are very real and very ambitious goals on behalf of our future. Whether I succeed in any or all of these goals remains to be seen. The only certainty is that without this drive and ambition, I wouldn’t even be trying.

Andrea Kasper
Leadership Dispositions
Knowledge Topics
Professional Leadership