A few months ago, I was talking with a friend I’ve known since elementary school. He’s going through a career transition and shared with me something his therapist told him that has stuck with me ever since. At our age (I’ll be 52 in December), we need to realize that we’re no longer Luke Skywalker, we’re Obi-Wan Kenobi. I laughed, nodded my head, and pleaded to be Han Solo. After all, Han has both the wisdom of experience and the moves to get in the fight (if he so chooses), while Obi-Wan has retreated to Tatooine, becoming old “Ben,” a hermit who appears to have no ability or interest in immersing himself in the battle.
Today, I’m hardly a hermit, but I’m no longer a school system leader who wakes up at 5 a.m., puts on a suit and tie, and works until 10 p.m. when the school board approves its final motion or I finish talking with constituents. A lot has changed, on multiple fronts. When I became a superintendent of schools at 35 years old, I was always the youngest (and the tallest) in the room. But when I came down to Maryland at age 41, I met Khalid Mumin, who was then superintendent of Caroline County, Maryland. Khalid is both younger and taller than I am, and when we first met I half-jokingly lamented to him that he had just stolen two parts of my core identity. That joking observation was the beginning of a realization that, while I was still young for my position, my relative youth could no longer define my leadership.
Today, I’m incredibly fortunate to have embarked on my second career of running a nonprofit and writing about leadership and change management at a relatively young age. In fact, my current position is exactly the work I imagined I’d be doing after leaving Montgomery County, Maryland. It happened a little sooner than I expected, but it’s all worked out incredibly well as I’ve been able to carve out a new career that builds on my previous experience.
As my friends of a similar age and I have talked about this stage of our lives and careers, we’ve found the idea of becoming Obi-Wan a compelling metaphor for where we find ourselves. We aren’t done working, not by any stretch of the imagination, but what made us relevant in our 30s and 40s may not be our strengths in our 50s and 60s. But what, exactly, does it mean to move from apprentice to master?
Lessons from Star Wars
When I first saw Star Wars in 1977, in the theaters, I was immediately enamored, as most 7-year-olds were back then. Over the years, I’ve shown the first three movies (episodes IV, V, VI) to my kids many times, bristled at the reboots focused on Anakin (episodes I, II, III), and thoroughly enjoyed the most recent episodes and off-shoots. I admit that I was never Star Wars obsessed (and I know that many readers will pick apart the details of my Star Wars metaphor). Yet, the movies were such a foundational part of my childhood (and of American culture) that I can’t help but use them to explore what it’s like to evolve as a leader.
What, exactly, does it mean to move from apprentice to master?
One of the most obvious lessons of Star Wars is that no one succeeds alone. We all know this, but too many leaders try to push an agenda by themselves. It took me time to realize this during my first superintendency, and I’ve always struggled to balance the boldness and passion that are necessary to lead others with a willingness to be led by them. There’s no algorithm that will tell a leader when to push forward and when to pull back and let others speak. But when you work with capable people, you’d be foolish not to listen.
When Luke goes after the Death Star in Star Wars: A New Hope, he seems to be acting recklessly by turning off his X-wing’s targeting system. But Obi-Wan’s voice in his head reminds Luke to use the Force to find his target, and hit the target he does. Because he trusts Obi-Wan to steer him in the right direction, he is able to take bold actions that aren’t in the playbook. A great team includes many voices like that. When superintendents are out in the community or in front of the school board promoting a new idea, they aren’t just speaking for themselves; they’re channeling the collective wisdom of their colleagues and mentors.
The original Star Wars movies don’t give us Obi-Wan’s perspective, but he models a kind of sagaciousness that rubs off on other people. He doesn’t tell Luke what to do, so much as he asks him important questions and challenges him to consider big ideas. In my experience, too many leaders think that their job is to have all of the answers, and certainly, there are times when they have to be decisive. But the real power of leadership rests in the ability to model certain kinds of behavior, encouraging others to listen carefully and act wisely in the face of complex problems.
Great leaders also know their limitations and understand that someone else may be a better messenger. When Obi-Wan (in his ghostly form) realizes that Yoda would be a better teacher for Luke, given the circumstances, he sends Luke to him. From then on, Yoda takes the lead in Luke’s education, with Obi-Wan stepping in only occasionally to provide support. All too often, superintendents think they have to be the only ones who tell the district’s story or communicate a vision for the future. But as Obi-Wan shows, there’s no shame in stepping aside and giving that role to someone else who will excel at it.
However, the most poignant of Obi-Wan’s actions occurs during his battle with Darth Vader. He knows he’s going to die. In fact, he sacrifices himself, knowing that he must do so in order for the others to succeed. That is, he understands when it’s time to pass the torch to someone who is better able to continue the mission. Unfortunately, though, many (perhaps most) superintendents never have the opportunity to create and implement a succession plan. School boards are fickle creatures, and when choosing a new leader, they often look for someone who will strike out in an entirely new direction, no matter the progress that the previous leader had made. But for board members who do recognize the value of continuity, there are some great examples to consider — such as California’s Long Beach school district, where a series of superintendents has moved forward with a well-crafted improvement strategy launched under Carl Cohn in the 1990s. Ideally, it would be the norm for all boards to ensure that every new generation of leaders has the knowledge, vision, and skills to expand upon whatever good work is already in progress.
Looking ahead
As I enter my 17th year as an organizational leader (10 as a superintendent of schools, six at PDK), I know that the work is never done, and that my job is to build capacity, with an eye to the future. I find myself constantly torn between the urge to take decisive action, on my own, and the recognition that my colleagues need space to learn and grow — and that they often have better ideas than I do. It’s hard to know precisely when to seize the reins and when to let others take the lead. Overall, though, I think I’ve become more of an Obi-Wan than a Luke Skywalker. My main job, these days, is to set clear standards and expectations for the organization and measure people on results. I have to recognize the passions, skills, and strengths of the people around me. I have to find the right mentors they can learn from. And I have to coach and model, while resisting the temptation to tell people what to do all the time. Ultimately, I’d like to become a helpful voice in their heads, like Obi-Wan providing guidance to Luke as he tries to blow up the Death Star.
Moving toward the Obi-Wan Kenobi state of being doesn’t mean I’m ready to lay down my lightsaber entirely. Rather, I’m trying to follow the lead of my friend Sarah Arnold Rossetti, the former public affairs director in Stamford, Connecticut. Sarah is 10 years older than I am and is an incredibly youthful fitness devotee with tons of positive energy. When I was turning 40, five years into my first superintendency, Sarah told me she’s never spent much time thinking about her next milestone birthday. Rather, she has always focused on where she wanted to be 10 years later. Sarah started her career as a news anchor, became a school district public affairs director, and during the last year of my superintendency, she started working on becoming a school social worker and counselor. So now, she’s spending the last 15 or so years of her career directly serving kids and families. She doesn’t lament turning older, but sees aging as an opportunity to learn, grow, and become a better version of herself.
The best leaders I’ve seen, and the one that I’m trying hard to become , have the self-awareness to know how they can best serve their organization and the people within it. A leader’s job is to ensure that the team they’ve helped build can continue winning battles when they’re not around. To do that, they need to know when to listen to the voices in their head and trust the Force, because they’re the only ones who can blow up the Death Star.
This article appears in the November 2021 issue of Kappan, Vol. 103, No. 3, pp. 60-61.
ABOUT THE AUTHOR
Joshua P. Starr
Joshua P. Starr is the managing partner at the International Center for Leadership in Education, a division of HMH, based in Boston, MA. He is the author of Equity-based Leadership: Leveraging Complexity to Transform School Systems.
