The Path of the Hero: Becoming a Risk-Taking School Administrator

become a risk-taking school administrator

It’s not easy to be a risk-taker. After all, “risk” involves the possibility that something unpleasant or unwelcome may happen. But risk also includes the possibility of something wonderful or amazing happening. This is why, historically, risk-takers are in a tight spot. Others often perceive them as heroes or villains, mess-makers or problem-solvers, crazy or innovative. 

Most of us likely agree: it’s a lot safer to don the status quo outfit and leave the risk-taking cape to someone else. Psychologically, we are more averse to loss than we are motivated by gain. That means when we make a decision, we are more concerned with what we may lose than about gaining something great. This mindset keeps us from risk. In school settings, no one particularly wants to rock the boat, and those who do, often encounter push back.

There is risk when you want to try something new—when it’s not how things have always been done. There is risk when we undertake something outside our wheelhouse. It’s risky to try something your peers aren’t doing. We are particularly opposed to risk when we’re not sure how something is going to turn out, especially when we’re not sure of the potential benefits. 

But what if the benefits outweigh the imagined risk? What if what everyone else is doing is mediocre? Great leaders are the ones willing to do something different when the status quo isn’t good enough. 

A Few Well-Known Academic Risk-Takers

Think about your heroes, fictional and real, from the legendary Captain America to Nelson Mandela or Liv Arnesen. Perhaps you picture an inspirational teacher from the silver screen like Robin Williams from Dead Poets Society. Or, perhaps you see the real-life characters of Erin Gruwell or Melvin B. Tolson. Why do you admire or revere them? 

Protagonists in all stories face challenges in various and intimidating forms. Isn’t part of the reason we admire such characters their exemplary courage or willingness to take risks in one form or another? Here are a few academic risk-takers we admire:

Jaime Escalante: Mr. Escalante taught calculus at Garfield High School in East Los Angeles from 1974 to 1991. Although the school had a reputation for poorly performing students, Mr. Escalante offered to teach an AP Calculus class. The administration disapproved of his method of asking students to answer a homework question before they could enter the classroom, but Mr. Escalante held his ground. Because of his willingness to be a risk-taker, Mr. Escalante earned a reputation for taking hard-to-motivate students and turning them into success stories. (Read more about Jaime Escalante.)

It was a risk to take poorly performing students and require more than just a bare minimum from them. Johann Wolfgang von Goethe said, “If we treat people as they are, we make them worse. If we treat people as they ought to be, we help them become what they are capable of becoming.” Mr. Escalante took this philosophy to heart and helped his students become more. We love Mr. Escalante’s courage to expect more from his students. 

Eric Sheninger: Mr. Sheninger was a principal at New Milford High School, spending his early days taking away cell phones from students. He recognized a need for change in the school’s leadership model and teaching practices to catch up with the digital age. His leadership oversaw the successful implementation of changes that “transformed the learning culture at his school” (source). Instead of taking cell phones away, they began to encourage digital technology use in the classrooms. Mr. Sheninger backed up these changes with communication strategies that won the support of the community. As a result of his willingness to be a risk-taker, the high school became “a globally recognized model for innovative practices,” and Mr. Sheninger went on to become an award-winning leader, best selling author, and speaker. (Watch Eric Sheninger’s TEDx talk from 2014).

Change is not something people typically embrace. For that reason, we tend to stick with the way things have always been done rather than push through resistance. We admire Mr. Sheninger’s courage to figuratively say, “This may not be easy, but it needs to be done.” Mr. Sheninger’s success in combating change resistance can be attributed to his innovative approach to using modern communications to engage families. 

Gloria Bonilla-Santiago: Dr. Santiago is the founder of LEAP Academies. She wanted to improve the education and opportunities available to poor children in urban communities. In one of the poorest and most violent cities in the US, her charter school has 100% graduation and 100% college acceptance rates. Who would have thought a charter school with extended school hours (7:00 a.m.–7:00 p.m.) in a crime-ridden neighborhood would be so successful?  (Read more about Dr. Santiago). 

Dr. Santiago wanted to be “an agent of change” and was willing to face the risks to get results. LEAP Academies are successful because they promote “engaged scholarship … where the entire community, students, parents, and local organizations and businesses have a vested interest in student success.” It takes great communication and public relations skills to engage that many people in the success of underachieving students.

The Enemy of Achievement

One of my daughter’s teachers would include this quote by Farrah Gray at the end of each email: “Comfort is the enemy of achievement.” There is comfort in normalcy—in maintaining a status quo. While it’s nice to have something to depend on, getting out of our own comfort zone helps us see with new eyes and even helps us resolve long-standing struggles. 

As a school administrator, there are tasks and challenges you have grown accustomed to facing and most likely other tasks that loom in front of you, daring you to tackle them. Don’t get discouraged! 

Be a risk taker

Times have changed; education has changed. We are in uncharted territory. There is no proven path—you must be the discoverer of it. 

Remember, challenges are risky, and they are an indicator that you are on the path of a risk-taking administrator. As you follow such a path, it’s important to communicate and to garner the support of your stakeholders. In doing so, you establish the trust of your community and the support to undertake new endeavors.  

Be a Risk-Taker

A friend once asked author Julie Berry (, “Are we flat characters or round?” As a school administrator, what exemplifies you? Are you a two-dimensional character, unwilling to change throughout the course of your work? Or are you willing to undergo development and change? If you want to make heroic change, the idea of risk-taking needs space in your mind. 

Taking risks can be intimidating; however, without risk, there is little excitement. C.S. Lewis wrote, “Do not dare not to dare.” The price of risk should things go awry may convince some to not venture; however, you’re not in your career in education solely for your own success, are you? We believe you are there because you hope to make a difference in the lives of those with whom you work. Perhaps you hope to be a hero, a problem-solver, an innovator. Is it realistic for any of us to look towards success, big or small, without the image of sticking our necks out a bit? With your mantle of responsibility at your school, there are problems to solve, and we’re not talking about the ones in math class. In order to overcome these problems, big or small, some risks are bigger than others, but remember, risk is not a dirty word.

Ms. Frizz, one of my family’s favorite fictional teachers often says, “Take chances! Make mistakes! Get messy!” At School Webmasters, we believe in the powerful potential we all have to make a positive difference in our community. As a school administrator willing to take risks, you appeal not only to students’ families but also to students, faculty, and staff. Finding innovative ways to connect with them strengthens your school public relations.

The Secret to Success

In all of our varieties, we have the potential to make a difference for good in the lives of those with whom we interact. How do you live? How do you lead? Mr. Escalante, Mr. Sheninger, and Dr. Santiago have this in common: they understood the importance of gaining the buy-in of their key audiences. Mr. Escalante’s students had to actively participate in their own success. Mr. Sheninger needed his school community’s support in his campaign for change. Dr. Santiago needed the entire community to be involved in her charter school. If you want to take risks, you must understand this concept: the act of garnering the support of your key audience is good school public relations

In an interview, Dr. Santiago said, “One thing I know how to do is organize parents and teachers.” Good communication and school public relations takes practice—and a little bit of risk. In our next blog, we’ll give you six tips to help you get out of your comfort zone and build strong school public relations. 

Emily Boyle, School Content Specialist