Making a Job Transition When Your Calling Is Also Your Career

E-mail from Student: “Ummm….You’re Leaving?!”

While I was on a flight from Beijing to Detroit at the end of February, my head of school announced to the community that I had accepted a new job. I had to come up with something to say when I got back to work.
I have taught since 2010 at Indian Springs School (Alabama), a place that boasts miniscule faculty turnover. In fact, an original faculty member from the school’s founding in 1952 still serves as school archivist. In my family’s three generations of independent school educators, career moves are nonexistent. Most lines of questioning as to my own search went something like, “Are you unhappy? What’s wrong? I thought that things were good? Are you being forced out?”
The job search in the world of independent schools can be exhilarating, draining, encouraging, and devastating all in the span of days. My experience is that, in teaching particularly, we tend to focus on our work as a “calling” more so than a “career” — perhaps rightly so. But we cannot forget that, though meaningful and wildly important, what we do is still work, employment.
Now, as I begin transitioning from one school community to another, I am equal parts full of hope for what will come and full of dread for leaving a place and people I love. I know that I am not alone in going through this, but in this moment of transition, I think it’s important to take stock of this liminal space.

My Search

So much of a search is trying to find the time and energy to thoughtfully respond to those schools that show interest in your candidacy. You have to imagine yourself at X school doing Y job and blending in socially in Z city. You look for indicators of school culture that are important for you. For me, I wanted to know that a particular community supported LGBTQ students and faculty; I wanted to see a collaborative faculty environment; and I wanted to see a robust commitment to professional development.
But the biggest struggle is going through the speed dating of interviewing while also serving the community in which you currently work. My search took me places far different from the Deep South I’ve called home my entire life. And each school offered me something new and presented new challenges.
What I know for sure: The search for a new job offers some of the best professional development I’ve done in my career. In meeting after meeting, I found myself energized about the future of independent education. I realized, too, that many of the struggles our individual school communities feel are present regardless of region. I couldn’t help thinking it strange that one of the times when I was learning the most from other excellent “school people” came at a moment of potential personal change. Why can’t those visits happen more often?
The biggest struggle I encountered came in early January, when conversations with four or five different jobs got very serious and managing the different timelines was almost untenable. But when I started to get stressed, I had to remind myself that I chose to undertake this search.
I knew from the fact that my own school had just completed a head search that the post-search process looks very different from the grind of actual searching. While clear goals and expectations guide the search process itself, the post-search period is murkier.
When I visited Western Reserve Academy (Ohio), the school that I will join in the fall, I had a feeling that this place was the right fit for me at this moment. So many times I heard the word “growth,” and it seemed to me that the faculty and the students were happy. I knew I could be happy, too.


In my first day back from China (after being gone two weeks), I was catching up with my classes. My Latin III class quickly said, “So, Ohio…?” What they wanted was an explanation. They were, self-described, “a little salty.” I found myself going rapidly through the language of break-ups, of separation: “It’s not you; it’s me” or “I think we should see other people” or “Haven’t you wondered what things would be like if….” But then I realized how ridiculous that seemed.
Then the students began to say things like, “Well, clearly we aren’t good enough for you,” which, while delivered in over-the-top fashion, made me think about how I could let them know that I value them. And I had to do so amid the continuous onslaught of Ohio jokes, which were in the same vein as the Alabama jokes they’d heard time and time again.
I resolved to talk to them as people who will undoubtedly make multiple career moves in the future. I thought it was important for them to thoughtfully practice understanding why people make career changes and for me to model how someone can conduct himself in such a transition.
Now, I am at the point of realizing that a series of “lasts” are coming up for me in this place. To savor and remember as much of this as possible, I am committed to being present — wholly present. I want to enjoy the great conversations with students, parents, and alumni that have sustained me and challenged me throughout my time here. These relationships are what I’ll carry with me.
It is a struggle, though, to negotiate the mourning of leaving one community with the hopeful anticipation of joining another. And all of these feelings cannot distract from the fact that I still have a job to do, moving arrangements to make, and relationships that are going to change. I must embrace the full range of emotions and responsibilities; I hope feelings of joy and gratitude will shine through.

11 tips when leaving.jpg
 When Transitioning to Another School

1.      Be generous with your current community. Think of the things that have sustained you and made you love the place into which you have invested a portion of your life.
2.      Understand that students take a lot of things personally even when those things have nothing to do with them. I should have realized that students tend to view the world through a “how does this affect me” lens. That includes your decision to take a new job. Be aware of how they are reacting to your news. My approach was just to ask them how they felt when they brought it up.
3.      Take care of any rough spots with current colleagues. Independent schools are interconnected through relationships among independent school professionals. If you have any existing tension with a current colleague, it might be good to work through that before you exit so that you don’t have tension with a future colleague.
4.      Be useful to your school in transitioning. Though my departure was known, I still engaged as much as I could in the school’s accreditation visit. When asked to help coordinate the search for my replacement, I was happy to do that as well.
5.      Journal your thoughts to reflect on where you are. Writing or journaling about the process can help you make sense of some complicated feelings.
6.      Keep organized. Myriad things are about to change — from retirement funds to insurance to tax liabilities. Stay on top of them, and don’t forget that professionals are available to give you great advice.
7.      Let your students know you care for them. Be present. You might also consider telling those students you’ve taught as juniors that you’re happy to write a college recommendation should they need it.
8.      Be excited about your new venture. When I told my head of school that I was leaving, I was filled with emotions. But — to be honest — the most overwhelming was sadness. He was keen to what I was feeling and gave me wonderful words: “This is a great thing. You have to be excited.”
9.      Don’t make promises you cannot keep. It’s important to know which people you can genuinely commit to staying in touch with and avoid spreading false hopes.  
10.   Realize that you represent two schools at once. Now that I am transitioning to a new school community, I know that to the people at my current school I represent both my home-to-be and them. As a double-ambassador, I strive to be a positive reflection of both places.
11.   Consider maintaining your giving to your current school once you are gone. I love my current school and what it means to the state of Alabama and to independent education in the South. My gifts will remind me of the people I love in a place I will always hold dear. In some small way, I am still present.

Douglas Ray
Douglas Ray

Douglas Ray teaches at Western Reserve Academy (Ohio). Author of He Will Laugh, a collection of poems, and editor of The Queer South: LGBTQ Writers on the American South, he is currently editing a book project called Supporting Transgender Students: A Guide for Schools and Teachers. For more information, visit

05/08/2016 11:48 AM
Jennifer, all the best in your transition and congratulations on your coming headship! Like you, after concluding my search, I realized how much energy I was investing in that process and that (probably necessarily so) I had substantially minimized considerations of what leaving looked like. It sounds like we are both fortunate to have time to invest in our transitions, time to honor the growth we've experienced in our current communities, and energy to anticipate the new opportunities we'll encounter. Again, my congratulations!

05/08/2016 11:41 AM
Thank you, Peter, for your comments. The clear, concise way you framed professional growth for your 10th graders makes a lot of sense, and I appreciate your emphasis on choice and growth. I know that, as an educator, I feel that it's important to model personal and professional growth for my students, and it's also vital for my staying fresh, engaged, and energized in the field of education.

05/05/2016 12:53 PM
Thank you for this Douglas. You capture the range of emotions that come with a job transition so well in your piece. I have been at the same school for 14 years and it's fair to say that not only did my two children grow up here, but I did too. Schools - as your title suggests - are so much more than just a job for so many of us. They call us to something bigger. My time at St. Patrick's has been nothing short of blissful and life-changing and I realize that I have spent far more energy on a search process this year than I have on internalizing the goodbye. June 30 will be a very tough day indeed.

I wanted to thank you for putting so much of what is on my mind into words! And for offering such a wonderful to do list for my last 6 weeks here. I am so excited to be moving on to become the Head of School at Grace Episcopal Day School in MD, and I am certain that it wouldn't even be a possibility without the support and love of my colleagues and my Head of School, Peter Barrett. So maybe my comment is an attempt at point #1! Best of luck as you make your transition this summer and fall.

Jennifer Danish, Assistant Head of School for Enrollment, Communication, and Marketing, St. Patrick's Episcopal Day School and Head-Designate, Grace Episcopal Day School in Kensington, MD.

05/05/2016 10:39 AM
I read Douglas Ray's comments on professional transition with interest. Years ago, when I was leaving one teaching position to move to another school, I explained my reasoning to my 10th grade students this way: "When you are a student, you are forced into periodic transitions that result in growth. You graduate from middle school, from high school, from some sort of post-secondary experience, like college. You may choose to go to graduate school. But when you're an adult, perhaps settled in your career choice, you sometimes have to make your own change. You have to force yourself to grow and to try new things. It's scary, it's sad, and it's also exciting and deeply rewarding." That seemed to make sense to my 10th graders, whom I still remember with great fondness. (They're now in their 40's!) Peter Baily, Executive Director of AIMS, the Association of Independent Schools in MD and DC.

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