The Grief of Unmet Expectations
44th Edition - January 16th, 2025 - Acknowledging emotions, curating consumption, and prioritizing focus.
A quick note before diving in: This post is arriving a few days later than my usual Sunday edition, and you may have noticed it’s been several weeks since I’ve released a podcast episode. Heading into 2025, I’ve been under the weather, which made recording a podcast unrealistic. I’m trying to be better about listening to my body. Also, I’ve been reflecting on how much I benefit personally from writing each week, which has me rethinking the rhythm of how I share content here.
For the foreseeable future, I’ll be experimenting a bit; adjusting my posting schedule to see if it impacts engagement (like email-opens, post likes, and comments), keeping to an every-other-week schedule for podcast episodes but releasing them midweek instead of having them replace a text edition. My goal is to prioritize writing weekly while balancing other creative projects. I should have a new podcast out next week.
As always, I value your input! If you have feedback on how this newsletter serves you or topics you’d like to read/hear about, I’d love to know. For now, I’m excited to get back to writing regularly—thank you for being here as I navigate these small but meaningful shifts! Now, let’s get to it…
If you work in public education—or, honestly, in any field that’s rooted in service of others and are also someone, like me, who feels things deeply—you probably understand the concept I am writing about today without me having to explain it. I spend a lot of time contemplating the concept of grief. I think about how we all experience it and yet rarely feel comfortable talking about it openly and honestly. It is one of the most universal emotions, something that impacts all of us in different ways and for different reasons. You would think that we would walk around talking about it with each other all of the time since we can all relate to it, and yet we have this tendency to hide it from all but our closest loved ones. We tend to think of it most often as it’s related to death, but there are other ways grief shows up in our lives. In this case, I want to talk about the grief of unmet expectations.
It’s been on my mind lately, especially as I reflect on my own 20+ year career as a school counselor, assistant principal, principal, and current role as a school district leader. When I first stepped into this world as a fresh-faced high school counselor way back in 2004, I carried what I thought was a clear vision of how my work life would transpire. I pictured sitting down with students each day, helping them triumph over the challenges of daily life, navigate decisions about their future, and providing guidance during difficult times. I envisioned being part of a system that functioned smoothly—a space where learning and growth were prioritized, valued, and celebrated. And for quite a while that is exactly what I experienced. I had wonderful colleagues who took me under their wing, mentored me, and helped me to find my own path forward as a professional while I did the same for my high schoolers. I had rich opportunities to work beside dedicated educators and kids as we all moved in the same direction. I traveled the world with groups of students, giving them the opportunity to connect with the world in unique and eye-opening ways. Of course there were challenges back then, kids and families who struggled, traumatic events that we had to navigate together in a post-Columbine, post-911 world, but those challenges did not dictate my entire professional experience.
Fast forward to 2025, and the reality looks… different.
The landscape of schools, and society for that matter, has changed dramatically since that 24 year old first put on a tie and sat behind his own desk. What students are carrying emotionally today is heavier, more complex, and often more heartbreaking, driven by a 24-7 inability to disconnect. Schools have become catch-alls for societal challenges that extend far beyond academics—mental health crises, social inequities, systemic barriers, rampant misinformation, and never-ending cultural tensions. Educators are no longer teachers, counselors, or administrators; we’re also crisis managers, communications specialists, advocates, and mediators. And we’re tired.
For many of us, the gap between how we imagined our 30+ year career would transpire and what we are experiencing now can feel overwhelming. And the emotion that comes with that gap—whether we name it or not—is grief.
“Anxiety, the illness of our time, comes primarily from our inability to dwell in the present moment.” - Thich Nhat Hanh
When you choose to work in education, it’s often because you feel called to it. There’s an idealism that draws you in—the belief that you can make a difference, change lives, and contribute to something bigger than yourself. You picture classrooms full of eager learners, schools as beacons of hope, and your work as a meaningful part of shaping the future. Thankfully I do believe that that is still the case. But then, reality sets in, and our current higher education programs do not do a great job of setting the stage for emerging graduates.
Instead of spending days focused on teaching and learning, you’re navigating constant interruptions: a fight in the hallway, a community member upset over something they saw on social media that may or may not be true, a student in tears over a social media interaction that happened the night before, an email about funding cuts or changing policies. The work becomes about survival—yours, your students’, and your school’s. And when you are the one tasked with leading people through all of this, the pressure is intense. That vision you carried into the field? It starts to feel less like a roadmap and more like a mirage. And that disconnect is where the grief begins.
“Grief can be a burden, but also an anchor. You get used to the weight, how it holds you in place.” - Sarah Dessen, The Truth About Forever
We usually associate grief with the loss of a loved one, but grief can also stem from the loss of an idea, a dream, or an expectation. For educators, it’s the grief of realizing that the world they hoped to shape isn’t the one they’re working within.
Here are some of the ways this grief shows up:
Loss of Control: The overwhelming feeling that no matter how hard you try, you can’t fix everything. You can’t control policies, funding, or even the pressures that students carry into your classroom.
Loss of Idealism: Coming to terms with the fact that the work doesn’t always look like you imagined—and may not always produce the outcomes you dreamed of.
Loss of Balance: When the joy of teaching and connecting gets overshadowed by the constant demands of just keeping everything afloat.
This kind of grief isn’t loud or dramatic. It’s quiet. Subtle. It creeps in slowly, lingering in the background as you try to keep going. And for many educators, it’s compounded by the guilt of even feeling this way in the first place. How do you reconcile loving your work with mourning what it was supposed to be?
“Grief is a very living thing. It visits at random. You can’t schedule it. I tried to work it away. I tried to drink it away. I booked myself like crazy, and all it did was wait for me to finish.” - Tyler Perry, in a conversation with Oprah Winfrey
Here’s the thing: Grief doesn’t have to be the end of the story. In fact, it’s often the beginning of something else—something quieter but just as powerful: resilience.
Even in the face of unmet expectations, educators continue to show up. They find moments of meaning in their work that remind them why they started this journey in the first place. For me, it’s the student who finally opens up after weeks of quiet struggle. It’s the colleague who offers a word of encouragement at just the right time. It’s the small, fleeting moments when you feel like you’ve made even the tiniest difference. It’s the funny text messages or moments of laughter between colleagues who have become great friends.
Those moments don’t erase the challenges, but they do remind us that the work still matters. The landscape may have shifted, but the heart of education—connection, care, and the belief in possibility—remains the same. In many ways it is even more important than ever before. We are the anchor of our communities.
“Tearless grief bleeds inwardly.” - Christian Nestell Bovee
As I reflect on my own journey, I’ve learned that part of processing this grief is giving myself permission to feel it. It’s okay to mourn the gap between what I imagined in school, what I lived as a young educator, and what the landscape looks like today. And it’s also important to honor the ways I’ve adapted, grown, and found meaning in the reality I’m living now. It’s also important to remember that I play a key role in making this reality an incubator for innovation and growth for our new and future colleagues.
And that’s the lesson I want to share with you. Whether you’re in education or another service-oriented field, unmet expectations are part of life. The question is: How do we move forward in a way that honors both what we’ve lost and what we still have? It means finding moments of gratitude for what’s still good, even in the midst of challenges. And it means recognizing that resilience doesn’t have to be grand or heroic. Sometimes, it’s as simple as showing up.
“No one ever told me that grief felt so like fear.” - C.S. Lewis, A Grief Observed
The grief of unmet expectations isn’t something we overcome in one big moment. It’s a process—a slow, deliberate choice to keep going, to keep caring, and to keep finding meaning in the work we do. If you’re feeling this grief right now, know that you’re not alone. And know that even in the hardest moments, the work you’re doing matters.
As we navigate this constantly shifting societal landscape together, let’s remind ourselves of the power of community connection, the importance of small victories, and the strength it takes to keep showing up. After all, that’s where resilience begins—in the quiet, everyday choices to roll out of bed, get dressed, grab that morning coffee, and be there for others, deliberately. Triumphantly.
Until next time, stay hydrated, and take good care.
Tim
What I’m Thankful For
This week, I’m thankful for the reminder that I have control over the information I take in each day. In a world that constantly bombards us with notifications, headlines, and endless social media scrolls, it’s easy to feel like we’re at the mercy of the noise. But we’re not. We get to choose where we place our attention, and that’s a powerful thing.
Lately, I’ve been more deliberate about curating what I consume. I’ve unfollowed accounts that drain my energy, limited the time I spend on platforms that feel more stressful than fulfilling, and focused on engaging with content that aligns with my values or inspires creativity and growth. It’s not about shutting out the world—it’s about being intentional in how I interact with it.
This small shift has reminded me that where I direct my attention is where my energy flows. And in a time when attention feels like one of our most precious resources, I’m grateful to reclaim it in ways that allow me to show up for the people, ideas, and work that matter most.
What I’m Reading
This piece by
that I came across on a recent scroll through Substack’s Notes feature felt extremely pertinent for this topic and my educator mind right now. I do appreciate how sometimes the algorithm shows up when you need. I appreciate the approach of, “Focus on what to protect rather than what to prohibit.” It feels like the balance I need since I have a tendency to approach such things from a doom-forward, all-or-nothing perspective.
I love letters. I love handwriting. I love the idea of our personal history being recorded through day-to-day correspondence that isn’t on a computer. We are losing a piece of our personal histories because the art of letter writing has essentially slipped away. That’s why I love the Letters of Note Substack by
, and this letter in particular from Marie Curie to her late husband Pierre in particular felt poignant for my theme this week.
Looking for More Ways to Discover Meaningful Writing?
One of the joys of writing this newsletter is discovering incredible articles and perspectives that inspire deeper thought, like the pieces I’ve shared above. If you're looking to enrich your own reading life, here are two tools I personally use to find fresh, thought-provoking content:
The Sample: Think of this as your daily dose of serendipity. The Sample sends a curated newsletter recommendation directly to your inbox, tailored to your interests and reading habits. It’s how I’ve stumbled upon some of the most unique and impactful writing I’ve shared here. If you’re curious about discovering new voices and expanding your reading list, this is a fantastic place to start. (And yes, I use it myself!)
Refind: Where The Sample feels serendipitous, Refind is like having a personal researcher. Every day, it delivers tailored links based on my own preferences. I find a lot of the articles I include in this newsletter through Refind, from thought-provoking essays to emerging trends in education, leadership, and mental health. It's a great way to stay curious and informed.
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It's fascinating how much time I've spent reflecting on how I read your writing rather than just the content itself. I'm a reader at heart—non-fiction is my go-to, particularly self-help books. As a lifelong learner, reading usually puts me in a specific zone. My eyes scan each letter, my brain processes and stores the information, and then I move on.
But when I read your work—and Mel Robbins' too—it's a completely different experience. My reading isn't as smooth or linear. I get through a sentence or two, and suddenly, my mind is off on a tangent, exploring thoughts that stir up vulnerability. Then I refocus on the text, only to be drawn into another web of connections, deeper reflections, and processing far beyond what I typically experience.
I truly appreciate this. Your writing resonates with me on multiple levels—touching on my past, my present, and my aspirations for the future. It helps me engage with my anxiety in a way that's not just tolerable but transformative. Your words offer a space for growth, insight, and a unique connection that feels both personal and profound.
Side note - You've inspired me to get back to writing more on a personal level. I haven't done this since my kids were babies. I miss it and had so many excuses as to why I didn't have time. No audience. Just to clear my brain, "talk through" ideas, and make sense of this crazy world we live in...little by little.
There is so much grief in the world. It can be shattering when the truth of situation cuts through like a knife. And yet Tutu and the Dali Lama say: “acceptance is the only place from which change can begin.” It is a grief to accept a situation as it is…and not as we would wish it. But as you say, it is in honoring that grief that we find the capacity and courage to change what we can. And the change starts with us.