Hope Is Not Optimism
The Learner-Centered Leader #257
“Hope is not the conviction that something will turn out well but the certainty that something makes sense, regardless of how it turns out.”
Hang on tight boys and girls. This newsletter is going to be be a little different. The first post is going to be an AI-generated synopsis of a chapter in a school leadership book some friends and I are writing. We wrote every word of the chapter, but I asked Claude AI to summarize it for a Substack post. The book is called “The Disciplines of School Leadership” and this chapter is Chapter 11: the Discipline of Hope.” I think AI captures the ideas well.
The second post is a the start of a short story I have written. I would LOVE to get your feedback on what I have written so far. As you read it, you will see that it is an obvious dystopian view of what our education system can become if we rely on analytics, algorithms, and numbers too much. Let me know if you think I should continue with the story. Ultimately, I want to introduce characters (both students and teachers) who do not fit the mold of the school I portray in the story and how those “rebels” show us the path forward for education. FYI: 100% of the words and ideas are mine and AI has not touched it. As a matter of fact, I wrote this three years ago before AI and LLM’s became ubiquitous.
The Discipline of Hope
Hope Is Not Optimism: What Václav Havel and Wendell Berry Taught Me About Leading Through Difficulty
Every leader faces seasons when outcomes disappoint and stakeholders lose patience. If your leadership runs on favorable forecasts, you’ll collapse when forecasts turn negative. But if your leadership runs on hope? You can sustain the work through brutal reality.
What Václav Havel Understood
The Czech playwright and president Václav Havel wrote:
“Hope is not the conviction that something will turn out well, but the certainty that something makes sense, regardless of how it turns out.”
Optimism is a state of the world—based on data showing things are trending positive. When spreadsheets look good, optimism is easy. When they don’t, optimism collapses.
Hope is a state of mind—not dependent on favorable conditions. You confront brutal facts but your hope isn’t invested in predicting outcomes. It’s invested in certainty that your work makes sense regardless of how it turns out.
Optimism is passive—a forecast, so you wait for favorable conditions. Hope is active—commitment to do what makes sense regardless of conditions.
Finding Hope on the Ground Under Your Feet
Wendell Berry adds another dimension: hope must be grounded in your actual place. Not “organizations in general” or “best practices from elsewhere.” Your organization. Your people. Your ground.
Berry writes, “If you can find one good example, you’ve got the ground for hope.”
Hope is grounded in specific things you’ve witnessed: excellent work happening, teams collaborating meaningfully, people thriving. Those aren’t predictions—they’re real examples happening now. That’s ground solid enough to build hope on.
Optimism forecasts improvement from data trends. Hope looks at actual ground—actual people, actual progress—and says, “This work makes sense. I’m committed regardless of whether I can predict the outcome.”
Berry also insists we “back out of the future into the present.” Stop obsessing over outcomes you can’t control. Focus on what’s right to do today. You can’t control when results materialize. But you can control whether you do what makes sense today. That’s how transformation happens—through accumulated weight of doing what makes sense, day after day, regardless of forecast.
The Practical Architecture of Hope
Research psychologist C.R. Snyder identified three components that give hope structure:
1. Clear Goals (what makes sense regardless of outcomes)
Your goal isn’t “improve metrics by 2027.” Your goal is what’s right to build in this place, for these people, regardless of guaranteed results. The goal gives hope direction without requiring predicted success.
2. Multiple Pathways (the heavy lifting)
You create multiple pathways because you can’t predict which will work. When one stalls, you adjust without abandoning the goal. This is disciplined hope—patient, persistent work with measurable benchmarks.
3. Agency (belief you can act regardless of odds)
Agency as optimism: “I’ll succeed because my plan is good.” That’s fragile. Agency as hope: “I can’t predict success, but I can do what makes sense today. I can learn from what doesn’t work. I can adjust while maintaining purpose.” That’s resilient.
And a fourth dimension—faith: believing in what you cannot yet see. Faith that right work compounds over time. As Hebrews says: “Faith is being sure of what we hope for and certain of what we do not see.”
When You Don’t Feel Hopeful, Practice It Anyway
Here’s what matters most: hope is a discipline, not a feeling.
There will be weeks when everything goes wrong—budget crises, key people leaving, public criticism demanding you abandon your work. You’ll go home feeling anything but hopeful.
Practice hope anyway. Not because you feel like it, but because it’s your discipline. Review your goal. Examine your pathways. Assess what you can do Monday that makes sense regardless of the crisis.
The discipline itself—not the feelings it produces—renews your hope. This is the heavy lifting. It’s patient, focused, sometimes fearless work. It’s returning to certainty about purpose when feelings fail you. It’s believing in what you’re building even when you cannot yet see the result.
Your hope must be rooted in a purpose that transcends your tenure, your reputation, your need for validation. If you’re building something that matters regardless of whether you personally see it completed, then setbacks become part of the work rather than reasons to quit.
The Paradox
You need hope most precisely when you don’t need optimism.
When conditions are favorable, when data is positive, when everything is trending well—you don’t need hope. You have optimism. Hope becomes essential when the state of the world doesn’t support favorable forecasts. Hope allows you to continue building what makes sense even when evidence doesn’t predict success.
When people watch a leader maintain purpose through difficulty, when they see someone do what makes sense regardless of whether it produces predicted outcomes, when they encounter faith that survives brutal facts—that’s when hope spreads. Not through optimistic predictions, but through encountering someone whose certainty about purpose survives brutal reality.
One person’s certainty about what makes sense, practiced through difficulty, can become many people’s shared commitment. That’s transformation.
What This Means for You
If you’re facing disappointing results, impatient stakeholders, resistance, or any of the thousand pressures that make leadership hard—the question isn’t “Can I predict success?”
The question is: “Does my work make sense for these people, in this place, today?”
If you can answer yes—if you can ground that answer in specific examples of good work you’ve witnessed on your actual ground—then you have hope. Not optimism. Hope. The certainty that what you’re building matters regardless of how it turns out.
This requires three things working together:
First, clear purpose rooted in your specific ground. Not abstract goals, but a concrete vision for what makes sense to build in your actual context, with your real people.
Second, disciplined practice through patient work. Multiple pathways because you can’t predict which will succeed. Incremental progress with measurable benchmarks. Learning from what doesn’t work without losing faith in what you’re building.
Third, active commitment regardless of conditions. Optimism waits for favorable circumstances. Hope acts because the work makes sense now, today, regardless of the forecast. You confront brutal facts honestly while maintaining absolute certainty that doing what’s right matters.
That certainty, practiced through brutal reality, sustained by duty to something greater than your comfort or reputation, becomes your organization’s hope. Not because you’ve convinced people transformation will definitely succeed, but because you’ve demonstrated that doing what’s right matters regardless of whether you can predict the result.
Hope is not optimism. Hope is better. Hope survives reality. And for leaders, hope is everything.
This is Chapter 11 from the superintendent leadership book I’m co-authoring with Dr. Duff Rearick, Dr. Jay Scott, and Dr. Pat Crawford. The book helps new superintendents navigate the transition into leadership and experienced superintendents reinvent their practice by focusing on essential disciplines rather than technical management. If these ideas resonate with you, I’d love to hear about your own experiences with hope vs. optimism in leadership!
#257
Grown-ups, on a good day, can screw things up. If you don’t believe me, just look around at the little sphere hurtling through space that we call home. I think their problem is that they haven’t accepted the fact that the human race is constantly “becoming.” “Becoming,” in my humble opinion, implies we need to approach life with a lack of ego about the present. An oversized ego does not allow wisdom to enter the psyche. Grown-ups seem to sleepwalk through their life, doing everything in their power never to be surprised. Surprise implies they are fallible. The lack of surprise in one’s life prevents learning and growth.
As I reflect on how I got to where I am today, I have to say that grown-ups’ lack of willingness to learn and grow is responsible. I am not happy about the realization. I just accept it.
I’ve decided humans don’t have humanity. You might ask yourself how a 16-year-old has reached this conclusion so early in life. That is a fair question, and I will gladly answer it. Right now, if I concentrate really hard, don’t look up, and have a look of “working” on my face, everything will be fine. Those three traits determine my score for this class period, and anything I can do to at least look as if I am concentrating and working, well, I’ll be good. Answering your question will help me stay focused on those three things.
“Number 257.”
I should start by telling you where I am. I am sitting in a classroom. It is a typical classroom, or at least we have been told it is a typical classroom. I am sitting at the fourth desk from the front of the room in the fifth row from the door. There is only one more row to my left. I feel bad for those sitting in that row because they sit right up against the bank of windows. I can feel the wind blowing through the window from where I am sitting, so I can’t imagine what it is like being right against the window.
Did I forget to mention that I am in a school? To be precise, I am in school Number 98…or at least I think it is school Number 98; it’s hard to keep track. It seems that those in charge of my education are determined to drain me and my friends of any natural vibrancy. It’s like naming your dog “Stay.” When you want them to move, you say, “Come, stay,” and it just confuses them more. That pretty much sums up my school…the more the grown-ups talk, the less I understand.
From my vantage point, I see the grown-ups are suffering from a fixation on numbers. They seem to believe that they can put a number to every human activity, whether it is appropriate to do so or not. The numbers then become their shibboleth
Besides the drafty window, good ol’ Number 98 has plumbing that is leaky, boards that are coming up in the hallways, and a weird smell coming from the basement. We are told that if the students do well in the next round of fidelity assessments, the Ministry of Fidelity Compliance (MFC) will start fixing some of those problems.
“Number 257.”
Just to let you know, it is winter outside, with snow and sleet pelting the window. I don’t dare look up, but I am afraid the windows will surrender to the elements and let the weather in. I am wearing the school-approved clothing for this time of year: snow boots laced up tightly, brown ski pants with the cuffs over the boots, and a school-issued biometric shirt that is overlaid with a mood sweatshirt.
Wait, maybe you don’t know about the biometric t-shirt and mood sweatshirt? This is wonderful because it allows me to look like I am thinking and working hard. The t-shirt has sensors that are fed into a computer (we call it The Monster) that analyzes our heart rate, perspiration, body temperature, and blood pressure. The Monster analyzes the data and gives the Fidelity Facilitator a second-by-second “student engagement score.” That score is averaged for each class period, and we are then given a Daily Engagement Score (DES).
“Number 257.”
As you might have picked up by now, my DES is always in the lower quartile…I am not sure what “lower quartile” means, but I know that it is not good. Anyway, we learned today that the MFC has given Number 98 the goal of increasing the median DES in students by 10.2% during this Fidelity Compliance Unit (FCU). We have just begun a new FCU, and our Fidelity Facilitator seems motivated to do their part to raise the DES by 10.2%.
“Number 257.”
Remember your breathing exercises, I keep telling myself. Managing your heart rate is a key factor in not increasing your Fidelity Confusion Score (FCS). If your heart rate is too low, then your DES goes down, which I think you can tell by now is a bad thing. But the shitty thing about your heart rate is that your FCS goes up if it goes too high. So what’s the big deal about that, you may ask? Well, if you…
Excuse me for a minute because I feel a persistent jab (almost a punch) in my back. I know that is Number 1 trying to tell me something. I’d better pay attention to what she is trying to tell me.
“Number 257, answer the question! Remember this is the first day of the FCU and you are now Number 257!”
That little bit of information made my FCS go through the roof, I am sure. You see, at the end of every FCU, all students undergo a Curriculum Fidelity Assessment (CFA) to make sure all of the curriculum was covered during the FCU. While taking the FCU, your FCS and DES must stay within one standard deviation of the classroom average during the CFA. Anyway, I can feel the sweat beading on my forehead and my face getting warm from stress.
“Number 257, the answer is The Ministry of Compliance and Control (MCC).” Number One says helpfully.
As confidently as I can, with doubt coursing through my veins and anxiety constricting my vocal cords, I answer.
“The correct answer for this specific question is The Ministry of Compliance and Control,” I answer with as much false bravado as I can muster. The hard thing about answering questions is that you have to answer in the correct format. The Fidelity Facilitator takes points off your DES if you do not use the proper “correct answer format.” The school’s average DES goes down if you just answer the question. The Fidelity Audio Audit (FAA) records every voice interaction in the classroom to ensure we use the correct format.
I pause to see what is going to happen next. Number One has bailed me out of so many of these situations that I trust her completely. And she risks a lot by helping me. Her DES will go to zero for the rest of the week if she is caught helping another student. We are told that helping other students is wrong because it messes up the CFA for the school, which in turn brings more attention to Number 98 by the MCC.
“That is the correct answer, Number 257. However, I see your FCS is rather high right now. If the score stays that high over the next 10 minutes, we will have to send you to the Fidelity Re-education Lab (FREL) for drills on coming up with the correct answers on the Daily Curriculum Essential Content (DCEC).”
I dodged a bullet on that one, for at least 10 minutes anyway.
Today is the first day after the results from our last CFA. At the start of every FCU, all students are renamed according to their rank in the school on the CFA. So, you see, I have a very good reason not to know my name. I remember now that my name changed from Number 228 to Number 257. This naming nomenclature makes it more efficient for the Fidelity Facilitator to assign Approved Structured Assignments (ASA’s) to help increase your answers on the DCEC.
It is all coming back to me now. I was told that if I moved below Number 259, I would be moved from School Number 98 (is it 98 today? I know that is what it was yesterday, but schools get reordered after every CFA as well according to their rank in the Fidelity Geographic Region (FGR). I will have to ask Number One what our new school name is during our five-minute Structured Free Time (SFT) we get every day.
I want to thank Number One for her help (again), but the Sensory Motion Veracity Unit (SMVU) will definitely see me turn around in my desk to talk to her. I will just lean back a little in my chair as a way to say “thank you.”
Number One is awesome, and to be honest with you, I am probably in love with her. I know what you are thinking. I’d better be in love with her because she bails you out all of the time. True. However, she is also brave, resourceful, and funny. She has figured out a way to counteract the biometric t-shirt and the mood sweatshirt and has cracked the code on how to do well on the CFA’s. She has been Number One for as long as I have known her, which is a long time…three years! I suspect she will always be a Number One no matter where she goes.
“You’re daydreaming, get your heart rate up, or your DES will go down!” Number One hisses to me under her breath.
She has saved me again!
I am curious to learn what you think of my short story and whether you think it is appropriate for this newsletter. Did something resonate with you in the story? Was the story just stupid? I am curious to find out what you think!
Book Of The Week
Fair warning, don’t read this book if you don’t want to get incredibly pissed about how the super wealthy in the United States game the tax system for their benefit.
