how do we lead with love through our mistakes?

Teaching children is an act of love. But love, as a concept, needs to be unpacked. It can so often be misunderstood! Love can be used as an excuse to avoid the bad stuff, to give ourselves credit for the intention rather than the execution. This is the third post on what it means, truly, to be an educator who is on the journey to lead with loveYou can read the first post here and the second post here.


I invite you to list 3-5 mistakes that you have made as an educator that stay with you, before reading the rest of this post.


In martial arts instruction, learning to fall is one of the beginner basics that kicks off instruction. We need to learn how to stay in the fight after we fall. We need to learn to fall and make mistakes and then, in our work, apologize for them, learn from them, and model the openness and transparency around them. We need to get back up, brush ourselves off, and jump back in.

Shawn Ginwright, in The Four Pivots reminds me of what it means to lead with love through a mistake. In his 2022 book The Four Pivots, Ginwright emphasizes the internal shifts that we must make if we are really to be leaders centering equity and justice. I recommend the full book as a treatise on what it means to lead with love, but for today’s question, I have one specific moment to spotlight.

In the introduction, Shawn Ginwright shares a moment when he went into autopilot and used the same syllabus for his graduate seminar on African American social theory semester after semester, until one semester he was confronted with the reality that his students hadn’t been doing the reading. When he asked them why they hadn’t come prepared for class, a couple of students called him out for what was a visibly stale selection of readings and topics.

Here’s how he describes the interaction that followed:

I was mortified that I had failed to update the readings and revise the materials for timely and relevant examples. Immediately my fear, the one that I thought had somehow disappeared, showed up and was staring me right in the face. So I did what any insecure, fear-filled professor would do – I lied to save face. I replied in my confident, proper, deep professor voice, ‘Well, the theoretical underpinnings of sociological phenomena remain in Black life and these readings, while dated, are classic and still relevant to … blah, blah, blah …’ They could see that I was bullshitting and hiding from them the truth, which was simply that I had majorly fucked up.

After escaping the embarrassment of this moment, I had two decisions to make. I could use my position and power as a professor to sweep my mistake under the rug, or I could come clean and tell the truth. I chose the latter, to tell the truth. The following week, after deep reflection and contemplation, I came into class and had an honest conversation about my mistake. I admitted that I hadn’t been as organized and thoughtful about the course as I should have been. I didn’t make excuses, but I explained that I was tired. Not the kind of tired you can just sleep off and wake up the next day and be cool. Naw, I was tired down to the roots, at my core. I was tired of meaningless meetings, tired of constantly raising money for my work, tired of not knowing where I was going in life. I apologized to them from my gut, because I really value my students’ learning. I didn’t just mimic the words “I’m sorry” or “my bad.” I was truly regretful, and they knew it, they could feel me. You feel me?

That conversation transformed the class, and my relationships with my students, in ways that I could not imagine. I suspect that somewhere in that clumsy apology they stopped seeing me as Professor Ginwright and began to see me as fully human. I imagine that in me standing in front of the class, somewhere in my stumbling over words, they saw something familiar, something they could relate to – my imperfection. They trusted what I said because it was real, no theoretical underpinning, no framework, no philosophical point, no bullshit, just damn honest. I said to them, ‘I messed up, I hope to regain your trust, I’m going to do better.’ I suppose that my being honest and vulnerable allowed me to let go of my fear, and in doing so opened something in us that connected us beyond the confines of teacher and student. For the rest of our semester together, we played, laughed, cried, and relished in simply being human; we healed.”

(The Four Pivots. Shawn Ginwright. p. 2-3)

Here are the three things I think we need to remember in leading with love through our mistakes:

  1. Mistakes are inevitable – we all have made them; we all will make them in the future.
  2. When we do, we have to honor the folks that we work with by talking to them, human-to-human.
  3. That conversation should be a beginning, after which there must be continued work on trust and relationships within the community.

Mistakes are inevitable – we all have made them; we all will make them in the future.

Here are five mistakes that stay with me from the last several years:

  1. Internalizing/normalizing a culture where personal/sick leave is discouraged since we have school vacations.
  2. Being resistant to the idea that ESL pedagogy should/must be different than lifting techniques/curricula/approaches from schools that are high-achieving and majority native English speakers.
  3. Not taking seriously what students needed to navigate in terms of the SSC textbook, school exams, and parental expectations when I was a Teach for India Fellow.
  4. Laughing during a washing-hands lesson with high school students right before COVID-19 hit.
  5. Deprioritizing knowledge and vocabulary relative to skills for the first few years of my teaching career.

Education will always feel high stakes. Nurturing our children is high-stakes. As part of what I read as an extraordinary love letter to school, Ijeoma Oluo writes,

You don’t have to be a parent or a student to care about what’s happening in our schools. It affects all of us on so many levels. The norms for how we treat one another are set in school. Our social and political identities are formed at school. Many of us find our lifelong passions at school. Most of us go through our most formative years in school.

There is no way we can hope to tackle systemic racism and think we can leave schools out of the equation.”

(Be a Revolution. Ijeoma Oluo. page 304).

Oluo is right – schools are important institutions that create and enforce the norms of our society, and educators have a lot of voice in what those norms are. That reality, though, can make it hard for us to acknowledge that despite – or actually probably because of the stakes, we WILL make lots and lots of mistakes along the way.

My dear friend Aishwarya’s post on remembering both our significance and insignificance feels relevant.

I agree with the basic argument that lowering the stakes can help us learn, grow, and change. So, here too, perhaps remembering that mistakes truly are inevitable can help us feel a little less afraid of making them and a little more prepared to handle the aftermath.

When we do make mistakes, we have to honor the folks that we work with by talking to them human-to-human.

So. We have acknowledged that we will make mistakes. Now, how do we deal with them?

First, we cannot, at any costs, convince others that the mistake didn’t happen – implicitly or explicitly. We cannot repeat the middle school behavior of, “No, you farted!” that most of us have experienced so often. Instead, there are many ways that we do this and they are all human responses protecting ourselves from embarrassment and humiliation. We sometimes:

  • Deny
  • Shift blame
  • Ignore
  • Redirect attention.

I’m sure you’ve experienced other strategies, too. Whatever the technique we choose, when we try to cover up our mistakes, no matter how small or large, we move away from leading with love and toward leading with fear.

In my work and in my life, I have seen a couple of instances where folks have really gotten this right. When a teacher realized that her lesson plans were actually creating a shortcut that made 9th graders more confused when they reached 11th grade, she reached out to the 11th grade teacher to make sure she learned the expectations of 11th and 12th grade so she could rework her 9th grade curriculum.

When a school principal participated in inappropriate staff work talk that hurt a teacher, she made sure to learn, apologize, and facilitate the creation of a new set of norms around professional talk at the school. When a teacher had a life event that got in the way of on-time grading, she stepped in front of the class to explain and chart out a revised plan for returning their assessments. When another teacher was discussing a student’s home situation with another teacher in a room that was open to students who needed supplies, she apologized to the student for violating her privacy.

These instances happen every day, and are examples of moments when the mistake-maker didn’t shy away from what they did and instead attended to it head-on. Ina s human a job as educating children, I think more often than not, this is the right path to choose.

That conversation should be the beginning, after which there must be continued work to build trust and community and relationships.

Apologizing is so hard that it can be really tempting to stop there. But stopping at an apology often comes at the cost of true repair and rebuilding and at its core, leading with love is about centering community and relationships.

I’ve certainly worked with folks who are extraordinarily self-congratulatory after a thoughtful apology, but then do absolutely zero work to actually address the problem they apologized for. Days or weeks later, teachers and students find themselves cleaning up the mess, and the extra work feels like it totally negates the apology.

Worst of all, because of the apology, teachers felt like they couldn’t complain, or that complaining would lead to accusations of “not being a team player” or “not empathizing enough with the manager who made the mistake and tried so hard to apologize.”

I hate being put in these situations. Let’s start by putting this scenario into a classroom context. Here’s one hypothetical:

A teacher neglects to grade a unit assessment for over a month. Students are clamoring to see their grades, and want to understand where they stand, and how to improve. One month in, their teacher comes in and apologizes. She shares with the students that she recognizes how much work they put into studying for these tests, and that they really want to see their results. She acknowledges that the more time passes, the less they may remember what they wrote, what the questions were, and how they studied, all of which are really important things for good reflections, learning, and future planning. She explains that grading quickly is a weakness of hers, something that she is working on, and she hopes that it will get better soon. She also shares that this month, due to a variety of variables, it was harder than usual to turn the tests around. She apologizes once again, and then shifts into the day’s lesson.

Now, what’s wrong with this picture?

In a lot of ways, this apology is great. She acknowledged the students’ feelings, affirmed the stakes/consequences of the mistake for the students, and modelled vulnerability (without oversharing) in sharing that this was a particular area of development for her. All great things.

A student listening to this apology, however, doesn’t come away with an understanding of when she will get her grades back, nor does she really get any concrete information that can robustly build back trust that her teacher is addressing and redressing this issue.

In a few days, whatever goodwill might have been generated by this teacher’s apology might be forgotten, assuming no additional clarity is provided in that time.

“When will I get my test back?” “Hey, she’s right, this is really unfair to me.” “I feel like she was just trying to calm us down.” “Is she really working on it?”

Doubt creeps in. That feeling of being unheard, unseen, or unattended to can get worse.

Most importantly though, when before there was frustration, indignation, or even anger, post-apology there may also be guilt or doubt or resentment, because they aren’t now allowed to feel annoyed, since “she did apologize.”

Following through is essential because of what happens to our community when we stop at the apology.


A lot of this can feel very generic and theoretical, so I encourage you to spend some time with your own mistakes. Here are some prompts to journal through, talk or think about, to get you started:

  1. List mistakes that you have made as an educator. What are the ones that stay with you?
  2. For each of these mistakes, reflect on some or all these questions:
    • Did you talk about the mistake, in the aftermath, in a way that you are proud of?How did making that mistake make you a better educator/leader?In what ways might you find gratitude for this mistake?
    • Who did this mistake harm? How long did that cost/consequence persist? Be honest here – I find often that we tend to struggle to sit with the harms we may cause others, because it is painful. But I think we can be kind to ourselves, forgive ourselves, and look ahead while still feeling and acknowledging the pain that we facilitate.
  3. Pick one mistake and rewrite the script if you had to do it again, and better, how would you go about it now? This is not about regret and being too tough on yourself. This is about practicing/exercising the muscles that you have built with a no-stakes event from your past so that you can be stronger and more flexible for the next test.  

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