I was about twelve, working in the yard with my dad, when our neighbor walked over. This in and of itself was odd, because these neighbors were not overly “neighborly” and did not often engage with others in the neighborhood. He approached my dad and exchanged a short round of pleasantries, and then announced he had won a swimming pool.
Wow. Who wins a swimming pool?
They’d entered their name at some event and actually won.
My father congratulated him. I watched my father’s face, and as only family can do, I noticed something. My father, who was the ultimate of composure and respect for others, did not give a top tier level of congratulations. This was a matter of fact congratulations that seemed required to say, but served as a curtain for something else. Now, I doubt anyone outside of the family would have noticed, but I did. I just couldn’t, at the moment, figure out what was on his mind with this bit of news.
Let me give you the layout. This neighbor lived on the corner lot at the entrance of our street—a smaller lot by design which held one of the smaller house models. Their backyard was narrow, wider than it was deep. Our house sat next door on a much larger lot.
My father was already piecing together the reality of the lot, the fact the neighbor had made the rarely exercised walk over to talk with him, and the words “Swimming Pool”. My father knew what lurked in the shadows of this conversation before the man had finished his sentence about winning the pool. They’d won a pool that wouldn’t fit in their backyard.
As the neighbor began laying out the situation, he finally introduced what was lingering in the shadows to the light of the conversation, and what prompted him to have to engage with his neighbor. It was an outrageous ask, really, and stretched the dynamics of neighborly actions and living with others to the limits. He wanted to put that pool in the side yard between our houses and use a hearty portion of our side yard. He started pointing and estimating exactly how close to our house that pool was going to sit, and how far forward it would be past the front line of the houses. It was not just a pool. It was a big pool. A big above ground pool, with filter equipment, hoses, decking and fencing…. It was quite the win.
Now, I do remember the neighbor throwing shade on his wife for entering the drawing. He presented it like, this is not my fault- it’s hers. While those words were floating around in the conversation, I was thinking, actually, you all did not have to accept the pool- you could have said no. But who says no to a pool? A big pool. Apparently not him. So, maybe don’t talk about your wife that way. But, that’s how he talked to her and about her all the time, so let’s not be too surprised.
My father listened intently to the ask and gave the man his time and attention. He did not react in any manner that was rude or indignant. (We were not allowed to be those kind of people). We were the kind of people who listened, reasoned, weighed options, and then made the most informed decision we could. Or, at least mom and dad did. I wasn’t quite there yet. Dad ended the conversation with a “let me think on this and talk to my wife.” There was no way dad would make a decision like this without mom. They were good partners and shared decision makers.
Mother was not pleased.
The kitchen table hosted a long conversation that included thoughts and opinions from each of us. My brother and I had very little to contribute, other than wondering if we could swim in it. The neighbor’s kids were younger than I was, and I did not hang out with them. One was a year younger than my brother, and he rarely played with him. They didn’t click, so actually wanting to swim with them was not anything my brother and I were advocating for. I think we wondered, if the pool is on our property, then do we get to use it too? Like, just us.
The answer was no. The neighbor did not offer, and mother made it very clear how dangerous pools were and how it was not ours.
Mom and Dad debated a long time. Mom was a solid no. She did not like the idea of how it would look, did not trust them to keep it looking neat and tidy, did not like where it would be, did not like that it would be sitting on a big portion of our yard, did not like the idea of how dangerous a pool can be…. All reasonable considerations.
Dad fell on the maybe yes side of the debate. He felt this was an opportunity to help that family have something nice and to be supportive of a neighbor. And, after a day or two that’s where the debate landed. That being a compassionate neighbor was more important than our personal interests in how things looked. Their situational need was what moved the needle. I can tell you now, it did not move the needle much past the mid point, but just enough.
The pool was installed. And, oh, wow. Was it installed!
Mother was not pleased.
Nor was she comforted by the thought they were helping their neighbor. It was a decision she had made, but regretted for years. Dad too, but he just didn’t talk about it as much.
For several summers, that pool and my parents’ decision to allow it to go in was the primo neighborhood conversation nucleus. Each summer, the pool was filled with their children, screaming at the top of their lungs, with no parent supervision, water toys everywhere, and because it stretched beyond the front of the house, everyone saw and heard everything. The equipment was loud, the kids were loud, and at times it was an eye sore. Sometimes the water would go green, and you could hear the kids screaming for their mom to fix it. She did not know how. So they had to wait for their dad to fix it, and he didn’t know much about taking care of a pool, and would be screaming about why his wife had let it happen. It was a mess that just kept getting messier year after year.
In the classroom, we make thousands of decisions. We don’t always get them right.
As educators, we see behavior patterns every day. Students, parents, and colleagues create situations through their own choices, then ask those around them to absorb the consequences. The trick is recognizing these patterns and learning how to respond to them. We face these decisional crossroads daily: the chronic procrastinator asking for “just one more extension” on a major project, the parent insisting their child needs accommodations that would fundamentally alter the learning experience for others, the colleague who wants us to cover their duty “just this once” – for the fifteenth time. Each request arrives wrapped in urgency, each requester certain their situation is unique, when in reality we’re watching the same patterns play out again and again.
I tell teacher candidates, you may find yourself being moved by those first sob stories, and those requests for “just one more day” may seem reasonable, as they come out of the mouth of a student. And it isn’t just students. The same patterns emerge with colleagues. There’s the teacher who always needs someone to make their copies ‘real quick’ because they’re ‘so swamped,’ never acknowledging that we’re all swamped. Or the teammate who consistently arrives late to collaborative planning, then asks you to catch them up on what they missed, turning a 45-minute meeting into an hour-long recap session.
You may want to be the compassionate teacher who understands that life is hard and sometimes we all need grace. It feels good to help others. There is an allure to being liked and thanked for understanding. But like my parents’ pool decision, endless accommodations can create a mess that serves no one.
The pattern is predictable: avoided eye contact during work time, sudden “confusion” about clearly posted deadlines, creative reinterpretation of assignment requirements, or continual extraordinary circumstances. Experienced educators have all encountered students, parents, and fellow educators who have mastered the art of the last-minute plea. First it’s a family emergency (which may be real and deserving of compassion). Then their computer crashes. Then they “misunderstood” the rubric or directions. In the end, they’ve learned that consequences are negotiable, that poor planning can always become someone else’s emergency.
The moment of clarity will come. Perhaps it happens during parent conferences. “They do this at home too,” parents confess. “Wait until the last minute then expect everyone to drop everything.” Then they look at us hopefully: “But you’ve been so understanding about extensions…”. Or the teacher who brags on you being so helpful and understanding in the lunch room then follows it up with yet another ask. ‘Since you’re so good with technology, could you just set up my Google Classroom?’ ‘You don’t mind proctoring my study hall while I run to make copies, right?’ ‘Can you talk to that difficult parent for me? You’re so much better at these conversations.’ Each request seems small, until they accumulate into a burden that disrupts your own teaching.
That’s when we realize we haven’t been understanding at all. We’ve been enabling. Just like my parents’ “kindness” didn’t help our neighbors learn better decision-making, excessive flexibility doesn’t teach responsibility. It teaches that deadlines are suggestions and accountability is optional.
Teachers need to approach these moments with critical thought. When that familiar pattern begins to show itself, be ready with clear boundaries that actually help. “I see you’re struggling with the deadline. Let’s look at your options within our class policy.” That policy – posted prominently and reviewed regularly – offers structured support while maintaining standards. The transformation can be remarkable. When students realize you are not accepting their burden, they have an opportunity to identify solutions never imagined. They start assignments earlier. They seek help during office hours instead of after deadlines. They learn to advocate for themselves proactively rather than reactively. The same applies to professional relationships. When colleagues realize you won’t automatically cover their duties or compensate for their lack of planning, something shifts. They start arriving to meetings on time. They learn the systems they’ve been avoiding. They discover they’re actually capable of having difficult conversations with parents themselves.
Are there genuine emergencies? Absolutely. Real illness, family crises, and unexpected hardships deserve compassion and flexibility. But like my mother’s instincts about that pool, we must trust our judgment about when help crosses into harmful territory. The difference between supporting and enabling often lies in patterns – one crisis might be life, but constant crises are often choices.
Some new educators might be tempted to think maintaining boundaries means we’ve lost our compassion. However, the most compassionate thing we can do is invest in supporting others in developing skills that will serve them beyond our classrooms, and beyond this single moment. They may not thank us for saying no in the moment, but, perhaps in the years to come, those boundaries will provide more support than fulfilling any last minute request ever could.
That pool eventually came down, weathered and broken, leaving only dead grass and drainage problems. The neighbors could have declined it entirely, but the allure of “winning” overshadowed realistic thinking. My parents wrestled with their decision and regretted where they landed, though they remained true to their generous nature.
The lesson remains: Sometimes the kindest thing we can do is hold the line. When we blur boundaries between helping and enabling, we prevent others from developing essential skills. Just like that pool became a constant source of stress for the entire neighborhood, our well-intentioned accommodations can become burdens that serve no one.
The boundaries we maintain today become the foundation for their independence tomorrow. That’s a lesson worth teaching, even when it’s difficult to learn.