East Side, West SIde

Wednesday, September 30, 2026, 4:02 p.m. to 4:20 p.m. – Words heard during a fast walk on Forty-second Street, New York City, from Grand Central Station to Port Authority Bus Terminal: brother, you got some change, God bless you ... it's this way ,,, and then she said ... a latte ... about three thousand, I said three thousand for that ... now it's your turn ... get over here ... when she was in Amsterdam ... you can't get them now ... don't ask me ... he would have said the same thing ... it's the same difference ...  next week sometime ... it was the spark plugs ... that was then, this is now ... how can anyone blame you for doing that after what they did to you ... ya no viene acui ... once in a while ,,, how do you get there ... it was way more than I was willing to pay ... let's go somewhere else, the line's too long ... not until then ... so he walks in, turns on the light and we all yell surprise and the jerk walks right back out and we're like all surprised like what was that all about and the cake is sitting there in the middle of the table, you know, and nobody thinks of going after him or if they do they ain't saying nothing, so Louise, she's a pisser, she starts cutting the cake and says oh well, more cake for us ... whenever you want ... sir, can you help me for a meal.

The Art of the Pause: Why Effective Writing Requires Unplugged Thinking

I asked Google Gemini, "Write a blog post for WORDS ON THE LINE by Philip Vassallo."  In less than five seconds, it replied, "Here is a draft for a new blog post tailored to the tone and philosophy of your blog." After the line break below, I have left intact the formatting and paragraphing, and I have not changed a word or punctuation mark of this post, including the title.

I have done this thought experiment for three reasons: First, I was curious about AI'sselection of content. Here I would give it a C because I have discussed the points it mentions in so many words repeatedly over the past 22 years of writing WORDS ON THE LINE. Second, I was interested in seeing how close AI comes to imitating my sense of structure (I would give it an A, as I have been teaching this organization strategy for decades) and my approach to style (here it gets a B since I would be more concise). Third, and most important, I wanted to know if AI could add value to WORDS ON THE LINE for my readers. To this point, I am undecided. But I promise not to fade away in the face of AI. To be continued.

The AI Revolution in Education, Part 3: Further Suggestions

No single policy will resolve the AI challenge in education. As technology changes, educators will have to change with it. Here are six evergreen practices that should be at the heart of instruction with AI.

1. Explain  the purpose of every assignment. If students are to practice independent writing, unrestricted AI assistance may defeat the purpose. If they are evaluating arguments, AI might provide useful material to critique.
2. Require students to disclose their AI use. This practice is no different from requiring students to cite their sources. In using AI, what did they request, accept, reject, or revise? Making AI use visible turns it from a hidden shortcut into an accountable part of the learning process.
3. Make AI itself an object of study. Give students an AI-generated response and ask them to find its factual, logical, or stylistic weaknesses. Through such an exercise, students can learn an important lesson: fluent language is not necessarily reliable knowledge.
4. Vary assessments. Discussions, presentations, drafts, demonstrations, reflections, collaborative work, in-class writing, and other teaching modes can provide evidence that a final product alone cannot.
5. Invest in teacher learning. Teachers need training to cultivate their AI knowledge, ethical understanding, pedagogical skills, and continuing professional competence. 
6. Create thinking spaces. The education system should place independent thinking at the heart of all learning. If students are to think for themselves, they must have facilitators ushering them into spaces, physical and otherwise, where AI answers are not immediate. Students and teachers alike must prize the uniquely precious human gift of abstract thinking. 

Not every problem needs an instant answer, nor does every sentence need technological assistance. Sometimes the questions are more important than the answers. Learning can be hard, and that's a good thing. Instead of removing all difficulties, add new challenges. Educators should not keep AI outside the classroom at all costs, nor to put it everywhere simply because it is available. They should include it where strengthens learning and exclude it where it replaces learning.

The AI Revolution in Education, Part 2: The Response

If educators cannot simply eliminate artificial intelligence from the classroom, how should they approach it? So far, we have devised some practical responses.

1. Start with the mindset that AI is an assistant, not the source of knowledge. Using AI purposefully will make students more responsible for learning. When they obtain information based on their results-driven, informed, and focused prompts, they will see AI as another powerful resource, not as the center of learning. 

2. Teach students to question AI rather than simply use it. Students can compare an AI response with reliable sources, identify errors, challenge its reasoning, or ask why one answer is more convincing than another. This approach brings critical thinking into AI literacy.

3. Recreate assignments. Instead of asking students only for a finished essay, teachers can examine outlines, drafts, revisions, sources, and reflections. The process becomes part of the learning.

These approaches suggest that educators do not necessarily have to choose between AI and no AI. They can instead ask whether a particular use of AI advances the learning objective. That question matters because the appropriate use of AI will differ by age, subject, assignment, and purpose, and a science laboratory, a literature discussion, and a college research paper should not necessarily have the same AI rules.

The essential shift is from asking, "How do we stop students from using AI?" to asking, "What do we want students to learn, and what evidence will show that they learned it?" AI may change the answers to those questions, but it must not eliminate those questions.

The AI Revolution in Education, Part 1: The Problem

Artificial intelligence has created dilemmas for educators with no simple solution. Should schools ban it, permit it, or regulate it? Each choice creates at least six problems:

1. Enhancing learning. If AI writes a student's paper, what has the student learned? Evidence suggests that students recall less of the AI-generated content in their assignments, suggesting they do not study the new information.
2. Legitimizing Writing. If AI can produce a competent essay in seconds, why should students struggle to write one? This question implies that writing may go the way of the slide rule.
3. Equalizing access. If students do not have equal access to technology and sophisticated AI tools, will the have-nots have  the knowledge required to use them effectively? AI can therefore create new educational inequalities, even as it promises greater access to information.
4. Protecting privacy. Might students and teachers enter personal information or student work into systems whose data practices they do not fully understand? UNESCO identifies privacy, human agency, accountability, and equity as important considerations in educational AI.
5. Assigning responsibility. If AI provides a wrong answer, who is accountable for accepting responsibility? This point is no small one because content verification can be untraceable.
6. Engendering relevance. What should education preserve when technology changes what people can do? Answering this question is not only at the heart of education but a major factor for giving people worldwide relevant employment.

AI technology is changing every imaginable industry from dairy to diamonds, from medicine to electricity. The challenge is not simply deciding whether AI belongs in education, but which parts of education should remain unmistakably human.

Key to the City

I don't remember the nightmare, but it bolted me out of bed. The clock showed I hadn't set the alarm and was late for work. I grabbed my keys and hopped toward the front door while putting on trousers, socks, shoes, and shirt. Half dressed, I tried unlocking the car door parked on the curb. It would not open. I darted back into the house. Honey, my car key doesn't work for some reason, may I have yours? Don't you remember today is D-Day? D-Day? Don't you remember I took ownership of the car and changed the key as part of the divorce agreement? What divorce agreement? You forgot you signed it? When? What difference does when make? How am I going to get to work? How should I know? Where's my phone? Don't you know it's always where you last put it? Why would I ask if I did? Do you remember that you stayed here last night as a courtesy I extended to you? What? Are you telling me you forgot that this house is no longer yours and I changed the house keys as part of the divorce agreement?

The walk to the train station, the wait for the train, the train ride itself, the run from the train to the office were painfully slow. I rushed into the office and said good morning to whoever I passed, but they all returned my greetings with strange stares. I tried unlocking my office, but couldn't get in. My manager walked up to me. What are you doing here? The key doesn't work. We changed the key. Why? You don't work here anymore. Since when? Close of business yesterday. Why didn't anyone tell me? You weren't around as usual. 

It was nine thirty and I had a hundred bucks in my pocket and the door to the bar across the street was wide open. The owner Charlie was there cleaning up the place and airing it out. Charlie, if I help you get things in order, will you sell me a bourbon neat? If you want to drink this early, knock yourself out. I took the chairs off the tables, swept the floor, and bought a bourbon. Charlie worked at the bar on his laptop all along. The only words we shared were, Give me another, Here you go. The more I drank, the cleaner and emptier the bar looked.

Six or seven shots and a hundred dollars later, I walked out of the bar with nothing in my pocket but three useless keys. I decided to walk home, wherever home now was. Down the block in City Hall Park, there was some commotion going on. A big crowd of people was cheering below the City Hall steps. At the top of the steps was the mayor handing the key to the city to someone famous, but I couldn't make him out. The crowd was chanting some rap lyrics, so I figured he was a recording artist. I stood there with a plan. After the rapper shook the mayor's hand and thanked his mother, music producer, entourage, and fans, he walked down the steps to embrace his following. I couldn't have planned it better. He was high-fiving some devotees and taking selfies with others, flashing his key to the city. He was heading in my direction, and I drew closer to him to quicken the process. Just when he stood in front of me, he raised his right arm for a high-five. From his left hand, I snatched his key to the city and made off for the busy streets hoping to disappear in the crowd. The rapper chased after me followed by two bodyguards, a half dozen police officers, and even some of his fans. But catching everyone by surprise gave me a pretty good head start. I was just a few steps from finding shelter in the mass of tourists and businesspeople scurrying around town. My heart was about to explode, in part because of the chase and in part because of the thrill of having the key to the city. Who would have thought this day would turn out so great?

Founded in 1996

August 2 marked the thirtieth anniversary of my quitting a steady, secure job to become the sole proprietor of a risky business in the educational services sector. The U.S. Bureau of Labor Statistics shows that 19% of such businesses fail within their first year, 46% fail within five years, and 61% after ten years. I'm not a big-time gambler, so I sometimes shake my head in bewilderment that I decided to go solo. Why would I take such a big risk at age 42 with a mortgage and two daughters, ages 14 and 11, meaning a quarter million dollars in college bills ahead of me, to walk away from a job with a reasonable salary, pension, health benefits, a company car, and good friends?  

I had a long time to answer this question. For seven years, I prepared myself to walk away from a role that I ultimately spend 19 years doing by calculating my potential income across the expanse of industry changes, learning whatever I could about the operational side of the business I wanted to enter, and honing my skills to succeed at it. I would have been happy with an equivalent income since I was fortunate to have a wife who had healthcare benefits from her work as a public-school teacher. Throughout those seven years, I continually weighed the pluses and minuses of going into business for myself.

It turns out that my predicted disadvantages and advantages, as well as my ultimate decision, were spot on. 

Starting with the downside, I would never again get a paid vacation, holiday, or sick day. I would work for billable time. I would lose the company car and the healthcare benefit. I would sit on a frozen abysmally low pension from my job, not payable for another 23 years, and I would no longer be able to contribute to a 403B plan reserved for nonprofit employees. I would have to surrender the company car, so I would now have to buy one of my own. Although I did not belong to a union, I enjoyed job security in an autonomous, specialized role. I would also miss the camaraderie of several friends.  

On the upside was the possibility of earning more income, but that was not a guarantee. I would have greater control of my time, even though I never shied from 75- to 90-hour workweeks. Important to me was the constant challenge of finding creative solutions to my clients' problems. I love learning, and surviving in this business depended on obtaining a great deal of self-education to stay at the top of my game. Without a boss, I would feel independent to make choices that mattered to me. I would never again argue with management. I would have only myself to blame for making poor decisions, holding on to bad clients, and partnering with ineffective collaborators.

It all has worked out. Despite formidable challenges, including recessions, natural disasters, an epidemic, and clients' strategic changes, I have earned far more than I expected, so my daughters went to colleges I would not have otherwise been able to afford, and my financial future is more secure. I traveled for work to China, India, and throughout the United States. I worked for some of the largest companies and municipalities in the world, and I have worked with brilliant, diligent people who have made me smarter. I remain close to my friends from my old job 30 years later.

Yes, risks arise in leaving a dependable job for an unknown future in a private business. I would not recommend it for everyone, but the ride continues to be worth it for me.