This piece originally appeared in the May 27 edition of the New York Post.
The curtain has fallen on the Oakland teacher’s strike, which, in its 11-day run, deprived students of critical learning time while reshaping the playbook for teachers’ rights and compensation. The inevitable compromise, announced last week, heralded a retroactive salary increase of 10% and trimmed class sizes. Yet, as I sift through the settlement’s fine print, what’s most notable about this battle is what the teachers didn’t ask for: anything related to artificial intelligence (AI).
Now, contrast this with a simultaneous drama unfolding 370 miles to the south, where the Writers Guild of America (WGA) stands firm against the tidal wave of AI, demanding, among other things, that Hollywood mustn’t employ these programmed poets in crafting their on-screen tales. The writers understand that this is likely their last chance to contain an existential threat to their profession. If I were on their negotiating team, I’d make this my number one priority because higher salaries only matter if studios employ actual humans to do the writing.
The stark difference in approach between the writers and the teachers makes you wonder why the latter haven’t been as expeditious in facing the AI threat as the former. Consider the impact of the most widely used digital learning platform in the world: Khan Academy. This site has been the 800-pound gorilla in education technology circles, having already garnered over 7.8 million Youtube subscribers and billions of views. Founded in 2008, Khan has built most of its content on pre-AI technology, but the site’s founder Sal Khan floored a Ted audience in April when he rolled out a new AI tool named Khanmigo. The program allows students to engage in an intellectual dance in which the machine tailors individual experiences and even conducts literary discourse as fabricated characters reminiscent of Hamlet or Jay Gatsby.
Khanmigo serves as a veritable gateway for students to dive freely into subjects ranging from mathematics and computer programming to history and writing, all under the vigilant assistance of AI. This tool, currently in beta but poised to spread its wings come fall, deciphers complex concepts into digestible nuggets while offering advice to those who find the subject matter challenging. And Khanmigo takes a step beyond the academic, extending personalized messages of encouragement to keep students engaged.
This is the state of one program mere months after the public launch of ChatGPT. Just imagine what this could mean five years from now. The AI education market is poised to grow from a $4 billion industry in 2022 to over $20 billion by 2032, according to Global Market Insights.
While the utility of such tools is undeniable in their ability to personalize learning and streamline lesson planning, we must dispel any illusion that these mechanical mentors will not eventually supplant flesh-and-blood educators. Every question Khanmigo poses to a student is one less for a teacher to ask. Every lesson plan it conjures up is one less for an educator to create. And every lecture it delivers negates the need for one imparted by a teacher.
And what happens when we add Education Savings Accounts (ESAs) to the mix? In a growing number of states, parents will soon be able to pull their kids from the public school system and use public dollars, ESAs, with very few restrictions. Many states allow the funds to be used for home schooling and hybrid instructional models resembling pandemic learning pods. I could see many taking advantage of free or low-cost platforms like Khan, which through AI and other advances, could provide an equivalent or perhaps superior instructional experience to their kids. Parents can then use the money they’ve saved for personalized enrichment programs, coaching, and equipment. If enough parents do that, districts will be forced to cut back, potentially hiring fewer teachers.
It is not a question of if, but when the next teacher’s strike will unfurl its banner with a demand that is as predictable as it is urgent: the restraint of AI in the classroom. Yet, this is a race against the relentless march of time and technology; indeed many school districts have already incorporated AI teaching into their official learning processes. As parents, teachers, and students become increasingly accustomed to the convenience and efficiency of AI tools, it may be too late for the unions to win this battle against their silicon substitutes. But that won’t stop them from trying.
For many years, I’ve been party to conversations with progressive donors and strategists about how to advance and then sell Democrats’ policy accomplishments. These conversations generally rest on two assumptions: (1) our policy views are correct and just need better messaging (the What’s the Matter with Kansas thesis), and (2) if not for obstructionism in Washington, Democrats would pass bold and transformative policy to lift up the marginalized. What’s stopping them, according to this line of thinking, is the filibuster, moderates in the Senate, the Supreme Court, and Republicans in the House.
Now, I’m as appalled by obstructionism as anyone (and have devoted countless hours to the issue on the Majority 54 podcast), and I am a Democrat in part because I believe the party is more often right than wrong. But if the above two premises were true, then we’d expect to see incredible results in my home state of New York, where Democrats hold not just a trifecta of government control but a supermajority.
What have they done with this absolute power?
The NY legislature’s marquee moves on education this past year include passing a bill requiring New York City to reduce classroom size, blocking a proposal to dramatically expand small-group tutoring for students, andhalting the expansion of public charter schools.
Class Sizes
The state is effectively mandating that New York City spend as much as $1 billion per year to cap class sizes at 20 students in K-3, 23 in 4-8, and 25 students in high school. This proposal was pushed by the leadership of the teachers union.
Most sensible people would want classes to be as small as possible, but we live in a world of limited resources. Is this the best use of money?
The data on the effects of class sizes is notoriously mixed. When Matt Barnum at Chalkbeat looked at available studies, he found that there’s “little rigorous evidence on how class size effects students in high school,” but quite a few studies showed modest results in elementary and middle school. The New York Times was even less impressed by the data:
An analysis of multiple studies found that the academic benefits of small classes are mixed. Generally, any academic gains for students are linked to relatively tiny classes, much smaller than what is required in the bill. . . Mr. Ready said the best evidence supporting smaller class sizes comes from studies in Tennessee and Wisconsin, where the classrooms studied had between 13 and 17 students.
Let’s assume there’s some modest benefit, in some grades, to reducing class sizes at the levels required by the New York law. The debate then becomes about the tradeoffs relative to other programs we could invest in. Here’s Barnum:
[T]hat doesn’t necessarily mean that New York’s class size cap is the right approach. The state is poised to force the city to choose reducing class sizes over other potential investments, and research doesn’t strongly support this either. Placing a hard cap on class sizes may also mean spending a lot to reduce class sizes in better-off schools, limiting the city’s ability to target resources to high-needs students.
This begs the question: if New York didn’t invest in a blanket class size reduction, what else would they invest in?
Tutoring
Sal Khan, in a recent TED Talk, cited data from 1984 that showed that small group tutoring can move a student from the 50th to the 95th percentile. Decades of studies since have confirmed that finding, including research by the Brookings Institution, which concluded that tutoring ranks among the transformative offerings a school district can make to families with struggling students. The think tank found that “over 80% of the 96 included studies reporting statistically significant effects.” Despite this data, Democrats in the legislature blocked $250 million put forward by Governor Hochul to help districts implement small-group tutoring.
This program would have cost a fraction of the total that New York City will spend annually to implement class size reductions. However, Democratic leaders from both chambers of the legislature inexplicably shut it down. It’s hard to tell why, though opposition from the New York Council of School Superintendents may have played a factor.
Charter Schools
New York has a statewide cap of 460 charter schools which has effectively prevented the issuance of any new charters since 2019. Governor Hochul proposed a series of measures that would lift that cap (though it’s complicated, read more here). Hochul faces stiff opposition both within the state legislature and the city council – as well as the teachers unions. As of today, Hochul is in a standoff over the budget with leaders of the Assembly and Senate who’ve both passed resolutions making clear their opposition to her charter school proposal. Even the city council, which has limited say in the matter, has come out against the proposal. This despite the fact that Democrats in the city support lifting the cap by a 24 point margin.
At a time where the Democratic Party is coalescing around a message of racial equity and championing difference, the best available evidence shows charters are a boon, primarily to Black and Latino students. In the 2018-19 school year in New York City, 62% of charter school students were proficient in math and 57% in reading, outperforming the traditional schools’ 45% and 47% respectively.
Critics often counter such data by claiming that charter schools “cream” students – meaning they recruit the higher performers and weed out the strugglers. But when the Stanford Center for Research on Education Outcomes (CREDO) compared “statistical match” students (ie, students with identical demographic, academic, and geographic characteristics), they found charter school students in New York City dramatically outperforming traditional public schools, with Black charter school students making nearly double the progress every year on reading and math than their zoned counterparts. This equates to receiving 23 additional days of instruction in reading and 57 days in math per year.
To sum it up, Democrats in New York this year passed a bill mandating an annual $1 billion spend on class size reductions based on anemic and often-contradictory research support, while rejecting two programs (tutoring and charter schools) which have for years produced jaw-dropping results. They did so largely because of adult politics: the unions love the class size cap and hate charters. The superintendents hate the tutoring expansion.
I helped elect many of these legislators – and without exception the candidates I worked with campaigned on platforms to help the vulnerable. These progressive politicians love to talk about kids, but when they get in a room with interest groups, they cave to raw political power. When I examine their record on the most important issue of the day – investing in our children – I am left wondering whether leaders of my party are truly worthy of the power we’ve given them.
If you like this piece, subscribe to Imbroglio, a newsletter from The Branch about how to bring about the education revolution.
In response to my newsletter on lifelong learning, I’ve gotten a ton of questions about the recommended resources for people trying to level up their productivity and learning. So I’ll take this opportunity to share what’s worked for me. In a separate post, I will share books and courses. Here, I’ll focus mostly on applications and tools.
Opal: This app will block any app on your phone whenever you want it to. I set it to block Instagram (the only social media app on my phone) from 8am to 5pm every day.
Timer Lock Container: I also have a plastic container with a timer. I place my phone in this contraption for 2-3 hours every morning when I am focused on deep work.
Centered: This website facilitates focus sessions. You clock in as part of a group, and each work independently, gaining points for stringing together many productive blocks. You can also set the app to block most other websites and apps on your computer and phone.
Focusmate: This website arranges “focus dates.” You are assigned a remote partner, and each commit to completing a task or project during the session – writing, chores, fitness, music, etc… The one rule is you must stay on camera and work the entire time.
Zoho Notebook: I tend to use a project-based organizational system (as opposed to a subject-based organization method). And though I use Apple Pages, MS Word, and Google Docs for final versions of documents, I tend to keep most of the embryonic work in a system called Zoho Notebook. Here’s what this looks like in practice:
Why do I use this system? For one, it’s beautiful. Each “notebook” has a unique and engaging cover, and the interface makes me excited to open it.
The risk in using this tool is that Zoho is a less established company than many alternatives, so if it ever goes out of business, I could lose a lot of important work.
In case you are wondering, here’s what the inside of a given notebook looks like.
This one is from a movie I started to write during the pandemic called “Varanasi Run.” I paused the project because I needed to travel to India to finish it.
Instapaper: I use this to clip news articles. The app saves them for later reference and relieves me of the need to keep multiple tabs open.
Noa: This app translates articles to audio. They include most publishers, like the New York Times, Bloomberg, Washington Post, etc…
Grammarly: A solid grammar editing program that also scores your writing. Be careful, as it often suggests nonsensical edits.
12 Foot Ladder: This gets you past the paywalls of many news sites. I pay for most of my news, but use this for extremist sites that I refuse to pay.
Journaling: I use a physical journal and tend to use the morning pages method.
Book Notes: After reading a book, I translate my notes to Pages documents. I tend to keep one pages document per book and then transfer key ideas into certain “writing guides” I keep for myself. Here’s a screenshot from the “metaphor” guide I keep for myself in Zoho:
Style Guide: I keep and update my own style guide that the teams at Arena and The Branch also use. It pulls from a bunch of external sources (a lot of the work is not my original stuff). Read it here.
Fitness Group: I’d mentioned in last week’s post about a fitness group I’ve started where we track workouts and habits as individuals and in teams. If you are interested in learning more about that, email me.
Apps I am testing but not committed to:
Roam: Key feature is bidirectional linking. More here on interesting ways to use it.
Superhuman: So many people have recommended this email tool to me, but I can’t seem to get into it.
Freedom: This app blocks the internet on my computer whenever I turn it on. You can enable a preference that prevents you from overriding the system.
I turned 40 on Friday. Coincidentally, I also moved apartments this weekend and stumbled upon old journals from over the years. Like most people, the vision I had for myself by this age is dramatically different than where I am now. No doubt, I had goals for myself that I didn’t meet. But as I leafed through those old diaries and took stock of some of my thirties’ most fulfilling moments and surprising accomplishments, I kept tracing them back to one decision I made five years ago.
Back in 2018, I was reflecting on a recurring dream I’d been having for years. Every night, I’d be back in either high school or college. This, as I’ve come to understand, is a common dream. In my version, I was over-prepared. I’d have my color-coded notes splayed out in front of me, engaged in a thoughtful discussion with my teachers and classmates. It was almost like an idealistic West Wing-esque version of school. Though the dream itself was positive, I’d wake up with a deep sense of unease because I missed the classroom experience.
I loved school. In college, I was often the first to arrive at class and would stay after to lob questions at professors. I attended every office hour I could and took advantage of every tutoring program the school offered. If I could have stayed in college forever, I would have. If I won the lottery tomorrow, I’d enroll in medical school or a neuroscience Ph.D. program.
Reflecting on my dream, I realized I’d been neglecting my love of learning. I needed to reconnect with the thrilling feeling of systematically mastering a skill or domain. I decided to choose one skill a year to obsess over and master. I wanted to select skills that I had little or no experience in — and for the past five years, I’ve gone from complete novice to intermediate or advanced in five different areas.
Year 1: Power Lifting
Year 2: Screenwriting
Year 3: Surfing
Year 4: Tennis
Year 5: Novel writing
Below, I briefly describe how I approached each skill or hobby and how you can choose your own.
Powerlifting
I’d always lifted weights but largely focused on beach muscles. I had no experience with technical lifts like deadlifts, squats, or cleans. I spent the year taking lessons from lifting experts and even attended a camp for Olympic lifters and CrossFitters. I picked powerlifting as my first skill because I was worried that as I approached 40, I’d suffer from sarcopenia — age-related muscle loss. I wanted to learn to lift heavy in a safe way.
By the end of the year, I was proficient in every major lift. Eventually, I went on to win the deadlifting event at a powerlifting competition. I took the lessons I learned that year and built a fitness community for my friends that is now in its fourth year. Through that program, I write and track workout programs for over forty people each week — including the founder of the powerlifting camp I attended in 2018.
Screenwriting
For my second year, I wanted to pick a completely foreign (and scary) skill. I chose screenwriting because I’d never before written anything fictional but always wanted to. I figured screenwriting was a more reasonable and achievable step than writing a novel.
I started the year by reading as many scripts as I could get my hands on. Then I’d watch the movie with my annotated script in hand — watching to see how the words on the page translated to the screen.
When I was finally ready to write, I traveled to Hawaii with a director friend, and we both committed to writing a screenplay by the end of the two-week trip. I finished mine and spent two months emailing the script to one person daily. I had no Hollywood connections, so I was shooting in the dark. Luckily, on the 63rd day, I emailed my friend MC, whose sister at the time worked at Imagine Entertainment, one of the most successful production companies in the world. MC emailed her sister the script, and her sister kicked the script up to the company’s top brass. Imagine wound up passing on the script (they had a planned show set in Staten Island that they felt was too similar – though it wound up being completely different), but I was able to parlay that interest into representation from Creative Artists Agency, the biggest and most powerful agency in Hollywood. They’ve represented me to this day, and I’ve written over a dozen scripts and been hired to adapt a novel into a movie.
Surfing
Ever since I was a kid, I wanted to surf. But I was cursed to grow up on an island with unsurfable waves and in a family that didn’t have the money to travel to tropical locations. But I never gave up the dream of learning the sport.
During the heart of the 2020 election season, I vowed that after election day, I would go somewhere and finally learn to surf. A friend recommended to me a place called Surf Simply, the world’s premier surf school (listen here for my interview with the school’s founder), but warned me that they had a many-year waitlist. By a stroke of luck, the day I decided to visit their website was the day they reopened registrations after the lockdown. I was in the air to Costa Rica as the election was called for Biden. I spent the next two weeks getting my ass kicked in double overhead waves — struggling with vicious tendinitis that prevented me from staying in the water any longer than half an hour. Yet I knew I loved it.
I had planned to return to New York after the camp, but the Delta wave was raging, so I extended my stay in Costa Rica. In a second stroke of luck, Tommy Potterton, my coach at that camp, left to start his own surf school and took me on as his first customer. For the next six months, I paddled out every morning at 5am. Tommy would collect video footage of me and send me the footage by the afternoon with his audio coaching commentary over my footage. My goal for that first six months was to become a “Level 2” surfer, which meant I wanted to be comfortable paddling out on my own, angling a take-off (going sideways down a wave instead of towards the beach), and executing basic turns. I was able to achieve that goal and was well on my way to “Level 3.” By the end of the year, I’d surfed in far-off destinations, including an advanced wave generated by a train. I’m now in my third year of surfing and am solidly a 3, and last week executed my first truly expert move when I got barreled.
Surfing can be a tool for longevity. I often see surfers in the water in their sixties and seventies. The balance, flexibility, and strength required for the sport perfectly matches the traits doctors recommend to avoid age-related physical decline. Most importantly, surfing is a great way to meet new friends late in life. When you paddle out, you leave your phone behind and spend hours in the water chatting with people you may never otherwise meet. Speaking of…
Tennis
As I rounded the bend on my surfing year, I was in the water early one morning in my favorite surf spot and started chatting up a stranger. I told him I needed to pick a new skill for the following year. He asked what was on my shortlist, and I mentioned tennis. By yet another strange stroke of luck, it turns out he was not only a tennis coach but was a former professional tennis player and the coach of the Costa Rica Davis Cup team. He offered to teach me the sport, which is precisely what he did over the next few weeks. He put me through an intensive boot camp that involved hours a day of drills and scrimmages. When I returned to New York, I would send him videos from my matches with friends, and he’d send me feedback. I spent the year playing anyone I could and went upstate a few weekends to a tennis camp (notice the camp theme?). More than a year later, I can play with friends who’ve been playing since high school. I rarely beat them, but I’m able to keep matches competitive.
I picked tennis partly because my favorite sport to play is basketball, a hobby I’ve largely abandoned because I kept getting injured. Tennis, like surfing, is something people do into their older years — and numerous studies point to the powerful longevity benefits of racquet sports.
And like surfing, tennis was something I couldn’t access as a kid because I didn’t grow up in a neighborhood with courts or a family with the resources to expose me to it.
Novel Writing
During my year of screenwriting, I started writing a novel but abandoned it in pursuit of more achievable goals. This year, I’ve decided to pick it back up and make completing the book my focus. I am going through a similar process that I took during the screenwriting year — reading and dissecting texts from authors I respect. I also take a weekly seminar conducted by one of my favorite authors. My goal is to finish the book by the end of the year. This has been the most difficult of the skills because I don’t just want to be intermediate; I want the book to be excellent. I often lose confidence and momentum when I inevitably and frequently fall short of my own expectations. I’m constantly reminding myself of this Ira Glass quote:
Nobody tells this to people who are beginners. I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be. It has potential. But your taste — your taste is still killer. And your taste is why your work disappoints you.
A lot of people never get past this phase. They quit. Most people I know who do interesting creative work went through years of this. Our work doesn’t have this special thing that we want it to have. We all go through this. And if you’re just getting started or you are still in this phase, you gotta know it’s normal, and the most important thing you can do is do a lot of work. Put yourself on a deadline, so that every week, you will finish one project. It is only by going through a volume of work that you will close that gap and your work will be as good as your ambitions. It’s gonna take awhile. You’ve just gotta fight your way through.
I’ve taken his advice and am submitting one chapter weekly to an editor. If I miss a deadline, she will donate money in my name to the Patrick Maholmes Foundation (I am a Bills fan).
Lessons Learned: The Four C’s
Looking back, there are certain themes to what has made each year successful. I call them the “Four C’s.”
Camps: Camps are a fun way to accelerate learning. I attended a powerlifting camp, surf camp, and tennis camp. I am currently in a writing seminar, which includes a two-hour block when I write alongside peers. The experience of intensive, social learning that camps and classes provide is invaluable. Of course, the cost can be prohibitive, but you can often find low-cost alternatives, like meet-up groups and apps (e.g., here’s an app that sets people up to play tennis with each other, and here’s one to help you find writing partners).
Coaches: Find mentors, and pay it forward in areas where you excel. I have been fortunate to find world-class coaches in each domain I’ve studied. This isn’t reasonable for most people, but you can find excellent coaching in almost every town in America — often for free or at a low cost. The CrossFit coach in your local box, the resident novelist teaching a class at the community college, the friend who’s mastered a sport you’ve been afraid to try. There’s also a wealth of online coaches to choose from.
Community: The hard work becomes easy when you do it with people you love and respect. Seek out people who are at or around your skill level. Learn and practice together, share tips, and motivate one another to stay the course. I would have never finished my first screenplay if I hadn’t committed with a friend to do so. I would have never stuck with surfing if I didn’t find a welcoming community of intermediate surfers who paddled out at the same spot every morning. If you can’t find the community you’re looking for, build one yourself. That’s what I did when I built a fitness community for my friends.
Commitment: When you start a new skill, stick with it for at least a year. Even if you feel totally demoralized, honor that commitment to yourself. You’ll find that most obstacles aren’t as intimidating as you originally believed — and that a few days or weeks of spinning your wheels will eventually give way to momentum. Under my framework, you can abandon each skill or hobby at the end of the first year, but thankfully I’ve kept up with all of mine thus far and made them a central part of my life.
Your Oxygen Mask
This is a newsletter for people interested in education. Many of you are school leaders or leaders of organizations or companies. Much of your energy goes into thinking about how to better teach those around you, whether they be kids or employees. Ask yourself: are you spending enough time on your own learning? As the now-cliche metaphor goes, you must affix your oxygen mask before worrying about those around you. That means rekindling your love of learning, that rush of going from clueless to proficient.
You may read this and think of all of the excuses. Your busy schedule, budget, children, and physical limitations. These are all important considerations that may limit what skill you choose and how much time you can devote to it. I, for example, have long wanted to learn to fly airplanes, but I don’t live near a place where it’s cost-effective to do so. But we can’t let these limitations stop us. I think of my mom, who always dreamed of becoming a history professor but had three kids to raise by herself on a nurse’s salary. She took night classes and eventually earned her bachelor’s and then master’s degree from the College of Staten Island, where she is now a professor of American history.