AI-driven microschooling, AI challenging jobs, and why degrees still have value

As far as most U.S. students are concerned, summer is now over and school is back in session. As we head into September, there’s a lot in this update. Among the items covered:

• The “AI-driven school”
• Whether one-room schools are actually disappearing
• A conversation with Michelle Rhee about the demise of college for all
• A heated conversation about whether AI is killing the entry-level job
• And the Western Governors University commencement I attended in Boston

First, there’s a lot of buzz in the news at the moment about the “A.I.-Driven” school founded in Texas and coming to you—and where students often opt for more school over vacation. This profile of what’s known as Alpha School and its founders in Colossus, for example, is comprehensive and fascinating. The New York Times also wrote about it, as did the Wall Street Journal in a story specifically about Bill Ackman’s involvement.

Longtime subscribers to my Substack will of course already know about the school. I welcomed MacKenzie Price , the founder of Alpha School and 2hr Learning—what’s now being called Timeback it seems—in June of 2024. If you want to refresh yourself and get some more context behind the story relative to other innovative schools and learning models out there, check out our conversation here at “Making Time for Passion: The 2hr Learning Model.”

The Boston Globe Media also had an interesting article about the last one-room schoolhouse in Massachusetts—and how it sits mostly empty on Cuttyhunk Island but can’t be closed. Yet it seems to me there are many one-room-type schoolhouses emerging in Massachusetts (and the nation, per the above on Alpha School). Maybe the distinction for the Globe is that these new ones aren’t district schools?

Hard to know, but just days later the Globe itself had a piece titled “A wave of Massachusetts students embrace unschooling, self-directed learning”—with a profile of North Star that sounded awfully like a one-room schoolhouse. You could also check out NuVu High School. Or, as Kerry McDonald told me, Elements Academy in Braintree. Or the Wildflower Montessori schools (you can refresh yourself about them by checking out the conversation I did in April 2025 with the founder here). And if you want to learn more, check out Kerry’s new book, Joyful Learning: How to Find Freedom, Happiness, and Success Beyond Conventional Schooling, which was just published.

Jobs > College?

Most of you know by now that my most recent book was the national bestseller Job Moves: 9 Steps for Making Progress in Your Career. I leveraged some of the insights from it in a few conversations over the past few weeks.

First, I joined former Chancellor of DC Public Schools and current venture capitalist for EO Ventures Michelle Rhee as a guest on OpenEd.co 's podcast. The episode was titled “College-for-All Is Breaking. What Replaces It?” In it, Michelle said, “Reformers, myself included, over-indexed on ‘college for all.’”

I spoke about how:

“What kids want depends on context. A decade ago, “purpose” was the rallying cry. Now many say, “I’ll have a couple gigs that pay, and my purpose may be outside work.” Both are valid. What’s not true anymore is the model our institutions assume: four years of college, a 40-year ladder. People change jobs every four years on average; roughly a billion job switches happen annually worldwide. Careers swirl and loop—side hustles, non-linear moves. Schools can’t pretend the outside world can be kept at the door. We need porous boundaries.”

This was a packed conversation with lots of insights—and I highly encourage you to listen here.

Second, I joined the “Leveraging Thought Leadership with Peter Winick and Bill Sherman” podcast in an episode titled “The Career Framework That Helps You Make Smarter Moves.” We talked about the power of ideas to transform education, careers, and the way we make big life decisions; how ideas and theories evolve; and some of the existential shifts facing colleges and universities.

Third, I moderated a conversation with hundreds and hundreds of parents in attendance for CGN titled “Is AI killing the entry-level job?” Diane Tavenner , founder of Futre.me; Joseph Fuller , co-lead and founder of The Project on Workforce at Harvard ; and Aneesh Raman , LinkedIn 's Chief Economic Opportunity Officer provided the insights on one of the most passionate conversations I’ve been a part of in years.

As CGN’s own recent national representative poll of parents showed, parents are highly anxious about AI’s impact on jobs and what it means for their children. The chat during the webinar displayed the same, as the parents in the audience were regularly and passionately piling in with a flurry of comments—sometimes in the form of questions, sometimes with anger, and sometimes with large doses of concern.

Counter to the prevailing pessimism in the virtual room, Diane, Joe, and Aneesh offered some practical optimism throughout. Here are a few nuggets I’ve pulled out for you:

Aneesh:

The thing I love about my job is that my job was made up for me. I've been in this role, Chief Economic Opportunity Officer at LinkedIn for about a year. It is a job that I don't think has existed anywhere else at any other company ever before. And our CEO created it entirely because the company needed someone with my specific skills, expertise, curiosities to go out into the world and to try and help all of us make sense of this moment of change. So what I love about my job is that it is my job. And I promise you, if we get this right as societies, the work that's waiting for your kids if they lean into this moment is gonna be jobs that they create for themselves. Work that is really indexing on their unique curiosities and interests the way that nobody beats them at being them. So that's what I love. And my hope is that we get to the other end of this moment that's starting with a lot of fear and anxiety where everyone or as many people as one are able to find jobs that they create themselves.

Diane:

I guess what I would say is there aren't entry-level jobs anymore that don't require experience. And so I think the most important takeaway I have is you're not gonna get hired out of college with your college degree if you don't have meaningful experience. And so… entry-level jobs now require two to four years of experience. And so what that means to me, and I'm sure we'll get into this, is you've gotta be getting that experience through your educational journey.

Aneesh:

I think especially if you're a parent, especially if like afraid, confused, like there's no final answer to this. There's no right answer. Are these jobs going away or not? We don't know. Is this sector gonna rise or fall? We don't know. It's way too early for anyone to have an absolute prediction about what's gonna happen. So don't rush to those conclusions for yourself. There's nothing inevitable about what about to happen. It's a moment of change that we're gonna go through. And that just means that entry-level jobs are gonna change. They're not gonna go away or stay. They're gonna change, and so one way to think about it is if entry-level jobs are kind of entering in into the basement of an organization and moving up, you're now gonna come in at the lobby or at the first floor. That means you've gotta come with work product. You've gotta, while you're in college, be becoming fluent in AI and really understanding the tools. And if your institution isn't giving you that help, you've got to go online and just get smart because that's becoming a prerequisite. … But then you're gonna get into jobs that are better jobs and entry-level jobs have been in the past. You're already starting to see, I did a New York Times op-ed recently, some examples of companies where entry-level folks are coming in to higher value jobs. That means that everyone across the organization has to up their game, too, as that happens. … And the last thing I'd say, in a way that is liberating, I think it matters much more where you work right now than what you do there. So as parents, as you're working with your kids, help them not get so worried about, well, I need this title and I need [this] function. I gotta be a sales person here, a marketing person there. Have them interview where they're looking to get internships or to work and really be rigorous in, how are you thinking about AI? What kind of learning and growth are you providing your employees? How are you rethinking the ways of work right now? Because over the next five years, we're all gonna learn best by doing and you're gonna want to put yourself in environments that are keeping pace with the chain. We can learn alongside that.

Joe:

You mentioned legal and tax. The law, tax is of course law, too, highly amenable to the use of AI to fully automate the preparation of most people's taxes or to fully automate the basic legal research that goes into a fairly simple case in the law. So there'll be a lot less demand for jobs like that. But by the same time, AI is going to be able to automate tasks that previously were things that the worker themselves had to have mastery of. So often had to have specialized background or credentials. So if you take a job like a financial analyst or a credit analyst, very often you needed pretty advanced finance skills… to do financial analysis to earn that job in the interview process. If AI, agentic AI is doing those highly technical tasks, the number of candidates who would be viewed as qualified for that job gets expanded because you don't have to have five course credits or even an internship in that field.

Aneesh:

Diane:

I think now we need to be about pathways for all. And there are, my organization [Futre.me] has mapped 17 different pathways into over 800 careers that exist in the country that are life, family sustaining careers. And each of those are very nuanced. They're, you know, not all of these career pathways require a four-year degree. And so if you, you have to really look at your own circumstances, how much money do you have invest? Are you gonna have to take on debt? You know, what are all of your personal circumstances to decide what the return on investment will be for you? But my big piece of advice there is it's no longer just blindly go to college and think it's gonna work out. …

Check out the whole conversation here.

Western Governors University Commencement

I had the honor to sit on the stage for one of Western Governors University’s commencement ceremonies in Boston last weekend. The speakers were all fantastic, and the student stories moving. I wanted to highlight one graduate, Ping Yan, who said the following in her speech:

There’s no “right” way to do education. There’s only YOUR way. This degree? It’s not just a piece of paper. It’s PROOF. It is proof of our dedication and relentless perseverance: All of us have struggled to juggle work and school, pulled all-nighters, dealt with tech issues and unkind proctors, and handled family stuff - all while holding tightly to our dreams with every fiber of our being. It’s proof that the non-traditional path…can be JUST as powerful…just as meaningful, and just as successful as any other.

For me, there’s a lot to take away there: that we don’t have to do things just because it’s the way it’s always been done, that we can innovate, and that degrees still do have value.

As always, thanks for reading, writing, and listening.