We dropped off our oldest, Ryan, at college this week, and one of the nights at our lakeside cabin Airbnb, sitting by a fire on Adirondack chairs after brief remarks saying how we’re glad Ryan landed in a good spot, Wendy and I began talking about our youngest and high school junior, Brandon.

This is the part of parenting nobody warns you about when your kids are two years apart, that the moment you finish supporting one college application odyssey, you immediately start auditing the next one. Brandon is a rising junior who wants to go to film school, and we spent about forty minutes projecting what his application will look like eighteen months from now. We could not talk ourselves into feeling like this endeavor was on a clear path for a slam dunk.

I want to be careful here, because there is a version of this sentence that sounds like a public complaint about my own kid, and it isn’t. Brandon spent this summer working, training, and recently getting named co-captain of his JV football team where his coach called him out as a model leader, which is a real thing that real teenagers do not get handed to them. He also lined up the documentary project he is making this year, which took actual coordination with actual adults who had no obligation to say yes. He also started preparing for AP US History in advance and did some SAT prep. He is not lying around.

The problem is that none of that is a no-brainer admitted student filmmaker’s packet; and while it’s not everything, the packet is the packet.

The checklist

Back in June, Brandon and I put together a list of what he wanted to accomplish over the summer. It was our list, with my fingerprints on it in the way that a college consultant’s or planning-intensive parent’s fingerprints end up on it. Last week I asked him to score himself against the checklist so we can see where we’re at now that the summer is over and junior year has begun.

He did do a line by line summary and numeric score (0.0 to 1.0); which is more than a lot of kids would have done with only one request at sixteen (Ryan his older brother was a big time procrastinator for these kinds of asks). But in terms of the actual inventory, Brandon is behind on more than one item; there were reasons for each but my sense is he is going to need to find another gear to land at the application he wants to submit in late 2027 for ED1 or early 2028 for RD.

I sat with that reality for a week before I brought it to Wendy, and what surfaced was not really disappointment. It was something closer to the feeling of watching a play develop from the sideline and knowing the read before the ball is snapped and having no way to say it in time.

The question I did not want to ask

Here is the uncomfortable version, the one I finally said out loud as the fire crackled and it was just me and Wendy (Ryan had retired to the cabin to play Plants vs Zombies Heroes which I guess is somehow defensible as a plant science major enjoying his last night before orientation starts). If Brandon really wanted to be a filmmaker, wouldn’t he have made more films this summer?

I wrote a post a few weeks ago called “The Hook Is Not the Kid,” arguing that the story we construct for an application can drift a long way from the kid it is supposedly about, and that what a child chooses when nobody is watching tells you more than the hook does. I believed it when I wrote it about Ryan, whose revealed preferences turned out to be genuinely more interesting than the narrative we had built for him.

The thing about a principle is that it does not check with you before it applies itself to the next case. Brandon’s revealed preference this summer was football, and I have been treating that as a problem to be managed rather than as information.

What he actually makes

There is a second layer to this, and it is even less flattering to me.

What Brandon likes to make, when he is making things on his own time with no assignment attached, is short vertical video: heavily cut, timed to music, built to make an athlete look like the best possible version of himself for about thirty seconds. He is good at it and multiple athletes at Paly, his high school, ask him for it and he got special recognition at the Track and Field team’s annual awards dinner for it (they even turned down the lights and featured his work to entire the room’s applause).

My honest first reaction to this, the one underneath the supportive-dad reaction, was that it isn’t filmmaking. Filmmaking in my head involves long-form narrative, a sustained argument, something with a second act. The person behind the camera with a beret and an espresso. What he makes is closer to marketing; as an MBA and business exec myself, I know marketing makes the world go round so this is more about an observation around hook accuracy versus value.

I have turned that reaction over enough times now to see what is wrong with it. The distinction I am drawing (art over here, promotion over there) is a distinction that mattered enormously to the industry I grew up watching and matters progressively less to the one he is walking into. Short vertical video optimized for a feed is not a lesser form of the thing. For an enormous share of the people who will pay for visual storytelling in 2035, it is the thing. My son may simply be early, and my discomfort may be a Gen X aesthetic or elitist status preference and the intellectual snobbery of a NESCAC grad wearing the costume of a strategic concern.

But to be fair this still does not settle the strategic question. If what he wants is to make brands and athletes look extraordinary in thirty seconds, that is a legitimate and probably lucrative career, and the question of whether it requires a conservatory film program or a D1 athletic powerhouse with a digital marketing major is a real question. .

He may not know yet. Brandon is only sixteen. I have written repeatedly that we ask these kids to declare in public what most adults are still revising at forty (as a career coach who works with professionals decades often after landing multiple Ivy League degrees who are still trying to figure out what to be when they grow up, I know this all too well). I do not get to exempt my own household from that observation because his college application deadlines are on the horizon.

The non-renewable resource

Here’s another argument that has been hard for me to answer.

You can make a film at twenty-two. You can make one at thirty. The equipment gets cheaper, your taste gets better, and nobody will ever ask you what you were doing with your summers in high school. You cannot be captain of your high school football team at twenty-two and he is definitely not going to be a professional athlete no matter how much leadership potential he has and work he puts in at practice. That window is open for one or two seasons and then it is closed permanently, and a kid who chooses to spend himself fully inside it is not making an error in judgment (assuming he’s making an informed trade off decision). In fact, in my own professional career, I’ve found that hiring people who played competitive team sports can be a huge positive signal.

On the other hand, it’s likely an admissions officer at a highly selective school is more inclined to admit a kid with either a recruitable athletic hook (Brandon plays well above his physical size but getting on a coach’s list even for D3 is not likely in the cards), a clear film portfolio hook, or a killer academic hook. In today’s arms race for youth achievement and elite college admissions, many admissions offices expect to see it all three or four.

The thing I actually want

I have spent the better part of a year on this publication arguing that the elite-private premium mostly evaporates for kids who could have gotten in either way; that credential-gating varies enormously by field, and that film in particular sits on the output end of the spectrum, where the reel decides and the diploma is decoration.

So when I ask myself what the downside case actually is, I have to be honest that it is not income. Nobody’s earnings change that much because of where they learned to cut on the beat but whether the output was a hit or not.

What I do want for Brandon is a very special room. I want for him to be surrounded for four years by people who are better than he is and more serious than he is, in a place where the ambient expectation is that you are working on something important. I think that room changes people (it did for me), and I think Brandon in particular is the kind of kid who rises to whatever the people around him are doing.

Father, consultant

There is also a structural discomfort here which is that I am also Brandon’s college consultant.

Families ask me to do this. What I tell them, when they call me in something like the state I was in this week by the fire pit, is that you can give a kid the best available information, you can help them see the causal chain between how they spend now and what they can choose in April of senior year, and then you have to let them own it. I tell them the kid will be fine at school A, B, or C. I truly believe this.

And then I get to my own family and discover that the advice survives contact with everyone’s family except mine; because when I say it to another family, I am describing a probability distribution and when I say it about Brandon I am describing my son.

We have landed, for now, on weekly check-ins. This is a defensible plan and also a slightly awkward one. It means that once a week I will sit down across from my child and become, for thirty minutes, a professional whose job is to help him see where he is and try my hardest to meet him where he is.

The right analogy

I have been using a football metaphor with Wendy, that we are on the sideline calling plays and Brandon is the quarterback. It is the natural analogy for a house with a captain in it, and it is wrong, because a coach can bench a quarterback.

But the analogy I have settled on now is talent agent, which fits better and hurts more. An agent knows the market, has seen a hundred careers develop, can read the situation faster than the client can; and has absolutely no authority. Everything an agent has is persuasion.

The difference is that an agent can be fired, and the relationship has a natural stopping point when the advice stops landing. I do not get that as Brandon’s dad. I will be in this conversation for the rest of my life, which means the cost of pushing too hard is ruining our father-son bond which would be heartbreaking – much more heartbreaking than him not getting into a fancy film school (and yes, that em dash was mine).

Where this leaves us

I do not have the resolution this post is supposed to have. Wendy pointed out that I had a version of this same anxiety about Ryan at this exact point in the calendar, and that Ryan is currently unpacking a dorm room at a school he is thrilled about.

What I keep coming back to is that the two failure modes are not symmetrical in the way I originally assumed. If I push too hard, the risk is a kid who stops trying, or who does it all correctly and arrives at college having learned that he performs for approval. If I say nothing, the risk is a far narrower set of options in one and a half years and a conversation in April 2028 or 2038 where we both know what happened and he asks “why didn’t you make it clearer in 2026?”

Note: I showed Brandon this draft before publishing it. His take was below.

If you have been on the other side of this, either as the parent who pushed or the parent who didn’t, I would like to know how you handled it in the comments below.

My oldest son Ryan starts at Cornell CALS in a few weeks as a plant science major, which is what he applied as, and which is what his entire application argued he was. The essays, the activities list, the recommendations, the whole tidy package pointed in one direction, and it pointed well enough that it worked.

What I did not anticipate is that we would spend most of this summer quietly relitigating it.

The detour that started it

The first wrinkle was benign. Ryan has been circling an idea about the intersection of robotics and ecological restoration (using automation to do the slow, unglamorous labor of putting damaged land back together), and if that is where he is actually headed, then biological and environmental engineering might serve him better than plant science. So we did what parents in our position do, which is treat it as a scheduling problem. How do you stack a first-year course load so that switching remains possible? What are the prerequisites, what are the sequencing constraints, and what has to happen in the fall so that a door stays open in the spring?

He talked to current students. He talked to advisors. The answer came back that yes, it is entirely possible, and also that the engineering path is dense enough that keeping it viable would consume most of the room he has for exploring anything else. You can argue that he is not attending a liberal arts college and did not sign up for four years of wandering, and that is fair, but the tradeoff is real. Preserving the option to become an engineer costs him the semester where he might find out he wants to be something we have not thought of yet.

And then, while we were deep in the course catalog for reasons that had nothing to do with it, landscape architecture surfaced.

It is right there in CALS. We knew about it the way you know about a restaurant you have driven past for years. But reading the actual course descriptions, the studio sequence where students spend their time designing ecologically restorative landscapes, it landed differently than the engineering track had. Not because it is easier or safer, but because I could picture him in it, and I had been having a harder time picturing him seven days a week in a robotics lab.

What he said next

Two things Ryan said in the middle of all this struck me as Raising Humanity worth of sharing.

The first was that back in high school, when he had to choose between putting his hours into a nationally ranked Robotics team or the Baylands Restoration Club, he chose Baylands. Not agonizingly, not as a close call, just as the thing he wanted to be doing on a Saturday and Sunday.

The second was sharper. He pointed out that he got into Olin College, and that if he were really Mr. Robotics (my phrase, not his), Olin over Cornell CALS would not have been a difficult decision. It would have been obvious. It was not obvious, and while he deliberated for a while, he did not choose it.

Those are two pieces of evidence he generated himself, before any of this came up, at moments when nobody was watching and there was no admissions officer to persuade or try to impress. Economists would call it revealed preference, and it is worth considerably more than anything he wrote in an essay.

The part I would rather not write

Here is where I have to be honest about my own role, because I did not observe this process from a neutral distance. I have a fair amount of experience in higher ed admissions both personally and as an informal admissions advisor to students over the years. I know how the hook gets built, and I worked with Ryan to build this one.

None of it was fabricated. Every piece of Ryan’s application was true. But the process rewards coherence, and coherence is something you construct out of a life that does not naturally have it. A seventeen-year-old with genuine interests in plants, in ecosystems, in building things, in a half-dozen other directions gets shaped (lovingly, collaboratively, with his full participation) into a single legible line that an admissions committee can read in seven minutes and remember.

The trouble is that the story does its job in March and then keeps working long after it should have stopped. It becomes the thing the kid thinks he is, partly because he wrote it down, partly because it got him in, and partly because we all congratulated him on it. And the underlying reality, which every parent knows perfectly well in the abstract, is that we are talking about children who will likely change majors more than a few times before they graduate and change careers several times before they turn fourty.

What I have come around to is that helping your kid apply to college involves two jobs, and they are not the same. The first is to get them admitted to as many places as possible, and that job requires the tight narrative with the bow on it. The second is to help them build a life, and that job has no deadline, no application portal, and nobody handing out sweatshirts at the end of it. The first job has all the urgency and all the scoreboard you can get on social media and at cocktail parties. The second one is the actual assignment of a parent and is probably the thing you’ll look back on with the most pride long after their college diploma becomes a distant memory. I am not sure I split my time between them correctly.

The practical version

If you want something actionable out of this, here it is: I think families systematically underprice the option value of changing your mind.

The default reasoning goes like this. We identified the hook, the hook fits the kid, we found programs that serve the hook, we are done. What that reasoning skips is the question of what happens when the kid comes home at Thanksgiving of freshman year and announces that he does not want to be The Hook anymore, he wants to be Hook Prime of Hook Reimagined. Is he stuck in one lane, or does the place he chose absorb it?

The mistake runs in both directions, which is what makes it hard. Choose the generalist school as insurance against a change of heart that never comes, and you have paid four years of premium on a policy you did not need, while your kid sat in a program that was merely fine when a specialist program would have been extraordinary. In the old days, you’d usually prioritize the well rounded school but in today’s post-AI employment market, I think the scales may be tipping the other way. On the other hand, choose the specialist program on the assumption that the hook holds, and if it does not hold, the exits are narrow and expensive.

So the real question is not which type of school is better. It is how durable you think the hook actually is, and that requires separating the surface expression from the thing underneath it. With Ryan, the surface has already moved twice this summer (plant science, then engineering, now possibly landscape architecture) while the thing underneath has not moved at all. He is a scientist, he is curious, and he loves being outside in the natural world. Every one of those three destinations sits inside CALS, which means the volatility we are experiencing is contained. We appear to have chosen well, though I would like to be clear that we chose well partly by accident. Had he chosen Olin and had the “maybe I don’t want to do robotics” epiphany in July before matriculation, we’d be sweating bullets.

Our younger son Brandon is a rising junior who wants to make films, and he is the harder case. If film holds, a Chapman is arguably a better place to spend four years than a UCLA. If film does not hold, Chapman gives him considerably fewer places to land than USC or UCLA would. Same kid, same decision, and the answer flips entirely depending on an assumption about a sixteen-year-old’s convictions that nobody, including the sixteen-year-old (no offense Brandon if you’re reading this), can honestly make right now. We have about eighteen months to think about it, and I will be writing about that process as it unfolds.

Where we actually are

As of this week, we are trying to get Ryan off the waitlist (yes, yet another waitlist in this era of scarcity) into the Intro to Landscape Architecture class for the fall, which is complicated by the fact that the course is reserved for students who were admitted into the landscape architecture major at CALS. The admissions office, entirely reasonably, asked whether he would like to apply to switch. Ryan said not yet, because committing to a major in order to take the introductory class that would tell him whether he wants the major was a strange piece of logic.

So he arrives in three weeks as a plant science major, hoping to get into a class in a department he might transfer into, having spent his summer seriously considering a third path he has now mostly set aside. Nothing about this is resolved, and I have decided to stop treating that as a problem.

I intend to keep reporting on it. What he takes, what he switches, what the advising actually looks like from the inside, and whether the door we spent all summer trying to keep open turns out to be one he ever walks through. If you are a year or two behind us and want to see how this goes before it is your turn, subscribe and follow along.

That leaves a practical question. If your kid takes the in-state path, lands a meaningful merit scholarship, or skips college for one of the trades, and you have roughly $200,000 sitting there that you’d budgeted for tuition, what do you actually do with it?

The reflexive answer is to leave it alone. Keep it in your brokerage account. He’ll inherit it someday with a step-up in basis at death, which wipes out the capital gains tax on decades of appreciation. The financial planners we talk to describe this as the tax-efficient default.

I’ve come to think it’s the wrong move, and the reason is mostly not about taxes.

The strategy in one paragraph

Gift the $200,000 to your kid now. Put it in a brokerage account in his name, buy a total-market index fund, and leave it alone. When he’s in his twenties and earning a modest income, have him sell appreciated shares each year and immediately rebuy them. Under current law, a single filer with taxable income under about $65,000 pays zero federal capital gains tax on long-term gains. Done annually through his low-income years, this resets the cost basis without ever triggering a meaningful tax bill. By the time he’s thirty, the position has compounded to roughly $400,000 with negligible federal tax paid along the way. By the time he’s fifty, it’s past a million in real, inflation adjusted, dollars.

The gift itself is straightforward. The federal lifetime gift exemption is well into eight figures, which most people reading this are not going to hit. You file IRS Form 709 to report it, and that’s the entire tax compliance picture. No tax is owed by you, your spouse, or your kid.

Why this beats the inheritance default

Capital does different things at different ages. At twenty-six, $200,000 is the difference between renting in the city where your kid’s career is and being able to buy a small place there. It is the difference between needing a steady paycheck and being able to take a sabbatical to try something risky. It is the difference between the conservative version of his early career and the version where he actually gets to swing. At fifty, a few hundred thousand is a strong addition to a retirement account but it isn’t life-shaping in the same way.

The real objection

The reason most parents won’t do this isn’t financial. The financial mechanics are simple enough that any competent accountant can run them in an afternoon. The reason is that a completed gift is irrevocable. The moment that $200,000 hits his account, it is legally his. He can spend it on a down payment, or seed a company, or buy a year of runway to take a real swing at his career. He can also spend it on a van and a year in Costa Rica or lend it to a shady friend. There is no clawback.

The case for holding the money until you die is mostly a hedge against your own kid. That’s a hedge you’re entitled to take, and there are kids you would not give $200,000 to at twenty-two for good reasons. If I had that kind of money in my 20s, I’d probably have spent some of it on living in a nicer place and maybe buying bigger TV’s and some nice watches but I actually also wanted to buy a townhome in the at-the-time less desirable Central Square neighborhood of Cambridge, MA when my landlord offered to sell it to me. Had I bought it, I’d either have a low cost place for my career in Boston or an income producing property for life.

A version of this strategy that some parents will find more comfortable is to hold the money in your own account until your kid is twenty-five or so, then make the gift. This costs you a few thousand in dividend taxes during the holding years, but it lets you make the gift with better information about who your kid is turning into. The harvest math still works, just on a slightly shorter runway. If you’re genuinely uncertain whether your kid is ready, this is the honest hedge, and I’d rather see parents do this than default to holding until death. The question worth asking is not whether to gift the money but when.

Wendy and I have decided the question, for us, is when. First, if he gets into an elite film school in a couple of years, do we take the leap of faith it’s worth it. It’s probably too early to know for sure.

If he ends up at a lower cost option for college, will the saved money will go to Brandon in his name soon enough that he can use it during the years it actually matters? We'll help him think about it, and we'll accept that some of what he does with it won't be what we would have done. That seems like the right shape of the deal.

Two weeks ago I published an honest accounting of what a $400,000 elite college degree returns for a full-pay family, and to my surprise it traveled (somewhere north of 200,000 views, and a comment section that stayed thoughtful long past the point where comment sections usually curdle). I read every comment. People who declined the Ivy and went to a state school on scholarship, people who paid full freight and would do it again, a professor, a couple of economists in disguise, parents in the exact spot I’m in. It was, hands down, the best conversation I’ve ever started online, and reading it I noticed something that has been bothering me ever since.

My own model had four outcomes in it, not three (the three I wrote up, plus the one sitting quietly at the top of the wealth chart). The path that won, by nearly a million dollars, was Scenario 1: the high-aptitude kid who skips college entirely, enters an electrical apprenticeship at eighteen, earns from day one, banks the $400,000 that would have gone to tuition, becomes a master electrician, and then owns the contracting business. That kid retires with roughly $3.2 million in today’s dollars, against $2.3 million for the honors-flagship grad and $1.0 million for the elite-private grad. (Two readers, ExtraStacked and Fenton L., ran their own back-of-the-envelope versions and came back telling me the result is robust, even conservative. They’re right, and the math isn’t the soft spot.)

So here is the thing I can’t stop turning over. Hundreds of numerate, accomplished people showed up to argue, and the argument was almost entirely Cornell versus UC Davis, elite-private versus honors-flagship, $400,000 versus $150,000. The option that beat both of those by a wide margin, the one my own spreadsheet crowned, barely came up. We were willing to debate paying $200,000 extra for a slightly more selective college, and we were not willing to look at the path where the kid skips the college premium altogether and ends up the richest of all. I want to understand why, because I caught myself doing exactly the same thing.

The recoil

Let me tell you about the moment I noticed my own flinch.

There was a stretch this spring when Ryan’s decision was genuinely live, when UC Davis was on the table against Cornell and I was running the numbers I later published, and somewhere in there I let myself sit with the most extreme version of the question. It wasn’t even Davis. It was this: what if the honest, wealth-maximizing answer for a kid as capable as Ryan was no college at all, an apprenticeship and a brokerage account?

I want to be precise about what happened in my own head, because it’s the whole point. I didn’t reach for a spreadsheet, I flinched, and the idea registered, instantly and beneath thought, as a step down, as something that happened to other people’s kids, as a waste of everything we’d built toward. I have spent my entire life inside the assumption that education is priceless, that you go to the best school you can get into, and that it pays off for decades. That assumption is so deep in me that “your brilliant son could be an electrician” didn’t land as an option, it landed as a loss.

Here is what I have to be honest about: when I interrogate that flinch, a lot of it isn’t economics. The economics actually cut the other way. The flinch is about class. It’s about what kind of family we are, what the holiday-table version of Ryan’s life is supposed to sound like, what I would be telling the other parents at that dinner. We dress these reactions up as prudence (”the trades are risky,” “not every kid makes it to master electrician,” “what about the body, the variance”), and some of that is real (the trade path in my model is a 90th-percentile outcome, and it assumes the discipline to invest the money instead of buying a nicer truck, which is a fair point that Alma K. raised in the comments). But if I’m honest with myself, the risk story is doing less of the work than the class story. I reached for “it’s risky” because it was more comfortable than saying “it’s beneath us,” which is closer to the thing I actually felt and don’t love that I felt.

H C. put words to the cost of this better than I could, in a comment I’ve reread several times: the parent who sat their kid down with the loan math, talked them out of the dream school, and is now living with the question, “Did we gaslight our own child?” Cathy S., who as a seventeen-year-old in the 1980s ran her own ROI analysis and chose the cheaper school, framed it as the question I keep coming back to, which is whether you would tell your kid to buy a Ferrari as an investment. We have somehow built a culture where steering a capable kid toward a $200,000-cheaper, higher-wealth path feels like a betrayal, and steering them toward the most expensive option on the menu feels like love.

It doesn’t help my flinch that the facts on the ground keep insulting it. Electricians earn a national median around $60,000 to $68,000, more like $80,000 to $110,000 in high-cost states, and master electricians who own contracting businesses routinely reach $150,000 to $200,000 and beyond. The field is structurally short-handed in a way the white-collar tracks are not (industry groups estimate that for every 10,000 electricians who retire each year, only about 7,000 enter, with tens of thousands of openings going unfilled). I have a Harvard classmate who became a real estate developer and loves his life. My wife is a Realtor with an associate’s degree and is thriving. And I can tell you from living in the Bay Area that it is 10X harder to get a good general contractor to call you back in Palo Alto than it is to find a software engineer or a product manager of which there are literally thousands out of work. The market has been telling us something for years, and we have decided not to hear it. I include myself in the “we.”

The research that both deflates and rescues the elite case

I am not going to tell you to pull your kid out of the college track and hand them a multimeter (you’ll see why shortly, and it has to do with the check I wrote to Cornell). But before I make the case for the elite degree, I have to deal with the comment that did the most intellectual damage to it, because it happens to be backed by some of the best research in the field.

Anthony C. offered a thought experiment in the comments: take a hundred pairs of identical twins, send one twin to Cornell and the other to a budget college, hold the career constant, and the lifetime earnings gap mostly disappears. The $1 million premium, he argued, is a statistical artifact of which kinds of students end up where, not a causal effect of the institution.

He is describing, almost beat for beat, the most important study in this entire debate. Stacy Dale and Alan Krueger spent years on exactly this question, and their method was clever. Instead of comparing elite grads to everyone else, they compared students who applied to and were admitted to the same selective schools, and then looked at the ones who chose the cheaper or less selective option anyway. Those students, the ones good enough to get into the elite school who went elsewhere, earned about the same over their careers as the ones who enrolled at the elite school. When the two of them re-ran the analysis years later using Social Security earnings records, the core finding held. The selectivity premium, for most students, washes out once you account for the kind of student who gets in.

With one enormous exception, and this is the part that matters for my readers specifically. The premium did not wash out for students from low-income and first-generation families. For them, the elite school delivered a real and lasting earnings boost. Which means the population for whom the elite degree pays off financially is, to a first approximation, the opposite of the population I was modeling. The full-pay W-2 family, the working wealthy, the families at that dinner: we are the group for whom the research says the credential adds the least to earnings, because our kids were largely going to be fine anyway. The elite premium turns out to be a redistribution program that works, just not for the people writing the biggest checks.

So if the earnings premium mostly isn’t real for our kids, why am I still paying for Cornell? Two reasons, and the first one is a framework that I think is the most useful thing in this entire post.

The real variable isn’t elite or state

Here is the reframe the comments pushed me toward, and once you see it you can’t unsee it. The question was never “elite or state,” it’s how much your kid’s field pays for a credential at all.

Some fields gate on the credential and the network. To get in the door at a white-shoe law firm, a top consulting shop, a bulge-bracket bank, or a tenure-track academic post, you need the right name on the résumé before anyone will look at you, and the network that name plugs you into is a large fraction of the actual value. On that end of the spectrum the elite premium is real, and Dale and Krueger’s exceptions multiply, because the credential is doing load-bearing work.

Other fields gate on demonstrable output. In software, in film, in the trades, in most kinds of entrepreneurship, the work speaks first and the diploma speaks last, if at all. Nobody asks a director where she went to school once they have seen the reel, and nobody asks a founder for a transcript. The market evaluates the thing you made. On that end of the spectrum the elite premium thins toward nothing, because you can demonstrate the output from anywhere.

Almost every “is it worth it” question collapses into “which end of this spectrum is my kid’s field on.” Tess J. said it plainly in the comments: it isn’t where you go, it’s what you do with the parchment once you’ve graduated. Baran E. watched one kid go elite and one go state and land on the same career trajectory. They are both describing the same truth, which is that the credential is a multiplier in some fields and a rounding error in others. The great mistake of the full-pay class (my mistake, the dinner-party mistake) is to pay the credential-gated price for an output-gated field.

Two sons, opposite ends

Which brings me to my two kids, who happen to sit on opposite ends of that spectrum, and who are the reason I am about to make two different decisions with the same set of values.

Ryan, the one heading to Cornell, is the generalist case. Cornell is an Ivy, and the thing an Ivy sells is breadth: a brand that reads as credible in finance, in consulting, at a startup, in a graduate program, in rooms that have nothing to do with the plant science he says he wants to study today. He is eighteen, and he does not actually know where he’ll end up, which is precisely the point. The honest value of the Cornell degree is that it’s a call option on a wide cone of futures, several of which sit squarely on the credential-gated end of the spectrum. If at twenty-six he decides he wants to raise venture money, jump to consulting, or do a JD, the Cornell line on the résumé quietly opens doors that Davis might have left a little stickier. I am not paying for a guaranteed earnings premium (the research says I shouldn’t expect one), I’m paying for optionality and for a set of intangibles I’ll come back to.

Brandon is the specialist case, and it’s why I’m probably going to make the opposite call.

He’s a rising junior who wants to make films, and his reach schools are the apex of that specific world: USC’s School of Cinematic Arts, NYU Tisch, Northwestern. USC SCA in particular gets called the Ivy League of film schools, and the comparison is both exactly right and exactly the trap. It is the best of its kind, and “the Ivy League of film schools” is still a fundamentally different purchase from an actual Ivy, for two reasons that stack on top of each other.

First, film sits at the far portfolio-gated end of the spectrum. Brandon’s ceiling will be set by his reel and his talent, not by the seal on his diploma, and a strong reel can be built at UCSB or at Chapman’s Dodge College (ranked top 5 in the country for film, with real merit money on the table) and shown to exactly the same industry. The USC network is genuinely valuable and I’m not waving it away, but it accelerates a career rather than gating it, and acceleration is worth a great deal less than a gate.

Second, the cone of futures is narrower and rougher. Where Ryan’s Cornell degree fans out into a dozen credential-gated industries, Brandon’s USC degree mostly pays off if he stays inside the commercial film and television pipeline, which is an industry with brutal economics in the best of times and real questions hanging over it as AI eats into production. A concentrated bet on a narrowing field carries a different risk than a broad bet on an optionality engine, even when both schools are honestly “the best.”

So here is roughly what I expect to tell Brandon, and I want to say it carefully, because he is sixteen, he’ll read this (hi Brandon!), and the admissions gods may make the entire conversation moot (the odds at USC SCA or Tisch are brutal, and there is a very good chance he won’t be choosing among them at all). If he gets the options, I’ll let him choose. But the bar I’m going to set for full-pay USC over Chapman-on-merit is that he has to come back from admitted students day genuinely over the moon, lit up in a way he cannot fake, certain in his gut that this specific place is where his work gets better. If he comes back merely impressed, or flattered, or quietly swayed by the name, that’s my signal that we are buying the brand rather than the reel, and we should take the merit money and the $200,000 and put it towards a studio apartment he can buy in LA to lower his living costs as a starving artist. For Ryan, the optionality justified the premium even at a wince. For Brandon, the premium has to justify itself, and the burden of proof sits on the expensive option.

The part I can’t put in the spreadsheet

I’ve made it this far as the guy with the model, so let me undercut myself, because the truest reason I wrote the Cornell check has very little to do with anything above.

I think Ryan is going to come out of Cornell a more interesting person. The talent density, the labs, the faculty doing serious work, the clubs, the late-night arguments with people who are sharper than he expected, four years of being surrounded by ambition: I believe that makes a kid more confident, more curious, more capable, and yes more hireable, in ways that don’t show up cleanly in a model and that I am not willing to pretend are zero just because I can’t price them.

There is also a quieter factor I’ll name, partly because a sharp commenter (Grey T.) made me, and partly because it’s real even though it’s a little uncomfortable to say in public. An elite campus is, among other things, an unusually dense market for meeting the person you build a life with. Economists have a clinical phrase for this, educational assortative mating, and the research (the standard reference is Eika, Mogstad, and Zafar) shows that who partners with whom, sorted by education and earning power, is a meaningful driver of household wealth over a lifetime. I am not paying Cornell tuition to arrange my son’s marriage, to be clear. But if four years in that environment raises the odds that he finds a hardworking, curious, accomplished partner to go through life with, I would be lying if I said that wasn’t worth something to me as his father, and on a pure dollars basis it may quietly be the highest-return line item in the whole analysis, sitting in the one place a spreadsheet can never reach. It is a secondary factor, but it is not a zero.

I’ll give the skeptics their due, because the comments did. Torger pointed out that he and his wife were both merit-scholarship students who found each other in a state honors program rather than at an elite school, and that the high-aptitude kids tend to find each other wherever they land, which is part of why the honors-flagship path is no tragedy. Lily L. took the full Vanderbilt ride over Columbia and watched her daughter quietly miss the density of peers she would have had, which is the same coin from the other side. The cohort is real and it is purchasable at more than one price point, and reasonable parents will weigh it differently.

Here is where I have landed, and it’s less a conclusion than a confession. I am paying for Cornell with my eyes open, knowing the earnings premium probably isn’t there for a kid like mine, because I believe in the optionality and the intangibles and I’m fortunate enough to absorb the cost. But I’ll more ambivalent with Brandon, with the same eyes open, because his field doesn’t reward the credential the way the price tag implies. Same dad, same values, potentially opposite calls, and the only thing that makes both of them honest is being willing to say out loud what we are actually buying in each case. (I’ll add one quiet admission about my own decision: had the $400,000 not already been sitting in a 529, or had the number been $500,000 instead, I think we’d have chosen differently. That should tell you something about how much of this is principle and how much is the comfort of already having the money.)

The hard part was never the math. The math, as the comments proved, is settled. The hard part is what I noticed when Ryan’s decision was live and I felt myself flinch away from the option that won, which is that I had spent a lifetime mistaking the most expensive path for the most loving one, and that untangling those two is the actual work.

Ryan, for what it’s worth, has already absorbed more of this than I had at his age. After he saw the numbers, he offered, unprompted, to pay me back $80,000 within ten years of graduating. I gladly accepted not because I need the money back but because I want him to feel like his next four years in Ithaca are an investment for him and he sucks the marrow out of every year of college life that he’s privileged to be there.

Tom is a parent, career coach, and the author of Raising Humanity, a Substack about parenting, education, and the future of work.

A few days ago I was at a dinner with a few other parents, all of us had high-achieving kids somewhere in the college funnel; none of us qualified for financial aid but all of us were working stiffs earning mostly W2 income (we do not have multi-generational wealth such that $800K in pre-tax income per child was a no-brainer). One family is about to start the college process with a rising high school sophomore. Another had younger kids but had not gone through the US undergrad educational system and was wide eyed and bewildered. I myself am already pot committed, check written for my oldest who starts college in August, no looking back but wincing from the sheer numbers.

The conversation kept circling the same question: if your kid manages to beat the odds and get into an elite college (no small feat for non-recruited, non first generation, over represented applicants), is it even worth it?

I’ve been sitting with that question ever since, partly because I’m living it. My older son Ryan is heading to Cornell this August to study plant science and environmental engineering, and we are writing the full check (no aid, no scholarships, no financial cushion from the university), just a bill that will total somewhere north of $380,000 over four years at published rates before you add flights between California and Ithaca every break, before supplies, before the incidentals that accumulate invisibly over four years of college life. The true all-in number for a family like ours at a school like Cornell is probably over $400,000.

In the old days, you just go to the best ranked school you get into and know that this is an experience, degree, and network that will produce a lifetime of intellectual, social, professional, and financial benefits. The financial return on investmenr was a no brainer. But surely there has to be a number right. If it’s not $100K a year, would you pay $200K a year or $300K a year for a Stanford degree? I don’t think I would.

I’m about to face a similar question for my younger son Brandon, a rising junior in high school, who dreams of a path that might take him to USC, NYU, or Northwestern for film. That would be another $400,000 conversation (or more given inflation). While Ryan wants to study engineering and life sciences, Brandon would be an aspiring filmmaker who might graduate with an elite film school degree and then try his best to land a production assistant job in Hollywood for the privilege of earning $20 an hour with no health insurance and going from gig to gig. That’s assuming people will still shoot films with crews and sets in six years.

To be clear, I’m not writing this to complain (at least not entirely). We made this choice for Ryan with open eyes; we funded the 529 (and the funded it more when the projected costs kept going up) assuming this day would come. But I’ve been been around long enough to know that we often convince ourselves of things because the alternative is too uncomfortable to say out loud. So I have actually run the numbers for all of us. Not to talk myself out of the decisions we’ve already made, but because the families at that dinner (and thousands more like them) deserve an honest analysis before they write the check.

OK, now let’s run the numbers and brace yourself -- it’s not pretty; it’s downright brutal. I literally just had a “come to Jesus” with Ryan this morning saying I’m supportive of him still going to Cornell over UC Davis but please make the most of those four years in Ithaca and try and do great things for humanity that are more possible because of a Cornell education, network, and brand. Otherwise, I could have bought him a small condo or started a retirement fund today that would generate passive income forever.

The Uncomfortable Thought Exercise: three paths

To make this analysis as bulletproof as possible, I modeled out three hypothetical scenarios. Same city for all three (Denver, a real but not extreme cost-of-living market). Same savings discipline for all three (10% of gross income invested annually). Same index fund return assumption (8% annually, conservative relative to the S&P 500’s 40-year historical average of roughly 10.5%). All results are reported in today’s dollars, adjusted for 3% annual inflation, so the numbers reflect real purchasing power rather than nominal figures that flatter with the illusion of size. The only variable across the three scenarios is what happened to the tuition money and what did they do for a living in their earning years.

Here’s the crucial framing: I’m not modeling a family of modest means who can go to a top college for free or a modest cost (e.g. $20K). Those families should truly go to the most rigorous school they can thrive at and be admitted to. You are all set.

For this post, I’m modeling the full-pay family (the W-2 professionals who earn too much for need-based aid and will write the full check). Based on Chetty et al.’s income distribution data and published financial aid figures, this working wealthy group (upper-middle-class families earning roughly $200,000 to $600,000, neither poor enough for meaningful aid nor wealthy enough to write the check without consequence) represents an estimated 25 to 35% of students at highly selective universities. They are, in other words, one out of four of every incoming freshman class (and almost certainly the majority of the parents reading this post).

Scenario 1: The trade path. A high-aptitude kid, smart and hardworking enough to get into a highly selective school, instead enters a Denver electrical apprenticeship at 18 where they (wait for it…) can earn income from day one. The $100,000 per year that would have gone to tuition goes into an S&P 500 index fund instead. Over four years, that’s $400,000 invested. The kid gets a journeyman license by twenty two, a master electrician license by thirty, and eventually owns an electrical contracting business where they’re the owner and boss (probably using AI to do most of their back office and marketing work). To be fair, this is not a median outcome; we’re modeling the 90th percentile, the high-aptitude kid applying the same drive and intelligence to a trade that he would have applied to a selective college. Also, if we all read this post, we probably don’t need a million more electricians every year but think about general contractors, next-gen small business owners, startup founders, plumbers, nuclear power plant operators, air traffic controllers, surgical technologists, etc.

Scenario 2: The elite private degree. A student attends a highly selective private university, full pay, four years. The working wealthy W-2 family writes checks totaling $400,000. The student graduates at 22, enters the professional workforce in Denver, and pursues one of several plausible career paths (ag-tech, environmental consulting, real estate development, law, or policy work). Blended across those paths and weighted by probability, the income trajectory peaks at roughly $233,000 in mid-career. Note: if the student went into high finance or business, the ceiling would be much higher but god help us, let’s not make that their only option (not to mention if you’re an innate genius entrepreneur or investor, did you really need to go to Princeton or MIT).

Scenario 3: The honors flagship. A student with the same ability attends a state flagship university with an honors program and modest merit aid, spending roughly $150,000 total over four years instead of $400,000 (think in-state tuition plus room and board at a strong public university like Colorado, Georgia, Ohio State, or Oregon, with some merit aid bringing the bill down from the $175,000-$190,000 sticker). The remaining $250,000 goes into that same index fund. Across the same blended career paths, the honors flagship grad earns a blended peak of roughly $192,000 (about 82% of the elite private grad’s ceiling) but carries a permanent invested capital base underneath the career earnings. A similar scenario is they go to a private university that offers generous merit based scholarships.

All three land in Denver, all three save 10% of their income every year, all three invest in the same index fund. The only difference is the nest egg and income. Let’s see how everyone fares by the time they’re approaching early retirement age.

What the numbers show

At age 57, here’s where each scenario lands in total wealth (invested nest egg plus career savings):

Scenario 1 (trade path): $3.2 million in today’s dollars. The $100,000 per year invested at ages 18 through 21 compounds individually (the first tranche has 39 years to grow, the last has 36), producing a nest egg of $2.37 million in today’s purchasing power. Career savings add another $856,000. This calculation excludes business equity entirely. A successful electrical contracting business in Denver (a real outcome for a high-aptitude person who applies themselves to the trade) would add meaningfully on top of that.

Scenario 2 (elite private): $1.0 million in today’s dollars. Career savings only. No invested nest egg, because the $400,000 went to the university at 18 and never entered the compounding engine. Despite earning more total income over a lifetime than either of the other scenarios, Scenario 2 finishes last in wealth by a wide margin. The elite degree generates roughly $1.06 million more in lifetime nominal earnings than Scenario 3 and still produces less than half the final wealth.

Scenario 3 (honors flagship): $2.3 million in today’s dollars. The nest egg from $250,000 invested across four years grows to $1.48 million in today’s dollars. Career savings add another $834,000. Scenario 3 finishes more than twice as wealthy as Scenario 2 despite earning $1.06 million less over a lifetime. The invested capital is doing work that salary simply cannot replicate.

The chart that tells this story most clearly is the wealth breakdown by source. Scenario 2’s entire pile is career savings. Scenarios 1 and 3 have a permanent base of invested tuition capital doing the heavy lifting underneath everything else. The gap isn’t about who earns more. It’s about who had $250,000 to $400,000 working for them at 18 versus who sent it to a university.

Here is the finding I keep coming back to: Scenario 2 earns more total lifetime income than either of the other scenarios (more than the electrician, more than the honors flagship grad by over a million dollars in nominal terms) and still finishes last in real wealth by nearly $1.5 million. The elite college network premium, modeled generously across five plausible career paths, generates roughly $165,000 in additional career savings in today’s dollars compared to the flagship in-state honors grad. The $250,000 invested at 18 generates $1.48 million. The hard truth: compound interest does not care about your fancy diploma.

Now let me tell you about Ryan

Ryan is going to Cornell, and I want to be honest about why, because I think a lot of parents reading this are having the same internal negotiation or wondering why I’m not following my own math.

Cornell’s College of Agriculture and Life Sciences is genuinely exceptional for plant science and environmental engineering. This is not a reach for prestige. Cornell’s biological and agricultural engineering program has ranked in the national top 10 for years. Ryan’s goal is to work in ag-tech, possibly with companies building environmental restoration robotics or agricultural sensing systems. It’s a real field with real growth ahead of it, and Cornell puts him in a network of researchers, faculty, and alumni who are doing serious work in exactly that space. The Ivy network in an emerging technical field (where connections to capital and research institutions matter) is not nothing.

But here is the honest version: Ryan’s most credible alternative was UC Davis. And I have to confront what that actually means.

UC Davis is ranked second in the world for agriculture and forestry by QS World University Rankings. Its environmental engineering program ranks eighth nationally. The university’s connections to California’s agricultural industry, to Silicon Valley’s ag-tech investment ecosystem, and to the practical, production-oriented culture of applied science are arguably stronger than Cornell’s for the specific career Ryan wants. A student graduating from UC Davis with strong grades and relevant research experience would have access to essentially the same job market as a Cornell graduate in this field (possibly with stronger West Coast connections, since that’s where the ag-tech funding is concentrated).

The in-state tuition for Ryan at UC Davis would have been approximately $15,800 per year in tuition and fees, with total cost of attendance around $43,000 to $47,000 per year including housing and living (figures sourced directly from UC Davis’s published cost of attendance for 2024-2025). Four years all-in: approximately $175,000 to $190,000. Compared to Cornell at approximately $400,000 total all-in, the capital difference is somewhere between $210,000 and $225,000.

Invested at 8% annually starting at age 18, $215,000 grows to roughly $1.4 million in today’s dollars by age 57 (which is not a rounding error -- it is a retirement).

I’m not saying we made the wrong decision for Ryan. The Cornell experience, the specific research environment, the peer cohort, the campus culture, the transformational nature of four years in a genuinely demanding Ivy League setting (these things have real value that doesn’t show up in a spreadsheet). Ryan is a specific kid, not a scenario in a financial model, and the intangibles of where he will grow and who he will become matter enormously.

But I do think we need to be honest about what we are buying. We are buying an experience and a network premium above a world-class alternative. For Ryan’s specific field, the financial premium we are paying for Cornell over UC Davis may not translate into a commensurate career earnings premium. We are, at least in part, buying a luxury product, and we are doing it knowingly (which is the only intellectually honest position available to us). We’ve been lucky to have less than generational wealth but enough that we’re not sacrificing our own retirement to make this call and loaded up his 529 during some key earning years (concurrent with enrolling him in a public high school and deferring some lifestyle upgrades over the years).

Now let me tell you about Brandon

Brandon is a different story, and it’s still being written and I’m not sure we’ll make the same call for him.

He’s a rising junior who has been telling stories on camera since middle school, received recognition at a film festival last year, and is currently in production on a full documentary this summer. He wants to study film at the college level, and the programs he’s aiming at (USC’s School of Cinematic Arts, NYU Tisch, Northwestern) are genuinely among the best in the world for what he wants to do.

The film industry saying about the top programs is worth knowing: “If you want to make a living, go to USC. If you want to make art, go to NYU.” Both are legitimate pipelines to the entertainment industry. Northwestern is exceptional for the combination of liberal arts rigor and professional film training.

The four-year all-in cost at any of these three is also north of $400,000 once you account for New York or Los Angeles cost of living layered on top of the sticker price and the fact that university costs are going up higher than inflation.

The alternative to USC SCA or NYU Tisch or Northwestern (assuming he were lucky enough to get in) would be a place like UCSB, UC Santa Cruz, or landing a merit scholarship at Chapman’s Dodge College of Film and Media Arts. As a California resident, Brandon would pay in-state tuition of roughly $13,700 per year in tuition and fees at a UC, with total cost of attendance around $36,000 to $40,000 per year. Four years all-in: approximately $150,000 to $160,000. Chapman, ranked fourth nationally by The Hollywood Reporter among film schools, offers merit scholarships up to $42,000 per year for strong applicants -- meaning a student good enough to get into USC SCA could realistically net the Chapman experience for $180,000 to $220,000 over four years, with alumni that include the Duffer Brothers and Justin Simien.

Here’s what makes the film calculation different from Ryan’s engineering calculation, and harder: in film, the portfolio is everything. The industry saying in these circles is that nobody asks where you went to school once they’ve seen your reel. What they ask is whether your work is any good. A talented filmmaker who graduates from UCLA or UCSB with a strong body of work and industry connections in Los Angeles (where proximity to the studios creates genuine access from day one) is not materially disadvantaged compared to a USC or NYU graduate with equivalent talent and work ethic.

The USC network in commercial film and television is genuinely powerful and worth something real. The connections, the alumni who take calls, the pipeline to studio internships (these things accelerate early careers in a relationship-driven industry) have real value, and I’m not dismissing it.

But here is the question I keep sitting with for Brandon: is the network advantage of USC or NYU over UCSB or Chapman worth $200,000 in capital that never enters the compounding engine? In a field where talent and a strong reel are the primary currency, where the industry evaluates you on your work rather than your institution, and where UCSB and Chapman are themselves well-respected and industry-connected programs, I genuinely don’t know the answer.

Brandon is two years away from this decision and the admissions gods may make the decision for us if he doesn’t get enough admissions offers in the first place. His portfolio will be significantly stronger by then and he’s doing really well in high school in the classroom, is gearing up for the SAT, and is emerging as a club leader to complement his film work so he should have a solid application. The right answer depends on what that portfolio says, what the actual admission and financial aid landscape looks like, and what Brandon himself concludes about where he will thrive. But I’m going into that conversation with my eyes open this time since the job prospects for an aspiring filmmaker in an AI world are even more unclear than for an aspiring environmental engineer.

The thing nobody wants to say

The value of an elite private undergraduate degree is real, but it is not primarily financial. It is experiential, social, and in some fields, network-based. For families who can genuinely afford to pay for that experience without compromising their financial futures because of their wealth or access to generous financial aid, the choice is easy.

But for the full-pay family that is stretching to write that check (the family for whom $400,000 represents a material sacrifice, a retirement account not funded, a financial cushion not built), the honest conversation is this: you may be paying a luxury price for a product whose functional performance, in most career fields, is not meaningfully better than a world-class public alternative or not going to college at all. If Brandon were more handy with tools and mechanical devices than he is with a camera, boom mic, and editing software, skipping college would definitely be on the table.

Scenario 3 is the finding I keep returning to as the most actionable insight from this analysis. The honors flagship kid, with $250,000 invested at 18 and a solid education at a well-respected public university, finishes at $2.30 million in real wealth at 57 (genuine financial independence, the kind that makes it possible to retire early, absorb a career disruption, take entrepreneurial risk, or simply live without the low-grade financial anxiety that stalks even high-earning professionals in expensive cities) and it costs roughly $150,000 in educational investment, not $400,000.

The question worth asking before you write the check is not “is this school good?” Almost certainly it is. The question is: “Is it good enough to justify what we are giving up by not investing that capital for their benefit long term instead?”

For some families, in some fields, for some specific kids, the answer is yes (and I think it might be yes for Ryan, though I hold that belief with some heartburn now that I’ve actually run the numbers). For Brandon, I genuinely don’t know yet. But I’m going into that conversation differently than I went into Ryan’s, and I think that’s the most honest thing I can say.

Tom is a parent, executive coach, and the author of Raising Humanity, a Substack about parenting, education, and the future of work.

This weekend, I was back on the Bowdoin campus for my 30th reunion. After a delicious breakfast in Moulton Union (it really is the best college dining in America), I found myself at a table with a former classmate and now Ivy League dean and two parents of college students at highly selective colleges we’ve all heard of. We had the kind of coffee-fueled conversation that reunions are actually for, the one you don’t plan and can’t quite replicate anywhere else.

The question that kept circling back was deceptively simple: what kinds of work will our kids actually do? And is a $400,000 elite undergraduate education still worth it?

I want to try to answer both here, honestly, from one parent to another.

First: yes, you should still send them.

If you’re a full-pay family, not wealthy enough that cost doesn’t matter, but carrying too many assets to qualify for meaningful financial aid, and your kid gets into an elite program, you probably have no real alternative but to write the check. I know that’s not the most inspiring framing, but let me give you the better version underneath it.

The elite undergraduate experience still delivers three things that are genuinely hard to replicate: it builds critical thinking at a level most environments don’t demand, it is one of the last protected spaces for genuine personal transformation before the pressures of adult life close in, and it produces the kind of friendships that last thirty years, as my weekend just reminded me.

What it no longer reliably delivers is the express pass into elite employment it used to provide. And parents deserve to understand why that’s happening, and what to do about it.

The two third rails

There are two categories of work being fundamentally disrupted right now, and the worst outcome is landing in the intersection of both.

The first is knowledge work, the research, synthesis, summarization, and coordination roles that have historically formed the backbone of white-collar employment. These functions can already be handled at roughly 70% quality by AI, and even if the ceiling turns out to be 90%, the implication is not that humans disappear from the equation. It’s that the team of twelve college grads becomes a team of three, each of them managing AI agents doing the heavy lifting. The work is still there but the headcount is not.

The second is large corporations. The era of the mega-employer, the firm with thousands of knowledge workers on corporate campuses and new-grad cohorts in the hundreds, is contracting. McKinsey, Goldman, even the NIH: none of them will be hiring the same number of recent graduates in three years that they hired five years ago. The organizational model that absorbed so many talented young people and gave them structure, mentorship, and a visible ladder is thinning at the entry level precisely as AI handles the work that used to justify those entry-level roles.

Grab both of these rails at once, knowledge worker at a large corporation, and you’ve found the highest-risk spot in the entire employment landscape. It’s where the disruption compounds. On the bright side, for those that do land those jobs and are the handful of humans in the loop, you will be very well compensated.

The gap no one is talking about

Here’s what struck me most in that breakfast conversation, and what I’ve been thinking about all year.

None of the NESCAC schools, and this extends to most of the Ivies, have entrepreneurship programs that are remotely commensurate with what the moment requires. There are student-led clubs at Bowdoin, a course or two at Middlebury, an inaugural cross-NESCAC entrepreneurship day that just happened for the first time at MIT. These are encouraging signs, but they’re modest. The schools that consistently top the entrepreneurship rankings are large research universities with business schools, places with a very different institutional culture than the ones most readers of this newsletter are paying $100,000 a year to attend.

The irony is significant. These potted ivy schools pride themselves on producing leaders who will change the world. They’re sending those leaders into a world where the primary vehicle for changing things is no longer a seat at a large institution. And they haven’t updated the curriculum to match.

I understand why. Entrepreneurship programs can feel pre-professional to liberal arts faculties, which pride themselves on something more elevated than vocational training. But there’s a version of entrepreneurship education that is deeply consonant with the liberal arts, one that asks students to identify a problem worth solving, understand it rigorously and from multiple disciplines, and figure out how to marshal limited resources toward a solution. That’s not pre-professional; it’s exactly what a great liberal arts education is supposed to teach. The schools just haven’t made the connection explicit yet. We can call it Entrepreneurship for the Common Good.

What’s actually on the other side

I want to be clear that I’m not writing this to scare anyone. The picture I’m describing has a genuinely bright side.

What will replace those top 100 corporate employers is not nothing. It’s closer to 1,000,000 new enterprises of one to ten people, each acting with the capability that companies of 100 to 1,000 people had a decade ago, because AI has collapsed the cost of building, operating, and scaling almost everything. Eldercare, preventative primary care, marketplaces that connect underserved communities to services they can’t currently access, climate resilience, education, local services, mental health, the list is endless. The problem space is not shrinking but the minimum viable team required to address it is.

We actually need the next generation of elite college graduates to become founders and founding team members more urgently than we need them to become new hires at blue-chip firms. Not because those firms don’t matter, but because the problems that most need solving in this economy are not going to be solved by large institutions moving slowly. They’re going to be solved by small, fast, mission-driven teams who can deploy AI as a force multiplier from day one.

Not everyone will be a founder; that’s probably about 20% of any cohort. But the other 80% will increasingly need to think like founding team members: which small enterprise, working on which specific problem, do I want to join and help build? The five-layer hierarchy of analysts, managers, directors, VPs, and SVPs will look like a quaint artifact of another era.

The question to change

Instead of asking your kid where they want to work, ask them what problem they want to solve. And then: what kind of one-to-ten person team could they imagine forming or joining to work on it?

This isn’t just a reframe for its own sake; it’s a fundamentally different preparation. A kid who has been thinking for three years about the problem they want to attack comes out of college with the orientation of an owner. A kid who spent the same three years optimizing for the most prestigious-sounding offer comes out as an applicant. In a world where the prestigious offers are fewer and the founding opportunities are more abundant than at any prior moment in history, that distinction matters more than it used to.

The degree is still worth it; the experience, the thinking, the people; those hold. What’s changed is what you build with it on the other side.

If this connects with something you’re navigating as a parent, I’d love to hear from you in the comments. And if you haven’t read the earlier post on what to actually encourage your kid to do while they’re in college, that’s here.

If you have more than one kid, you already know the biggest joke in parenting: what works perfectly for your first child is almost guaranteed to fail for your second. I am learning this in real time as we get ready for the second college application gauntlet.

This summer, our oldest Ryan heads to Cornell to study plant science and environmental engineering. He is a budding scientist and student environmental restoration leader who spent his high school years buried in AP coursework, grinding SAT prep, landing ecology support grants, and ultimately publishing peer-reviewed research on soil restoration. We researched the levers to pull, he pulled them, and while the multi-year process had plenty of ups and downs, it worked. Due to his hard work and a good dose of luck, he’ll be attending his dream school.

Now I turn around and our youngest, Brandon, is preparing to enter junior year, and we are starting from scratch. Two kids, two completely different paths forward.

The moment it really clicked for me was at a track and field awards dinner a few weeks ago. To my surprise, Brandon got extra recognition as the team photographer and hype content creator (when he’s not long jumping and competing in the 100M). They even turned down the lights and pulled up one of his Instagram reels on the big screen: a highlight edit from a recent meet, fast cuts, music timed perfectly, genuine energy. The room loved it and watching Brandon’s face in that moment, it was clear this is not a hobby; this is his thing.

It all started with him taking pics using my phone when he was barely able to walk to some photography classes in middle school and some amateur horror films in junior high. Gradually it became something more serious where he was competing in student film festivals. Now the plan is to spend this summer producing a documentary about the Paly football team, following what could be a remarkable turnaround story from a winless season last year. Brandon plays on that team so he has access nobody else has and he dreams of working full-time for the Seattle Seahawks video content team after college.

If he pulls it off, that film could be a scroll stopper for admissions officers in a way that a bullet point on a resume never could be.

Brandon wants to go to film school like USC SCA, NYU Tisch, or Northwestern. This weekend on a car ride, I asked him: if film school does not work out or you change your mind, would you consider a more general path? A liberal arts college, maybe study history or a great university and study marketing? He looked at me like I had suggested something mildly absurd. “Why would I do anything other than what I love?”

And honestly, that was the moment I thought, we cannot run the Ryan playbook. Film school admissions is not environmental science admissions; it does not care nearly as much about your transcript. It cares mostly about your portfolio of creative work. No SAT score and sterling transcript with great essays is getting Brandon into USC SCA. What gets him in is a body of work that answers one question: who is this filmmaker, and what does he uniquely see? Now, don’t get me wrong; USC and NYU still look at the transcript to ensure he can handle the academic rigor. But the grades only get him to the door; it’s the reel that actually opens it.

So Brandon and I talked it over a few months ago and decided to make a bet. A lot of parents in our position would put their kid in a summer film program that’s structured, inspiring, and name-droppable. It sounds great on paper and the peer exposure and industry feedback are real benefits. But we decided to go a different direction and bet on Brandon actually making something awesome.

The football documentary is the centerpiece of this summer. If he produces it, and he does what I think he can do and makes a great film, that piece could do more work in an admissions portfolio than any summer program credential could.

That is the thing though. He has to grab the ball and run with it, the same way Ryan had to with his independent soil research. I can give guidance and nudges and reminders. But at this stage they have to own it. If he wanders around this summer and doesn’t have much to show for it, that’s gonna be a miss and in a way, a test for him as well.

Brandon’s path is specific, but the underlying principle is not. Whether it’s a kid building their own coding project, writing a novella, or launching a local community initiative, elite schools with seemingly unlimited qualified applicants want to see independent execution, not just a list of camp certificates.

I will be honest; this is less comfortable than the Ryan process. With a transcript-centered application, you have levers. The numbers move and you can see them move. With a portfolio-centered application, the criteria are more subjective, the feedback is slower, and at a certain point you are making the best work you can and hoping the right reader connects with it.

I am not a filmmaker; I cannot teach Brandon how to color match or cut a sequence. But I do know how to help someone find his authentic voice, figure out what he is actually trying to say, and build a body of work with intention behind it. And some things really are the same no matter what kind of kid you are working with:

Find the spike and opportunities genuinely aligned with that spike. Build a package that captures who this specific person actually is. Then let go, because you only have so much control aside from helping the kid put together as compelling a packet as you can.

We figured it out once. Now we figure it out again with a completely different set of tools. I will be sharing more here as junior year at Paly unfolds so feel free to subscribe to this free Substack for updates.

One more thing: I have spent over a decade doing career coaching for professionals, helping people mid-career figure out what they actually want to do next. I also did admissions consulting for a stretch and just finished navigating this whole process on our own with a STEM kid from Northern California.

Every kid needs a different playbook. If you’re trying to figure out how to help your teenager find their unique spike, or if you’re realizing the standard AP/SAT grind isn’t the right path, happy to chat. Whether you just need a single strategy session to map out the summer or ongoing guidance, feel free to shoot me an email (tom@tomleungcoaching.com).

Over ten years ago, I walked into my yard in Seattle to find my son Ryan, seven years old at the time, doing something I couldn’t quite explain. He had taken an outdoor play table, tilted it at an angle, stretched a piece of plastic mesh he had scavenged from an old construction project across the surface, and was running a garden hose over a pile of dirt. He was processing soil, separating minerals from sediment, doing what any reasonable third-grader would do on a Saturday afternoon.

My first thought was that this kid had lost his mind. My second thought, several years later, was that he had been telling me exactly who he was all along, and I almost missed it.

After I published “The Spike and the Soul,” a reader wrote in asking a version of the same question: okay, but how do you actually find the spike? How do you know when you’ve found it versus when you’re just chasing a phase? That’s what I want to try to answer here, with the caveat that this is as much a retrospective as it is a framework, because if I’m being honest, a lot of what I now recognize as obvious clues looked like noise at the time.

Flare Before You Focus

The first thing I’d tell any parent is to resist the urgency to specialize early. Walk through any middle school in a wealthy zip code and you’ll find the same cohort: kids who started fencing at age ten because someone told their parents that fencing was a differentiator, kids logging forty hours a week on piano because the Ivies supposedly love instruments, kids doing robotics not because they love robotics but because it signals STEM aptitude on a transcript. What you rarely find is a kid who woke up at seven years old and said, “I have decided that fencing is my life.”

We call the antidote “flaring,” which is essentially the wide part of the funnel: trying as many disparate things as possible before committing to anything. Science camp one summer, improv class another, a season of travel soccer, a weekend coding workshop, whatever creates stimulus. The goal isn’t breadth for its own sake; it’s exposure, because you cannot develop a taste for something you’ve never tasted. The danger of premature focus isn’t just that your child might be optimizing for the wrong thing, it’s that you’ve foreclosed the serendipitous encounter that might have changed everything. Ryan’s entire environmental arc began because his school had a mandatory community service requirement and he happened to choose a Bay Area restoration event as his qualifying activity. If his schedule had been full, he never would have gone.

Learn to Read the Scent Trail

Once you’ve created enough exposure, your job shifts from activating opportunities to watching and listening, because the signal, when it finally arrives, is almost never announced but is usually a faint pattern.

Ryan is, by any reasonable measure, a teenager who enjoys his sleep and has a complicated relationship with putting back dirty dishes after dinner. But at the beginning of his restoration work, he would wake up on his own at dawn on a Saturday, in the rain, and ask me to drive him to the San Francisco Baylands. That was not a child being pushed. That was a child being pulled.

The distinction matters enormously. Plenty of kids will do things when pushed; that’s compliance, not passion. What you’re watching for is the child who volunteers to do more than you asked, who finishes the minimum and then keeps going because stopping didn’t occur to them. Ryan was supposed to do a certain number of volunteer hours for school. When I eventually asked him how he was tracking against the requirement, he told me he had finished months ago. He had just kept going because he wanted to; that’s the scent trail.

There’s something else worth watching for, which I think of as the sophistication escalator. When a child is genuinely in a flow state around something that could become a spike, they naturally seek harder and more complex versions of the challenge without being asked. Ryan went from attending restoration events to bringing friends to founding a club of thirty students to spending a summer doing back-breaking planting work as an restoration intern to co-authoring a peer-reviewed journal article on native plant rehabilitation. None of those escalations were my idea. I asked questions, floated possibilities, drove the car and he did the rest.

Compare that with passive consumption, which can look engaged from the outside but isn’t the same thing. My youngest, Brandon, went through a period of overdosing on Fortnite, and that’s not the same as Ryan building elaborate, collaborative worlds in Minecraft that he would give me tours of and host his friends inside. Even the gaming tells you something, if you watch it closely enough. To Brandon’s credit, he’s now becoming an accomplished storyteller and budding documentary filmmaker so maybe Fortnite wasn’t entirely bad.

The Saturday Morning Test

If you want a quick heuristic for distinguishing a fad from a genuine scent trail, I’d offer what our family calls the Saturday Morning Test. Not whether your child will do something when you schedule it and drive them there. Whether they are asking you to take them somewhere at a time when they could just as easily be asleep.

The Saturday Morning Test isn’t just about early rising; it’s about what a child chooses to do when they have completely free agency and zero external pressure. Family vacations are one of the best diagnostics I know, particularly if you can create some device-free space and just watch. Ryan was always in the woods building something or examining plant life. Brandon was always taking pictures, posing, finding angles, narrating what he saw. Those weren’t performances for our benefit; they were just what those boys naturally became when no one was managing their time. Brandon is a sophomore and still finding his arc, but he’s writing and producing short documentaries that are already getting recognized at student film festivals, and none of that surprises me at all.

You’re not looking for a single moment. You’re looking for a pattern of behavior, repeated over time, that persists when the child has every other option available to them.

Know When to Let It Breathe

This is the part I find most counterintuitive to talk about, because it runs against almost everything the competitive parenting culture tells you to do.

During Ryan’s junior year, he was carrying a full course load, running his restoration club, volunteering across multiple sites, and trying to finish a plant research project that had started as a spring experiment and stretched into a year-long undertaking. At some point, I could see he was hitting his limit. The research was intellectually serious, it would almost certainly help his college applications, and every instinct in me wanted to say just push through. But that’s not what I said. I told him the research was genuinely cool and genuinely useful, and that if he decided it was too much and needed to let it go, the earth would continue rotating on its axis and life would go on. He decided to keep going, on his own, and eventually the work was accepted in a peer-reviewed scientific journal. But I want to be clear that I was prepared for the other outcome, because I think that preparation is part of what made it possible for him to choose well.

The tiger parent approach, which would have been to set a firm deadline and hold the line, might have produced the same result in this particular case. But it also might have curdled his relationship with the research, or with me, or with the whole domain. By the time your kids are teenagers, part of their development is making real decisions and living with real consequences, and the parent who can step back from being the enforcer long enough to become a genuine thinking partner is, I believe, doing something more valuable than holding the line. They don’t work for you; it’s their life.

For the Parent Whose Kid Hasn’t Found Anything Yet

I want to speak directly to the parent reading this whose child is fifteen or sixteen and hasn’t lit up about anything, because I think that parent is probably the majority, and the anxiety is real.

Finding a spike is a little like fishing. Sometimes you get a bite in the first ten minutes and sometimes you’re casting all over the lake for hours with nothing to show for it, and the lake doesn’t care about your schedule. What you cannot do is rush the fish. What you can do is make sure you’ve cast in enough different parts of the water, and that you’re paying close enough attention to notice a nibble when it comes.

The late bloomer finding an authentic arc in junior year is not behind the kid who committed to a faux spike in eighth grade. I would much rather Ryan had found his true thing at sixteen than locked into something plausible at twelve, because the spike that takes longer to surface is often the one that will actually serve him for decades. He’ll arrive at college knowing who he is and what he cares about, and that’s worth more than a great sweatshirt and a vague sense of forward momentum.

If you have a child who hasn’t found their thing yet, treat summers as concentrated exploration opportunities, try new things every weekend during the school year, and create as much unstructured, device-optional time as you can manage. Not every experiment will produce a reaction, and that’s not failure. A child who has tried twelve things and rejected eleven of them now knows eleven things they don’t want to do, and sometimes the inverse of what you don’t like is the arrow that points you toward something you do.

That backyard wash plant is no longer in our yard, no longer tilted at a slight angle, but not forgotten. Ryan is heading to college in the fall to study plant sciences and environmental engineering. It turns out the third-grader processing dirt in the rain knew exactly what he was doing. I just didn’t have the language for it yet.

Tom Leung is a Director of Product Management at major tech corporation, a volunteer instructor at Foothill College, a student advisor at Stanford GSB and UC Berkeley Skydeck, and a Bowdoin College and Harvard Business School alumnus. He is also the father of two boys navigating the education system in real time (one at Palo Alto high school and one about to start at Cornell), which means he is doing this research whether he wants to or not. Raising Humanity is where he thinks out loud about what it actually takes to prepare the next generation for a world that keeps changing the rules.

He recently started working with a small number of families each year as college readiness coach, focusing on spike discovery and long-game admissions strategy for rising sophomores and juniors. Reach him at tom@tomleungcoaching.com.

For fifteen years, I’ve sat across from VPs, Directors, and startup CEOs, helping them navigate career transitions and product roadmaps. But recently, I had a coaching client that was more complex than any tech rollout: helping my oldest son navigate the college admissions process.

As we went through it, I realized that the traditional college application approach is often missing the forest for the trees. They are often obsessed with the packet; I became obsessed with the arc.

I had so much fun acting as his coach and advisor with this process that I’m opening up a few spots in my exec coaching practice to do this for a few families.

The Problem: Sweatshirt Hunting vs. Life Building

Most admissions consultants are purely outcome oriented. They want to get your kid the sweatshirt. That’s a fine business goal, but it’s not really a life goal (or at least shouldn’t be).

If we only focus on building a resume, we risk getting a kid into a school that doesn’t actually fit their flow state. My approach for my son Ryan was a 1/3 split:

1/3 Life Coach,
1/3 Academic Advisor, and
1/3 Admissions Strategy.

The admissions outcome is a benefit of the coaching, not the point of it.

My Approach: Product Management of the Self

When I worked with Ryan, we treated his journey like a PM exercise:

• Finding the Spike: In freshman year, he thought he liked robotics. He tried it, but it didn’t stick. Then he found environmental science and fell in love. Instead of forcing a well rounded (but boring) resume, we leaned into that spike. That became his hook and his authentic arc.

• Starting with the Kid, Not the List: We didn’t start with a spreadsheet of Ivy League schools. We started with where he loses track of time. We looked at earlier life experiences to find out what actually makes him tick.

• The Parent as the Insight Partner: In my process, parents aren’t just project managers. You are the people who know the kid best. My onboarding includes deep listening to the parent’s perspective to help me triangulate the student’s true potential the same way my wife and I would talk about Ryan’s magical moments as a kid.

The Long Game

The ultimate goal isn’t just an acceptance letter. My definition of success is catching up with your son or daughter when they are a junior in college or in their first job and hearing them say that the introspection we did now set them up for that bigger life arc. I want to help them play an important role in society and be happy, successful people. The admissions process is just the first big strategic project of their adult lives.

The Side Quest Experiment

I’m currently a Director of Product at a big tech company and have been an executive coach for over ten years (including as a top-rated internal exec coach during my over decade as a senior manager at Google). I’m only looking to work with 1-2 families at a time who want this Long Game approach.

If you have a rising sophomore or junior and you want a partner to help them find their flow (and a great school), I’m happy to hop on a few Joint Discovery Calls for parents and students together.

We’ll spend 45 minutes acting as a sounding board for your student’s current path. No pitch, no pressure. I just want to see if my coaching style can help more kids find their spike.

If you’re interested, email me at tom@tomleungcoaching.com

Picture this: It’s late April. Ryan, my oldest son, is a high school senior, and the final deposit deadline for his chosen college is two weeks away. The months-long, gut-wrenching rollercoaster of applications, deferrals, rejections, and waitlists appeared to be over. After applying ED1, he got deferred but declined to apply ED2 anywhere to keep his options open. He then got in RD to the ED1 school but wait listed at his other top choice. After attending admitted students day, he put down a deposit and was looking forward to attending the original ED1 school.

Then, an unexpected text. Ryan got pulled off the waitlist at his other dream school one week before the May 1 deadline. Suddenly, anxiety floods back in. Instead of excitement, his reaction is, “This sucks.” The very school he would have given anything to attend just a month ago now only brings dread. Does he abandon the college he’s just committed to? Were his choices just rationalizations?

This is the chaos of college admissions.

It is time to replace it with something better. The current system, cluttered with Early Decision traps, waitlists, and constant updates, generates “admissions inflation.” Students apply to more schools because they are terrified of being excluded, schools try to appear more selective by rejecting more applicants, and the entire process feels random.

How it Works: The RED System

Ranked Early Decision (RED) offers a way out. It is a blind, ranked-choice system where students submit their top choices, colleges convey who they want, and an algorithm matches them optimally. While this sounds futuristic, the fundamental matching logic is based on the Gale-Shapley algorithm—the same stable, computationally efficient math used to match medical residents to hospitals for decades.

The Student Experience: Instead of a single, high-stakes Early Decision deadline, you create a prioritized list. Put your absolute dream school at the top, followed by your next choice, and so on. To further reduce the burden, we would implement a Common Video Interview. Similar to the process at schools like Bowdoin, students answer a random, candid question once, and that video is shared with all ranked colleges. No more interviewing at 20 different institutions.

The Financial Aid Lever: RED allows working-class families to compete on equal footing with wealthy ones. During the ranking process, students choose one of three financial modes:

1. Academic Priority: Ignore financial aid and match with the highest-ranked school possible.

2. Hybrid Balance: Prioritize an offer from a lower-ranked school if the financial aid package is significantly better.

3. Financial Optimization: Optimize for the highest-ranked school that provides the most generous plan available.

Eliminating the “Early Decision Gamble”

The current ED system forces families into a game of strategic “overshooting” or “undershooting.” If you aim too high with your single ED choice and miss, you’re thrown into the chaos of Regular Decision with no remaining leverage. If you play it too safe and aim low just to secure a spot, you’re left with the “buyer’s remorse” of wondering if you settled.

RED eliminates the need for game theory. Because the system allows you to rank multiple schools, you can—and should—put your “moonshot” school at #1. If you don’t match there, you haven’t “wasted” your early energy; the algorithm immediately looks at your #2, #3, and #4 choices with the same level of priority. It removes the fear of aiming high while simultaneously ensuring you don’t have to “settle” early just to be safe. You get to be ambitious and practical at the same time.

The Quantifiable Cost of the Status Quo

To understand why RED is a necessity rather than a luxury, we have to look at the sheer scale of the waste in the current system. As of the 2026 admissions cycle, the average student now applies to 6.56 colleges, with many high-achievers in wealthy suburban districts targeting 15 or more. This “application inflation” forces the average senior to burn nearly 80–100 hours just on the mechanics of writing supplements and managing deadlines not to mention the hundreds of hours thinking, Googling, ChatGPT’ing, and kvetching about it with friends, parents, and family.

RED, combined with a Common Video Interview, could cut this time burden by more than 70%. Beyond time, the financial toll is staggering; the average cost to apply to a competitive set of schools—including fees and test reporting—now hovers around $2,700 and many families hire professional consultants to meet with their kids weekly for up to $100K. By shifting to a matching model, we aren’t just changing a policy; we are returning billions of dollars and thousands of hours of senior year to American families, while stabilizing a process that 76% of students currently describe as the most stressful experience of their lives.

A Proven Path

We should acknowledge that we aren’t reinventing the wheel from scratch. The innovators at QuestBridge have already figured this out for high-achieving, low-income students. RED simply takes those proven principles and scales them for everyone, adding the flexibility of financial aid “modes” to make it practical for every family.

The Path to Adoption: Start with a Consortium

We don’t need the entire Department of Education to sign off on this for it to work. We only need a consortium of peers. Imagine a pilot program involving a natural grouping of schools with similar applicant pools, such as the NESCAC schools, the Ivy League, or a regional consortium of West Coast schools. By running a “RED Pilot Cycle,” these schools could prove the stability of their enrollment while being the “heroes” who lowered the collective blood pressure of their applicants. The match would be handled by a neutral, third-party nonprofit to protect the integrity of the “blind” match. If they want to be extra innovative, they could review RED applicants in the summer of junior year and have a min GPA senior year to maintain the offer if matched.

See It in Action

The Outcome

Once a match is made, it is final and binding. No more anxiety, no more guessing games, and no more “April surprises” from waitlists. This approach takes the pressure off colleges trying to manage their “yield” and gives students the confidence of knowing exactly where they are going.

The only scenario where a match isn’t made is if a student’s entire list consists of schools where they aren’t admissible. But for everyone else, if you rank a college and they think you are a fit, a match is guaranteed.

Tom Leung is a Director of Product Management at a major tech company in Silicon Valley, a volunteer instructor at Foothill College, a student advisor at Stanford and UC Berkeley, and a Bowdoin and Harvard alumnus. He is also the father of two boys navigating the education system in real time. Raising Humanity is where he thinks out loud about what it actually takes to prepare the next generation for a world that keeps changing the rules.

A few weeks ago I found myself back on the Bowdoin College campus for an alumni panel on AI and the future of work, sitting across from a room full of students who were trying to figure out what the next few years were going to look like for them.

Before the panel, over dinner with faculty and career counselors and a handful of students, I kept hearing a version of the same anxiety: the world is changing faster than anyone can track, the jobs that seemed safe a few years ago don’t feel safe anymore, and the question of whether four years of a liberal arts education is the right preparation for what comes next was sitting in the room like an uninvited guest.

Walking between buildings that evening, I recognized the feeling. It is the same one I hear from parents of college-bound kids all the time, and one I have felt myself: in a world moving this fast, is breadth a luxury students can afford? Wouldn’t a more specialized, pre-professional curriculum be the safer bet?

I have come to believe that instinct, while completely understandable, is asking exactly the wrong question, and that most of the conventional wisdom guiding parents through this decision right now is optimized for a labor market that is already changing underneath us.

The Path That Used to Work Is Narrowing

For most of the last fifty years, the deal was implicit but durable. You got your kid into a good school, they worked hard, they graduated, and a large institution absorbed them. The analyst class at McKinsey or Goldman, research analyst at a major university or government body, the rotational program at a Fortune 500, these organizations took in thousands of talented junior people every year and did the work of turning them into professionals. They provided structure, mentorship, credentials, and a clear ladder. Many of those kids went on to graduate school before the real ascent began, but the point was that the large entity was the on-ramp, and the on-ramp was reliable.

That on-ramp is narrowing, and parents sending kids to college today deserve to understand why.

The work that once required a class of twenty-five analysts, most of it research, synthesis, first-draft document production, data modeling, and structured problem-solving, can increasingly be handled by a much smaller team equipped with AI. This is not a prediction about some distant future. It is already showing up in hiring numbers, in shrinking analyst cohorts, and in the quiet restructuring of what entry-level roles are actually expected to do. The competition for those spots is intensifying at exactly the moment the developmental scaffolding they used to provide is thinning out. Your kid may get the job, but it will not look the way you remember jobs looking, and it will not develop them the way you were developed.

The students who will navigate this well are not the ones who optimized hardest for those shrinking spots. They are the ones who started preparing for a different kind of territory.

The Other Thing That Happened

At exactly the same moment that the large-institution path is contracting, something else has occurred that most career conversations aimed at college students, and the parents advising them, have not yet absorbed.

The cost of building something from scratch has collapsed.

A company, a nonprofit, a research initiative, a service that matters to a community that has been underserved, any of these things used to require years of accumulated credibility, a network of connections, and enough capital to hire a team. Your kid would have needed to wait until they were senior enough to have resources, or until they had saved enough to take a real risk, or until they had spent a decade inside an organization learning how things worked before they could try anything independently. The team that once required a seed round and eighteen months of recruiting is now available for the cost of a few software subscriptions. Marketing, engineering, research, strategy, communications, finance, all of it, ready to deploy this afternoon on whatever problem your kid actually cares about.

No generation in history has had access to this before theirs.

Which means the question for your graduating senior is no longer only which large organization will hire them and develop them. It is also, for the first time, what do they want to build, and what is actually stopping them from starting? If they care about rural education, chronic disease, climate resilience, democratic participation, or any of the other problems that have historically been too underfunded or too daunting for a small team to tackle, they no longer need to find a billionaire philanthropist or wait until they have enough seniority to matter. They can start now, with the team they already have.

The Two Ways to Think About AI

There is a mindset question underneath all of this that I have started to think is the most important thing a parent can help their kid internalize before they graduate.

There are two fundamentally different ways to relate to AI. The first is that AI is the thing coming to replace you, in which case every new model release is a threat, every capability announcement is a reason for fresh anxiety, and your entire orientation is defensive.

The second is that AI is your superpower, a set of capabilities that multiplies what you can do by an order of magnitude, in which case every new model release is a reason to celebrate, because your team just got more powerful. The difference between these two orientations is not optimism versus pessimism. It is the difference between thinking like an employee and thinking like and in many cases becoming an owner and chief executive, and the students who come out of college with the owner orientation are going to have a fundamentally different experience of the next decade than the ones who didn’t.

Your job as a parent is not to teach them the tools. The tools will change completely between now and graduation, and whatever prompt engineering course they take as freshmen will be quaint by senior year. Your job is to help them develop the orientation underneath the tools.

What Actually Prepares Them

This brings me back to that campus, and why I now think the anxiety about breadth versus specialization has it exactly backwards.

The skills that determine whether AI makes someone exceptional or merely efficient are not technical. I have written about them at length here on the Raising Humanity substack, but the short version is this: critical thinking, strategic judgment, the ability to communicate clearly and persuasively, and the capacity to lead other people through uncertainty. These are the skills that determine whether someone treats AI as a genuine thought partner, pushes back on its reasoning, brings real context and judgment to bear, and produces work that actually changes something, or whether they take the first output, call it done, and wonder why their work looks the same as everyone else’s.

I watch this divergence inside my own corporate Silicon Valley job every day. Give two people the exact same AI tools on the exact same problem, and they produce work products that are not even close in quality. The difference is never the tool. It is whether the person on the other end of the conversation has the judgment to know what good looks like, the curiosity to keep pulling on the thread, and the critical thinking to recognize when the AI has gone confidently off a cliff. That judgment layer is not something you can learn in six months. It accumulates through years of struggling with hard problems, defending positions out loud, having your thinking pushed back on by someone who knows more than you, and being forced to synthesize across disciplines in ways that don’t have clean answers.

Which is, not coincidentally, a fairly accurate description of four years at a rigorous liberal arts college.

There is also a concern worth addressing directly, because I hear it from parents and from students themselves. If AI is doing so much of the work, how does someone build real judgment? Aren’t we screwing over the future leaders by not training them the old way? If you never had to struggle through the problem the hard way, do you ever develop the instincts that struggling produces?

It is a serious question with a genuinely counterintuitive answer. Consider what a product manager’s first two years might look like now compared to mine. In my early years, I shipped a handful of products. The cycle times were long, the organizational friction was real, and each launch was a months-long ordeal. A junior PM today, working with AI-assisted workflows, might ship ten times that volume in the same period, which means ten launches, ten rounds of user reactions, ten post-mortems, ten sets of patterns deposited into their accumulating sense of judgment. Lewis Hamilton did not become the driver he is because he understood every component of the engine at a mechanical level. He became who he is because he drove more tracks, in more conditions, more times than almost anyone else. The reps are not gone for your kid’s generation. They are multiplied.

The Practical Advice

So what should you actually be encouraging your kid to do while they’re there?

Go broad. The student who takes economics and philosophy and environmental science and statistics and a writing seminar is not diluting their preparation. They are building the cross-domain pattern recognition that allows them to see connections that specialists miss, and that AI cannot manufacture on its own.

Go deep in something. Breadth without at least one area of genuine depth produces generalists who lack the judgment to know when they’re out of their depth. The independent research project, the thesis, the thing they pursued beyond the assignment because they couldn’t stop thinking about it, this is what produces the kind of curiosity that separates people who use AI to discover interesting problems from people who use it to produce slightly faster versions of mediocre work.

Lead things with real teams. Not just join organizations, but take on roles where they are responsible for other people, where their judgment affects outcomes for a group, where they have to communicate a vision and bring skeptical people along. The seminar teaches them to think. Leading the student organization teaches them to move people. Both matter, and the second one is considerably harder to develop later than the first.

The students who come out of college with all three of these in their toolkit are the ones who will look at that team of AI agents and know exactly what to do with them. The ones who spent four years optimizing for a credential, picking the most legible major and the most prestigious-sounding internship and the most predictable path, will find that the path they optimized for has fewer spots than it used to, and that they skipped the development that would have made them formidable anywhere else.

Congrats, your kid is going to college. What they do with it matters more now than it ever has.

Tom Leung is a Director of Product Management at Meta, a volunteer part-time instructor at Foothill College, a student advisor at Stanford GSB and UC Berkeley Skydeck, and a Bowdoin College and Harvard Business School alumnus. He is also the father of two boys navigating the education system in real time. Raising Humanity is where he thinks out loud about what it actually takes to prepare the next generation for a world that keeps changing the rules.

Last week, I was in a state of euphoria.

My oldest son had just finished his college application process, coming out the other side with incredible options despite the daunting odds we all hear about. My wife and I were taking a victory lap, scrolling through old photos, reliving the chapter of raising these boys. It was one of those rare moments when you feel like you did something right.

So I asked him, riding the high: “When were you the happiest growing up?”

He said eighth grade, back in the States, hanging out with his core group of friends, and I smiled because that tracked completely with the kid I knew.

Then, just curious, I asked: “When were you the most unhappy?”

He said Zurich, and I did not know what to say.

By any objective measure, those years were supposed to be extraordinary. We lived in an idyllic landscape of rolling hills, forest farms, and grazing cows, traveling to a new country almost every month in a place that was safe and organized and beautiful beyond anything I had grown up with. The Sound of Music upbringing, I used to call it. I had given my sons the world, and it turned out that the world was where he was the most miserable.

Here is what I did not know at the time, and what he could not tell me then.

I was a Director of Product at a major tech firm, working brutal hours, often not wrapping up until 10 or 11 p.m. local time, which meant my window with the kids was basically weekends. I wanted to make sure my sons did not grow up as spoiled rich brats, especially in a culture as disciplined as Switzerland’s, so I designed a system. I built them a micro-economy: a ledger of points earned through chores and good behavior, offset by fines for bullying, breaking things, or being disruptive, with a running balance that could be redeemed for toys or screen time or docked down into debt.

On the surface, it worked magnificently. I would reach for my phone the way a gunslinger reaches for a sidearm, and they would immediately stop whatever they were doing, sometimes even laughing about it. I thought I was an ingenious, progressive father, teaching accountability and responsibility through elegant game design.

What I was actually building was a cage.

My son told me, ten years later, that he felt a state of total helplessness. While his friends might get grounded for a week and then start fresh at zero, he lived under a compounding debt with no end in sight. Even birthday money felt like it had to be taxed to pay down the ledger. He did not have the words at eight years old to say “Dad, this is not fair,” and he had no mechanism to negotiate his way out of a system that an adult had designed specifically to be airtight.

So he went outside and sat by a large rock under a tree.

I even had a name for it: Ryan’s Rock. I thought he was just blowing off steam, processing frustration the way boys do, and I would give him space and then go back to whatever I was doing. It seemed healthy to me, independent even. Now I understand what he was actually doing out there. He was sitting with powerlessness, a kid who had run out of moves inside a system with no mercy clause, no reset, no path to winning. And his father was too busy feeling proud of himself to notice.

That is the part that breaks my heart the most, not that I made mistakes, because every parent makes mistakes, but that I was actively congratulating myself while it was happening.

My younger son had his own version of this story, and I handled it just as badly.

Before his ADHD diagnosis, I read his impulsivity as defiance, responding with lectures and taken privileges and the firm conviction that I was preparing him for the world by teaching him that behavior has consequences. What I was actually doing was punishing him for something he literally could not control yet. I would get emails from teachers once a week, sometimes more, across multiple schools over several years, and each time I would respond the way I knew how: more structure, more accountability, more pressure.

A friend of mine, a psychiatrist, finally sat me down and reframed it without lecturing me. He just said: there is a cost to not treating this. Your son might be losing friendships he does not know he is losing. His grades reflect something that is not actually his capability. And when he eventually has to work inside an organization, the gap between what he can do and what he is actually delivering will compound. There are opportunity costs on both sides of this decision.

I was deeply anti-pharmaceuticals at the time, carrying this fear that medication would flatten my son and drain the color out of him, take away the magnetic energy that was so much a part of who he was. I held out far longer than I should have.

When we finally tried it, I asked him how his first week of school felt, and he told me it was like night and day. The emails from teachers stopped entirely, not tapered off over time but simply stopped, and his grades climbed to meet what I had always suspected was his actual capability. He started building real friendships, the kind that stick. Somewhere in that window, he found filmmaking and threw himself into it with a seriousness that surprised us both. He was not a different kid. He was finally the kid he had been trying to be all along, the one who had been there the whole time, just fighting his own brain chemistry to get out.

That is the nuance I got wrong for years. I thought treating his ADHD meant making him more compliant, more manageable, easier to handle. What it actually did was get out of his way. And then, as he grew older, he eventually did not need the medication anymore, which was the outcome I had barely let myself hope for. He grew into himself, and the magic did not go anywhere. It just got a foundation underneath it.

I have spent a lot of time trying to understand where this instinct came from in me.

I grew up in a demanding household where the expectation was that you would always be near the top, and I had bosses over the years who operated the same way. I absorbed a kind of ambient belief that pressure was what produced excellence, that the gap between where someone was and where you expected them to be was itself the motivating force. I used to run job interviews by trying to prove I was smarter than the candidate, which in retrospect was just insecurity dressed up as rigor.

The shift did not happen in one moment. It accumulated. I remember watching a video of Tyler Lockett, the Seahawks receiver, being asked before a game how he was feeling. He said: “This is another day to discover the best version of myself.” I must have watched that clip four or five times. Something about it landed differently than all the motivational content I had consumed over the years, because it was not about competing with anyone or proving anything. It was just the quiet orientation of someone who had found a sustainable reason to push.

I started reading about abundance mindsets and whole-person leadership, about the difference between helping people grow and simply raising the bar and watching who clears it. I gradually started to apply those ideas at work first, and then tried to bring them home. I think I became a better manager before I became a better father, honestly, but the direction was the same.

There is a real tension I have not fully resolved, and I want to be honest about it here.

It is genuinely true that many of the people who have had the most impact in the world carried a chip on their shoulder, had imposter syndrome that never quit, and never quite accepted their own success, and that restless hunger drove them to keep going. The data on that is hard to dismiss. It is also true that plenty of people who grow up with everything handed to them end up wandering, because security without purpose is its own kind of trap.

So where does that leave those of us who want to raise kids who are capable and driven and do meaningful things in the world?

I keep coming back to what I think of as the seven-out-of-ten question. Not every kid is going to become a Nobel laureate or build a billion-dollar company, and honestly, the ones who do are probably going to get there somewhat irrespective of whether their father gave them a ledger system in Zurich. Those people are outliers, and trying to manufacture that outcome by making your child feel like a failure unless they achieve it is not preparation. It is just cruelty with good intentions.

What I actually want for my sons is something more specific and harder to optimize for: that they push themselves, that they do big things and know they are capable of big things, but also that they have deep relationships and are healthy in mind and body and give something back to the world beyond accumulating a trophy case. I want them to feel, when they sit down next to someone they love, that they have a shot at winning rather than a mounting debt to pay off.

The goal was never to build a micro-economy. The goal was to raise people, and you cannot do that from a spreadsheet or from a distance. You have to be there. You have to watch. And sometimes the most important thing your kid is telling you is not what he is saying out loud, but why he keeps going to sit alone by that rock.

p.s. Thanks to Ryan and Brandon for allowing me to share these lessons learned and thanks to both for so graciously accepting my apologies.

Something that would have been unthinkable a decade ago is now happening more often each year: some middle class families are turning down offers from elite universities and choosing in-state honors programs instead. Not because their student wasn’t admitted to the better-known school. Not because they couldn’t afford it. But because they ran the numbers and the math no longer worked.

I watched this dynamic up close this past year while going through the college admissions process with my son and trading notes with other parents. The conversations happening among families in our community, families with every resource available to them, were different from anything I had heard before. For most of the last century, higher education was treated like healthcare. You didn’t scrutinize the line-by-line invoice. You paid the bill because the alternative, whatever it was, seemed worse. Asking about the cost was like asking for the price of the specials at a fine dining restaurant; you didn’t ask and just convinced yourself it’ll be more but it’ll be worth it. That era is over.

Three things are happening simultaneously, and together they are more destabilizing than any one of them is on its own.

The first is the compression of employment outcomes across the institutional prestige hierarchy. It would have been genuinely shocking, five years ago, to hear about a Stanford CS graduate or a Harvard magna cum laude struggling to land a blue-chip job six months after graduation. That is no longer shocking. It is not yet common but it’s happening. The credential that once reliably converted into lifetime employment and high earnings is losing some of its automatic conversion power, and the gap between ultra-elite, elite, near-elite, and very good is narrowing in ways that discerning families eyeing a potential $400K investment for each kid are starting to notice and price into their decisions.

The second is that the competencies elite admissions has historically selected for are precisely the skills that generative AI has made broadly accessible. For decades, high AP scores and SAT results were proxies for the ability to acquire, retain, and synthesize knowledge. Those proxies made sense when those capabilities were scarce. Today, you do not have to be exceptional at analyzing information and connecting the dots entirely in your head to do strong analytical work. You can become a capable writer with an AI editor. The cognitive moat that the admissions process was designed to identify is not gone, but it is shallower than it ever was.

The third is a decades-long inflation in tuition costs that has finally crossed a psychological threshold for middle class families. Families who are ineligible for financial aid (but not so wealthy that cost is irrelevant) are asking a question they never had to ask before: what is the incremental value of Private University B over the in-state honors program? At $400K total, and with employment outcomes compressing and the cognitive credential eroding, a lot of them cannot find a compelling answer.

Add these three forces together and you have a perfect storm. So if I were the president or dean of admissions at an elite institution today, here is how I would rebuild it.

1. Rebalance Admissions: From Academic Performance to Landed Impact

Strong academic ability should remain a baseline expectation. But it should no longer be the primary differentiator. The question I would want the admissions process to answer is different: has this student taken initiative, worked on a complex long-term project, ideally with a team, and delivered measurable, lasting impact?

It is not enough to say “I wrote some code and made a video game.” The bar is: “I wrote some code, made a video game, marketed it, iterated on it, and now it has 10,000 users.”

It is not enough to say “I started the environmental club.” The bar is: “I led a restoration project, secured a third-party grant, published peer-reviewed research, and earned a recommendation from a community leader who worked directly alongside me for over a hundred hours.”

Impact is most meaningful when it is quantified and validated by third parties. Admissions readers can already tell the difference between a manufactured extracurricular and genuine landed impact. If a college gets exceptionally good at finding students who use every tool available, including AI, to solve real problems, their graduates will have high-impact careers. That is the selection signal worth optimizing for.

The common counterargument is that this model advantages wealthy families who can fund these projects. I do not find that persuasive. The truly curious, driven, determined student with a phone and an internet connection has access to the same AI tools, the same research databases, the same distribution platforms as a kid in the most resourced zip code in America. If anything, measuring landed impact rather than polished credentials flattens the playing field.

The student who actually executed a meaningful project in a low-resource environment and can prove it is a more compelling candidate than one who had a college counselor craft a narrative around a club they nominally led. The brilliant, hardworking first-generation student, given the tools that now exist, can run circles around more typical students in highly resourced environments if the measure is actually building and finishing something real.

2. Question the Four-Year Default

Nobody ever rigorously justified why a degree should take four years. It has always been four years because it has always been four years. Five years? Two years? Three years? The question is rarely asked.

Start from first principles. After high school, if a student is pursuing the next credential, the goal is to leave genuinely more capable and more valuable than they arrived. The right length is an optimization: weighing the cost of each additional year against the incremental formation that year actually produces. By that logic, the most transformative years are almost certainly the first, second, and third. The fourth year is still accretive, but not nearly accretive enough to justify one quarter of a $400K price tag.

Compressing to three years would require real discipline: earlier declaration of major, fewer elective requirements, and a curriculum designed around what actually produces transformation rather than what has always filled the catalog. That discipline, applied honestly, would almost certainly result in a better product for society.

The accreditation question is real but answerable. The 120 credit hour standard for a bachelor’s degree is not a federal law, it is a standard set by regional accrediting bodies, and those bodies can approve redesigned programs. Ensign College launched fully accredited three-year degrees in 2026 by eliminating required electives without touching core or major requirements. Employers recognize the degree as equivalent. The path exists. Elite universities simply have not chosen to walk it.

3. Require a Live Oral Defense for Every Class

You cannot hold a student in 2026 to the same standard as a student in 1996. The student in 1996 was in the library stacks with dusty books and index cards. The student today has access to all of the world’s knowledge and generative AI tools that can produce a competent paper on modern Chinese economic reform in an afternoon.

The bar for great work has to rise. The new standard should not just be writing the paper nor taking the test. It should be developing original predictions based on the analysis and tracking whether they bear out. It should be generating genuinely novel insights by combining current discourse with publicly available data. And because the baseline is so much higher, the expectation should be work that is publishable for peer review.

How do you prevent this from becoming an AI prompting arms race? You take a page from the oldest playbook: the live, in-person thesis defense, required for every class, not just the capstone. Whatever work you produce must survive a panel that challenges you with nuanced follow-up questions in real time, in front of your peers. If you do not know the material and cannot think on your feet, you will not survive it. This is exactly what happens in executive reviews, state capitols, investor pitches, job interviews, and board meetings in the real world. It is nearly impossible to fake your way through a live defense. It is also, done well, the most accelerated form of learning available.

4. The Three Legs of the Stool

In the traditional university, academics are the core and everything else is extracurricular. That model is obsolete.

In the post-AI university, academics should be one leg of a three-legged stool standing on equal footing with two others: extracurricular leadership measured not by title but by outcomes (if you are president of the consulting club, your club needs to have delivered a real project with real impact for a real client) and team-based project work that produces tangible results in the world. This is not a soft addition to the academic experience. It is a restructuring of what the experience is for.

What This Looks Like

A handful of institutions are already pointing the way. Olin College built its entire model around project-based engineering education and produces graduates who are disproportionately capable relative to its size. The University of Waterloo’s co-op program has long embedded real-world work into the degree in ways that most universities have not matched. MIT has been deepening project-based learning across several of its programs for years. These are not fringe experiments. They are proof of concept.

The likely trajectory is not that a handful of small innovative schools corner this model while large research universities stay frozen. It is the opposite. The project-based, impact-driven model will become the mainstream expectation, and the pure academic experience will invert into what it probably should have been all along: a specialized path for students pursuing research careers and doctoral study, not the default for everyone.

The elite universities that move first will define what elite means for the next generation of students and employers. The ones that wait will find that the families with options have quietly stopped waiting.

As someone who interviews, hires, and does performance reviews and promotions of many elite college alumni, I can tell you that where a person went to school registers briefly and then fades. What I am actually probing for is their biggest accomplishment - why it was hard, what fell apart, how they adapted, whether they got it done. There are plenty of people with elite degrees who struggle to execute and plenty of people from less famous schools who end up running divisions or entire companies. The skills the admissions market selects for overlap with, but are not the same as, the skills that produce high-impact leaders.

If you are a university president or a trustee reading this, you do not need a five-year strategic plan to start. Pick one program. Design a pilot around project-based learning, real-world team impact, and oral defense requirements. Launch it this September. The families making decisions about the class of 2031 are watching. Give them a reason to choose you.

Tom Leung is a Director of Product Management at a major tech company in Silicon Valley, a volunteer instructor at Foothill College, a student advisor at Stanford and UC Berkeley, and a Bowdoin and Harvard alumnus. He is also the father of two boys navigating the education system in real time. Raising Humanity is where he thinks out loud about what it actually takes to prepare the next generation for a world that keeps changing the rules.

1. Identify the hottest industry.

2. Earn a specialized degree from a prestigious institution.

3. Get a job at a top-tier firm in that field.

4. Spend years mastering the craft, climbing the ladder, and enjoying the benefits of expertise.

This model has been remarkably stable for over a century.

In the 1950s and ‘60s, aspiring financiers pursued economics degrees from Ivy League schools before joining Wall Street firms like Goldman Sachs.

In the ‘80s and ‘90s, management consulting became the golden ticket, with Harvard and Wharton MBAs leading to careers at McKinsey and Bain.

In the 2000s, the rise of Silicon Valley meant a Stanford CS degree practically guaranteed a spot at Google, Microsoft, or Facebook.

By the 2010s, data science and AI became the hottest fields, with Princeton, MIT, and Carnegie Mellon graduates filling the ranks of hedge funds, adtech startups, and robotics firms.

Every decade or two, a new discipline emerged as the most lucrative and prestigious, creating cycles of educational demand. Those who graduated at the wrong time had to retool, but it was a gradual shift.

That world is now disappearing.

AI is Changing the Game

For the first time in history, specialized expertise is no longer confined to those with elite degrees or years of apprenticeship. Large AI models can now perform many of the tasks that once required years of training.

AI can write and debug code — often better and faster than junior engineers. AI can draft complex legal contracts with precision. AI can analyze vast datasets and generate market research insights in minutes. AI can write a PRD, optimize a portfolio, and even generate working prototypes of robots.

The implications are massive. The traditional pathways to career success — long periods of deep specialization — are losing their exclusivity.

When machines can handle so much technical work, what skills will be most valuable in the coming decades?

The Era of Decades-Long Careers at Dominant Employers is Ending

With AI dramatically reducing the need for massive workforces, smaller, more capital-efficient companies will increasingly challenge industry giants.

Employees may still work at the top firms, but only for 3–8 years at a time before facing periodic restructuring or layoffs. High-impact work will increasingly shift to smaller, nimble firms that can leverage AI to compete without needing thousands of employees. Professionals will need to navigate a more fluid career landscape, moving between large and small companies based on opportunity, innovation, and personal growth.

What This Means for the Next Generation

The AI revolution should radically reshape how you think about education and career preparation.

A helpful historical analogy is the Industrial Revolution. Before mass production, skilled artisans handcrafted goods, passing down their specialized knowledge through apprenticeships. Then, machines arrived. Suddenly, what mattered wasn’t knowing how to shape wood by hand — it was understanding how to operate, fine-tune, and improve industrial machinery.

The same shift is happening now in knowledge work.

Consider this: As recently as 2023, “prompt engineering” and “model tuning” were considered hot skills. People rushed to learn how to craft the perfect AI prompt or fine-tune large language models. Fast-forward to 2025, and those skills already feel quaint — as AI models have become vastly better at understanding natural language and self-optimizing their outputs.

The pace of change is staggering. What seemed like an essential skill two years ago is now automated. This cycle will only accelerate, making deep specialization in any one technical skill less valuable over time.

The AI Whisperer

If AI is going to be a part of almost every job, then the skill of working effectively with AI will be just as important as any domain expertise.

Knowing how to get the most out of AI will separate high performers from those who simply accept mediocre results. Just like the best engineers don’t just copy and paste Stack Overflow answers, the best AI-powered professionals won’t simply accept AI’s first draft.

1. Learn How to Get the Most Out of Your AI Co-Pilot

AI tools can be astonishingly powerful — but only when given the right context, specificity, and constraints. The best AI users will know how to frame problems effectively, provide context and structure to improve outputs, and iterate intelligently rather than settling for a first draft.

2. Learn How to Evaluate, Coach, and Correct AI Outputs

AI outputs aren’t perfect — and often contain hallucinations, key omissions, and inconsistencies. To succeed in the AI-driven workplace, people will need to develop rigorous fact-checking and logical reasoning skills: knowing when to trust AI and when to verify its work, recognizing logical inconsistencies, using secondary sources, and refining responses rather than using them blindly.

3. Learn How to Integrate AI Into Your Workflows

Knowing where AI fits into your workflow is critical. Trust AI for structured tasks (summarizing meeting notes, generating reports). Review AI for creative and strategic tasks (brainstorming, campaigns). Take full control for high-stakes decisions (hiring, negotiations). The best professionals will blend AI automation with human judgment.

The Return of the Renaissance Generalist

We may see the resurgence of the Renaissance generalist — people who have a broad knowledge base across the sciences, humanities, and business fundamentals; develop depth not just in a subject matter but in the skill of rapidly acquiring expertise; and are curious and adaptable, able to synthesize new information quickly and apply it in innovative ways.

In the AI era, the ability to learn, unlearn, and relearn may be more valuable than any single domain expertise. This doesn’t mean deep specialization is obsolete, but the purpose of mastery is changing. Instead of specializing to do a job, you specialize to understand a system well enough to guide, manage, and optimize AI-driven workflows.

The Takeaway: The 21st Century Superpower

The 20th century was about mastering a trade. The 21st century is about mastering learning, adaptation, and leadership.

The New Career Playbook:

• Develop portable skills that transfer across industries.

• Learn how to leverage AI to multiply productivity.

• Build strong networks to access new opportunities.

• Become comfortable with transitions and uncertainty.

For parents and educators, a better question than “What job will my child have?” might be:

How can they develop the skills to thrive in any field, even as AI reshapes everything around them over and over and over again?

How do you see careers evolving in the age of AI? Let’s discuss in the comments.

Tom Leung is a Director of Product Management at a major tech company in Silicon Valley, a volunteer instructor at Foothill College, a student advisor at Stanford and UC Berkeley, and a Bowdoin and Harvard alumnus. He is also the father of two boys navigating the education system in real time. Raising Humanity is where he thinks out loud about what it actually takes to prepare the next generation for a world that keeps changing the rules.

We seek out degrees from elite institutions, obsess over logos on our resumes, and aim for the next promotion or title bump. We might even see ourselves as living a “high-performance” career — one that signals success in a world that rewards credentials and upward motion.

But lately, I’ve been rethinking the idea of performance.

The High-Performance Life vs. the High-Performance Career

We often assume that a high-performance career automatically equates to a high-performance life. But what if that’s only part of the picture? What if career success is necessary but not sufficient?

What if, by living a truly high-performance life — one that’s multidimensional — we not only improve our well-being but also increase our career success and overall impact?

This isn’t about “balance” in the vague, work-life sense. It’s about performance across multiple domains, sustained over decades.

Here’s a framework I’ve been playing with: five dimensions of a high-performance life.

The Five Dimensions of a High-Performance Life

1. Physical and Emotional Wellness
Performance starts with your body and mind. Without sleep, energy, and mental resilience, even the smartest strategy won’t get executed.

2. Intellectual Growth
Read. Listen. Explore. Stay curious. The most interesting and impactful people I know treat learning like a lifelong liberal arts education.

3. Relationships and Leadership Outside Work
It’s easy to lead a team or launch a product. But how are you showing up for your spouse, kids, friends, and community? That’s leadership too.

4. Career Impact
This is your domain-specific contribution — what you build, lead, or transform in your company, industry, or mission. It’s where achievement culture shines, and that’s okay — as long as it’s in harmony with the other dimensions.

5. Financial Foundations
Not glamorous, but essential. Having a plan around earning, saving, and investing buys you freedom, resilience, and the ability to say no to misaligned work.

So How Do You Know If You’re on Track?

Metrics matter — just not the ones we usually track on LinkedIn or in performance reviews. Try scoring yourself from 1 (struggling) to 5 (thriving) across each of the five dimensions. If your total is above 18, you’re likely in a healthy place. If it’s not, that’s useful information.

What patterns do you see? Where are you overperforming? Where are you deprioritizing or coasting?

Tom Leung is a Director of Product Management at a major tech company in Silicon Valley, a volunteer instructor at Foothill College, a student advisor at Stanford and UC Berkeley, and a Bowdoin and Harvard alumnus. He is also the father of two boys navigating the education system in real time. Raising Humanity is where he thinks out loud about what it actually takes to prepare the next generation for a world that keeps changing the rules.

For as long as most of us can remember, institutions like Bowdoin have been the launchpads for our highest paid workers: business execs, scientists, artists, educators, founders, public servants. For generations, the promise was simple: if you sharpened your mind here, you would be insulated from the winds of economic change. We knew that while machines might take the back-breaking labor of the fields or the repetitive labor of the factory floor, they would never touch the “head-work” of the strategist, the analyst, or the leader drawn from the top few percent of high school grads and put through four years of a classic liberal arts education in small classes, labs, and studios with outstanding faculty on a 215 acre campus comprised of 120 historic and state of the art buildings on the southeastern coast of Maine.

Since graduating from Bowdoin in 1996, I’ve spent most of my career at the heart of the tech industry including at Microsoft, Google, Meta and a variety of startups. Three years after the launch of ChatGPT, the outlines of how people work in the tech industry are starting to appear. I could see that being a harbinger of changes in other industries as well.

At the risk of sounding dramatic, we may be entering a period of “great inversion.” For the first time in human history, the most elite cognitive tasks (the very things companies pay new Bowdoin grads $80,000 a year to perform) are the ones most vulnerable to frontier technology. Computer Science, economics, biology, physics, english, and interdisciplinary majors are all impacted.

The J-Curve of Disruption: We’ve Seen This Movie Before

To understand where we are going, we have to look at the “J-curve” of previous revolutions where you see an initial decline followed by a sustained recovery surpassing the initial level. In the early 1800s, it was the power loom replacing the hand-weaver. In the 1830s, it was the mechanical reaper transforming the American farm. In each case, a specific type of human effort was displaced. The automobile destroyed the carriage industry but gave us the interstate highway system and suburban real estate.

Historically, technology has acted as a “complement” to high-skill labor. The spreadsheet didn’t kill the accountant; it killed the “calculator” (a job title that, in the 1940s, described a human being with a pencil). This freed the accountant to move “upstream” into strategy. The ATM replaced some bank tellers but increased the demand for human personal bankers for more complex transactions like refinancing a mortgage or opening a new account.

The pattern is always the same: routine tasks are automated, the “skill premium” for those who can use the new tools sky-rockets, and entirely new industries emerge. But in every previous revolution, there was a safe harbor or higher ground. If you used your brain to move into more complex knowledge work, you were safe. From 1950 to 2000, we lived through the “Golden Age of the Knowledge Worker.” During this period, “Information Workers” grew from 37% of the U.S. workforce to 59%. Knowledge-producing occupations were the fastest-growing group in every decade.

This Time is Different

But now let’s look at the 2024–2034 Bureau of Labor Statistics projections. The “Information” sector is no longer the engine of job growth. Instead, the gains are concentrated in healthcare delivery teams (not MD’s), renewable energy installation (not design), and high-touch personal services (not their lawyers or financial planners). We are seeing a return to the physical.

The “moat” of specialized knowledge is evaporating. When an LLM can pass the Bar Exam or MCAT in the 90th percentile, “knowing the law” or natural sciences is no longer the differentiator. The question for a Bowdoin grad is no longer “What do you know?” but “What do you do when the machine knows everything?”

Five Playbooks for the Future

Outside of focusing on physical jobs or physical adjacent jobs that are hard for agents and robots to perform, I see five common playbooks for navigating this shift (not mutually exclusive):

The Skeptic: Believing AI is “just hype” like Dutch Tulip Mania. This is the “Complacency Trap.” You can take this approach if you’re about to retire or have generational wealth. Otherwise, I would not recommend this approach.

The Power User: The “person driving an AI tractor” approach, using AI to handle the first 80% of any task. This is the baseline for 2026. Most people are in this camp and there’s little downside and it will keep your head above water.

The Orchestrator: Moving from doing the work to directing a team of AI agents. You provide the “taste” and the “connective tissue.” The key thing here is going from asking questions and getting answers to overseeing agents do actual work. With your AI team, you are doing things that a human team of twenty people would have been required to do in 2022.

The Humanity Problem Solver: Using these tools to solve intractable problems like the 7% annual rise in medical costs or climate-driven migration. Think of all the things non-profits have tried to solve for but were underfunded. What if they had 10X the funding in the form of free highly intelligent AI agent labor?

The Long-Tail Entrepreneur: Since AI collapses the internal cost of assembling a firm, a single person can now wield the power that once required a mid-sized corporation in the 1990s. Is now the time to start a non-profit, startup, or small business because you don’t need to raise $10M to do it and can get started today with $1K?

AI Proof Your Future: The Irreducible Three

If you are a junior right now, the role and company you are thinking of taking after college may look very different by the time you graduate but the skills that will keep you relevant may not. If knowledge is a commodity, what is valuable? I believe there are three skills that AI cannot, and perhaps should not, replicate in the next few years.

I. Judgment (Be right a lot)

Judgment is the ability to know when to correct the AI and the courage to see when it has steered you off a cliff. This is the professional equivalent of knowing when to ignore your Google Maps navigation because you can see the road is washed out in front of you. To have this judgment, you need “cockpit hours” of doing the work from first principles so that the AI remains a tool, not a replacement for your own cognition. The biggest risk for early-career professionals is that they may become the equivalent of students who went straight to calculators without ever doing math with a pencil and paper. If you haven’t built the foundation, you cannot be the pilot who knows how to land the plane on the Hudson when the systems fail.

II. Efficacious Curiosity (The “Inspired” Spark)

We can ask AI to generate a thousand ideas, but it cannot tell us which problem is worth solving in the first place. Curiosity that leads to action — what I call “efficacious curiosity” — is the ability to ask the question no one else thought to ask, and then to pursue it with enough energy to actually produce something. This is the skill that turns a research project into a published paper, a frustration into a startup, or a classroom observation into a new pedagogy. AI can execute; it cannot be genuinely inspired.

III. Human Influence (Move people)

The ability to change what people believe and what they do — through writing, speaking, listening, and leading — is the last irreducible human skill. AI can draft the memo, but it cannot read the room. It cannot notice that the CFO is skeptical and adjust in real time. It cannot build the trust that makes someone follow you into an uncertain situation. The leaders who will thrive in an AI-augmented world are not the ones who know the most; they are the ones who can move people.

The Chamberlain Moment

At Gettysburg, Colonel Joshua Chamberlain of the 20th Maine — a Bowdoin professor before the war — faced a situation no training manual had prepared him for. His regiment was out of ammunition, his flank was about to collapse, and the Union line with it. He ordered a bayonet charge downhill. It worked. The Confederate advance broke.

What Chamberlain had was not information. He had judgment, the courage to act on it, and the ability to inspire exhausted men to do something that looked insane. No AI would have made that call. No AI could have made those men follow.

That is the standard. Not “can you use the tools?” but “when the tools fail, what do you have left?”

The “Human-First” skills are no longer the “soft skills”; they are the only “hard skills” left.

P.s. While not as dramatic as Gettysburg, many of us probably encounter these moments every day working with AI where you are taking the output and correcting it, redirecting it, and refining it. Even this post you’re reading was started with a long three paragraph prompt from me and then went through 15 iterations between me and Gemini, Claude, Grok, Manus, and me reading it all as a human and tying it all together.

Discussion

Finally, some questions to discuss over dinner this week:

• Ten years from now, what will you be able to do that a bright high school grad using AI can’t do almost as well?

• What happens to society if an even small fraction of frontier AI labs people capture most of the economic value?

• How much access should we give AI to our lives? Should it be able to adjust your spending and saving to keep you out of debt?

• Is there an upcoming human renaissance? Does “losing” knowledge work mean we can do more fulfilling activities? Will we finally see the four day workweek?

• Do the right incentives exist for using AI for the common good? Why are so many AI entities focused on sales automation, contract writing, and insurance claims adjustments?

• The “Internship” Question: You have three summer internship offers. One is at McKinsey using AI to automate 80% of your work. One is at a startup building the AI tools McKinsey will use next year. One is at a non-profit addressing climate change. Which do you choose?

• The “Accountability” Question: An AI makes a significant error that costs your company millions. Who is accountable — the AI, the engineer who deployed it, or the manager who signed off?

• The “Value” Question: If an AI can pass the bar exam, the MCAT, and write a flawless essay, what is the true value of a college degree in 2030?

Tom Leung is a Director of Product Management at a major tech company in Silicon Valley, a volunteer instructor at Foothill College, a student advisor at Stanford and UC Berkeley, and a Bowdoin and Harvard alumnus. He is also the father of two boys navigating the education system in real time. Raising Humanity is where he thinks out loud about what it actually takes to prepare the next generation for a world that keeps changing the rules.

The short version: Ryan got into some highly selective colleges despite not having straight A's junior year, an SAT on the lower end for admitted students, and not being in the top 10% of his class. He's an AAPI kid interested in STEM from the Bay Area — not exactly the most sought-after admissions profile to work with. But that's who he is, and that turned out to be exactly the right approach: lean into who he actually is, not who you think admissions committees want to see.

We skipped the professional consultant. Instead, we relied on his authentic passions, my coaching, advice from friends and family, and a lot of AI-assisted research. Here's what I learned.

The Thing That Mattered Most: Real Work, Not Resume Padding

Ryan spent months on an independent research project that became a published, peer-reviewed scientific journal article. No school credit. No adult pushing him to do it. Just genuine curiosity, months of field work, and daily measurements. It connected directly to the environmental restoration club he had founded — and schools using holistic review could see he was the real deal.

This is the thing I’d tell every parent first: the most powerful thing your kid can do is produce something real in the world. Not an internship arranged by a parent’s contact. Not a club they joined junior year to fill out a resume. Something that came from actual curiosity, sustained over time, that produced a tangible result.

Admissions readers are very good at spotting the difference between manufactured achievement and genuine passion. They read thousands of applications. The kid who spent two years studying soil microbiomes in local wetlands because he genuinely couldn’t stop thinking about it reads completely differently than the kid who did a six-week summer program at a university to check a box.

The Story Matters as Much as the Stats

Blemishes in a transcript or test scores are not fatal if the kid has an authentic, specific story backed up by real actions. Not something dreamed up senior year. Not something the kid couldn’t care less about. A real story, with real evidence, that only that particular kid could tell.

Ryan’s story was coherent: environmental curiosity → founding a restoration club → independent field research → published paper. Each element reinforced the others. The application didn’t feel like a collection of achievements; it felt like a portrait of a person.

If your kid doesn’t have that story yet, the time to build it is sophomore or early junior year — not the summer before applications are due. The story has to be lived before it can be told.

Fit Beats Rankings

This is the one I feel most strongly about, and the one most families get wrong.

Ryan is passionate about plants, soil science, and environmental restoration. The schools that are genuinely strong in those areas noticed it immediately. The more generalist schools — the ones that are highly ranked but don’t have a particular identity around environmental science — were less impressed by the same application.

This is counterintuitive but important: a specific kid with a specific passion is more compelling to the right school than a generic excellent student is to any school. The rankings don’t tell you which school is the right fit for your kid’s particular obsessions. That requires actual research — visiting, talking to professors, reading department pages, understanding what each school is actually known for.

We toured schools junior year with this lens: not “is this a good school” but “does this school have the specific thing Ryan cares about, and does it feel like a place where he would thrive?” That question led us to some schools we might have overlooked based on rankings alone.

The Application Doesn’t End at Submission

This was the thing I didn’t fully appreciate until we were in it. Updates, letters of continued interest, new achievements after you submit — all of it matters, especially for waitlists and deferred decisions.

December for ED1 is the start, not the finish line. If your kid gets deferred from their first-choice school, that’s not a rejection — it’s an invitation to keep making the case. A well-written letter of continued interest, combined with a meaningful update (a new award, a new publication, a new development in a project they described in the application), can genuinely move the needle.

Most families treat the January 1 deadline as the end of the process. The families who understand it’s the middle of the process have a real advantage.

The Stress Is Optional (Mostly)

Our son was genuinely happy with his target and likely schools, which we toured junior year. This made swinging for the reaches a lot less stressful for everyone. When you know there are schools on the list where your kid would be genuinely excited to go — not just “fine” with going — the whole process feels different. The reaches become upside, not the only acceptable outcome.

I think a lot of the anxiety families experience around college admissions comes from treating it as a pass/fail test with only one acceptable answer. The families I’ve seen navigate it most gracefully are the ones who did the work early to identify multiple schools where their kid would genuinely thrive — and then treated the selective schools as exciting long shots rather than existential necessities.

What I’d Tell Parents Starting This Process

If your kid is a sophomore or junior right now, here’s the short version:

Help them find the thing they can’t stop thinking about, and then get out of the way while they pursue it seriously. That’s it. That’s the whole strategy. Everything else — the test prep, the essay coaching, the school list — is secondary to having a real story to tell.

College applications can be an opportunity for self-discovery and for learning important life skills: how to articulate who you are, how to advocate for yourself, how to handle rejection and keep going. It doesn’t have to be only a grind. To be clear — it definitely is a grind. But it can be more enriching than the final outcomes suggest.

If you’re heading into this next year and want to compare notes, feel free to reach out.

Tom Leung is a Director of Product Management at a major tech company in Silicon Valley, a volunteer instructor at Foothill College, a student advisor at Stanford and UC Berkeley, and a Bowdoin and Harvard alumnus. He is also the father of two boys navigating the education system in real time. Raising Humanity is where he thinks out loud about what it actually takes to prepare the next generation for a world that keeps changing the rules.