I want to be careful about how I say this, because I’m not interested in generational blame-shifting. Every cohort of students gets criticized by the one before it, and most of the time the criticism says more about the critic than the cohort.
But I teach entrepreneurship at Toronto Metropolitan University. I’ve been doing it for fifteen years. And what I’m seeing in the classroom right now is different from what I saw ten years ago in a specific, measurable way.
Students are arriving with less capacity to tolerate ambiguity, figure out problems without guidance, and take initiative when the path isn’t clearly marked.
I don’t think it’s a generational character flaw. I think it’s a structural outcome — and I think it has direct implications for anyone building a small business who plans to hire from this cohort over the next decade.
I talked about this recently on the Unscripted Small Business Podcast with Jeremy Rivera, and I want to expand on it here, because I think the business owner’s framing of this question is different from the cultural one.
Bulldozer Parenting
There’s been plenty of discussion about helicopter parenting — parents who hover anxiously over their children, always monitoring, always available. That’s one pattern.
But what I’m seeing is something further along the spectrum. I’ve started calling it bulldozer parenting. The parent doesn’t just hover — they go ahead and remove every obstacle before the child ever encounters it. Every conflict resolved before it becomes a conflict. Every challenge softened before it becomes a challenge. Every failure cushioned before it can land.
By the time children raised this way arrive in my classroom — and later, in your hiring pool — they haven’t developed the muscle for navigating difficulty. They’ve been protected from the very experiences that build that muscle.
Jonathan Haidt’s Framework
Jonathan Haidt at NYU makes this argument rigorously in The Coddling of the American Mind, which I’d put on any business owner’s reading list regardless of whether they have children.
His core argument: we’ve made a categorical error about children’s nature. We treat them as fragile — as though exposure to difficulty will damage them. But the evidence suggests the opposite. Children are anti-fragile. Challenge makes them stronger. Uncertainty develops their capacity for ambiguity. Failure that they have to recover from builds resilience.
The glass doesn’t get stronger when you drop it. But the child does.
And we’ve been protecting children from falling for thirty years.
What It Looks Like in the Classroom (and Later, in Your Business)
In practical terms, here’s what I observe:
- Students treat rules as lists of things they’re allowed to do, rather than things they’re not allowed to do. They look at a new situation and ask ‘Is this permitted?’ rather than ‘Is this prohibited?’ The entrepreneurial orientation — the bias toward action unless something explicitly prevents it — is less instinctive.
- They struggle with a bias toward action. The bird-on-a-wire problem: when all four birds decide to fly, how many actually do? The answer in too many cases is zero. Deciding isn’t doing.
- They find it difficult to work through ambiguous situations without explicit direction. Not because they’re lazy — most of them are earnest and hardworking — but because ambiguity is a muscle, and it hasn’t been exercised.
Jeremy pushed back on this during our conversation, gently. He mentioned running a homeschool science fiction club and experiencing firsthand how much effort it took to get students to go further — to take the next step without being explicitly told what it was.
That’s the pattern. Not inability. Not laziness. Underdeveloped capacity for initiative.
The Pandemic Didn’t Help
The structural conditions of the last five years compounded this. Locking young people down for the formative years of early adolescence and young adulthood — removing social friction, unstructured time, and peer-to-peer navigation of conflict — accelerated a trend that was already underway.
This isn’t about blame. It was an impossible situation. But we should be honest about the outcome.
What This Means for Business Owners
I want to shift the frame here, because the cultural debate about parenting choices isn’t particularly useful for someone trying to build a team.
What is useful is this: if you’re hiring from a cohort that has less natural tolerance for ambiguity, less default bias toward action, and less practice with self-directed problem-solving, then the organic vs. mechanistic question I write about becomes more important than ever.
Organic roles — the ones that require someone to own an outcome and figure out the path themselves — need extra vetting for initiative and ambiguity tolerance. Don’t assume it. Test for it.
Mechanistic roles — where you’re defining the task and measuring consistency — may actually be a better fit for candidates from this cohort in their early career. Clear expectations and measurable outcomes give them something to anchor to.
For anyone you put in an autonomous role: invest deliberately in developing the muscle. Assign problems without solutions. Ask what they’d do before telling them what to do. Don’t rescue immediately.
The goal is to recreate in your organization some of what over-protection removed. Not harshly — but deliberately. Anti-fragility has to be built. It doesn’t arrive pre-installed.
The Bigger Picture
We’ve produced a generation that, in significant ways, struggles to solve problems independently. I said this on the podcast and I’ll say it here: I blame the parents primarily, and the public school system secondarily. It’s a structural problem with structural causes, not a character judgment.
And the business case for caring about it is simple. If you’re building a team over the next decade, the people you’re hiring will disproportionately come from this cohort.
Understanding what that means — and building your hiring, onboarding, and development practices accordingly — is a competitive advantage.
The business owners who treat this as a complaint and do nothing about it will keep struggling to find people who can ‘just figure it out.’ The ones who understand the dynamic and build deliberately for it will end up with better teams.
For more on the hiring and org design side of this, my post on what actually motivates people and my planning system at Confident Operator both get into the structural questions in more depth.
Full conversation: Unscripted Small Business Podcast · Watch on YouTube.
