Don't fly too low

The antidote to stagnation is a curriculum of ambition.

Most people remember the myth of Icarus for its cautionary tale of hubris. Don’t fly too high or else ambition will melt your wings. But what's often conveniently forgotten is Daedalus's other warning. Don't fly too low, or the ocean mist will soak your wings and weigh you down. This neglected counter-warning captures the true modern paradox of ambition. For all our fear of overreaching, we're far more likely to be dragged down by stagnation and unexamined potential.

Ambition. Despite all its contributions to modern-day progress, we still tiptoe around it like an elusive Pandora’s Box, wary of what we might unleash.

We carry deeply flawed ideas about ambition, often assuming it's an innate gift you're simply born with or not. Or we vilify it as a direct path to burnout and inevitable suffering. Too often, ambition only appears in public discourse as a convenient scapegoat for narcissism or political misdeeds. These beliefs, however widely held, oversimplify and understate one of the most powerful forces driving human behavior.

And this tension plays out in how we raise and educate young people. Parents grapple with the extremes. Do we risk gentle parenting our kids into aimlessness, or tiger parenting them into burnout? Traditional school promotes a narrowly defined view of success, where genuine ambition (not the one tied to standardized testing) isn’t a core outcome. Ambition, then, becomes the elephant in the room, especially when graduation looms and private worries mount about what kids will actually do with their lives.

But we need to get past this idea that ambition is reserved for the brilliant and select few, or that nurturing it is a precursor to burnout. Contrary to the bad rap ambition often gets, it doesn’t have to be all or nothing. There’s a healthier third alternative that is much more intentional and personally defined. Cultivating ambition in young people and creating environments where it’s nurtured is a moral imperative. We should care a lot about creating better conditions for more young people to develop this earlier on, if we care about greater prosperity and progress for individuals and humankind as a whole.

The trap of unexamined ambition

For the first fifteen years of life, the typical path to becoming a “high-achieving” young person today is narrowly defined by some combination of 1) getting high grades; 2) balancing a variety of extracurriculars; all typically in pursuit of 3) attending a prestigious university.

The tides are changing as credentialism declines and merit markets increasingly take root. For the record, I don’t think these benchmarks of grades and college admissions are what we should be optimizing for, but traditional school makes it difficult to avoid and has convinced most families and kids this is what being “ambitious” means. For some time this type of shallow ambition might seem relatively acceptable or even impressive—the pipeline-to-university artificially supports this narrowly defined track. But it doesn’t take long for the cracks to surface.

Eric Wei, CEO of Karat, is a model example.

Eric’s story is one you might not be familiar with, and yet it is hardly an outlier.

Eric has been transparent on many podcasts about his journey. He was your high-achieving kid under immense pressure by his immigrant parents to succeed.

And so he did what he was told “success” looked like and collected all the infinity stones: Harvard → Blackstone → McKinsey → Instagram.

Except he was miserable. Getting to each of these milestones felt empty because he actually didn’t care about any of these things.

I think the very first thing I’d tell him is please don’t give a shit and care about any one of the things you’ve listed. Because it’s all these external validators of prestige. Frankly, they’re all things I did because I didn’t know what I wanted to do and I cared so much about what other people thought, so getting into Harvard was my life’s dream. And once I got there I was like ‘oh my gosh what was this all for? I’ve no sense of what I actually care about and immediately latched on to what I saw was the next ladder up.’ — Eric Wei, jayhoovy interview

After a lot of soul-searching he discovered what he actually cared about was being creative and working with other creatives, leading him to start Karat, a leading financial services platform for creators.

Eric’s ambition initially was motivated by external validators and it was narrowly defined. That path led to inevitable burnout. It required taking a step back to consider what he truly cared about so that he could channel his ambition into something more personally motivated.

He’s still audaciously ambitious with Karat. The company is YC-backed, has raised $100M, and has extended over $1.5 billion in credit and advances to creators.

And that’s the point.

Wouldn’t we want more young people to come to these realizations much earlier in life?

Embracing the builder's mindset

This powerful third alternative of ambition is something psychologist

Dr. Gena Gorlin

has coined the “builder’s mindset” after observing behavior, especially among startup founders in Silicon Valley.

She argues this type of mindset sits on an entirely different plane of what she rejects as a false dichotomy of drill sergeant vs. zen master. The drill sergeant tends to follow conventional paths of success at the expense of their own desires and often mental well-being, and the zen master—often in response to oppressive hustle culture—is more passive about outcomes. People often oscillate between these two, but neither offers real agency. The drill sergeant is driven by what society expects of him and the zen master overcompensates by downsizing their ambition.

But the builder’s mindset is an agentic form of ambition that declares “we are the sole owners of our lives.” The builder’s mindset is a much more reflective approach to ambition. You take real ownership over what you choose to put effort into and ultimately aspire to achieve.

In the case of Eric Wei’s story, it took real reflection to acknowledge how depressed he was from aimlessly climbing the social ladder (drill sergeant) in order to connect with his “why” as an entrepreneur (builder’s mindset).

In a recent interview with Shane Parrish on The Knowledge Project, this is the type of agentic ambition Harley Finkelstein, President of Shopify, was referring to when he described “outcaring” as a superpower that supersedes IQ, EQ, and raw talent. He uses the term “innate” but I think what he’s really referring to here is the presence of a “why” behind individual motivation. One that can be realized early and further cultivated over time.

Ambition’s controversial reputation + how we got here

Developing a healthier, more intentional relationship with ambition sounds relatively straightforward. So, why haven’t we figured this out?

First, we know surprisingly little about ambition even today. Despite its influence on progress, we don’t study it nearly enough. Academia and psychology touch on related concepts like motivation and leadership, but ambition is seldom studied as a standalone concept, often seen as a secondary variable of other traits. William Casey King is one of few who has dedicated a direct, in-depth study of the concept of ambition, and his book, Ambition, a History: From Vice to Virtue (2010), is frequently cited as the definitive scholarly work.

Ambition’s tumultuous, dual-natured past also plays a role in our confusion. And it's a story that has played out over centuries.

Antiquity viewed ambition with ambivalence, a “hidden plague” that fueled Rome’s ascension to greatness but also engendered its demise. But in Christendom, ambition entered a dark age, condemned completely as outright sin. This was a period that fiercely promoted mediocrity that defined generations.

The Renaissance prompted reevaluation. Thinkers like Francis Bacon reframed ambition as a powerful condition to be balanced—"malign and venomous" if stifled, but "noble" if managed. This fueled an era of intellectual and artistic rebirth, paving the way for ambition’s rebrand.

Once condemned, ambition transformed into an instrument of empire during the Age of Exploration, driving unprecedented conquest and global reshaping. This later became the force behind the American Revolution, where ambition was publicly championed as a civic virtue essential for nation-building. Yet, private fears of its corrupting influence persisted.

These shifting historical attitudes we’ve inherited about ambition were far from straightforward. And this extends into contemporary biases and design flaws that continue to take root today.

For instance, advocating for raising psychological ambitiousness is controversial among psychologists. Namely because the idea of becoming more ambitious stirs fear that it will perpetuate harmful perfectionism and judgmental tendencies psychologists work hard to fight against.

A call to “raise your ambitiousness” seems to fly in the face of all those therapeutic efforts, unless of course you disentangle the fake “ambitiousness” of the drill sergeant from the genuine ambitiousness needed to build your own flourishing, fully-lived life. — Dr. Gena Gorlin, Embracing Healthy Ambition

But also because psychology, as a helping profession, is mainly concerned with alleviating suffering and, as a result, frequently neglects “raising the ceiling” for those who are already doing considerably well by modern standards. While it can certainly appear less urgent in the face of a mental health crisis, what might we stand to gain if we dedicated more attention to unlocking new heights of competence and purpose? Could it even build greater mental resilience?

This professional hesitancy is hardly the sole culprit holding us back. Traditional school’s inherent design flaw fosters a much more insidious cultural zeitgeist.

Education’s narrow definition of success, centered on testing and standardization, misguides hundreds of thousands of children and families into believing this is the natural way to measure and acquire ambition. Unfortunately, this is often when young, fervent ambition is squashed and with it, so much potential is lost.

Modern education, in its current form, is not teaching young people to “fly high enough” nor “fly their own way.”

Raising psychological ambitiousness

But this problem is not insurmountable.

There are very practical, concrete ways of raising the ceiling and cultivating a better kind of ambition in young people, much earlier:

• Elevate aspirations: Start by believing in young people's immense potential. Expose them to a broader vision of what's possible, far beyond conventional expectations. Tyler Cowen wrote about this as a “high-return activity” referencing his strategy of encouraging strong candidates who initially applied for Master's programs to pursue PhD admissions instead:

  At critical moments in time, you can raise the aspirations of other people significantly, especially when they are relatively young, simply by suggesting they do something better or more ambitious than what they might have in mind. It costs you relatively little to do this, but the benefit to them, and the broader world, may be enormous. — Tyler Cowen, The high-return activity of raising others’ aspirations

• Exercise the Pygmalion effect: A recent study extending on the research in Pygmalion in the classroom (1968) concluded that high teacher expectations were associated with higher achievement in reading in earlier years. Having high expectations isn’t inherently bad, and in fact influences a young person’s perception of their ability.

• Encourage self-definition of success: Don't prescribe narrow paths; instead, create space for young people to discover and pursue what genuinely excites them. Expose them to a wide range of avenues for success.

• Make it real: Healthy ambition flourishes in optimism and psychological safety. This means creating environments where young people consistently see their effort yield visible, achievable progress like mastering a bike or successfully coding an app. These positive feedback loops help young people discover what they are good at and what they genuinely enjoy.

• Expose them to heroic individuals: To combat apathy and evoke awe in young people, it’s crucial we share the stories of heroic, high-agency individuals who have made remarkable contributions to humankind. After all, you cannot be what you cannot see. I wrote more about this in a recent post.

While traditional school hardly optimizes for any of these strategies, many alternative schools are building intentionally with healthy ambition as a core outcome. And this design feature is particularly attractive for many high-agency families who want their child to discover their “why” sooner.

The Socratic Experience led by

Michael Strong

, runs a daily Purpose class around Ikigai, a Japanese concept referring to what an individual defines as the meaning of their life ("What do you love? What are you good at? What does the world need? What will it pay for?"). There, he encourages ongoing reflection around what truly matters to his students and what they want to strive for.

Two others that come to mind are Acton Academy microschools, which adopt the hero’s journey as a core philosophy to encourage students to pursue ambitious, real-world projects aligned with their personal mission; and Praxis, which offers an accelerated alternative to college, focused on apprenticeships and direct career launches.

Don’t fly too low, fly your own way

For all its controversy and confusion, ambition remains the most influential human instinct for progress. To stifle it is to suppress human potential in action.

As my own parents liked to say, “We know you have a mind of your own, and whatever you choose to do, work hard and you’ll figure it out.”

This is the very spirit of the builder's mindset, and what we ought to strive for in raising the next generation.

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As always, thanks for reading.

-Sam