The Chip on Your Shoulder

"A chip on the shoulder is too heavy a piece of baggage to carry through life" - John Hancock

I was having dinner with founder friends recently and we came to discuss how we all identified with “having a chip on our shoulder”. For widely different reasons, we all came to the same internal narrative.

That made me wonder - do all entrepreneurs feel compelled to ‘right the wrongs’ they have experienced?

Moreover is this type of mindset (essentially carrying the energy of someone with a grudge) both desirable and useful for entrepreneurs?

While I can’t A/B test a cohort of founders with chips vs. one without chips on their shoulders, I did find some surprising data and science insights to help make sense of a common, yet paradoxical entrepreneurial concept.

Defining the Chip

“Having a chip on your shoulder” generally means to hold a grudge or feel resentful, leading to an angry or argumentative attitude because you believe you have been treated unfairly or are disadvantaged. In other words, it’s a deep-seated resentment or defensiveness stemming from past slights or perceived injustices.

Perhaps nowhere is the “chip on your shoulder” mentality more discussed than in entrepreneurship and high-performance careers. In the business world, there’s a common narrative that many great innovators and leaders were driven by a personal grudge or a burning desire to prove themselves. Venture capitalist Mark Suster explicitly says he looks for founders who have a chip on their shoulder—those with something to prove. “Good entrepreneurs have a chip on their shoulders. They are out to prove something,” Suster notes, arguing that this attitude often translates into extraordinary hustle and perseverance.

TechStars entrepreneur-in-residence Chris Heivly similarly wrote that “to some extent every great founder gets started with a chip—a chip that basically tells the established way of doing things that they can go jump in a lake.” In other words, successful startups often emerge from a spirit of defiance, a rebel mentality that says, “I’ll show the doubters and disrupt the status quo.” This contrarian drive can be essential in a field where one must challenge incumbents and persist through countless setbacks. Investors often find it valuable when a founder has a personal mission or frustration fueling their work—it can be the “something special” that keeps them going through the low points of the startup journey.

Entrepreneurial folklore abounds with examples: the kid who was told “no one will ever want your product” and becomes determined to prove everyone wrong, or the underprivileged founder who uses each rejection as motivation to hustle harder. Research on entrepreneurial resilience suggests that moderate levels of early adversity can bolster later success by building grit. A recent study found that entrepreneurs who experienced some childhood hardship often developed higher resilience and resourcefulness, translating to better career outcomes—up to a point. This aligns with the notion that an underdog mindset—feeling like one has to fight for one’s place—can drive creativity and persistence.

Psychological Roots: Resentment, Insecurity, and Motivation

From a psychological perspective, a chip on one’s shoulder often originates in unresolved emotional trauma or feelings of inferiority. Psychologists note that holding onto past grievances can become a defensive mechanism—a way to preempt further hurt by remaining on high alert for disrespect. For instance, someone who felt undervalued in childhood might carry that “chip” into adulthood as hypersensitivity to slights: even minor comments are interpreted negatively, triggering disproportionate anger. In this way, the mindset becomes a lens through which they view the world, breeding a negative bias in interactions and a tendency to collect evidence of being wronged.

Such a mindset can be self-defeating. Carrying a chip can lead to chronic anger, cynicism, and self-sabotage. It’s like lugging around a heavy backpack of bitterness that weighs down one’s ability to move forward. Studies on emotion suggest that persistent resentment (a form of chronic anger) correlates with poorer mental health and strains the body’s stress responses—echoing Nietzsche’s warning that nothing “burns one up faster” than the toxic effects of ressentiment, which exhausts energy and poisons us from within. Modern therapists often liken holding grudges to “drinking poison and hoping the other person dies,” emphasizing that the primary harm is to the bearer of the grudge.

Anger Psychology & Approach Motivation

Psychology also acknowledges a motivational side to this mindset. Feeling underestimated or unfairly treated can spark a powerful desire to prove oneself. The chip can act as emotional fuel: anger and indignation, when controlled, can drive people to overcome obstacles.

A recent series of peer-reviewed experiments published by the American Psychological Association found that induced anger consistently improved participants’ performance on challenging tasks compared to a neutral mindset. Across trials with over 1,000 people—from solving difficult puzzles to playing demanding video games—those put in an angry state exerted more effort and achieved higher scores or faster times than those who were emotionally neutral. “These findings demonstrate that anger increases effort toward attaining a desired goal, frequently resulting in greater success,” reported lead author Dr. Heather Lench.

Notably, the performance boost appeared only for tough, high-effort goals; anger didn’t help with easy tasks but provided an edge in the face of difficulty. (One caveat: anger’s energizing effect was so strong that it even increased the likelihood of cheating to succeed in one experiment—a reminder that this motivation can bypass ethical restraint.)

Psychologists interpret this through the lens of approach motivation: anger, despite being a negative emotion, often pushes people to approach challenges aggressively rather than avoid them. It creates a sense of urgency to set things right. For someone with a chip on their shoulder, the desire to rectify an injustice or “show them” can translate into persistence and grit. In sports psychology, this phenomenon has been dubbed the “chipped shoulder effect.”

Researcher Myisha Cherry, writing on emotions in athletics, describes it as a combination of “a lasting grudge, controlled anger, and a desire for payback at being overlooked or slighted.” She argues that playing with a chip on one’s shoulder can enhance athletic performance by keeping athletes intensely motivated to prove themselves. Crucially, it’s controlled anger—channeled into training harder or competing fiercely, rather than undisciplined rage. Cherry even suggests that athletes “can and should have a chipped shoulder forever” to sustain their competitive fire. This is a provocative stance, since conventional wisdom often extols letting go of anger; yet here anger is reimagined as a permanent drive for excellence.

Chips in Social Contexts

What about the effects of a chip on your shoulder on relationships and leadership? Unfortunately, the “chip” often exacts a toll on interpersonal dynamics. People harboring grudges tend to be defensive and quick to argue, which can strain friendships, family bonds, and workplace relationships. Counselors observe that such individuals live in a state of “negative sentiment override,” meaning they interpret even neutral or positive actions by others as hostile due to their lens of resentment.

This creates a self-fulfilling cycle: expecting hostility, they provoke or perceive conflict everywhere, reinforcing their grievance. As one therapist put it, “Holding onto past grievances keeps us stuck in a state of anger and prevents us from moving forward.” Indeed, carrying a chip can become a self-imposed limitation, hindering personal growth and happiness.

For these reasons, “chips on shoulders” often make bad managers. Depending on how grievance is channeled, it can lead to borderline aggressive or antisocial behavior. A person with a chip is often blind to feedback. The best leaders cultivate self-awareness, and having a chip can prevent them from truly listening to others, stunting learning and growth. A leader chronically fixated on past slights rarely has the insight to recognize their own negative impact. An unchecked chip can grow heavier over time, turning into cynicism or a victim mentality that undermines leadership potential.

Chips Help Drive Social Change

On a broader social level, entire groups can develop a “chip on the shoulder” ethos if they feel systematically wronged. Sociologists note that collective grievances (e.g., among marginalized communities) can fuel social movements. In this context, a chip on the shoulder might spur activism and demands for change.

Philosophically, this ties into discussions of recognition and resentment. As political theorist Axel Honneth explored in The Struggle for Recognition, social conflicts are fundamentally driven by struggles for recognition—experiences of disrespect and being denied dignity motivate social movements and demands for justice. Honneth argues that “subjects perceive institutional procedures as social injustice when they see aspects of their personality being disrespected which they believe they have a right to recognition.” In this view, while personal resentment can be toxic, principled resentment (anger at unfair systems, for example) might lead to justice or excellence.

Thus, what might appear as a character flaw can also be a completely reasonable reaction and the main driver of justice, progress, and reform. Nothing pisses people off more than witnessing or being the subject of injustice.

“That’s not a chip on my shoulder, that’s your foot on my neck.” - Malcolm X

Nothing Burns One Up More Than Resentment

Many philosophical traditions view resentment with caution, seeing it as a corrosive emotion. The Stoics taught that holding grudges or dwelling on past injuries is pointless suffering. A Stoic might say that having a chip on your shoulder gives external events too much power over your inner peace. Instead, one should practice forgiveness and focus on what can be controlled—namely, one’s own response and effort. From a Stoic lens, the ideal is to replace resentment with rational acceptance—not to condone injustice, but to refuse it the satisfaction of dominating one’s emotional life.

Friedrich Nietzsche offered one of the most famous critiques of entrenched resentment. He coined the term “ressentiment” in On the Genealogy of Morals to describe the bitter, repressed anger of those who see themselves as oppressed. Nietzsche argued that this feeling, when stewed upon, becomes “poisonous”—it leads to blame-based values and eats away at vitality. He wrote that “nothing burns one up faster” than ressentiment; it is a self-consuming fire that can literally sicken the body. From this viewpoint, living with a chip on one’s shoulder is living in thrall to past injuries—a kind of spiritual imprisonment that prevents growth and nobility.

How to Live Happily Ever After With A Chip on Your Shoulder

After researching all insights I could find, I came to the view that the best way to have a chip on your shoulder—in order to let it drive you and not destroy you—is to aim it towards a constructive, bigger-than-yourself ideal, and absolutely not on getting back at others due to past events.

It’s also key to understand that one day your chip will have done all it can for you to fix the wrongs in your life—and you must then let it go. There is always a point where your chip is no longer useful—nor justified. Some other kind of energy will need to drive you on your journey.

Balance your strong will with a more gentle type of energy: Wu Wei. Wu Wei is the art of effortless action—such as when you work in a deep flow state—that makes the work so much easier and enjoyable than trying to ‘right the wrongs’ of the world. Chips on your shoulder make you less self-aware, blind to feedback, while flow states allow you to detach naturally, by quieting your inner critic, to clearly observe your own patterns and feel less self-absorbed. In my experience, it is much harder to do important, creative, collaborative work when you’re burning with resentment and rumination. Chips on shoulders may provide you with the inner motivation to start on your journey, but it can’t be the only thing moving you forward.

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