Opening
A missed investment in Warby Parker pushes Adam Grant to investigate what makes “originals” succeed. Across two chapters, he reframes originality as a choice and a process—less about fearlessness, more about smart risk management and sharp idea selection.
What Happens
Chapter 1: Creative Destruction
Grant opens with the founding story of The Warby Parker Founders. He had the chance to invest early but declined, a decision he calls his worst financial mistake. That regret becomes his launchpad: what actually defines an “original,” and how can anyone increase their odds of making an impact? He defines originality as introducing and advancing a novel idea that improves a domain, and he ties it to rejecting defaults and Challenging the Status Quo. The browser study—where employees who proactively download Chrome or Firefox outperform those who stick with Internet Explorer or Safari—embodies this mindset. Small acts of initiative predict larger habits of questioning and improving the familiar, a pattern he calls vuja de.
He dismantles the myth that originals are thrill-seeking daredevils. Many figures we consider bold—George Washington, Martin Luther King, Jr., Michelangelo, Steve Wozniak—hesitate before stepping into transformational roles. That reluctance reflects a healthy fear of failure and a desire for security, which Grant reframes as strategic. Originals, he argues, maintain a “risk portfolio,” balancing bold bets in one domain with caution in others. Polaroid’s Edwin Land models this approach: create stability in most areas so you can take focused creative risks where it counts.
This principle of Risk Mitigation and the Myth of the Risk-Taker explains why Grant initially misreads Warby Parker. Their “hedging”—staying in school, keeping internships, lining up job offers—seems like doubt, but it actually supplies the financial and psychological safety to persist. Data backs it up: entrepreneurs who keep their day jobs at launch reduce failure odds by a third. Even icons like Nike’s Phil Knight, Apple’s Steve Jobs, and Google’s founders temper risk. Originality, Grant concludes, is not an innate daredevil trait; it’s a deliberate choice amplified by smart risk management.
Chapter 2: Blind Inventors and One-Eyed Investors
Grant shifts from generating ideas to selecting them, arguing that the central hurdle is The Challenge of Idea Selection. He contrasts two famous misreads: the Segway, a “false positive” hyped by luminaries yet commercially doomed, and Seinfeld, a “false negative” dismissed by executives and test audiences that becomes a cultural phenomenon. Creators themselves struggle to judge their work—overconfidence and attachment distort their view—just as even geniuses like Beethoven and Picasso fail to predict which creations will last.
The fix isn’t perfection; it’s volume plus feedback. Great creators ship broadly—Shakespeare writes unevenly across masterpieces and duds, and Edison’s thousand-plus patents yield only a few breakthroughs—because more variation increases the odds of a hit. But secrecy undermines selection: Segway’s inventor, Dean Kamen, cloisters development and misses user realities that could have corrected course. Exposure to critique is the throttle for better picks.
Managers and test audiences aren’t reliable either; they’re “prisoners of prototypes,” biased toward what succeeded before and wary of mold-breaking ideas. Research shows peers—fellow creators—forecast novelty best: open enough to recognize originality, detached enough to judge rigorously. Rick Ludwin, the executive who saves Seinfeld, exemplifies this “insider–outsider” vantage point: deep comedy experience paired with perspective beyond the sitcom lane. Grant widens the point—Nobel laureates are likelier to have artistic hobbies—arguing that breadth fuels better judgment.
Finally, he explains why Jobs’s bullish Segway bet falters: intuition works only in predictable environments where judgment has been calibrated, and transportation is not Jobs’s home turf. Charisma misleads too; passion in a pitch predicts little. Passion in execution—iterating on price, name, and user experience the way Warby Parker does—systematically de-risks originality until it’s no longer a leap but a measured step.
Character Development
Grant presents himself as a guide who learns in public, using his Warby Parker miss to interrogate his own biases and refine his methods. The founders emerge as disciplined originals whose caution powers their boldness. Jobs appears as a domain-bound genius—brilliant where calibrated, vulnerable where intuition outstrips experience.
- Adam Grant: Shifts from confident evaluator to evidence-driven investigator; centers peer review, risk portfolios, and experimentation.
- Warby Parker founders: Model methodical originality—retaining safety nets, testing assumptions, inviting feedback, and iterating.
- Steve Jobs: Serves as a caution on cross-domain intuition; shows how charisma and passion can cloud evaluation outside one’s expertise.
Themes & Symbols
Originals begin by Challenging the Status Quo. Vuja de captures the practice: see the familiar differently, then act on it. The browser study turns a tiny choice into a diagnostic of mindset—the move from default to chosen signals the willingness to question inherited settings, whether that’s pricing in eyewear, the design of a product, or the format of a sitcom.
Risk Mitigation and the Myth of the Risk-Taker reframes courage as portfolio management. Originals don’t court danger everywhere; they cordon it to where impact demands boldness and buffer the rest. Meanwhile, The Challenge of Idea Selection argues that success hinges less on brilliance than on judgment. Volume, diverse feedback, and peer evaluation counteract the biases of creators and gatekeepers.
Symbol: Web browsers. Choosing a non-default browser symbolizes the move from passive conformity to proactive improvement—a daily micro-act mirroring the macro-behavior of originals.
Key Quotes
“He argues that the hallmark of originality is rejecting the default and questioning the status quo, a phenomenon he calls vuja de—seeing a familiar situation with a fresh perspective.”
This distills the book’s operating lens: originality starts with how you look, not just what you make. Vuja de trains attention on overlooked leverage points in everyday systems.
“He introduces the concept of a ‘risk portfolio,’ suggesting that successful originals balance extreme risk in one area of their lives with extreme caution in others.”
The portfolio metaphor replaces the myth of the fearless founder with a practical model of how bold work survives. It explains why safety nets don’t dilute originality—they enable it.
“Grant argues that the biggest barrier to originality is idea selection, not idea generation.”
By moving the bottleneck from creativity to curation, the book shifts readers toward process: generate widely, test early, and choose with evidence, not attachment.
“The most accurate forecasters … are not managers or creators themselves, but fellow creators—peers.”
Peer judgment balances novelty and critique. It justifies building creator-to-creator feedback loops instead of relying on hierarchy or gut alone.
Why This Matters and Section Significance
These chapters reset common assumptions about how change happens. Chapter 1 makes originality accessible by decoupling it from fearlessness and grounding it in risk management; Chapter 2 equips readers to navigate the trap-filled path from idea to impact by privileging volume, feedback, and peer evaluation. Together, they outline a methodology—challenge defaults, hedge smartly, create prolifically, and select scientifically—that the rest of the book develops into a practical toolkit.