Unlearn

When was the last time you realized that what once made you successful might now be holding you back? In Unlearn: Let Go of Past Success to Achieve Extraordinary Results, Barry O’Reilly challenges you to confront the habits, mindsets, and methods that were once useful but have turned into anchors. His central claim: in an age of disruption, the biggest barrier to growth isn’t the inability to learn more—but the unwillingness to unlearn what no longer works.

O’Reilly contends that today’s leaders—from tech CEOs to teachers—are stuck in the paradox of success. The very approaches that once propelled them forward—rigid processes, proven playbooks, and predictable thinking—now limit innovation. Unlearning is the antidote: the deliberate process of questioning, reframing, and letting go of outdated mental models so you can relearn and break through to extraordinary results. In doing so, he builds a system called the Cycle of Unlearning, which consists of three perpetual stages: unlearn, relearn, and breakthrough.

The Core of Unlearning

O’Reilly opens with a powerful example—Serena Williams’ slump after years as the world’s number-one tennis player. Despite training harder, she began losing. Her trusted routines had become limitations. When she hired an unconventional coach, Patrick Mouratoglou, she took the biggest risk of her career—abandoning proven strategies to discover new ones. This act of courage and adaptability exemplifies what O’Reilly calls the paradox of success: the more successful you are, the harder it is to change. Serena’s story sets the tone for the book—not as a lesson in talent, but in mental flexibility.

Why We Resist Change

Humans crave certainty. Success breeds comfort, and comfort breeds rigidity. O’Reilly points out that organizations and individuals alike often fail to acknowledge when their environment has changed. They cling to “what worked before.” This resistance isn’t ignorance—it’s a psychological trap rooted in ego, fear of uncertainty, and reward systems that favor short-term results. He draws from leaders at NASA, Disney, Capital One, and T-Mobile to reveal how even world-class organizations can be blinded by their own achievements until change becomes a necessity.

The Cycle of Unlearning

The solution lies in building a new habit loop: Unlearn outdated assumptions, Relearn new information or behaviors through experimentation, and use those insights to achieve a Breakthrough—then repeat. This framework isn’t a one-time fix; it’s a continual system for adaptation. Unlearning begins with identifying limiting beliefs, relearning requires deliberate practice and experimentation, and breakthroughs emerge when reflection transforms mindset. It’s the organizational version of personal growth combined with agile innovation. Leaders who intentionally apply the cycle—rather than waiting for crises—can stay ahead of disruption, not just survive it.

Why It Matters

O’Reilly argues that the speed of change today demands adaptability as a core competency. In business terms, adaptability beats efficiency. Companies like Amazon and Google thrive not because they know more than competitors, but because they learn, unlearn, and relearn faster—powered by experimentation and safe-to-fail systems that treat mistakes as sources of information rather than weakness. In a broader sense, he reminds you that unlearning isn’t limited to companies; it’s a mindset applicable to improving any part of life—from leadership and creativity to stress and performance.

Across twelve chapters, O’Reilly expands this principle from personal transformation to corporate innovation, drawing vivid examples from Serena Williams, NASA’s learning culture after the Challenger disaster, Disney’s billion‑dollar MagicBand experiment, and even the UK’s National Health Service rebuilding massive IT failures. Each story shows that true innovation often starts with the uncomfortable act of letting go. Unlearning is courage in action—a skill that, once mastered, lets you drop the safety of past success and embrace the uncertain path toward something far greater.

Barry O’Reilly’s central framework—the Cycle of Unlearning—shows how growth happens not through accumulation of knowledge, but through cycles of release and renewal. It’s a simple yet transformative model consisting of three interconnected stages: Unlearn, Relearn, and Breakthrough.

Step 1: Unlearn

Unlearning means accepting that what brought you success before may now limit your progress. It begins by identifying behaviors or beliefs that once served you but are no longer effective. O’Reilly urges you to write an “Unlearn Statement”—a simple commitment defining what to let go, what success looks like, and how you’ll measure progress. For example: “I will unlearn micromanagement in three months. I know I have when my teams make decisions without my approval 80% of the time.” This forces clarity, accountability, and measurable growth.

Step 2: Relearn

Relearning replaces obsolete habits with new ones through deliberate practice. It’s about thinking big but starting small—tiny, safe-to-fail experiments that build confidence. O’Reilly draws from psychologist BJ Fogg’s Tiny Habits method, explaining how micro‑actions compound into major change. Leaders at Disney’s parks, for instance, prototyped ideas in abandoned lounges and tested them daily with customers. Small experiments—prototype first, PowerPoint later—helped reveal what customers actually wanted, not what executives assumed.

Step 3: Breakthrough

Breakthroughs are insights gained from reflection. Feedback loops transform experience into wisdom. In the NFL, RFID sensors in players’ gear give real‑time data for refining performance, mirroring how leaders can use feedback to continuously evolve. In companies, breakthroughs often come when individuals realize the system—not the people—is flawed. After NASA’s Columbia disaster, leaders unlearned their culture of silence, relearned through open knowledge-sharing, and achieved long‑term safety and innovation improvements.

The power of this cycle is repetition. Each loop builds competence, courage, and curiosity. Those who integrate it into daily practice—like Amazon’s philosophy of constant experimentation—create organizations that evolve without waiting for crises. O’Reilly’s message is that personal and organizational excellence follow the same rhythm: let go, learn anew, and reflect forward.

At the center of unlearning lies courage—the willingness to step into uncertainty without guaranteed success. O’Reilly stresses that this emotional shift distinguishes leaders who adapt from those who stagnate. Drawing on Brené Brown’s research on vulnerability, he defines courage not as reckless action but as acceptance: knowing you will fail sometimes, yet proceeding anyway.

Embracing Vulnerability

To unlearn, you must embrace discomfort. That means recognizing when perfectionism or ego blocks growth. Brown calls this “the physics of vulnerability”—if you’re brave enough often enough, you’ll fall, but rising stronger requires openness. O’Reilly connects this idea to real‑world leadership: executives at International Airlines Group learned to challenge their own “comfortable” approaches to innovation by deliberately practicing uncertainty. Their breakthrough came only after embracing awkward, messy feedback cycles and realizing old success formulas no longer worked.

Creating Safe-to-Fail Environments

Courage doesn’t mean chaos—it means designing safety for experimentation. O’Reilly advocates “safe‑to‑fail” contexts where mistakes become learning inputs. After initial resistance, Disney’s Founding Five created prototypes, learned quickly, and evolved the $1‑billion MagicBand project. Their courage wasn’t blind risk‑taking; it was methodical unlearning supported by evidence. As Brown and psychologist Edgar Schein both note, when learning anxiety drops and psychological safety rises, performance soars.

Choosing courage over comfort lets you break free from incremental improvement. It transforms fear into feedback. Once you master this mindset, unlearning becomes a habit—an intentional act of renewal rather than reaction to crisis.

Before you can change behavior, you must understand what’s stopping you. O’Reilly lists eight core obstacles to unlearning: leadership conditioning, knowledge thresholds, biases, ego, reward systems, fear of uncertainty, lack of curiosity, and environment. These forces conspire to keep people repeating the past.

The Trap of Success

Success reinforces behaviors that may later limit future growth. The more successful you are, the more you fear failure—and avoiding failure kills experimentation. This explains why 84% of digital transformations fail: leaders cling to old methods that made them successful. (Marshall Goldsmith summarized it perfectly in What Got You Here Won’t Get You There.) O’Reilly’s point is simple: continuous achievement requires continuous renewal.

Cultural Conditioning

Social norms reinforce conformity. From schooling that stigmatizes mistakes (Ken Robinson’s famous TED talk: “Do schools kill creativity?”) to corporate reward systems that punish failure, environments teach people to fear being wrong. O’Reilly references sociologist Ron Westrum’s Three Cultures Model—pathological (fear, power), bureaucratic (rules, compliance), and generative (trust, learning). Only generative cultures, which value information flow and cooperation, support unlearning.

Turning Obstacles into Opportunity

Drawing from Intel’s Andy Grove, O’Reilly encourages leaders to view obstacles as “strategic inflection points”—moments of radical change. Grove’s pivot from memory chips to microprocessors saved Intel, demonstrating how questioning everything leads to reinvention. The takeaway: challenge assumptions deliberately and frequently. Unlearning isn’t accidental; it’s intentional adaptation.

The more you confront these obstacles, the more you’ll see patterns of resistance in yourself, your teams, and your organization. Recognizing them is the first act of courage that opens the door to transformation.

Relearning is where theory turns into practice. It means re‑examining how you acquire new skills and deliberately designing behaviors that reinforce learning. O’Reilly integrates research from BJ Fogg’s Behavior Design lab, defining the conditions required for relearning: clarity of outcome, options for small steps, finding the right behaviors, and starting smaller than you think.

Thinking Big and Starting Small

Big visions require tiny beginnings. If you want to run a marathon, start with walking around the block. This principle—safe, simple progress—is crucial to habit formation. In business, Disney’s MagicBand project worked because leaders began with inexpensive prototypes instead of $1‑billion full builds. Success compounded through evidence, not faith.

The Fogg Behavior Model

Fogg’s model (B=MAP: Behavior = Motivation + Ability + Prompt) adds scientific clarity to relearning. You can succeed when motivation, ability, and prompts converge. The most effective change makes behaviors easier to do and prompts people naturally. O’Reilly suggests attaching new habits to existing routines—like flossing one tooth after brushing—to trigger success quickly. In organizations, this works when leaders embed reflection time or brief feedback rituals into regular meetings.

Relearning demands patience and humility. When you start small, celebrate micro‑successes. Each small win rewires your identity—from learner to experimenter—making the discomfort of change rewarding rather than frightening.

Breakthrough is the reward for cycling through unlearning and relearning—it’s when reflection brings clarity and courage compounds into confidence. O’Reilly defines breakthroughs as evidence‑based insights that permanently change how you think and act.

Reflect and Feed Forward

Reflection, not activity, drives growth. O’Reilly tells of Edward Deming silently observing an executive for a week before pointing out that none of his actions aligned with company priorities. The lesson: busyness isn’t progress. You must reflect on outcomes, not outputs, and use insights to feed forward into your next experiment. Many leaders, like Capital One’s CEO, discovered breakthroughs only after redefining success from task completion to customer outcomes.

Scaling Breakthroughs

Breakthroughs expand when learning anxiety drops and psychological safety grows. Google’s Aristotle Project proved that high‑performance teams aren’t the most skilled; they’re the most safe. When people feel safe to fail, feedback becomes fuel. Leaders can scale breakthroughs by encouraging reflection and designing experiments for continual improvement.

Increasing the Rate of Unlearning

The ultimate goal is acceleration. Edison’s lab optimized the number of experiments conducted—not hours worked. Amazon deploys software every few seconds to maximize learning. Repetition builds adaptability: the more often you unlearn, relearn, and reflect, the faster your organization innovates. Breakthroughs aren’t luck—they’re engineered through constant iteration.

Reflect, feed forward, and repeat—that’s how you turn insight into momentum. Each breakthrough makes you braver for the next.

O’Reilly calls leadership the linchpin of organizational transformation. To unlearn effectively, leaders must model it first. Most executives still operate with nineteenth‑century management conditioning—command and control—enforcing rigid structures that stifle creativity. The challenge is to evolve leadership from managing things to leading people.

From Command to Mission

The military long ago abandoned pure hierarchy. Through mission command (as used by Napoleon and later by Helmuth von Moltke), leaders define intent—what and why—not orders. Every soldier has autonomy to decide how. Submarine commander David Marquet’s Turn the Ship Around! demonstrates this perfectly: by delegating decisions, he turned the worst-performing sub into the Navy’s best.

Clarity vs. Competence

Effective leadership balances clarity (purpose) and competence (skill). Leaders must define goals clearly so employees can act independently. As competence grows, control can be safely transferred. BJ Fogg’s behavior design and Toyota’s coaching method both reinforce this gradual growth—make it easy at first, then increase challenge as people gain confidence.

The Flow Zone

O’Reilly borrows Mihaly Csikszentmihalyi’s concept of flow—optimal balance between challenge and skill. Leaders should design work that puts people in this zone, where engagement is highest and fear is lowest. Dynamic difficulty adjustment (from video games) serves as metaphor: increase autonomy as competence rises, creating scalable trust systems like those at Amazon and Toyota.

Leadership that unlearns micromanagement and relearns intent-based empowerment transforms organizations into adaptable ecosystems. The best leaders don’t direct—they design environments where learning happens continuously.

O’Reilly argues that to truly innovate, companies must also unlearn how they engage with customers. The standard model—build first, ask later—is reversed. Listening becomes the first act of creation.

Raw Feedback Over Reports

T-Mobile’s CEO John Legere sits in his office for hours each day listening to actual customer service calls. He treats feedback as unfiltered truth rather than sanitized dashboards. His approach birthed the “Un‑carrier” strategy—eliminating phone contracts and hidden fees after hearing how customers hated them. The result: millions of new subscribers and billions in revenue. Legere’s lesson? Distance from customers breeds delusion.

Shortening Feedback Loops

Technology enables faster unlearning. Elon Musk famously turned a single tweet into a companywide Tesla policy change within six days, implementing idle‑time fees at charging stations after one customer complained. O’Reilly calls such acts “cycles of unlearning at velocity”—where real‑time input drives immediate improvement.

Breaking Ivory Towers

Executives isolated on top floors make poor decisions based on filtered data. Companies like Disney and British Airways broke this barrier by placing leaders directly in front of customers—testing prototypes inside terminals and lounges instead of offices. The result: empathy became data, and assumptions turned into insights.

Unlearning with customers transforms organizations from assumption‑driven to evidence‑driven. Listening doesn’t just improve products—it reinvents leadership.

The culmination of O’Reilly’s framework is organizational transformation—creating companies that continuously unlearn and relearn. NASA, Netflix, and Toyota serve as case studies of how systems, not slogans, sustain learning cultures.

From Mistakes to Mastery

After the Challenger and Columbia disasters, NASA learned that silos and fear of accountability kill innovation. Chief Knowledge Officer Ed Hoffman built programs encouraging engineers to share mistakes without punishment. His Pyramid of Advantage model teaches teams to catch errors early before they become catastrophes. Psychological safety replaces blame with learning—a system mirrored at Google and Toyota.

Cultural Design for Learning

Creating a learning organization means designing mechanisms for feedback, collaboration, and experimentation. Netflix institutionalized this through its “Chaos Monkey”—software that randomly breaks systems to test resilience. The goal isn’t perfection but continuous adaptability. Toyota’s “daily destruction of preconceptions,” as founder Taiichi Ohno called it, embodies the same principle.

Continuous Unlearning

Organizations that thrive—Amazon, NASA, and Capital One—treat unlearning as habitual, not reactive. They design sandboxes for employees to run safe experiments, simulate failures, and surface new insights. This practice keeps complacency from creeping in and ensures evolution never stops.

O’Reilly reminds us: you’re either building a learning organization or being beaten by one. Continuous unlearning is the defining skill of the twenty‑first century—for companies and individuals alike.