Chapter 1
Breaking Free from Success: The Revolutionary Power of Unlearning
When Serena Williams suffered a devastating first-round loss at the 2012 French Open, it wasn't just another defeat-it was the catalyst for one of the most remarkable transformations in sports history. Partnering with coach Patrick Mouratoglou, Williams didn't just work harder; she did something far more revolutionary-she unlearned. By systematically discarding techniques that had previously brought her success but were now limiting her potential, Williams achieved what many thought impossible: a second "Serena Slam" and 10 more Grand Slam victories, including winning the 2017 Australian Open while pregnant. This phenomenon of unlearning-the deliberate abandonment of outdated knowledge and behaviors to make room for innovation-has become the secret weapon of today's most successful leaders and organizations. Named one of Bill Gates' top five leadership books and praised by executives at companies like Amazon and Microsoft, Barry O'Reilly's "Unlearn" reveals the counterintuitive truth that what brought you success today will likely be the very thing that prevents your success tomorrow.
Chapter 2
The Cycle of Unlearning: A System for Extraordinary Results
Leaders today face immense pressure to transform their organizations while struggling with rigid thinking patterns developed over years of success. Despite American businesses spending approximately $160 billion annually on training (with $356 billion spent globally), only 25% of participants believe this training critically impacts business outcomes. The disconnect is clear: traditional learning isn't enough-we must also unlearn.
The Cycle of Unlearning is a three-step system that high performers use, often unconsciously, to achieve extraordinary results. The first step, Unlearn, requires courage, self-awareness, and humility to accept that your current beliefs and behaviors are limiting your potential. This isn't about forgetting knowledge but recognizing when it no longer serves you. As Einstein noted, "We cannot resolve a problem by using the same thinking that created it."
The second step, Relearn, involves taking in new information that challenges your existing mental models. This requires creating an environment outside your comfort zone where you can experiment safely. The key principle here is to think big but start small-creating safe-to-fail experiments that allow exploration without catastrophic consequences.
The final step, Breakthrough, emerges from the first two steps-it's the powerful insights that transform your mindset. The path to thinking differently runs through acting differently; when you act differently, you experience the world differently, which changes how you think. After breakthrough, the cycle begins again as you push forward with new innovations.
This system works by starting with small challenges and gradually applying the cycle to increasingly complex situations. Think big but start small, try many alternatives, and remember that the only real failure is doing nothing-any action provides valuable information for your next iteration.
Chapter 3
The Success Trap: Overcoming Obstacles to Unlearning
Success itself often becomes the greatest obstacle to unlearning. People with histories of positive results become attached to behaviors they associate with those rewards, making them reluctant to try different approaches for fear of failure. Many executives have built entire careers on methodologies that are now outdated, yet they resist evidence-based approaches that challenge their established patterns. As Bill Gates observed, "Success is a lousy teacher. It seduces smart people into thinking they can't lose."
Our brains are wired to resist change through our intense desire to be correct. While children naturally adjust through trial and error, this changes when we enter formal education systems that train us what to think rather than how to think. As Sir Ken Robinson noted in his famous TED talk, children aren't afraid of being wrong, but adults lose this capacity as schools and companies stigmatize mistakes. This conformity continues through higher education and into corporate careers, where making mistakes isn't tolerated.
Rather than waiting for crisis to force change, it's better to adopt the Cycle of Unlearning proactively. Andy Grove demonstrated this at Intel when he pivoted the company from memory chips to microprocessors after asking, "If we got kicked out and the board brought in a new CEO, what do you think he would do?" Grove called these moments "strategic inflection points"-times when business fundamentals change, creating opportunities to rise or signals of decline.
Disney's transformation of their theme park experience illustrates successful unlearning in action. When faced with the crisis of half their first-time visitors not returning, the "Founding Five" team relocated to an abandoned theater to break calcified mindsets. Inspired by a magnetic wristband, they developed the MagicBand-a wearable device containing everything guests needed. Today, more than half of guests use MagicBands, helping increase park attendance by 7% and year-over-year income by 24%.
The key insight is that transformation isn't hindered by a lack of ideas but by resistance to behavioral change. When leaders step outside their comfort zones and tackle challenging missions, they let go of legacy thinking that holds them back. Acting differently changes how you experience the world, which shifts your mindset, creating a virtuous cycle of new thinking and behavior.
Chapter 4
The Four Necessary Conditions for Effective Unlearning
Unlearning requires openness to new approaches, curiosity, and belief in possibility, but it also demands specific conditions to break old patterns holding us back. Through working with leaders worldwide, I've identified four necessary conditions that enable successful unlearning.
First, identify a specific challenge you wish to address-an obstacle to remove or opportunity to enhance that will positively impact your performance. Look for areas where you're avoiding challenges, taking easy options, or not meeting expectations. Don't wait for the perfect moment to start-begin where you are right now.
Second, define success as though you have already conquered the challenge. Tell stories about behaviors that would demonstrate success-these are observable and measurable. Quantify these behaviors using rates or ratios rather than averages. The 0-100% thought experiment helps think big: "100% of customers book digitally" or "0% of partner integrations take more than a week." Write unlearn statements like "I will unlearn [challenge] before [constraint]. I know I have when [measurable outcomes]."
Third, channel courage over seeking comfort. Unlearning requires moving beyond your comfort zone and embracing uncertainty. As Brene Brown explains in "Rising Strong," vulnerability is essential-committing to falling while remaining fully engaged. Rather than pursuing perfectionism, which hampers success and leads to anxiety, strive for excellence. Pick courage over comfort, bravery over fear, and excellence over perfection.
Finally, commit to, start, and scale the Cycle of Unlearning. This isn't a one-time event but a scalable system allowing you to tackle increasingly ambitious challenges as you iterate more quickly through the cycle. Each iteration builds upon previous ones, developing your courage, curiosity, and capabilities as you strive for excellence.
IAG's leadership team demonstrated these conditions when they removed six key leaders from their organization for eight weeks to focus on company challenges. Initially struggling by using familiar methods, their breakthrough came after presenting underwhelming early ideas to stakeholders. This forced them to reflect on their comfortable but ineffective approaches, triggering their unlearning journey. By thinking big and challenging implicit assumptions, they pushed beyond comfort zones and rekindled curiosity.
Chapter 5
Relearning: The Art of Small Steps Toward Big Change
While unlearning focuses on what aspiration you want to achieve and why, relearning addresses how to accomplish it. The process begins by thinking big about your desired outcome, then starting small with easily achievable steps that build quick success. When paired with deliberate practice, this approach builds confidence and momentum for tackling greater challenges.
Three necessary conditions make relearning effective. First, after establishing your big aspiration, don't try to achieve it all at once. Instead, brainstorm numerous small, achievable steps that create fast feedback loops and build momentum. List all possible options-new behaviors, old behaviors, skills you have, or ones you're curious to try. This approach is exemplified by President Kennedy's moon landing vision, which NASA broke down into thousands of small, incremental steps to achieve the seemingly impossible goal.
Second, find the right behavior that matches your motivation and ability-what BJ Fogg calls "behavior matching." Different people respond to different approaches, like visual versus auditory learning when studying guitar. You need to experiment with various behaviors to find what works specifically for you. Starting with smaller, faster, cheaper iterations helps you discover effective behaviors more quickly and recover gracefully from failures.
Third, recognize that starting small is even smaller than you think. Rather than deconstructing a big solution into tasks, focus on truly small, experimental steps toward your aspiration. Consider the "couch to marathon" training program-it doesn't start with running a mile but with simply walking around the block for 10 minutes. Starting extremely small makes people feel successful quickly and builds momentum.
BJ Fogg's Behavior Model (B=MAP) explains that behavior occurs when Motivation, Ability, and a Prompt converge. The model shows that when designing new behaviors, it's best to make them easy to do rather than relying on high motivation. Fogg's maxims are: "Help people do what they already want to do" and "Help people feel successful."
To create new behaviors, start small with something easy rather than relying heavily on motivation. This creates a safe-to-fail environment where people feel successful quickly. By linking small steps to larger aspirations, you generate momentum and confidence. When coaching executives to increase effectiveness, I get them to specify what effectiveness means to them, envision success, and identify small behavioral changes. A tiny tweak like pausing five minutes before the end of meetings to gather feedback can have systemic impact by modeling new leadership behavior that ripples throughout the organization.
Chapter 6
Breakthrough: Transforming Insights into Action
Breakthrough is the final step of the Cycle of Unlearning-the result of unlearning and relearning that provides powerful new insights that transform your perspective. This changed perspective impacts your mindset, making you more open to unlearning behaviors more frequently, creating an accelerating cycle. The challenge is that people resist letting go of their ideas, as we're so conditioned to our ways of thinking that we tend to ignore information that challenges our basic assumptions about achieving success.
Four necessary conditions must be met to achieve breakthrough. First, reflection enables us to consciously examine our results rather than just staying busy. The famous story about Deming observing an executive who spent a week not working on his top priorities illustrates how being visibly busy is often mistaken for progress. True breakthrough comes from stepping back and reflecting on whether our efforts are yielding the intended outcomes.
Second, feeding forward means taking feedback from small experiments and using those results to inform subsequent experiments, creating exponential benefits. This approach involves declaring a hypothesis, defining outcome-based measures of success before starting experiments, gathering information quickly and cheaply, and recognizing that the only true failure is failing to learn.
Third, to scale breakthroughs, we must align impact and increase safety. This requires psychological safety-Google's Aristotle project found it's the #1 indicator for high-performance teams. When people can connect their efforts to meaningful outcomes rather than just outputs, they recognize how their new behaviors work, feel successful, and gain confidence to tackle greater challenges.
Finally, increasing your rate of unlearning is key to achieving extraordinary results. By pairing experimentation with deliberate practice, you can respond effectively to rapid change. Thomas Edison optimized for experiment quantity at his "Invention Factory," while Leonardo da Vinci maintained "to-discover" lists of questions rather than to-do lists, fueling constant curiosity.
Today's most innovative companies like Amazon run thousands of experiments annually. Jeff Bezos attributes Amazon's success to "how many experiments we do per year, per month, per week, per day." In 2011, Amazon could deploy software every 11.6 seconds, enabling constant discovery. Unlearning is a deliberate practice that pushes everyone to embrace uncertainty rather than comfort, helping teams discover breakthroughs that enable letting go of past success to achieve extraordinary results.
Chapter 7
Unlearning Command and Control Leadership
CEOs and managers who cling to command-and-control leadership are micromanaging through self-designed control systems that limit organizational potential. This approach kills innovation and strips creativity from work, turning followers into robots focused solely on execution without thinking or questioning. People become squeezed to deliver more output faster, forgetting how to problem-solve independently and embracing disempowerment.
Most managers have risen to their positions by knowing all the answers rather than helping others discover solutions. This leads to the Peter Principle-rising to their level of incompetence while inhibiting others' progress. Many leaders remain in "unconscious incompetence," failing to recognize their deficits or take in new information. They miss crucial inflection points to unlearn, not realizing that true leadership means making others successful by helping them discover answers themselves.
Many managers still operate with outdated Industrial Age mindsets rooted in Frederick Taylor's 1911 "Scientific Management" principles. In this model, managers determine the exact steps workers should follow, dismissing worker ideas because problems are considered "already solved." Despite living in a 21st-century world, most organizations run on 19th-century management principles.
Contrary to popular belief, the military abandoned rigid command and control after the Napoleonic War. Napoleon pioneered "maneuver warfare," giving small teams authority to make battlefield decisions based on clearly communicated mission intent. The Prussian Army further developed this under Helmuth von Moltke as "Auftragstaktik" or "mission command," where leaders describe their intent and trust those closest to the situation to make aligned decisions.
Captain Marquet demonstrated this approach on the USS Santa Fe by vowing to never give another order except for launching weapons. Instead of giving orders, he gave intent and asked for intent in return. This transformed decision-making authority to those closest to the information. Under Marquet's leadership, the USS Santa Fe went from worst to first in Navy history for operational efficiency.
The concept of "flow zone" from video game design offers a valuable model for leadership transition. When designing games, developers seek a balance where challenges match player abilities-avoiding both frustration (too difficult) and boredom (too easy). Similarly, effective leaders must recognize different capability levels in team members and adjust accordingly, considering both clarity of intent and competence in taking action.
Great leadership isn't innate but can be systematically developed. High-performing organizations create systems allowing people closest to information to make decisions, as they have the most context and competence. Toyota exemplifies this by empowering ordinary employees with Andon cords that allow any worker to stop the entire assembly line when problems arise. The journey for leaders begins small-designing feedback loops into work systems and gradually building confidence to delegate authority appropriately.
Chapter 8
Customer-Driven Unlearning: The Power of Direct Feedback
Businesses often lose sight of customers, especially those who quietly pay without complaint. The traditional approach of seeking customer feedback only after investing significant resources in product development is fundamentally flawed. T-Mobile CEO John Legere demonstrates a better way-spending three hours daily listening to customer service calls through a special line in his office and personally engaging with millions of followers on social media. Unlike most executives who avoid direct customer contact, Legere embraces unfiltered feedback to inform what T-Mobile needs to unlearn and relearn.
Candid customer feedback is one of our best mechanisms for recalibrating perspective and making unconscious incompetence visible. The feedback gathered from customers becomes the key input for the Cycle of Unlearning, helping identify what works, what doesn't, and what needs transformation. Today's most effective leaders embrace removing friction in customer communication, seeking raw, unsanitized information that's true, accurate, and as close to real-time as possible.
Most executive reporting systems produce what I call "watermelon reports"-green on the outside but red on the inside. Information gets sanitized and filtered as it moves up the organization, especially when employees fear sharing negative outcomes. As Deming said, "Whenever there is fear, you will get wrong figures." Leaders who make decisions based on this poor information lead their companies in terrible directions.
There's a massive perception gap in most organizations. Bain & Company found that while 80% of companies believed they delivered "superior experience" to customers, only 8% of customers agreed. Despite 95% of management teams believing they're customer-focused, only 50% actually tailor products to customer needs, only 30% organize functions to deliver superior experiences, and only 30% maintain effective customer feedback loops.
Elon Musk exemplifies responsive customer engagement through social media. When a customer complained about Tesla Supercharger stations being used as parking spots, Musk replied the same day acknowledging the problem. Within six days, Tesla implemented a fleet-wide idle fee policy charging $0.40 per minute for cars remaining connected after charging completed. Customer problems rarely change, but the technology to gather feedback evolves constantly, enabling leaders to unlearn outdated beliefs with faster, tighter feedback loops.
When British Airways renovated Terminal 7 at JFK Airport, they moved executives out of offices into an abandoned lounge where they could test ideas with real customers instantly. This direct engagement helped them unlearn their beliefs about what customers wanted. The team abandoned 100-page PowerPoint presentations in favor of battle-tested prototypes, creating safe-to-fail experiments that allowed them to iterate through the Cycle of Unlearning.
Chapter 9
Creating Learning Organizations Through Systematic Unlearning
On January 28, 1986, the space shuttle Challenger exploded 73 seconds after launch, killing all seven crew members. Despite engineers warning against the launch due to low temperatures, their concerns were dismissed by management. This disaster demonstrated how success can breed complacency. When work becomes routine and guards are let down, performance suffers-precisely when concern should be heightened.
NASA's tremendous successes from Mercury through Apollo created a false sense of intellectual superiority and impermeable information silos that ultimately led to catastrophic failures. With the Columbia disaster in 2003, program managers had normalized the "deviance" of foam shedding from the external fuel tank. Despite video evidence showing a large chunk of foam striking Columbia's wing during launch, the routine nature of foam shedding had created a dangerous blind spot.
Dr. Ed Hoffman, NASA's first chief knowledge officer, spent three decades at the agency transforming its learning culture. Despite understanding the importance of organizational learning, NASA required catastrophic failures like Columbia to truly embrace unlearning. Ed applied space problem-solving approaches on the ground, building systems that encouraged sharing stories of both success and failure.
Creating sustainable organizational transformation requires designing systems that scale learning and unlearning. Start by gathering data from all organizational levels, identifying successful competencies, and designing work systems that enable desired behaviors. Begin with small, high-impact changes that are easy to implement. Provide tools and training to a small group first, create safe opportunities to practice new behaviors, and test the system with actual users throughout development.
Google's Aristotle project revealed that psychological safety-not intelligence or experience-was the primary indicator of high-performing teams. When team members feel safe to be vulnerable and share mistakes, it becomes a competitive advantage. Creating a culture of shared lessons and reduced learning anxiety grows organizational capability, improving information quality, decision-making, and results.
Organizations risk backsliding without ongoing vigilance. NASA prevents complacency by conducting an annual Day of Remembrance, where families of astronauts lost in Apollo 1, Challenger, and Columbia tragedies share stories, keeping the lessons alive for newer employees. Similarly, Netflix deliberately creates controlled failures through their "Chaos Monkey" software, which randomly shuts down production systems to test resilience and force teams to collaborate on solutions.
As Andrew Clay Shafer states, "You're either building a learning organization, or you're losing to someone who is." Learning organizations systematically gather information from all sources, synthesize it, and use it as a foundation for innovation. They create safe environments for experiential learning through informal settings, simulations, and play.
Chapter 10
Aligning Incentives with Outcomes: The Key to Sustainable Unlearning
Financial incentives often prevent people from letting go of past successful behaviors. Research shows pay-for-performance can actually drive negative behaviors, as people focus on "getting that" reward rather than doing what's necessary for organizational excellence. The percentage of company payrolls dedicated to bonuses has grown dramatically since 1991 (from 3.1% to 12.7%), while raises have declined. For CEOs, about 90% of total compensation comes from performance bonuses, with median payouts reaching $7.1 million by 2014.
With such high stakes, leaders almost inevitably choose the safe path that guarantees their bonus rather than taking risks that might produce extraordinary results but could jeopardize their compensation. These incentive structures, intended to drive innovation, actually inhibit it by rewarding individual performance while extracting systemic-level costs.
According to Gallup's 2017 State of the Workplace report, 85% of employees globally are either actively disengaged (18%) or not engaged (67%). This lack of engagement results in approximately $7 trillion in lost productivity globally. Nobel Prize-winning economist Bengt Holmstrom identified the "principal-agent problem"-how to motivate one party to act on behalf of another. His research revealed that focusing on single, easy-to-measure incentives leads people to ignore harder-to-measure tasks that often drive desired outcomes.
Employees want appreciation more than just financial rewards. According to TINYpulse research surveying 200,000+ employees, the top motivators for going the extra mile were: camaraderie and peer motivation (20%), intrinsic desire to do good work (17%), feeling recognized (13%), having real impact (10%), and professional growth (8%). Money and benefits ranked seventh at just 7%.
Drew Firment, former technology director of cloud engineering at Capital One, learned firsthand how to create systems that encourage employees' best efforts. Rather than using abstract maturity models for measuring cloud adoption, he created the "Cloudometer"-a system that measured what truly mattered: speed, quality, cost of cloud migrations, and individual talent transformation. To incentivize skill development, he created a "Cloud of Fame" displaying names of certified employees, making certification a badge of honor while gamifying personal development.
With individual actions aligned to visible system-level outcomes, Capital One saw the emergence of learning communities where individuals worked cooperatively to master cloud computing. Unlike technologies with longer shelf lives, cloud computing evolved rapidly with constant new AWS features. Traditional training methods couldn't keep pace, forcing the organization to unlearn how to learn and shift to continuous learning through self-sustaining communities.
When designing incentives, remember Charlie Munger's words: "You get what you reward for." Identify desired system-level outcomes, then clearly signal to employees what behavior you seek. Changing KPIs impacts behavior, and both financial and non-monetary incentives can be effective-even small bonuses can have great impact.
Chapter 11
The Path Forward: Embracing the Unlearning Mindset
Unlearning doesn't begin with words but with action. Rather than trying to change others' mindsets first, we must lead by example, making small steps toward desired outcomes while adapting our own behavior. The most serious barriers to change exist in organizational culture, leadership, and strategy-all of which can be transformed through unlearning outdated behaviors. By changing our actions first, we begin to see and experience the world differently, which eventually changes how we think.
Most people avoid uncomfortable situations and uncertainty, pulled toward mediocrity by small-minded thinking and office politics. These individuals rarely achieve extraordinary results. Instead of chasing success directly, prioritize experiential learning and personal transformation-success will naturally follow. Choose greatness over mediocrity in all aspects of life by taking small steps toward desired outcomes. True greatness occurs at the intersection of courage and vulnerability to failure.
The Cycle of Unlearning begins with you-start immediately rather than waiting for a crisis. Define your aspiration, then quantify it by asking someone to rate your current performance on a scale of 1-10. This quantitative feedback helps your brain understand precisely where you stand. Ask what behaviors are helping or holding you back, and what small step would help you improve by half a point. Implement this as a tiny habit in your routine, then check back later to see if you've achieved your breakthrough.
As C.S. Lewis wisely noted, it's not beginnings but endings we should focus on changing. Whether you're a business leader facing disruption, an athlete seeking to break records, or simply someone wanting to grow personally, the ability to unlearn-to let go of past success to achieve something extraordinary-may be the most valuable skill you can develop in our rapidly changing world.
