The Gap and the Gain

The Gap and the Gain Plot Summary

Introduction

Have you ever felt that no matter how much you achieve, you're still not satisfied? You reach a goal, but instead of celebrating, your mind immediately shifts to the next target, leaving you in a perpetual state of striving but never arriving. This is what Dan Sullivan calls "the GAP" – the space between where you are and where you think you should be. It's a mindset that traps countless high achievers in a cycle of perpetual dissatisfaction. This book offers a revolutionary perspective shift: instead of measuring yourself against ideals that continually move further away, learn to measure backward from where you are to where you started. This simple yet profound change – moving from the GAP to the GAIN – transforms how you experience success, happiness, and progress in every area of life. By adopting this approach, you'll discover that happiness isn't something to pursue in the future but something to expand in the present by appreciating your progress and transforming every experience into a gain.

Chapter 1: Escape the Gap: Break Free from Unhealthy Comparison

The GAP is a toxic mindset that prevents people from experiencing happiness and appreciating their lives. When you're in the GAP, you're constantly measuring yourself against ideals – perfect standards that by definition can never be reached. This creates a perpetual state of dissatisfaction, where no achievement ever feels like enough because there's always more to do, more to accomplish, more to become. Consider Thomas Jefferson, who penned the famous phrase "the pursuit of happiness" in the Declaration of Independence. By framing happiness as something to pursue, Jefferson inadvertently suggested that happiness is always ahead of us, never here in the present. This pursuit mindset has shaped American culture profoundly – a recent poll found that only 14 percent of American adults say they're very happy. When your happiness is tied to something in the future, your present is diminished. Take Edward, a successful businessman with a multi-million-dollar portfolio. Despite growing his investments from $2.5 million to $17 million over sixteen years – far exceeding his original goal of $5 million – he remained anxious and worried. Each time he reached a financial milestone, instead of feeling secure, he simply moved the goalpost further. Eventually, his GAP-thinking became so extreme that he abandoned the very investment strategy that had created his wealth, convinced the financial world was going to collapse. The GAP creates a fundamental disconnect between your achievements and your ability to appreciate them. It's like running on a treadmill – no matter how fast you go, you never actually arrive anywhere. The solution isn't to stop setting goals; it's to change how you measure your progress toward them. Instead of measuring the distance between where you are and your ideal, measure the distance between where you are and where you started. This shift from the GAP to the GAIN is transformative. When you're in the GAIN, you appreciate your progress. You recognize how far you've come. You feel successful right now, not at some distant point in the future when you've finally "arrived." This doesn't diminish your ambition – in fact, research shows that positive emotions and confidence actually fuel better performance and greater achievement. The first step to escaping the GAP is simply becoming aware of it. Notice when you're measuring yourself against ideals rather than appreciating your progress. Then consciously shift your focus to the GAIN by asking: "Where was I before, and how far have I come since then?"

Chapter 2: Define and Pursue Success on Your Own Terms

Society trains us to measure success against external reference points – test scores compared to national averages, income compared to industry standards, achievements compared to competitors. These external comparisons put us squarely in the GAP, constantly measuring ourselves against standards we didn't choose. To live in the GAIN, you must become self-determined by defining success on your own terms. Dean Jackson, a marketing expert and entrepreneur, had an epiphany about this twenty years ago. He realized that using the phrase "I'll be successful when..." led people to chase the wrong forms of success. Instead, he flipped the question to "I know I'm being successful when..." and created a list of ten personal criteria, including "I can wake up every day and ask, 'What would I like to do today?'" and "I'm working on projects that excite me and allow me to do my best work." This list became his personal compass, allowing him to make decisions aligned with his own definition of success. Sandi McCoy experienced the power of self-determined success during her remarkable weight loss journey. After losing over 240 pounds, she still faced criticism about her appearance and excess skin. She learned to ignore external judgments and define success for herself: "There used to be a time where I based my success on what I thought others wanted from me. I felt like I was always letting everyone down. It wasn't until I decided to make a list of what I actually wanted in life that I was finally able to succeed on the goals I set for myself." Creating your own success criteria is surprisingly simple. Set aside 20-30 minutes with no distractions and answer this question: "I know I'm being successful when..." Be completely honest with yourself – no one else needs to see this list. Include both tangible achievements and emotional states. For example, you might write "I know I'm being successful when I'm financially independent" alongside "I know I'm being successful when I feel calm and present with my family." Once you've created your list, use it as a filter for decisions. The British rowing team transformed their performance by developing a one-question filter for every decision: "Will it make the boat go faster?" This simple criterion helped them win Olympic gold after decades of mediocre results. Similarly, entrepreneur Lee Brower uses six filtering questions to guide his decisions, starting with "Is this opportunity aligned with my values?" Your success criteria become more powerful as you use them. They help you say "no" to opportunities that don't align with your true priorities, preventing you from being pulled into the GAP of external expectations. They also create confidence and momentum as you make decisions that consistently move you toward your own definition of success rather than someone else's. Remember that your success criteria can evolve over time. What matters is that you're measuring yourself against standards you've thoughtfully chosen, not unconsciously absorbed from society, social media, or others' expectations.

Chapter 3: Build the Gain Habit: Train Your Brain for Progress

The GAP isn't just psychologically damaging – it physically harms you. Research shows that the stress of continually feeling inadequate taxes your body and shortens your lifespan. Studies of Catholic nuns found that those who expressed more positive emotions in their journals lived nearly 10 years longer than those whose entries were more negative. Other research shows unhappy people get sick more easily, taking an average of 15 extra sick days per year. The way you mentally filter experiences literally shapes how your body responds to them. In one fascinating study, hotel room cleaners who were told their work constituted "good exercise" showed measurable improvements in weight, blood pressure, and body fat compared to a control group – despite no changes in their actual behavior. In another study, participants who believed they were drinking a high-calorie milkshake felt fuller than those who thought they were drinking a low-calorie shake, even though both groups consumed identical beverages. Your brain is constantly filtering reality based on what you're looking for. When you're in the GAP, you're trained to spot what's missing, what's wrong, or what could be better. When you're in the GAIN, you notice progress, growth, and positive changes. The good news is that you can retrain your brain to default to the GAIN perspective through consistent practice. Jeff, who recently went through a painful divorce after 15 years of marriage, demonstrates this principle powerfully. Despite the heartbreak, Jeff made a conscious choice to frame his experience as a GAIN. He viewed the 15 years they were married as a beautiful adventure he wouldn't take back. He chose to see his ex-wife with compassion rather than bitterness. He focused on their three wonderful children and the lessons he'd learned. By staying in the GAIN, Jeff was able to move forward rather than being derailed by resentment. To build your own GAIN habit, start by catching yourself when you go into the GAP. This might happen dozens of times daily at first. When you notice it, simply call it out: "I'm in the GAP right now." Then immediately look for the GAIN in the situation. Share the concept with people you trust and give them permission to gently point out when you're in the GAP. Use language like "What's the GAIN here?" or "How can we turn this into a GAIN?" when facing challenges. Mental subtraction is another powerful technique for strengthening your GAIN muscle. Inspired by the classic film It's a Wonderful Life, this exercise involves imagining the absence of something positive in your life. Research shows this practice increases gratitude and happiness more effectively than simply thinking about positive things. Try mentally subtracting an important relationship, achievement, or capability from your life. How would things be different? This exercise helps you appreciate what you have rather than focusing on what you lack. Finally, implement the "five-minute rule" used by a championship women's soccer team. When something disappointing happens, allow yourself exactly five minutes to feel frustrated or upset – to be in the GAP. When the five minutes are up, deliberately shift to the GAIN by identifying what went well and what you learned. This simple time-bound approach acknowledges negative emotions without letting them dominate your experience. With consistent practice, spotting GAINS will become second nature. As investor Naval Ravikant noted: "I used to get annoyed about things. Now I always look for the positive side of it. It used to take a rational effort. It used to take a few seconds for me to come up with a positive. Now I can do it sub-second."

Chapter 4: Measure Backward to Boost Hope and Resilience

Jill Bishop, a physical therapist who works with children with severe disabilities, makes phone calls that regularly bring parents to tears – tears of joy and hope. During annual reviews, she reminds families of where their children were a year ago compared to now. "Last year, Rosie was learning to walk on grass," she'll say. "Remember how impossible that seemed? I was just reviewing her annual report and was reminded how far she's come. I'd actually forgotten about that since she now walks on grass like a champion!" These calls are powerful because humans quickly adapt to their "new normal," forgetting the progress they've made. Psychologists call this automaticity – the process by which conscious skills become unconscious habits. Once you master something, you rarely think about how difficult it once was. Without deliberately measuring backward, you lose sight of your GAINS, which undermines your confidence and motivation. This forgetting happens because memory isn't like a video recording – it's a reconstruction influenced by your current perspective. As psychologist Dr. Brent Slife explains, "It is more accurate to say the present causes the meaning of the past, than it is to say that the past causes the meaning of the present." When you draw on a memory, you always do so through the lens of your current knowledge and abilities, making it difficult to accurately recall how far you've come. The solution is to deliberately measure backward by keeping records of your progress. Harvard psychologist Daniel Gilbert found that when people reflect on their former selves, they're often surprised by how much they've changed. Looking back 10 years, most people realize their interests, priorities, and capabilities have evolved significantly. Yet without concrete reminders, we underestimate this growth. Try this exercise: Where were you 10 years ago? What were you focused on? How did you measure success back then? What do you know now that you didn't know then? Make a bullet-point list of your GAINS – not just external accomplishments, but also experiences, lessons learned, and relationships built. Be as specific as possible. For example, instead of writing "My business did pretty well," write "My revenue increased from $50,000 to $250,000, and I built a team of five people." Then zoom in closer – repeat the exercise for the past 3 years, then the past 12 months, and finally the past 90 days. Josh Waitzkin, former chess prodigy and author of The Art of Learning, asks himself every 90 days: "What did I believe 3 months ago that I no longer believe today?" This question helps him track his intellectual evolution and stay open to new ideas. When entrepreneurs in Dan Sullivan's Strategic Coach program first try this exercise, many are shocked to realize how much they've accomplished. Despite objective success, they've been feeling like failures because they've been measuring themselves against their ever-advancing ideals rather than against their starting points. Once they shift to measuring backward, their confidence and motivation surge. Don Bradley experienced this transformation firsthand: "I've been taking the practice of enumerating my wins for the year, month, and week and I've been applying it on the level of the day. Seeing how much I'm actually getting done in a day is creating this wonderful upward spiral in my self-efficacy: I feel unstoppable. Consequently, I get even more done." The more you practice measuring backward, the more you'll appreciate your progress and the more confident you'll become in your ability to create future GAINS. This isn't about lowering your standards or ambitions – it's about acknowledging how far you've come while continuing to move forward.

Chapter 5: Win Every Day: Daily Practices for Momentum

There is one specific hour – the "sweet spot" of your day – that has the biggest impact on both your short-term and long-term success. What you do during this hour affects how well your brain functions, how productive and purposeful you are, and ultimately how successful you feel. This critical time is the hour before you go to sleep. Research shows that the behaviors you engage in before bed are coded into your long-term memory. While you sleep, your brain processes everything you experienced that day, with special emphasis on your final waking activities. This is why top athletes like Olympic gold medalist Kayla Harrison visualize success just before sleep: "Every night I visualize myself winning the Olympics, standing on top of the podium, hearing the national anthem, watching the American flag go up." Unfortunately, most people squander this powerful hour. Studies show that nearly 97 percent of people use their smartphones before bed, despite evidence that screen time disrupts sleep quality and next-day alertness. Instead of ending the day intentionally, they scroll mindlessly through social media or news feeds, filling their minds with comparison, anxiety, and distraction. A simple yet transformative alternative is to spend the last 30-60 minutes before sleep in reflection and preparation. Dan Sullivan has taught his entrepreneurial clients to write down three "wins" at the end of each day for decades. This practice serves multiple purposes: it boosts gratitude, increases happiness, improves sleep quality, and builds confidence by focusing your attention on progress rather than gaps. After recording three wins from today, write down the three most important wins you want to achieve tomorrow. Not ten or twenty items – just three. As leadership expert Jim Collins said, "If you have more than three priorities, you don't have any." Make these wins important rather than merely urgent. This practice primes your subconscious to work on these priorities while you sleep and gives you clear direction when you wake up. The benefits compound quickly. As Dan explains: "I would go to bed feeling good, but excited about the next day. I would wake up the next morning excited. Then, that day, I'd go out and try to have those three wins. But oftentimes, what would happen is I'd have wins that were bigger than the three I had imagined the night before. And then I'd come home and have the same exercise. What happens out of this exercise – and this has been going on for 15 years with me – is I'm always winning." This daily practice retrains your brain to see GAINS rather than GAPS. Psychology has a term for this – selective attention – which explains that we notice what we're looking for. William James, the father of American psychology, put it this way: "My experience is what I agree to attend to." By deliberately attending to your wins each day, you train yourself to notice more wins throughout your life. For even greater impact, share your daily wins with an accountability partner. This combines the power of measurement with the power of reporting – what's known as Pearson's Law: "When performance is measured, performance improves. When performance is measured and reported back, the rate of improvement accelerates." Simply text your three wins for today and three intended wins for tomorrow to a trusted friend or colleague. This creates gentle accountability and makes the process more enjoyable. The beauty of this practice is its simplicity. It takes just a few minutes each day but fundamentally shifts how you experience your life. Instead of going to bed feeling inadequate about what you didn't accomplish, you'll fall asleep appreciating what you did achieve. Instead of waking up without direction, you'll start your day with clear priorities. And instead of living in the GAP, constantly chasing but never arriving, you'll live in the GAIN, creating and celebrating progress every single day.

Chapter 6: Transform Every Experience Into a Gain

On September 29, 2008, Howard Getson woke up having lost over $2 million before his morning coffee. The financial crisis had begun, and the stock market was crashing. Later that day, while working out at the YMCA, his trainer noticed his pale complexion and asked if everything was okay. Howard replied, "Today is the worst day in the market since the Great Depression." As the words left his mouth, he realized they were false – it was the worst day for him, but not for everyone. This realization led to an epiphany: "No system works all the time, but there is always something that's working." Trading is a zero-sum game – while many people were losing money, others were making it. The next day, Howard had a breakthrough conversation with an analyst on his team that revealed a fundamental flaw in their investment approach. They had been using a rule that shut off any trading system that ever lost more than 20% during testing, which inadvertently eliminated specialized systems that could have performed exceptionally well in specific market conditions like the 2008 crash. Instead of remaining devastated by his loss, Howard transformed this painful experience into a GAIN. He completely redesigned his investment strategy, developing systems tailored to different market conditions with an overarching AI-driven approach to switch between them as conditions changed. This insight became the foundation for everything he's done in the thirteen years since the crash. Howard's story illustrates the profound difference between being in the GAP versus the GAIN when facing challenges. When you're in the GAP, you're reactive to your experiences – viewing them as negative events that happened to you. When you're in the GAIN, you're proactive – you take ownership of your experiences and utilize them to become more adaptive and successful in the future. This approach develops what psychologists call psychological flexibility – the ability to manage emotions effectively and move toward goals even when facing setbacks. Research shows that psychological flexibility is associated with lower anxiety and depression, better work performance, greater learning capacity, and higher quality of life. The more flexible you are, the more pathways you can find to your goals when obstacles arise. Richie and Natalie Norton demonstrate this flexibility in the face of extraordinary tragedy. They lost their three-month-old son, Gavin, in 2010. Two and a half years earlier, they had lost Natalie's 21-year-old brother (also named Gavin). Later, they lost three foster children in a failed adoption, Natalie suffered a stroke, and their 11-year-old son was hit by a distracted driver and placed in a coma. Despite these heart-wrenching experiences, the Nortons made a conscious decision: "We will be better because of this, not bitter because of this." Richie quit his corporate job, went back to school for his MBA, and wrote the book he'd been procrastinating on for a decade. The tragedies became a wake-up call that time is finite, leading the family to prioritize creating meaningful experiences together. They now live in Hawaii, take extended vacations, and focus intensely on family connection. To transform your own experiences, Dan Sullivan created a tool called The Experience Transformer. The process is simple: Think about any specific experience, positive or negative. Ask yourself: What about this experience worked? What usefulness can I get from it to improve my future? What did I learn about what I don't want? How will I approach my future differently based on this experience? What about this experience am I grateful for? This deliberate rumination process – actively thinking about an experience and creating meaning from it – is how you transform experiences into GAINS. Research shows this process is enhanced when done in written form, such as in a journal, and when it includes gratitude. The alternative is intrusive rumination, where uncomfortable thoughts and emotions randomly hit you because you haven't processed and transformed the experience. When you're in the GAIN, you become what Dr. Nassim Taleb calls "antifragile" – not just resilient to shocks but actually strengthened by them. Every experience, even the most challenging, becomes fuel for growth rather than a source of regret or resentment. This doesn't mean pretending difficulties don't exist; it means choosing to extract value and learning from them rather than being defined or diminished by them. As Dan explains: "We're not usually given encouragement to deal with the negative aspects of our experiences, but when you can take a negative experience and learn a lesson from it that you can apply positively to the future, you're transforming the negative experience. In my own life, I've found that the more I transform my experiences, the more confident I feel that I'll be able to deal with anything new, negative, or jarring in the future."

Summary

Thomas Jefferson's formula of "Life, Liberty, and the pursuit of happiness" makes happiness an unachievable ideal. By framing happiness as something to pursue, we inadvertently place it always in the future, never in our present. The fundamental insight of this book is that happiness isn't something you pursue – it's your starting point, which you expand every time you measure backward and appreciate your GAINS. The shift from the GAP to the GAIN transforms everything. Instead of measuring yourself against unreachable ideals, you measure your progress based on where you were before. This simple yet profound change liberates you from the hedonic treadmill, allows you to define success on your own terms, and enables you to transform every experience – even painful ones – into learning and growth. As Dan Sullivan writes, "Everyone who grows achieves their progress and improvement by transforming frustrating and painful failures into rules and measurements for satisfying success." Today, make the choice to be in the GAIN by writing down three wins from your day and planning three wins for tomorrow. This single practice will begin retraining your brain to see progress everywhere, creating an upward spiral of confidence, achievement, and genuine happiness that expands with each passing day.

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Benjamin P. Hardy

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