Never Play It Safe

Never Play It Safe Plot Summary

Introduction

Have you ever felt that nagging sensation that something is missing in your life? That despite checking all the societal boxes of success, there's a lingering emptiness within you? This feeling is more common than you might think. Many of us have been conditioned to prioritize safety and security over authenticity and fulfillment. We've been taught to listen to external voices rather than our own intuition, to fear failure rather than embrace it as growth, and to sacrifice our dreams on the altar of practicality. But what if the greatest risk isn't taking a chance on your dreams, but rather never pursuing them at all? Throughout these pages, you'll discover powerful levers that already exist within you—tools for directing your attention, transforming your relationship with time, trusting your intuition, embracing constraints, rediscovering play, leveraging failure, and building lasting practices. These natural resources, when activated, can help you break free from the illusion of safety and create a life of meaning, purpose, and joy—a life that truly reflects who you are and what matters most to you.

Chapter 1: Harness the Power of Attention

Attention is your most powerful resource, yet most people give it away freely without realizing its value. In today's world, our attention is constantly being hijacked by notifications, news cycles, and the opinions of others. But when you learn to direct and protect your attention, you gain the ability to shape your experience of life and create meaningful change. Consider the story of Viktor Frankl, who found himself in the most dire circumstances imaginable during World War II. When the Nazis invaded Austria in 1938, he could have escaped, but he refused to leave his parents. Eventually, Frankl and his entire family were deported to concentration camps, where most of his family perished. In the midst of this horror, Frankl made a crucial decision about where to focus his attention. Rather than surrendering to despair, he concentrated on treating suicidal patients in the camps and set up suicide prevention groups. By directing his attention toward helping others and finding meaning in his circumstances, Frankl not only survived but emerged with insights that would help millions through his book "Man's Search for Meaning." Similarly, Mihaly Csikszentmihalyi survived his time as a prisoner in an Italian work camp by focusing his attention on chess. The game provided an escape into flow state, where the world around him faded away and only the task before him existed. This practice of directed attention became the foundation for his groundbreaking research on flow states and optimal experience. To begin harnessing your own attention, start by becoming aware of where it's currently going. Try setting random alarms throughout your day to check in with yourself and notice what you're focusing on in that moment. Is it the present? Are you ruminating on the past or anxious about the future? This awareness alone can be transformative. Next, create regular practices of stillness and presence. This could be meditation, mindfulness, prayer, journaling, or expressing gratitude. The specific practice matters less than the consistent act of training your attention. Even five minutes each day can begin to strengthen this muscle. Remember that attention works like a flashlight—whatever you shine it on becomes illuminated while everything else fades into the background. You can choose to focus on problems or possibilities, on what's lacking or what's abundant. As psychologist William James wrote: "My experience is what I agree to attend to." When you truly understand the power of attention, you'll recognize it as your first and most fundamental lever for creating the life you desire. Your experience of the world isn't determined by what happens to you, but by what you choose to focus on.

Chapter 2: Transform Your Relationship with Time

Time is not the rigid, linear construct we've been taught to believe. Despite what conventional wisdom suggests, time is incredibly malleable—expanding and contracting based on our perception and experience. While calendars and clocks give the impression that time moves at a uniform pace, our lived experience tells a different story. Hours can feel like minutes when we're fully engaged, or minutes can drag on like hours when we're bored or anxious. Brent Underwood's story perfectly illustrates this transformation. As a digital media manager and hostel owner in Austin, Brent had a successful career by most standards. Yet when a friend asked him, "So what's your thing?" he realized he didn't have an answer. Despite his accomplishments, something was missing—a purpose bigger than himself. Then came a text message that would change everything: an article about buying a ghost town for under a million dollars. Within days, Brent found himself standing in Cerro Gordo, an abandoned mining town perched high above Death Valley. Something about this place spoke to him deeply. Despite the obvious challenges, he took a leap of faith—bringing on investors, taking out loans, and using every penny he had to become the owner of this historic ghost town. This decision led to years of hardship including fires, floods, and earthquakes. He lost thirty pounds and lived in desolate conditions without running water, far from modern conveniences. Yet through this journey, Brent discovered something profound—a completely new relationship with time. "I used to get a lot of anxiety thinking, 'What's next? What's next? What's next?'" he explained. "But now I've found presence, and this presence has given me purpose. I know that I have time. I know what the next project is." By focusing his attention on rebuilding Cerro Gordo, Brent found that his experience of time expanded. What once seemed impossible now felt achievable, even if it would take decades. To transform your own relationship with time, start by questioning the myth of busyness. There's nothing noble about filling every moment with activity. Instead, create systems rather than rigid schedules. Systems are the practices and routines that support your creativity and adaptability, while schedules are often dictated by others. Practice being fully present. The next time you're "waiting" in line or at a doctor's office, replace waiting with practicing being here. Feel your feet on the floor. Notice your breathing. These moments are not intermissions from your life—they are your life. Also, recognize that life is long. Many of us hear "life is short" and interpret it to mean we must rush, never make mistakes, and get everything right the first time. But this mindset often leads to playing it safe rather than truly living. Statistically, most of us are "time billionaires" with at least a billion seconds (over thirty years) left to live. We have time to experiment, fail, learn, and reinvent ourselves multiple times. Time is both precious and abundant. When you stop trying to manage it and instead learn to flow with it, you'll discover there's always enough time for what truly matters.

Chapter 3: Trust Your Inner Compass

Deep within you exists an extraordinary guidance system—your intuition. This inner compass points toward what's truly right for you, but it's often drowned out by external voices, societal expectations, and self-doubt. Learning to trust yourself again may be the most crucial step in creating an authentic life. Captain Chesley "Sully" Sullenberger's story vividly illustrates the power of intuition in action. On January 15, 2009, just seconds after taking off from LaGuardia Airport, his passenger plane collided with a flock of geese, causing catastrophic engine failure. As the aircraft plummeted toward densely populated New York City, Sullenberger had to make a split-second decision. Despite standard protocol and air traffic control both directing him to return to the airport, his intuition told him this was impossible. "We can't do it," he said. "We're gonna be in the Hudson." In that critical moment, with the lives of 155 people in his hands, Sully trusted his gut. Drawing on his decades of flying experience, including time as a glider pilot, he executed a textbook emergency water landing on the Hudson River, saving everyone aboard. This "Miracle on the Hudson" demonstrated how intuition, informed by expertise and experience, can guide us through seemingly impossible situations. For most of us, trusting our intuition doesn't involve life-or-death situations, but the principle remains the same. Your body often knows what's right before your rational mind does. When you're trying to make a decision, notice how your abdomen feels. Are you tense or relaxed? Does your stomach feel unsettled or calm? These physical sensations are your intuition speaking to you. To reconnect with this inner wisdom, try taking an "intuition field trip." Set aside a day with no technology where you ask yourself, "What next?" throughout the day. Listen for the soft voice of intuition and follow where it leads. Let feelings of expansion and openness in your body signal "yes," while constriction suggests you should choose differently. Remember that your intuition isn't something you need to create—it already exists within you. The challenge is becoming quiet enough to hear it. This often requires creating space away from the noise of daily life, opinions of others, and your own self-critical thoughts. As you practice listening to and acting on your intuition, you'll develop greater trust in yourself. This trust compounds over time, making each subsequent decision easier as you build confidence in your ability to navigate life's complexities without someone else's map. Your compass always knows the way home—to your authentic self.

Chapter 4: Use Constraints as Catalysts

Contrary to popular belief, limitations aren't obstacles to creativity and fulfillment—they're essential catalysts. When everything is possible, nothing is possible. It's by embracing constraints that we unlock our greatest potential and discover unexpected paths forward. Graphic design legend Stefan Sagmeister taught me this powerful principle while I was struggling to create a book cover design. Feeling stuck, I sought his advice, and what he shared changed my creative process forever. Instead of approaching the problem head-on, Stefan suggested thinking about the solution through the lens of something completely unrelated—a glass of water. What if the cover were clear? Could reflections play a part in the design? Could there be a connection between water flow and creative flow? Suddenly, by imposing this seemingly arbitrary constraint on my thinking, ideas began flowing effortlessly. The limitation forced my brain to make new connections rather than falling into familiar patterns. This technique, developed by lateral thinking expert Edward de Bono, illustrates how constraints can spark innovation by challenging us to think differently. We see this principle at work in the creative process of Chris Ballew, founder of the platinum-selling rock band The Presidents of the United States of America. Early in his career, Chris kept breaking guitar strings. When replacing them became too costly and time-consuming, he began experimenting with purposely removing half the strings on his guitar and using heavier-than-normal strings for the others. This constraint led him to pioneer a unique sound and style that contributed to the band selling over three million records. To leverage constraints in your own life, start by identifying which type you're facing. Self-imposed constraints are limitations you intentionally place on a problem to drive focus—like time limits, budgets, or creative parameters. Externally-imposed constraints come from circumstances beyond your control, such as the weather or health conditions. Perceived constraints are the limiting beliefs you've unconsciously adopted. Environmental constraints relate to your physical surroundings and circumstances. Once you understand your constraints, you can begin using them strategically. Rather than seeing them as barriers, view them as boundaries that give shape to your creativity. Like the banks of a river that direct water's flow, constraints channel your energy and attention in powerful ways. Remember that the best ideas often emerge from working within limitations rather than having unlimited resources. When you're forced to think differently, you discover solutions you might never have considered otherwise. As artist James Victore says, "The things that made you weird as a kid make you great today." Your uniqueness—including your particular set of constraints—is your greatest asset.

Chapter 5: Rediscover the Magic of Play

In our achievement-oriented culture, play has been relegated to childhood—a frivolous luxury we outgrow as we enter the "serious" business of adulthood. But what if play isn't just recreation? What if it's actually the most important work we do? Tennis champion Novak Djokovic discovered this truth at a critical moment in his career. After a series of painful defeats and injuries in 2018, Djokovic decided to quit tennis entirely. He announced his retirement plans to his team and walked away from the sport. Shortly afterward, while on vacation with his family, he watched his wife and children playing tennis—simply enjoying the game without pressure or expectation. Seeing their joy rekindled something in him, and he asked to join them. That playful reconnection with tennis—approaching it with curiosity rather than competitive pressure—reignited Djokovic's passion. After that vacation, he called his coach and announced he was ready to return. He went on to win another dozen grand slams, becoming arguably the greatest tennis player in history. He had forgotten that at its heart, tennis wasn't just work—it was play. This transformation isn't unique to elite athletes. Charlie Hoehn, a young professional who had worked with Tim Ferriss and other high-profile entrepreneurs, experienced debilitating anxiety after years of overwork. He tried every remedy—medication, meditation, therapy, diet changes—but nothing helped. Then he read about the power of play and decided to try a thirty-day experiment of playing every single day. Charlie went on mini-adventures, tried improv comedy, took walks, and worked on puzzles. Most memorably, he purchased a bucket of baseballs and a bat, meeting a friend at a park where they'd take turns pitching and hitting—something he'd loved as a child. This simple activity brought him immeasurable joy and effectively eliminated his anxiety symptoms. "Play utterly destroys anxiety," Charlie discovered. To rediscover play in your own life, try approaching routine tasks with playfulness. The next time you fold laundry, make it a sensory experience—notice the warmth of the clothes, the softness of the fabric, the colors and patterns. Turn the movements into a dance. This shift in perception can transform even the most mundane chores into opportunities for presence and joy. Remember that play isn't just about having fun—though that's certainly part of it. Play helps us build neural networks, adapt to change, connect with others, and solve problems creatively. As psychiatrist Stuart Brown found in his research, "Nothing lights up the brain like play." Far from being frivolous, play is essential to our well-being, creativity, and ability to navigate an increasingly complex world. When we stop trying to do what everyone else is doing and start experimenting to discover what truly brings us joy, our ability to focus becomes greatly amplified. This creates a virtuous cycle: focused attention on what we love, in turn, creates more focused attention.

Chapter 6: Embrace Failure as Growth

We all fail—and we will continue failing a little bit every day until we die. This isn't something to fear or avoid, but rather to embrace as an essential part of growth and discovery. Failure, when approached with the right mindset, becomes one of our most powerful levers for creating a meaningful life. Mountain climber Melissa Arnot Reid understands this better than most. While attempting to summit Mount Everest without supplemental oxygen—a feat accomplished by only about 220 humans in history—she overheard fellow climbers questioning why she was trying again after previous failed attempts. Lying in her tent at base camp, she found herself crying tears of rejection. But instead of giving up, Melissa made a pivotal decision. She stopped expecting universal support and moved to a quieter side of the mountain where she could focus on her goal without distraction. This strategy worked. After five attempts—five!—Melissa finally became the first American woman to summit Everest and return to base camp without supplemental oxygen. What she learned through this journey is that failure isn't just something to endure on the way to success—it actually contains the seeds of that success. When we face setbacks, most of us react in one of two ways: either we beat ourselves up or we minimize the experience with toxic positivity ("everything happens for a reason!"). Neither approach serves us well. Instead, we need to develop what psychologist Michael Gervais calls "neutral thinking"—not swinging between extremes but staying objective when things go wrong. Dashun Wang, professor at Northwestern's Kellogg School of Management, conducted extensive research on failure and found that the mantra "try and try again" doesn't actually work. What matters is how quickly you recover from failures with a new, demonstrably different approach. Those who succeed don't just keep trying the same thing—they study what went wrong, make strategic adjustments, and then try again with renewed focus. To embrace failure as growth, start by practicing "radical ownership." Navy SEAL Jocko Willink demonstrates this principle through his response to a tragic friendly-fire incident under his command. Rather than blaming circumstances or others, he told his superiors, "It was my fault." By taking complete responsibility, he positioned himself to learn everything possible from the experience and prevent similar mistakes in the future. Next, reframe how you view failure itself. Entrepreneur Jia Jiang tackled his fear of rejection by seeking it out—deliberately putting himself in situations where he would likely be rejected for 100 days straight. He asked for $100 from a security guard, requested to drive a police car, and asked a Krispy Kreme shop to make Olympic-ring-shaped donuts. Through this experiment, he discovered that rejection wasn't as painful or personal as he'd imagined, and that people were often kinder than expected. Remember that not all failures are equal. Harvard professor Amy Edmondson identifies three types: basic failures (simple cause-and-effect mistakes), complex failures (with multiple causes in dynamic environments), and intelligent failures (valuable learning from experimentation). Whenever possible, aim to engineer conditions for intelligent failure—controlled experiments that provide maximum learning with minimal risk. As you practice failing well, you'll develop resilience and self-trust that can't be gained any other way. Ultimately, the cost of trying to avoid failure is far greater than the sting of failing itself.

Chapter 7: Build a Practice of Success

Success doesn't happen by accident—it's built through consistent, intentional practice. The world's most extraordinary performers understand this at a fundamental level, developing routines and mindsets that turn momentary triumphs into lasting achievement. Take Stephen Curry, widely regarded as the greatest shooter in basketball history. What sets him apart isn't just natural talent but his approach to practice. Curry treats every repetition with incredible precision and intention. Even after becoming a multiple-time NBA champion and MVP, he continues to approach practice with the same focus and dedication that got him there. As former coach Alan Stein Jr. observed, "He wipes the slate clean after every shot and always believes his next shot is going in." This same pattern appears in architect Yasmeen Lari's daily practice. Rather than focusing solely on design, she begins each day walking through the historic streets of Lahore, engaging with residents and connecting with locals at heritage sites. Her practice is rooted in understanding the people she serves, aligning her work with the fundamental purpose of architecture—to improve human lives. Cellist Joshua Roman demonstrates yet another dimension of deliberate practice. Beyond technical mastery, he incorporates mindfulness and a holistic approach to his craft. For years, he practiced one of Bach's Unaccompanied Solo Cello Suites every day—arguably the most technically demanding pieces ever written for the instrument—building both technical proficiency and a deeper connection to the music's emotional core. What unites these masters across different domains are three pillars of practice. First, they focus ruthlessly on fundamentals. While they may possess extraordinary fringe skills, they consistently return to the basics of their craft. Second, they've fallen in love with the process itself. Practice isn't a chore but a joy—something they genuinely look forward to. Third, they've aligned their practice with their identity. They don't just do what they do; they are who they are. To build your own practice of success, start by identifying the fundamentals in your area of interest. What are the core skills or principles that everything else builds upon? Then find ways to make practice enjoyable rather than obligation. As philosopher Alan Watts observed, "If you are a great artist, your periods of practice will not be effective unless it is a pleasure for you. You have to come to the point that going over it again and again is a dance." Most importantly, connect your practice to your identity. As James Clear writes in Atomic Habits, "Every action you take is a vote for the kind of person you want to become." Consider your future self—if you could snap your fingers and become the person you dream of being, what would your daily habits look like? How would you think and act? Begin incorporating these elements into your life now. Remember that practice isn't about perfection but momentum. The goal isn't to always be improving but to always be practicing. Even Maya Angelou, one of literature's greatest voices, maintained a strict daily writing ritual in a rented hotel room for decades. She understood that to be the noun (a writer), she simply had to do the verb (write)—consistently and with intention.

Summary

Throughout these pages, we've explored seven powerful levers that already exist within you—attention, time, intuition, constraints, play, failure, and practice. These aren't external resources you need to acquire but internal capacities waiting to be activated. As you learn to harness these tools, you'll discover that playing it safe is actually the riskiest choice you can make. True freedom comes from the courage to create your own path, guided by your authentic self. Remember the wisdom of Francis Ford Coppola: "It's so silly in life not to pursue the highest possible thing you can imagine, even if you run the risk of losing it all. You can't be an artist and be safe." Whether your dream is to climb mountains, create art, build a business, or simply live with greater joy and presence, the path begins with refusing to settle for less than what your heart truly desires. Your journey won't be without challenges, but as you've seen through countless stories in these pages, those challenges are precisely what make the journey worth taking. Your first step is simple: choose one lever that resonates most strongly with you and commit to a small daily practice. Perhaps it's five minutes of meditation to train your attention, a daily intuition check-in, or deliberately introducing play into a routine task. Start where you are, with what you have, and trust that these small actions will compound over time, creating powerful momentum toward the life you're meant to live. The world is waiting for your unique contribution—it's time to embrace the unknown.

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Chase Jarvis

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