Never Play It Safe: Embracing Risk for a Meaningful Life

Chase Jarvis, an award-winning photographer, director, artist, entrepreneur, and bestselling author, presents a compelling argument for embracing risk to achieve a life of true fulfillment. His new book, "Never Play It Safe," serves as a "training manual" for navigating the inherent risks that lead to our most profound experiences. Jarvis contends that while external pressures exist, we often do the most harm to ourselves by choosing to play it safe.

The Illusion of Safety and the Call to Authenticity

Jarvis clarifies that "never playing it safe" does not advocate for reckless physical endangerment. Instead, it challenges the emotional and psychological safety we often seek, which he deems an illusion. He asserts that "all of the best stuff in life is on the other side of our comfort zone." Our culture, loved ones, and even our own minds frequently discourage risk-taking, pushing us towards perceived security. His book aims to counteract this by drawing on his personal journey, insights from over a thousand podcast guests, and his experiences with creative invention and reinvention.

Jarvis himself embodied this principle when he scrapped an entire draft of "Never Play It Safe" eight weeks before his deadline. He felt it was too safe, too polished, and lacked the raw honesty he intended, realizing he was presenting a sanitized version of struggle—what he calls "gold-plated grit." The current version of the book is a direct result of that difficult, yet authentic, decision.

The CreativeLive Journey and Personal Betrayals

A significant influence on the book is Jarvis's experience founding CreativeLive, an online learning platform launched over 15 years ago. This pioneering venture in live-streamed education achieved considerable financial success and attracted top talent. However, as the company grew and became venture-backed, Jarvis, a lifelong artist, found himself in the role of CEO—a position he felt ill-suited for. He describes this period as a "betrayal" of himself, where he ignored his true nature to fulfill an expected role.

Despite the personal cost, CreativeLive became profitable and was eventually sold to a publicly traded company. Reflecting on this, Jarvis acknowledges that while it was a massive risk involving personal compromises, it also fostered immense growth. He learned that "we will all betray ourselves over and over again, and the goal is to just return to ourselves with a little more kindness and get 1% better every day." This continuous process of self-correction, even minor adjustments, prevents us from drifting too far from our authentic selves.

The Trap of Success and External Validation

Jarvis highlights the "trap of success," where external validation and material rewards can divert us from our core values. When the world celebrates our achievements, it's easy to overlook internal dissonance. He recounts earlier ventures, including a pre-Instagram mobile app that, despite initial success, didn't achieve the billion-dollar valuation of Instagram. He learned to accept such outcomes, recognizing he "just got [his] ass kicked by a lot of money and smart people."

He emphasizes that all these experiences—from photography to tech startups—are expressions of creativity. However, when these expressions flourish, they can easily lead to a "betrayal of the sensibility that birthed it in the first place." This is because societal incentives often prioritize a narrow definition of success: a good salary, a respected job title, and material possessions. These external pressures can drown out our internal compass, leading us to make choices misaligned with our true desires.

The Seven Tools for an Authentic Life

Jarvis's book proposes seven innate tools to help us reconnect with ourselves and live more authentically. He argues that just as creativity is often "trained out of us," so too are our abilities to focus, listen to our intuition, and seek joy and play. The world, he contends, isn't inherently evil, but it often functions to talk us out of these essential aspects of ourselves.

The book's core message is one of empowerment: "the answers were always there." We don't need to move to a new country or change our friends; the transformation is an "inside job." If we are willing to do the work, the tools are readily available.

Playing It Safe vs. Living Fully

Jarvis defines "playing it safe" as "not showing up as who you really are" and being "unwilling to take a chance for fear of not looking like your absolute best." This insidious behavior often masquerades as a virtue, as seen in societal pressures to pursue financially secure and respected careers. However, he argues that such paths are often "someone else's prescription for your one precious life."

He challenges readers to reflect on their best life experiences, asking if they occurred within their comfort zone or on the other side of fear. Invariably, he finds, the answer is the latter. This raises the question: why does our culture default to safety? While biological wiring for survival plays a role, Jarvis asserts that this wiring is for reproduction, not for joy, freedom, happiness, or fulfillment. His book aims to provide a "compass" for navigating towards those best experiences, emphasizing that the goal isn't to "light it all on fire" but to find a methodical way to embrace risk.

The Cost of Compromise

Jarvis refers to the compromises we make as "tiny betrayals." He acknowledges that perfection is unattainable, but the goal is to become more aware of these betrayals and to listen more closely to our true selves. He highlights the societal emphasis on intellect over heart, where rational thought is celebrated at the expense of intuition. This imbalance makes us more susceptible to external incentives that pull us away from our inner wisdom.

He shares personal examples of the costs of playing it safe: hundreds of thousands of dollars in student debt from following a traditional path, and nearly losing his marriage due to an all-consuming career that looked successful on the outside but was internally hollow. He argues that the "riskiest thing you could do" is to pursue a path that isn't authentically yours, as the costs, though different, are just as real as those associated with taking risks.

The Power of Attention

The first tool Jarvis discusses is attention, which he considers our most precious resource. He asserts that "your experience of your life is entirely contingent on where you place your attention." He cites Victor Frankl's experience in a concentration camp as an extreme example of how directing attention can create meaning even in the most horrific circumstances.

Jarvis encourages us to consciously direct our attention, rather than allowing it to be hijacked by external stimuli or internal narratives. He uses the analogy of a flashlight: when we focus our attention on something, it illuminates that area while darkening others. This deliberate focus is a skill that can be developed through practice, leading to a more intentional and fulfilling life. He also emphasizes the importance of observing our internal thoughts, recognizing that we are not our thoughts, and that we have the power to choose the narratives we feed ourselves.

Time and Intuition

Following attention, Jarvis addresses time and intuition. He argues that effectively directing our attention changes our experience of time, making it more malleable and allowing for "flow states" where productivity and joy align. He challenges the notion that life is short and we must rush, suggesting that this leads to reactive and impulsive living. Instead, he proposes that if we had more time, we might be more willing to experiment and pursue our true passions.

Intuition, he explains, becomes accessible when we create enough space in our lives to hear our inner voice. This doesn't require becoming a monk but rather cultivating "little glimpses" of quiet awareness. He emphasizes that the purpose of these practices is not to achieve perfect meditation but to reconnect with ourselves, to understand our true desires, and to make choices aligned with our authentic selves.

The Role of Constraints

Drawing from his artistic background, Jarvis views constraints not as impediments but as drivers of creativity. He explains that a blank canvas can be daunting, but imposing even basic constraints—like choosing a medium or a color palette—can immediately focus creative energy. He cites designer Stefan Sagmeister's exercise of using an unrelated object, like a glass of water, to inspire the design of a tennis shoe, demonstrating how constraints can shatter well-worn mental ruts and unlock new ideas.

He distinguishes between external constraints (lack of money, time, etc.) and internal constraints (self-limiting beliefs). While external constraints can be seen as powerful directors, guiding us towards what is possible, internal constraints are often the biggest hurdles. He encourages readers to view these as opportunities for decision-making, emphasizing that we are "one decision away from taking a step in the direction of your dreams."

Re-evaluating Failure

Jarvis challenges the often-fragmented discourse around failure. While acknowledging that failure can be painful, he suggests reframing it as "tiny experiments." This approach lowers the stakes, making us more willing to try new things. He argues that if experiments don't sting when they go wrong, we won't put in the effort to learn and adapt.

The key, he believes, is to uncouple our identity from the success or failure of a particular project. When our self-worth is tied to outcomes, the fear of failure can lead to paralysis. By viewing endeavors as experiments, we can foster resilience and growth without the existential threat of personal failure.

The conventional discourse around failure is often polarized: either dismissing it as a non-issue or glorifying it to an extreme. Jarvis argues against both, acknowledging that failure can be painful and costly, citing examples like the space shuttle disaster. He criticizes Silicon Valley's dismissive attitude towards failure, advocating for a more nuanced examination.

Failure is simultaneously glorified ("fail fast, fail forward, fail often") and deeply painful. Jarvis suggests that if failure doesn't sting, true learning might not be occurring. He proposes reframing failures as "tiny experiments." These experiments should sting if they don't go well, as this motivates effort and iteration, leading to adaptation, growth, and resilience. The definition of "tiny" can evolve, and even seemingly large endeavors, like expanding a network of shows, can be considered tiny experiments within a broader life context.

Uncoupling Identity from Outcomes

A crucial aspect of navigating failure is to uncouple one's identity from the success or failure of a particular project or task. When identity is deeply intertwined with outcomes, failure becomes an existential threat, leading to fear of starting and paralysis during the process. This is counterproductive to actualizing goals. Jarvis views failure as an essential tool for building resilience and learning. Just as a child learns to walk by falling repeatedly, individuals learn and grow through failed attempts. He highlights that many people give up after a few failures, unlike the persistence seen in children learning basic skills.

Jarvis stresses the importance of not tying one's identity to failure, which requires significant internal work but offers immense freedom. This resilience is built through taking chances and struggling, which are valuable characteristics in life. He summarizes this by stating, "if you're afraid to fail, you're afraid to live."

The Science of Meaningful Failure

Research on failure indicates that it is a valuable tool for building resilience and skill. However, it's important not to become too comfortable with failure, as a lack of sting can lead to insufficient effort. The key is to create a framework around failure:

1. Try something.
2. If it doesn't work, quickly deconstruct what happened.
3. Try again with a slightly different approach.
4. Repeat this process.

This iterative, non-random approach to learning from mistakes is what constitutes meaningful failure. Jarvis notes that many people fail to apply this principle in their own lives, often repeating the same mistakes without changing their approach.

Overcoming the Fear of Others' Opinions

A significant obstacle to embracing failure is the preoccupation with what other people think. This is linked to identity and can be a major impediment to taking risks. Jarvis shares a valuable tip from Brené Brown: identify a small, select group of people whose opinions truly matter. Brown suggests writing their names on a 1-inch by 1-inch piece of paper. For Jarvis, this list contains fewer than five people. The opinions of everyone else should be disregarded.

This approach allows individuals to be "willing to be misunderstood by large swaths of people for long periods of time," a concept echoed by Jeff Bezos. This willingness is crucial for achieving significant goals and transforming one's world.

However, charting one's own course can lead to challenges from those in one's immediate environment. When individuals break from established norms, they may inadvertently hold a mirror up to others, challenging their worldviews and potentially leading to resentment or lashing out. Jarvis reflects on his own experiences with sobriety and transitioning from a legal career, acknowledging the difficulty of navigating others' judgments. While he has developed resilience, he admits to being a people-pleaser and sensitive, making criticism hard to bear. The key, he suggests, is to have an internal compass that propels one forward, even when facing external negativity.

The Value of Play

Jarvis identifies "play" as the most challenging concept for him to embody. He admits to a Protestant work ethic that equates suffering with hard work and value, often robbing him of joy and presence in his life. He believes play is our natural state, much like creativity, which is often trained out of us as we age.

He argues that joy doesn't have to be deferred until work is done, and that fun doesn't diminish the value of an activity. He encourages reframing mundane tasks, like folding laundry, as opportunities for play and gratitude. This involves a "tiny defiance" against societal norms that dictate what is considered work versus play.

Jarvis emphasizes that the goal is not to pretend that difficult tasks are easy, but to decide that they can be positive experiences. This shift in attitude, rather than a change in the task itself, can transform the experience. He uses the example of digging up his septic system by hand, which he decided to make fun, leading to unexpected positive interactions and learning.

The Story of Paul: A Testament to Embracing Risk

Jarvis illustrates these principles through the inspiring story of Paul, a young man from Ghana. Paul, facing immense cultural and financial pressure after having a child out of wedlock, sold everything he owned to buy a camera. He taught himself photography, built a portfolio, and was accepted into the International Center of Photography in New York, a seemingly impossible feat given his circumstances.

Through a chance encounter with Brandon Stanton of Humans of New York, Paul's story reached Jarvis. With their support, Paul eventually made it to New York, completed his studies, and became a successful commercial photographer. However, his ultimate dream was to create a center for photography in Africa, where Africans could tell their own stories. He collected over 30,000 books and, with the help of a fundraiser organized by Stanton, built the Deacon Center, the largest center for creativity and photography in Africa.

Paul's journey, Jarvis explains, embodies all the levers discussed in the book: his singular focus, his trust in intuition, his ability to overcome immense constraints, his joy in the creative process, and his consistent practice. His story serves as a powerful testament to the transformative potential of embracing risk and pursuing one's authentic calling. Jarvis emphasizes that while Paul's story is extraordinary, the underlying tools and principles are accessible to everyone, offering a path to "loving your life and feeling free rather than pulled in a hundred ways."

The author emphasizes a gentle approach in his book, using personal anecdotes of self-betrayal and responsibility-avoidance to connect with readers. The goal is to inspire and show accessibility, rather than shame.

The Superpower of Directed Attention

The book's core message is counterintuitive. While society often teaches us to seek attention, the true superpower lies in the ability to direct one's attention purposefully. Similarly, while grinding through work might feel productive, finding joy in the process can lead to better outcomes and a more fulfilling experience.

Jarvis's personal journey, from photographer to venture-backed startup founder, and now to a new phase, illustrates these principles. After selling his company, he realized the toll of relentless work and is now focused on finding "simple joy." He is looking back at what truly lit him up in the past to guide his future projects, including writing the book, rebuilding his personal brand, and exploring new ventures in AI and creativity. This process of "cleaning out his closet" has left him feeling lighter, smarter, and propelled by a 51% conviction over 49% doubt.