PDF Summary:Never Play It Safe, by Chase Jarvis

What if the safest paths are the least likely to make you happy? In Never Play It Safe, entrepreneur and award-winning photographer Chase Jarvis argues that life’s biggest rewards lie beyond your comfort zone. Yet, fear often drives you to choose safety over your true desires—leading you to live a life that looks good on paper but ultimately feels unfulfilling.

In this guide, we’ll lay out Jarvis’s advice on how to commit to your true desires by developing your intuition, reclaiming your attention, and managing your time. We’ll then examine strategies for embracing obstacles as growth opportunities and putting in the work to achieve your goals. Along the way, we’ll compare Jarvis’s ideas to those of other self-improvement authors and offer more tips for choosing a fulfilling life over a safe one.

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To prevent this, Schwartz suggests creating “second-order decisions”—automatic choices that free up your mental energy. You can do this by:

• Setting rules (like always stopping at stop signs)

• Creating presumptions (like waking up at the same time each workday)

• Establishing standards (like only considering restaurants that serve food you enjoy)

• Building routines (like ordering the same satisfying meal at your favorite restaurant)

How to Design Helpful Limitations

Jarvis explains that there are two types of limitations in life:

First, there are limitations you can’t control—for example, health conditions that limit your mobility or unexpected events that disrupt your plans. You can’t eliminate these limitations, but you can change how you think about them and view them as opportunities instead of roadblocks. Many successful people turn their unchangeable limitations into fuel for creativity and motivation rather than using them as excuses to give up.

(Shortform note: In The Happiness Hypothesis, Jonathan Haidt writes that adversity can make you stronger and happier. He explains that when you face and overcome hardships, you prove to yourself that you’re stronger than you thought, and you gain confidence to face future challenges with less fear. You may also realize that your support network of family and friends runs deeper than you know, which can shift your focus from seeking material success to building meaningful relationships. Most importantly, overcoming difficulties allows you to rewrite your personal story—what Haidt calls your “self-narrative”—from one of frustration to one of triumph over adversity.)

Second, there are limitations you create yourself—such as setting specific work hours or reducing your social commitments. Jarvis writes that creating helpful limitations can make you more focused and creative. For example, when you decide to stop checking work emails after 6 p.m., you create better boundaries between work and personal life. When you limit your social events to one per weekend, you protect your time for rest and other priorities.

(Shortform note: Creating helpful limitations requires mastering a skill most people struggle with—saying no. In Essentialism, Greg McKeown explains that we avoid saying no because we’re afraid of creating conflict or disappointing others, but you can learn to do it gracefully while earning more respect. Remember that you’re rejecting the request, not the person, and have a repertoire of techniques ready: You can pause to let the person making the request fill the silence, buy time by saying you’ll check your calendar, or suggest someone else who might help. McKeown emphasizes that saying no to nonessential activities is actually saying yes to what’s more important.)

However, cautions Jarvis, don’t confuse helpful self-imposed boundaries with harmful limitations you set for yourself. Harmful limitations are false beliefs like “I’m too awkward to make new friends” or “I’m not smart enough to start a business.” Identify and challenge these beliefs since they’re not real limitations—they only exist in your mind.

(Shortform: In The Big Leap, Gay Hendricks says you can identify self-limiting beliefs by reflecting on behaviors you do every day. Constantly worrying about things you can’t control, deflecting compliments, being overly critical of others, or mysteriously getting sick after good things happen are all red flags that point to deeper limiting beliefs about yourself. He suggests you observe and gently correct these behaviors. In doing so, you weaken the power of limiting beliefs—proving they really do exist only in your mind.)

2) View Failure as a Learning Tool

In addition to taking advantage of limitations, Jarvis encourages you to acknowledge failure as a necessary part of creating a meaningful life. We’re naturally afraid to fail because we worry about what others will think of us. For instance, it’s normal to feel uncomfortable when you make a mistake in front of your friends or coworkers. This feeling comes from our biology—we’re wired to be social creatures who want to belong to our groups. When we fail or make mistakes, our brains trigger a fear response because failure threatens our acceptance in whatever group we’re trying to fit into.

(Shortform note: If you’re a parent, your response to failure shapes not just your own life but how your children react to failure. According to Kristin Neff in Self-Compassion, practicing self-compassion when you make mistakes—especially in front of children—teaches them that failure is a normal part of being human, not something that makes you unworthy of belonging. You can do this in three ways: 1) Apologize to your child after losing your temper (showing that mistakes are learning opportunities), 2) avoid self-criticism in front of children (“I’m so stupid!”), and 3) correct children’s behavior without attacking their character. By practicing these behaviors, you can help your children develop healthy responses to their own failures.)

Today, social media makes this fear worse by only showing people’s successes, not their failures or struggles. When we only see others succeeding, we start to think success should come easily. This leads us to view our mistakes as shameful rather than what they really are: normal steps in learning something new.

(Shortform note: When you scroll through social media, your brain naturally zeros in on posts from people who seem successful—and tech companies know this. According to researchers, social media algorithms amplify prestigious content—posts that signal someone’s success or high status—because our brains evolved to pay special attention to successful people as a survival strategy. These algorithms learned that showing you influencers in private jets or friends announcing promotions keeps you scrolling longer, so they flood your feed with success stories instead of the everyday struggles and failures that don’t generate as many clicks.)

Jarvis argues that failure teaches more valuable lessons than success does. When you fail at something, you have to figure out what went wrong and adjust your approach. For example, if you’re a writer, you might write several mediocre books that teach you to better structure your plot, leading you to eventually write a successful novel. Failure also makes you more resilient. The more you face smaller failures and recover from them, the more capable you’ll be of handling bigger challenges later.

(Shortform note: Research suggests that the difference between people who succeed after failure versus those who don’t is that successful people build on their previous attempts instead of starting from zero. You can even predict who will succeed by watching how quickly they try again after failing. People with fast retry times are those who keep the useful parts from their last attempt and only change what didn’t work. Therefore, failure can be a powerful teacher—but only if you absorb and apply its lessons rather than just blindly trying again.)

How to Learn From Failure

To learn from failure, Jarvis says you shouldn’t pretend failure doesn’t hurt. Popular self-help advice often tells us to openly embrace failure or act like it doesn’t affect you, but this isn’t realistic. Instead, accept that failure hurts while recognizing that it helps you grow. This mixed feeling toward failure—not loving it but not completely fearing it either—allows you to take worthwhile risks, learn from your mistakes, and keep trying.

(Shortform note: Failure may hurt a little less if you realize that people are paying far less attention to your mistakes than you think. Social psychologists say that due to the spotlight effect, we tend to overestimate how much others notice about us. This happens because we’re naturally more aware of our own thoughts and feelings than anyone else’s. When you make a mistake or fail at something, it feels glaringly obvious to you, so you assume everyone else must be watching and judging just as closely. But in reality, most people are too caught up in their own lives to pay much attention to your failures.)

Jarvis suggests two ways you can start using failure as a learning tool:

1. Experiment: Treat everything you do as an experiment where you come up with a theory, try it out in a controlled way, record what happens, and learn from the results. This way, you can start viewing failure as a learning tool rather than a source of shame. Jarvis notes that successful innovations often come from people who are willing to fail many times while learning what works.

(Shortform note: In The 5 Elements of Effective Thinking, Edward D. Burger and Michael Starbird suggest one way to learn from experiments: simulating mistakes. You can do this in two ways: 1) Make deliberately bad leaps in logic to see where they lead. For example, a Spanish teacher might imagine taking students to Spain—an impractical idea and logistical nightmare—which could spark a more realistic idea of visiting local Spanish-speaking businesses. 2) Wildly exaggerate your ideas. For example, if you design trampolines, imagine an elephant jumping on one—this absurd scenario could reveal structural flaws that could affect humans too, helping you improve your product design.)

2. Get rejected on purpose: Intentionally make requests that people will likely say “no” to, like asking for free dessert at a restaurant or requesting an upgrade at a hotel. This exercise teaches you that rejection isn’t as devastating as you may think. It also helps you build the confidence to take chances with less fear holding you back.

(Shortform note: This “rejection therapy” has become a viral trend on social media platforms like TikTok. Psychologists say that while it can help some people expand their comfort zones, it’s not right for everyone. For people dealing with trauma, self-esteem issues, or social anxiety, rejection therapy could make fears worse. There’s even a condition called rejection sensitivity dysphoria, where people experience intense emotional responses to both real and perceived rejection. If rejection prevents you from enjoying social events or maintaining relationships, it may be better to work with a mental health professional who can properly guide you through exposure therapy techniques.)

Put in the Work

Once you’ve identified your true desires and learned to handle hardship, you need to put in consistent effort to achieve the life you want. In this section, we’ll explore three of Jarvis’s strategies for doing the work required: being consistent with your practice, making the most of your time, and maintaining a sense of fun.

1) Be Consistent

Jarvis writes that to succeed at anything, you must practice consistently, even when you don’t feel motivated. While beginners often look for quick and easy ways to improve, experts spend a lot of time mastering basic skills. For example, a professional artist might warm up by sketching volumes and studying anatomy each day, while a beginner artist might jump straight to complex character poses without practicing fundamentals.

(Shortform note: In The Art of Learning, Josh Waitzkin says there are two benefits to practicing fundamental skills first: You build resilient skillfulness, and you learn to appreciate the process of growth. By drilling basics until they become automatic, you can later combine them creatively to handle new challenges, unlike someone who only memorizes rigid strategies that work in specific situations. For example, learning a language by understanding its basic sounds and grammar helps you form your own sentences, while just memorizing common phrases leaves you stuck when conversations go in unexpected directions.)

How to Practice Consistently

To practice your craft consistently, Jarvis suggests that you:

1. Enjoy the journey. High performers find enjoyment in practicing their craft, not just succeeding at it. When you find joy in the everyday work, not just the result, you’re more likely to stick with it even when you hit rough patches or experience failure.

(Shortform note: Enjoying the journey can be hard if you’re stuck in a rut. In Anatomy of a Breakthrough, Adam Alter says that in the middle of long-term projects or crafts, we often face a point where progress becomes so incremental that we can’t see it anymore. He offers several strategies to overcome these ruts, like breaking your project into smaller chunks, practicing mindfulness, and lowering your standards temporarily to play with new ideas. When you understand that these slowdowns are normal parts of any journey, you can stop seeing them as failures and start seeing them as just another step in the process.)

2. Make practice part of your identity. Instead of seeing practice as something you must force yourself to do, make it part of who you are. For example, instead of thinking, “I want to run more,” think of yourself as a runner. When you see yourself as a runner, you’ll want to run on a regular basis because it matches who you believe you are. This shift from seeing running as an external task to seeing it as part of your identity creates a natural motivation that is stronger than willpower alone.

(Shortform note: In Atomic Habits, James Clear echoes Jarvis’s advice, explaining that lasting change happens when you work from the inside out, starting with your identity, rather than focusing solely on external goals. You can make practice part of your identity because of the feedback loop between actions and identity. When you consistently take small actions aligned with your desired identity (like running every morning), these actions serve as votes that gradually convince you that you are indeed that type of person (a runner). Each run reinforces your runner identity, which then makes you more likely to go running again, creating a cycle of positive change.)

2) Make the Most of Your Time

We all have limited time in the day to work toward our goals. Jarvis argues that getting more out of your time isn’t just about better scheduling or working faster—it’s about understanding how you experience time and learning to use it more effectively. He offers strategies for stretching your perception of time and organizing your work schedule to maximize productivity.

How to Stretch Your Perception of Time

Jarvis explains that time can pass more slowly or more quickly depending on your mental state and how present you are. For example, if you’re bored while waiting for an appointment, minutes can feel like hours, but when you’re playing video games with friends, hours can feel like minutes. You can work with time’s elastic nature to be more productive and get more hours out of the day.

To stretch your perception of time, Jarvis recommends you:

1. Live in the moment. Jarvis explains that we often waste time thinking about things we can’t change (the past) or things that haven’t happened yet (the future). He suggests you focus on what’s happening right now—the conversation you’re having, the task you’re doing, or even simple things like the food you’re eating. When you put all your focus into what you’re doing, you can savor the moment, work more efficiently, and make the most of your time instead of letting it slip by as your mind wanders elsewhere.

(Shortform note: In The Power of Now, Eckhart Tolle explains two ways we think about the past and future: “Clock time” is practical and tied to the present moment—like learning from mistakes or planning future actions. “Psychological time” is when we get stuck thinking about the past or worrying about the future in ways that don’t help us. For example, after a job interview, you might spend some time thinking about how to improve your answers next time—that’s useful clock time. However, worrying about everything you said wrong and feeling bad about yourself is psychological time, and it only creates stress.)

2. Choose to see life as long instead of short. When you think life is too short, you’ll feel stressed about making perfect decisions and avoid exploring and taking risks to avoid wasting your time. Jarvis recommends you instead recognize that you have decades ahead to learn, grow, and try new things. This longer view allows you to explore different careers or interests with less pressure and anxiety. You’ll be OK with making mistakes since you have time to recover and start fresh in a new direction, even later in life.

(Shortform note: Though Jarvis recommends viewing life as long, not short, Stoics argue that remembering you could die at any moment actually helps you live better. In Meditations, Marcus Aurelius says that focusing on every task as if it’s the last thing you’ll ever do forces you to focus on what’s important and avoid wasting time on distractions or worrying about what others think. He points out that whether you live 50 years or 5,000 years, you only ever have the present moment—and that’s all you lose when you die—so there’s no real benefit to longevity. When you accept death as natural and focus on living well right now, you stop fearing the future and can face whatever comes with calm acceptance.)

3. Do new things. When you perform routine activities, your brain operates on autopilot, and time goes more quickly. In contrast, when you experience something new, like visiting a city you’ve never been to or taking a class on an unfamiliar subject, time feels like it moves more slowly because your brain is paying more attention. Therefore, Jarvis recommends seeking out new experiences—a year filled with new experiences might feel much longer than a year of doing the same old routine.

(Shortform note: In Moonwalking With Einstein, Joshua Foer explains that our brains have a biological tendency to compress similar experiences, which makes routine-heavy periods feel shorter. This is because our brains are designed to record change, not sameness. When every day follows the same pattern, our brains lump those experiences together, causing months to blend in our memory. This is why time seems to pass more quickly as we grow older: We have fewer new experiences than we did as children, when we were constantly taking in new sights and information.)

How to Schedule Productive Work

In addition to stretching your perception of time, Jarvis also recommends working in blocks of 90-120 minutes. This timeframe matches your natural attention cycles while still being long enough for you to tackle complex problems or creative challenges. When you work this way, you’re more likely to enter flow—a state of deep focus where you become completely absorbed in your work and lose track of time.

(Shortform note: Working in 90- to 120-minute blocks matches energy cycles called ultradian rhythms that control how your body produces and recovers energy throughout the day. After 90-120 minutes of focused work, your brain and body have burned through significant amounts of oxygen and glucose while metabolic waste builds up in your system, making you feel tired, spacey, or distracted. When you ignore these signals and push through, your next peak performance will be significantly lower. By mid-afternoon, you’ll feel completely drained, and no amount of coffee will save you.)

Jarvis suggests you take a 30-minute break after each work period because your body needs rest to work well. Rest allows your brain to make new connections and come up with fresh ideas. Beyond daily breaks, take longer rest periods too. Schedule days off for fun, take breaks from technology, and go on vacations where you completely unplug from work. Many people think they need to be available for work 24/7, but Jarvis disagrees. He warns that if we don’t choose to rest, our bodies will eventually force us to rest by getting sick.

(Shortform note: If rest is so important, why don’t we prioritize it more? In Laziness Does Not Exist, Devon Price explains that our culture has trained us to view rest as laziness and to measure our worth by how much we accomplish. When you feel tired or unmotivated, you might push yourself to keep working, seeing these feelings as character flaws rather than your body’s natural warning signals telling you to slow down. To rest well, you must let yourself be lazy and separate your self-image from your productivity levels. Price explains that by taking care of your needs and energy limits, you’ll actually be able to give more to your work and relationships over time.)

3) Bring More Fun Into Your Life

Lastly, to work sustainably toward your goals, make life more fun. Jarvis writes that many people think fun is optional—it’s something you do only after you finish your work. School and work both teach us to focus on goals and deadlines, so we learn to rush through our days, checking off tasks rather than enjoying what we’re doing. Because of this, we feel empty and drained even when we succeed at work or school because we’ve forgotten how to slow down and appreciate what’s happening in the moment.

Thus, Jarvis argues that having fun is vital to living a good life. It helps us learn, grow, and stay mentally healthy, making it just as important as work or other responsibilities. Instead of taking life too seriously, focus more on being playful and having fun. This mindset allows you to venture more bravely from your comfort zone and engage with life’s challenges with curiosity, creativity, and openness.

(Shortform note: The idea that fun is optional actually goes against human nature. Though play may seem unproductive, both humans and animals spend much of their time doing it. Evolutionary biologists theorize that when animals and humans play, they develop better social skills, reduce stress, and improve motor coordination and problem-solving abilities. Wolves, for instance, use play to learn important social rules and strengthen group bonds. Therefore, when you make time for fun, you’re supporting your mental and physical well-being.)

Why We’re Having Less Fun Than Ever Before

In The Power of Fun, Catherine Price writes that we’re having less authentic fun than previous generations due to two major shifts in modern life:

First, the Industrial Revolution changed our relationship with time—suddenly every hour was worth money. This made people view time spent on fun as “wasted” time that could have been spent earning. The pressure to be productive has only increased since then, making it harder to justify taking breaks just to play and enjoy life.

Second, technology has also reduced fun in our lives. While scrolling through social media might feel entertaining, Price argues it’s just a shallow distraction that isolates us and prevents us from experiencing real joy and connection. Even worse, phones make us less likely to strike up conversations with strangers or invest in meaningful face-to-face interactions—the very things that create true fun.

How to Make Everyday Tasks Fun

To add fun and playfulness to your life, Jarvis suggests you transform mundane tasks into playful experiences. You can do this by being completely engaged in what you’re doing instead of rushing through tasks while thinking about other things. For example, instead of scrolling on your phone while walking your dog, tune into your surroundings and explore different paths together. Being mindful about simple activities can make everyday tasks feel less like work and more like play.

(Shortform note: In The Happiness Project, Gretchen Rubin echoes Jarvis’s recommendation to be more playful during everyday activities. She explains that we forget to be playful in these moments when we try to get things done efficiently, even when there’s no real reason to be efficient. To avoid this, Rubin recommends asking yourself two questions: “Does this task need to be done now?” and “Can we spare a couple of moments to be goofy?” These questions can remind you that you don’t need to be so serious when trying to complete tasks, which improves your mood and the happiness of everyone around you.)