Whether it’s leaving a stable job, breaking a social rule, or trusting your instincts when everyone else disagrees, risk-taking can feel both thrilling and terrifying. Yet, as Wayne W. Dyer argues, playing it safe may quietly drain your life of meaning. The question, then, isn’t whether to take risks—it’s how to take them wisely.
This article explores how to take risks by drawing ideas from Your Erroneous Zones by Wayne W. Dyer, On the Edge by Nate Silver, and The War of Art by Steven Pressfield. We examine why we avoid uncertainty, how successful people and artists navigate it, and what separates reckless choices from courageous ones. By blending insights from psychology, strategy, and creativity, we offer practical ways to challenge “shoulds,” embrace uncertainty, and move forward with purpose.
Table of Contents
Why It’s Important to Take Risks
To illustrate how to take risks, Wayne W. Dyer in Your Erroneous Zones explains why it’s important to do so in the first place. He says that one way you play it safe is by sticking to what’s familiar. You value security over spontaneity, preferring a well-worn path over something new or unusual. You refuse to take risks that lead to unpredictable results because you’re afraid of having to figure things out or hearing what other people might say if you don’t succeed.
For example, you might get a job that earns you enough money to buy a house because that’s what’s expected of you, do things you’re good at instead of trying something new because you’re afraid to fail, and hang out only with people who are similar to you because they won’t challenge your views. Living in this way takes any excitement out of life and keeps you from difficult situations that challenge you and help you grow.
(Shortform note: As Dyer says, many people tend to stick to what they know because they want predictability. But in The War of Art, Steven Pressfield contends that losing the comfort that comes from predictability isn’t a bad thing. He writes that anything you lose in the process of walking a different path is not something you need as you move forward. Additionally, walking a new path means you gain new people and experiences that enrich you.)
Another way you play it safe, says Dyer, is by being a prisoner of protocol. You adhere to “shoulds” and “musts” dictated by society because you don’t want to rock the boat, even if those rules and expectations don’t make sense and stifle your freedom, growth, and happiness. For example, you agree to be a bridesmaid because you think it would be rude to say no—even if saying yes would strain your finances and add to your stress.
Dyer contends that rules are dictated by outside sources, which means you’re ceding control over your choices to an external force. While he says that laws are necessary to impose order, some rules are nonsensical, and you should trust your judgment to determine which rules are sensible and worth following. For instance, you might question why a woman “should” wait for a man to make the first move.
| How the Patriarchy Traps Men and Women in “Shoulds” and “Musts” While society imposes “shoulds” and “musts” on everybody, these expectations differ for men and women. Research suggests that in the US, men face greater pressure to provide financial support and be successful in their careers, while women face greater pressure to be good parents and be physically attractive. These expectations are a manifestation of the patriarchy—the rigid division of gender roles—which one expert says was meant to uphold stability (or impose order, as Dyer puts it), but it came at the expense of intimacy and happiness. That said, women arguably have more confusing, conflicting “shoulds” and “musts” to contend with: The 2023 movie Barbie featured a monologue capturing how the patriarchy has made it impossible for women to meet contradictory expectations. For example, women are expected to be attractive for men, but not too attractive that it threatens other women; women are expected to always be grateful while at the same recognizing that the system works against them. |
How Can You Learn to Take Risks?
In On the Edge, Nate Silver argues that understanding the approach that gamblers take to risk-taking can help us deal with uncertainty, manage risk, and make decisions in many situations where other people’s actions will play a role in determining the outcome. He explains that in fields from poker to venture capitalism, it’s crucial to know when to take risks, when to walk away, and when to raise the stakes. Top performers in various industries have a mix of confidence and strategic decision-making skills that help them navigate high-risk environments.
Silver explains that successful risk-takers have several key characteristics that help them thrive. You can cultivate the same skills and mindset to learn to take risks:
1. Adopt an Independent Mindset
First, Silver explains that members of the River share a willingness to go against the grain. Rather than following conventional paths, they chart their own course and are attracted to unconventional or rebellious pursuits. This nonconformity allows them to see opportunities that others miss and take calculated risks that others overlook due to conventional thinking or risk aversion. By going against the grain, they can find edges that the crowd misses.
Silver writes that to adopt an independent mindset, you should invest time and effort in honing your skills and knowledge in your field, and question the assumptions others make about the status quo. He explains that you can practice making decisions based on your analysis rather than following the herd.
| The Art of Calculated Risk While Silver presents nonconformity as a path to success, Wes Anderson’s 2005 film The Life Aquatic with Steve Zissou illustrates that risk-taking and rebellion can sometimes go sideways. The film follows Steve Zissou, an oceanographer modeled on Jacques Cousteau, who takes increasingly dangerous risks—from leading his crew into pirate-infested waters to piloting an unsafe helicopter—in pursuit of both scientific discovery and personal revenge against a mysterious “jaguar shark.” Like Cousteau, who revolutionized underwater filmmaking with inventions like the Aqua-Lung but also infamously damaged coral reefs with dynamite in his 1956 film The Silent World, Zissou embodies both the promise and peril of going against conventional wisdom. Zissou’s willingness to chart his own course leads to genuine breakthroughs in marine biology and cinematography. But his refusal to acknowledge limits ultimately contributes to his son’s death. The film suggests that true innovation requires not just breaking rules, but knowing which ones matter—something Cousteau himself learned over time as he evolved from reckless explorer to passionate conservationist who founded organizations to protect marine life. This complicates Silver’s framework by showing how successful risk-taking often involves finding a balance between bold nonconformity and responsible stewardship, between pursuing your unique vision and protecting what matters. |
2. Be Conscientiously Contrarian
Second, members of the River have well-reasoned theories about when and why the conventional wisdom is wrong. According to Silver, they don’t simply rebel for the sake of rebellion, but rather have a deep understanding of when the crowd is misguided and are willing to bet against popular opinion when their analysis suggests an edge. Contrarian thinking grounded in sound analysis is essential for identifying situations where the market or conventional wisdom is wrong. Without this ability, risk-takers would simply be reckless gamblers rather than calculated risk-takers.
Silver writes that you can hone your contrarian thinking by studying past instances where the market or consensus was wrong, and developing frameworks for identifying such situations in the future. You can also practice articulating clear rationales for your contrarian views.
3. Have a “Raise or Fold” Mentality
Third, Silver explains that members of the River have the flexibility to embrace bold aggression or prudent caution as the situation demands. They avoid the mediocre middle ground of passivity, instead making decisive moves to capitalize on promising opportunities or cut losses on unfavorable situations. A “raise or fold” mentality is important because mediocrity and passivity are often the biggest risks in high-stakes environments. Bold action is required to capitalize on promising opportunities, while prudent caution is necessary to cut losses and preserve capital when the odds are unfavorable.
To cultivate a “raise or fold” mentality, Silver recommends setting clear criteria for when to be aggressive and when to exercise caution. You can practice making decisive moves based on these criteria, avoiding the temptation to take a passive middle ground.
| Beyond Mere Rebellion While Silver emphasizes the importance of being “conscientiously contrarian” and having a “raise or fold mentality,” Christian Dior’s revolutionary “New Look” shows both the promise and complexity of this approach. In 1947, when most designers were still creating practical, fabric-conserving styles due to post-war austerity, Dior made the bold decision to launch dresses that used up to 40 yards of fabric—a move that sparked both acclaim and outrage. This wasn’t mere rebellion: Dior had calculated that after years of wartime restrictions, women were ready for a return to luxury and femininity. When it came time to launch his collection, he exemplified Silver’s “raise or fold” mentality by going all in: Rather than hedging his bets with a mix of practical and luxurious styles, he committed fully to his dramatic new silhouette, even designing elaborate architectural underpinnings to achieve his vision. His decisive action paid off spectacularly, reviving both his business and French fashion. Dior’s contrarianism wasn’t just about seeing where the market was wrong: It was about understanding deeper human needs and desires after a period of hardship—and came from an artist’s intuition about what people needed even before they knew they wanted it. |
4. Prioritize the Process Over the Results
Fourth, Silver characterizes members of the River as being process-oriented rather than results-oriented. They focus on making optimal decisions based on their analysis rather than being swayed by short-term outcomes. They understand that even with sound decision-making, random ups and downs are inevitable in the short run, so they play the long game and trust their process.
A process-oriented mindset is vital because even the best decisions can sometimes lead to disappointing results in the short term due to factors outside your control. By focusing on the quality of their decision-making process rather than being swayed by temporary setbacks or wins, risk-takers can maintain the discipline and consistency required for long-term success. This can involve reviewing decisions objectively, identifying areas for improvement, and maintaining consistency in their approach regardless of the immediate results.
| The Art of the Process While Silver emphasizes the importance of focusing on process rather than immediate results, artist Alex Katz shows what this looks like in action. For over 60 years, Katz has maintained a rigorous approach to painting that prioritizes method over outcome: He begins with quick sketches, develops them through multiple studies, and only then attempts the final work—often completing large canvases in a single day of intense focus. When a painting fails (and he has destroyed “thousands”), he just starts again, focusing on the work of creating the painting rather than fixating on the end result. This process-oriented mindset has allowed Katz to take bold artistic risks while maintaining consistency: Rather than chasing immediate success or avoiding failure, he trusts in his method and keeps working. Yet Katz also shows how process-orientation can enable innovation. By focusing on refining his technique rather than achieving specific results, he developed a distinctive style that influenced generations of artists. This suggests that truly successful process-oriented thinking isn’t just about following established methods—it’s about using disciplined practice to discover new possibilities. |
Miscellaneous Tips
In Your Erroneous Zones, Wayne W. Dyer has the following tips to help you take more risks and break illogical rules:
1) Challenge norms and accept the consequences that come with living by your principles. If you find that things you “should” do end up making you unhappy, assess where this pressure to conform is coming from, free yourself from it, and deal with the backlash. For example, if wearing white after Labor Day makes you happy, then put on that white outfit—but be prepared to handle criticism from your busybody aunt.
(Shortform note: Challenging norms is easier said than done and can come at a great price. For example, Nelson Mandela fought against racist policies of apartheid and as a result spent 27 years in prison. Pakistani activist Malala Yousafzai spoke out against the Taliban’s rule that women and girls should stay home and not go to school, and she ended up getting shot. However, their courage to challenge norms brought about much-needed change, showing that speaking out against unfair “shoulds” can have broader implications beyond personal happiness: Mandela became South Africa’s first Black president, and Yousafzai has been instrumental in increasing girls’ and women’s access to education.)
2) Introduce spontaneity and rule-breaking in small doses. You don’t have to immediately do anything drastic like quitting your job and pursuing an unconventional career. Instead, start with small acts like trying a new coffee shop instead of going to the same one every morning, having lunch with a coworker who seems very different from you, or (as in the previous example) wearing white after Labor Day. Doing so can push you out of your comfort zone, help you become more open and flexible, and introduce more excitement into your life.
(Shortform note: Aside from changing up your routine, another way to encourage spontaneity and rule-breaking is by tapping into your creativity, which requires originality, thinking beyond convention, and cultivating playfulness. You can foster creativity by regularly challenging your beliefs—exposing yourself to films and art you wouldn’t normally consume—and ditching technology and doing something like communicating and navigating the “old-fashioned” way.)
3) See failure in a different light. Try something new without putting pressure on yourself to do it successfully or perfectly, especially if it’s not crucial to your goals. If you don’t accomplish what you set out to do, just accept that it’s the way things turned out and that this doesn’t reflect your value as a person.
Learn More About How to Take Risks
To understand more about taking risks in a broader context, check out these Shortform guides to the books referenced in this article:
