A woman taking a risk as she walks in the middle of the street in a city.

Do you live life by rules and expectations? Why should you take more risks?

Some rules in life shouldn’t be broken, but some are okay to break every once in a while. When you’re playing it safe for the sake of security, you’ll never be able to do anything new in life.

Find out how to take more risks so you can forge new paths for your future.

Playing It Safe

To illustrate how to take more risks, Wayne W. Dyer 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 to Break Free From Rules and Expectations

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.

(Shortform note: Other authors have offered tips for reframing failure: In The Mental Toughness Handbook, Damon Zahariades says you should view failure as an inevitable part of life and valuable feedback you can learn from, which trains your brain to see future challenges as opportunities to grow from. In Big Magic, Elizabeth Gilbert suggests seeing creative misses as “interesting,” which encourages you to wonder what can be improved. The same principle can be applied to failures outside the creative field—in Think Like a Rocket Scientist, Ozan Varol writes that scientists approach their failures with genuine, disinterested curiosity. All authors echo Dyer in saying that you should believe it’s OK to not be perfect.)

How to Take More Risks (& How They’ll Help You Grow)

Katie Doll

Somehow, Katie was able to pull off her childhood dream of creating a career around books after graduating with a degree in English and a concentration in Creative Writing. Her preferred genre of books has changed drastically over the years, from fantasy/dystopian young-adult to moving novels and non-fiction books on the human experience. Katie especially enjoys reading and writing about all things television, good and bad.

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