Risk Taking and Creativity

Who hasn’t daydreamed at about quitting their 9-5 job and jet setting on a fulfilling adventure? Be it a life-changing volunteer trip in South America, writing the next great American novel, or developing a must-have app, fear holds us back from achieving our dreams. The fear of failure, ridicule, and monetary loss prevents us from embracing our creative spirits and keeps us sticking to the status quo. The good news is that risk taking is easier than you may think.

In this article, I’ll guide you through the relationship between risk taking and creativity, discuss fearless risk takers, creative endeavors you can dive into, and tips for achieving creative success.

The Relationship Between Risk Taking and Creativity

Ask yourself one question: Are you living your passion? Most of us were ushered in college by our parents the moment we finished high school, then into a steady job, solid marriage, and finally buying a house with a heavy mortgage. In this predicated path, countless people have to give up on what they are passionate about in lieu of living a cookie-cutter “successful” life.

Your 20s are the easiest time to take risks because you do not likely have to worry about taking care of a young family, paying off a mortgage, or attending high stakes meetings. By risk taking, we don’t mean buying a fancy car way out of your price range just to impress everyone you know; We are talking about creative risks. Dare to put your creative endeavors out into the world, regardless of the challenges, disinterest, or ridicule you may face.

Most people find themselves paralyzed at the thought of the rejection they might face by living creatively. Roman philosopher Seneca once said, “We suffer more often in imagination than in reality.” Often, we create the worst possible scenarios in our minds that are so far removed from what would likely ever happen.

We have all heard that luck favors the bold, but we can’t forget that it is the bold that dare to take action. To live filling, creative lives, we must embrace risks, challenge the status quo forced onto us, and create fearlessly.

The Man in the Area, an Ode to Risk Takers

From presidents, to TED talkers, actors, and world-class athletes, countless risk takers have been inspired by President Teddy’s Roosevelt’s famed speech, “Citizenship in a Republic.” After leaving office, Roosevelt traveled the world, attending events and giving speeches. On April 23, 1910, Roosevelt delivered an outstanding 35-page speech called “Citizenship in a Republic.”

Of his speech, a passage that later became known as “The Man in the Arena” captured the hearts of listeners and quickly became widely published for its inspiring message to the doers of the world. The phrase “the man in the arena” refers to someone who is in a position that requires great courage, skill, or determination. In his famed speech, Roosevelt spoke out against people who criticized those that were trying to make a positive difference in the world.

The passage reads:

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, and comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows the great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who know neither victory nor defeat.

This powerful and widely quoted speech still holds plenty of weight over a century later. For anyone who is struggling with the fear of failure, take Roosevelt’s words to heart. Do not let the critics in your life prevent you from taking action. Roosevelt clearly admires the doers of the world, even those who meet failure when he states, “there is no effort without error and shortcoming. . . if he fails, at least fails while daring greatly.”

Famous Creative Risk Takers

Achieving greatness does not come without risks. Let’s take a close look at three famous risk takers who did not let fear get in the way of their creativity.

Stephen King: Famed horror writer Stephen King did not live a glamorous life before he became the king of horror. In 1973, King was living in a trailer with his wife, Tabby, and their young children. To support his family, King worked as a high school English teacher and took on countless odd jobs like being an industrial launderer and janitor.

Crammed in his laundry room, King wrote short stories during every free moment he had. King submitted his stories raunchy men’s magazines with only a few lucky pieces ever getting published. Eventually, the high school King worked at needed a new faculty advisor for the debate team and would pay him an extra $300 a year if he took on the role. Though King was excited by the prospect of more income for his family, Tabby told her husband that he would lose his writing time and could not accept the position.

King’s first novel, Carrie, went on to becoming a best seller, kicking off his illustrious writing career and giving his family the means to moving out of the trailer. Thanks to the wisdom of Tabby and his passion for macabre storytelling, King has published over 60 novels and hundreds of short stories to the delight of horror fans across the world.

Bill Gates: With a net worth of well over $100 billion, Bill Gates is easily one of the richest people in the world. Gates riches did not come without major risk taking. As a teen, Gates was enthralled by computers and coding. He wanted to be part of the personal computer revolution and dreamed of a future where personal computers were in every home and office, which was laughable at the time.

While Gates was a Harvard student, the affordable Altair 8800 computer was realized, which Gates developed a programing language for. Gates knew that with such an affordable personal computer on the market, more people would buy them. He felt that staying in school was delaying his role in developing software that would change the world of computers.

Gates dropped out of Harvard after two years of study to develop his software company Microsoft. Decades later, no one can deny that Gates made the right decision and every computer user thanks him for his daring. Will billions of dollars to his name, an iconic company, and outstanding philanthropy work, Gates never let the fear of failure stop his dream.

Ken Jeong: Not everyone knows that the outlandish actor and comedian Ken Jeong actually worked as a doctor for seven years. Despite his desire to perform, Jeong’s parents pushed him to enter med school and put his acting and comedy passions to the side. Jeong went on to work as a doctor by day and standup comedian by night, even for just $10 gigs.

In his late 30s, Jeong took a week off work to play a burnt-out doctor in the 2007 film Knocked Up. When the executive producers told Jeong that they truly believed that he was a burned-out doctor, he told them that he really was. When Jeong returned to his actual job after filming, life just wasn’t the same.

Just two years later, Jeong stared in the Hangover as the iconic Mr. Chow, became a favorite of director Judd Apatow, and took on countless comedic roles. Jeong is renowned for his fearlessness and has said that he is, “totally uninhibited at the risk of making myself look idiotic.” After all, what would the Masked Singer be like without Jeong’s brand of unabashed humor?

Creative Endeavors

Creativity can take on countless forms. Check out some of our favorite creative endeavors and see if one sparks your interest:

  • Travel to Ecuador for volunteer work and learn more in a week than you ever did in your high school Spanish class.
  • Launch a podcast in your favorite niche that you can talk about for hours with your best friend.
  • Dare to take a job in a city that you have never been to.
  • Share your borderline crazy yet genius campaign idea that had been fermenting in your head with your boss.
  • Send in your short stories and poems to indie literary zines and publishers.
  • Put your passion project on Kickstarter and interact with thousands of people who believe in your dream.
  • Sign up for a time slot at your local comedy club and deliver your best set.
  • Put together a ragtag band and upload your music online.
  • Launch a cooking blog and publish your wildest recipes that have you feeling like an avant-garde Gordon Ramsay.
  • Write out your ideal business plan and follow that up with an elegant resignation letter for your soul-sucking job.
  • Develop the next greatest gaming app that will have everyone competing for the highest score.
  • Channel your inner Jackson Pollock and live out your expressionist artist dreams.

Tips for Success

Taking risks doesn’t need to feel like a cliff dive. There are simple measures you can take to ensure that you are prepared for the next phase of your boundlessly creative life:

  • Evaluate your goals: Be sure to clearly define what your goals are. From long term and short term goals, having a defined purpose will help you power through any challenges.
  • Be ready to adapt: Success is not a straight line and you have to be ready to adapt to whatever challenges and opportunities come your way. Actress Audrey Hepburn once said, “Opportunities don’t often come along. So, when they do, you have to grab them.”
  • Failure does not equal defeat: Smooth seas never made a skilled sailor, and you should never give up at the first rough seas you encourage. Embrace all obstacles in your path and moments of failure as challenges to overcome and learn from.
  • Believe in yourself: Beyoncé once said, “sometimes you have to just believe in yourself and take a risk.” As trite as this sounds, you have to fully commit to whatever you are doing and be your number one supporter.
  • Have funds: No one really wants to be a starving artist, so make sure that you have enough money in the bank to cover a few months of rent and bills.
  • It’s about the journey: You must enjoy the process and not fixate on one day being able to buy an outrageously priced sports car and mega yacht. It may take years for you to profit from your creative endeavors, so don’t get hung up on not instantly living like an A-lister.


Feeling ready to take charge of your life and dare to take risks? What creative passions have been bubbling in your heart that you are ready to embrace? Let go of the fear that has preventing you from achieving your dreams and see just where your creative risk taking will get you.

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