Top 200 Risk-Taking Quotes (2025 Update)
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51. “Cows run away from the storm while the buffalo charges toward it – and gets through it quicker. Whenever I’m confronted with a tough challenge, I do not prolong the torment, I become the buffalo.”

— Wilma Mankiller

52. “I want to stand as close to the edge as I can without going over. Out on the edge you see all kinds of things you can’t see from the center.”

— Kurt Vonnegut

53. “Security is mostly a superstition. It does not exist in nature, nor do the children of men as a whole experience it. Avoiding danger is no safer in the long run than outright exposure. Life is either a daring adventure, or nothing.”

— Helen Keller

54. “If you want to move to a new level in your life, you must break through your comfort zone and practice doing things that are not comfortable.”

— T. Harv Eker

55. “If you aren't making waves, you aren't kicking hard enough.”

— Unknown

56. “I constantly get out of my comfort zone. Looking cool is the easiest way to mediocrity. The coolest guy in my high school ended up working at a car wash. Once you push yourself into something new, and whole new world of opportunities opens up. But you might get hurt. In fact you will get hurt. But amazingly when you heal – you are somewhere you’ve never been.”

— Terry Crews

57. “You jump off a cliff and you assemble an airplane on the way down.”

— Reid Hoffman

58. “Our doubts are traitors, and make us lose the good we oft might win, by fearing to attempt.”

— William Shakespeare

59. “If you don’t invest in risk management, it doesn’t matter what business you’re in, it’s a risky business.”

— Gary Cohn

60. “If you can’t take a small loss, sooner or later you will take the mother of all losses.”

— Ed Seykota

61. “Do not be afraid. Do not be satisfied with mediocrity. Put out into the deep and let down your nets for a catch.”

— Pope John Paul II

62. “There are risks and costs to action. But they are far less than the long range risks of comfortable inaction.”

— John F. Kennedy

63. “Always think, ‘what’s the worst that can happen’ and have some kind of strategy to deal with it.”

— Richard Branson

64. “There are two options: adapt or die.”

— Andy Grove

65. “What is the point of being on this Earth if you are going to be like everyone else and avoid trouble?”

— Arnold Schwarzenegger

66. “When I started SpaceX I thought that the most likely outcome was failure. And I think to have any other expectation would have been irrational.”

— Elon Musk

67. “Thinking will not overcome fear but action will.”

— W. Clement Stone

68. “Think about it: What’s the worst thing that can happen to you if you just totally go for it?”

— Grant Cardone

69. “You better lose yourself in the music, the moment You own it, you better never let it go You only get one shot, do not miss your chance to blow This opportunity comes once in a lifetime, yo.”

— Eminem

70. “I hope that in this year to come, you make mistakes. Because if you are making mistakes, you're doing something.”

— Neil Gaiman

71. “I say, ‘Why not’ to everything.”

— Russell Westbrook

72. “Take action now, because tomorrow never comes.”

— Marshall Sylver

73. “I learned to always take on things I’d never done before. Growth and comfort do not coexist.”

— Ginni Rometty

74. “Buy the ticket, take the ride.”

— Hunter S. Thompson

75. “Risk more than others think is safe. Dream more than others think is practical.”

— Howard Schultz

76. “Don’t be afraid to fail big, to dream big.”

— Denzel Washington

77. “If you want to be successful, you have to jump, there’s no way around it. When you jump, I can assure you that your parachute will not open right away. But if you do not jump, your parachute will never open. If you’re safe, you’ll never soar!”

— Steve Harvey

78. “Speak up. Believe in yourself. Take risks.”

— Sheryl Sandberg

79. “Make voyages. Attempt them. There’s nothing else.”

— Tennessee Williams

80. “So please ask yourself: What would I do if I weren’t afraid? And then go do it.”

— Sheryl Sandberg

81. “The time to go into a new business is when it’s badly run by others.”

— Richard Branson

82. “I have two basic rules about winning in trading as well as in life: 1. If you don’t bet, you can’t win. 2. If you lose all your chips, you can’t bet.”

— Larry Hite

83. “We have to continually be jumping off cliffs and developing our wings on the way down.”

— Kurt Vonnegut

84. “No pessimist ever discovered the secret of the stars or sailed an uncharted land, or opened a new doorway for the human spirit.”

— Helen Keller

85. “The best way to do it, is to do it!”

— Amelia Earhart

86. “To any entrepreneur: if you want to do it, do it now. If you don’t, you’re going to regret it.”

— Catherine Cook

87. “If you don’t make bold moves, the world doesn’t move forward.”

— Richard Branson

88. “Action cures fear. Indecision, postponement, on the other hand, fuel fear.”

— David J. Schwartz

89. “The real risk is doing nothing.”

— Denis Waitley

90. “When we got Tesla going at the very beginning, if you asked me what I thought the odds of success were, I would have said less than 50%. I would have said that failure is the most likely outcome.”

— Elon Musk

91. “The only way of discovering the limits of the possible is to venture a little way past them into the impossible.”

— Arthur C. Clarke

92. “It’s now or never. I ain’t gonna live forever. I just wanna live while I’m alive. It’s my life.”

— Jon Bon Jovi

93. “The future belongs to the risk-takers, not the comfort-seekers .”

— Brian Tracy

94. “It’s not an adventure until something goes wrong.”

— Yvon Chouinard

95. “Take risks in your life. If you win, you can lead! If you lose, you can guide!”

— Swami Vivekananda

96. “The greatest risk in life is to risk nothing. The person who risks nothing, does nothing, has nothing, is nothing and becomes nothing.”

— Norman Vincent Peale

97. “If you are going to try, go all the way or don’t even start. If you follow it you will be alive with the gods. It is the only good fight there is.”

— Charles Bukowski

98. “Only the person who risks is truly free.”

— William Arthur Ward

99. “You know, sometimes all you need is twenty seconds of insane courage. Just literally twenty seconds of just embarrassing bravery. And I promise you, something great will come of it.”

— Benjamin Mee

100. “It’s a terrible thing, I think, in life to wait until you’re ready. I have this feeling now that actually no one is ever ready to do anything. There is almost no such thing as ready. There is only now. And you may as well do it now. Generally speaking, now is as good a time as any.”

— Hugh Laurie