Quotes about Taking Risk

“The idea of ‘Fuck Yes…or N’ is far too simple and has caused me quite a lot of grief. Dropping out of college, I was maybe 51/49 on it. Leaving my corporate job to become a writer, maybe 60/40. Right now I’m about to do something big that I am both excited and terrified about. The point is: The certainty comes later. The truly life-changing decisions are never simple. If I had only ever done things I was absolutely certain about, I’d have missed out on experiences I love. Conversely, I regret a good chunk of my ‘Fuck yes’s’ because I was caught up in a fit of passion or bias. The whole point of risk is that you don’t know.“
Ryan Holiday

“The future is shaped by men and women with a steady, even zestful, confidence that on balance their efforts will not have been in vain. They take failure and defeat not as reason to doubt themselves but as reason to strengthen resolve. Some combination of hope, vitality and indomitability makes them willing to bet their lives on ventures of unknown outcome. If our forebears had all looked before they leaped, we would still be crouched in caves sketching animal pictures on the wall.”
John W. Gardner, Self-Renewal (Page xiii)

Choose the adventure.

“All paralyzed people—psychologically paralyzed, spiritually paralyzed—live life in hell. And how do they create it? The secret is that they live in fear; they only do a certain thing when there is no fear, but then there is nothing left worth doing. All that is worth doing has certain fears around it.”
Osho, Everyday Osho (Page 58)

Do it.

“Never settle for any mediocrity, because that is a sin against life. Never ask that life should be without risk, and never ask for security, because that is asking for death.”
Osho, Everyday Osho (Page 41)

“That’s what many people have managed to do; afraid of the depth, they have missed the peaks. One has to take risks. You have to pay for the peak, and the price is to be paid by your depth, your low moments. But it is worth it. Even one moment at the peak, the magic moment, is worth a whole life in the darkest depths. If you can touch heaven for one moment, you can be ready to live for the whole of eternity in hell. And it is always proportionate, have and half, fifty-fifty.”
Osho, Everyday Osho (Page 39)

“Life is a struggle and the potential for failure is ever present, but those who live in fear of failure, or hardship, or embarrassment will never achieve their potential. Without pushing your limits, without occasionally sliding down the rope headfirst, without daring greatly, you will never know what is truly possible in your life.”
William A. McRaven, Make Your Bed (Page 63) | ★ Featured on this book list.

“If you’d like to do something bold with your life, you will have to choose to do something bold on a specific day. There is no perfect day. There is no right time. For the trajectory to change, there has to be one day when you simply make the choice.”
James Clear, Blog

“Reputation is invaluable. Freedom and independence are invaluable. Family and friends are invaluable. Being loved by those who you want to love you is invaluable. Happiness is invaluable. And your best shot at keeping these things is knowing when it’s time to stop taking risks that might harm them. Knowing when you have enough.”
Morgan Housel, The Psychology of Money

How to be exhilarated later:

“With every pilgrimage one encounters the temporality of life. To die along the road is destiny. Or so I told myself.”
Bashō, Narrow Road To The Interior (Page 14)

Risk it.

“Nature is merciful and does not try her children, man or beast, beyond their compass. It is only when the cruelty of man intervenes that hellish torments appear. For the rest—live dangerously; take things as they come; dread naught, all will be well.”
Winston Churchill, via The Daily Stoic (Page 280)

“All that we do
Is touched with ocean, yet we remain
On the shore of what we know.”
Richard Wilbur, via Sunbeams (Page 72)

“It has become ever more clear to me that if I had spent my life avoiding any and all potential risks, I would have missed doing most of the things that have comprised the best years of my life.”
Phoebe Snetsinger, via The Happiness of Pursuit (Page 262)

35 Osho Quotes on Courage and Why Life Is Better Lived Dangerously

Excerpt: These 35 Osho quotes on courage were all hand selected and organized from his book, Courage: The Joy of Living Dangerously. Ready to drop fear? Read on.

“Those who are courageous, they go headlong. They search all opportunities of danger. Their life philosophy is not that of insurance companies. Their life philosophy is that of a mountain climber, a glider, a surfer. And not only in the outside seas they surf; they surf in their innermost seas. And not only on the outside they climb Alps and Himalayas; they seek inner peaks.”
Osho, Courage (Page 119)

Beyond the Quote (330/365)

What’s most interesting to me is how deeply connected both types of adventuring are. It is very similar to the connection between breathing in and breathing out. Adventuring on the outside is the expansion of the lungs—it is the breathing in of all that the world has to offer. Adventuring on the inside is the contraction of the lungs—it is the breathing out of all that you have inhaled and synthesized from your experiences. One leads to the other and the other leads to more of the one.

“Have you ever gone climbing the mountains? The higher the climb, the fresher you feel, the younger you feel. The greater the danger of falling, the bigger the abyss by the side, the more alive you are… between life and death, when you are just hanging between life and death. There is no boredom, then there is no dust of the past, no desire for the future. Then the present moment is very sharp, like a flame. It is enough—you live in the here and now.”
Osho, Courage (Page 120)