Risk Quotes

“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

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.

“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.

“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.

“Life can only be lived dangerously—there is no other way to live it. It is only through danger that life attains to maturity, growth. One needs to be an adventurer, always ready to risk the known for the unknown. And once one has tasted the joys of freedom and fearlessness, one never repents because then one knows what it means to live at the optimum. Then one knows what it means to burn your life’s torch from both ends together. And even a single moment of that intensity is more gratifying than the whole eternity of mediocre living.”
Osho, Courage (Page 51)

“[Listen] to the heart consciously, alertly, attentively. And follow it, go wherever it takes you. Yes, sometimes it will take you into dangers—but remember, those dangers are needed to make you ripe. Sometimes it will take you astray—but remember again, those goings astray are part of growth. Many times you will fall—rise up again, because this is how one gathers strength, by falling and rising again. This is how one becomes integrated.”
Osho, Courage (Page 10)

“Basically courage is risking the known for the unknown, the familiar for the unfamiliar, the comfortable for the uncomfortable, arduous pilgrimage to some unknown destination. One never knows whether one will be able to make it or not. It is gambling, but only the gamblers know what life is.”
Osho, Courage (Page 2)

James Clear Quote on Decisions and How Understanding If One Is Reversible Or Not Can Help You Decide

“If a decision is reversible, the biggest risk is moving too slow. If a decision is irreversible, the biggest risk is moving too fast.”
James Clear, Blog

Beyond the Quote (212/365)

Let’s start by figuring out which types of decisions are which. Not going to college, for example, is a decision that can easily be reversed. You can always go back to college at a later point in time. Going to college and getting a degree in something that you aren’t passionate about or uninterested in pursuing is a decision that is irreversible. Quickly committing to college when you’re unsure, undecided, or confused about your path is a big risk. Especially if the college you’re committing quickly to has a high tuition cost.

“When you are young spend at least 6 months to one year living as poor as you can, owning as little as you possibly can, eating beans and rice in a tiny room or tent, to experience what your “worst” lifestyle might be. That way any time you have to risk something in the future you won’t be afraid of the worst case scenario.”
Kevin Kelly, Blog

Quote About Showing Up For Life—On Collecting Scars Not Avoiding Bruises

“Maybe life isn’t about avoiding the bruises. Maybe it’s about collecting the scars to prove we showed up for it.”
Unknown

Beyond the Quote (67/365)

Good judgement comes from bad judgement remembered. Bad judgement happens when we interact with the world in a way that doesn’t align with the nature of reality. The only way we can ever know if our judgement is “good” or “bad” is by interacting with the world. Reality is the judge and the jury. By avoiding reality, we avoid finding out. By not finding out, we avoid getting bruised, yes, but we also avoid the deeply felt lessons that only those bruises can ever deliver—the lessons that only reality can teach us.