Throughout the ages, many have tried to put into words exactly what risk is and what it means to them.

Some have been more successful than others—cutting to the heart of the matter, appealing to sensibility, or just putting an idea that’s difficult to explain into words we all can understand.

Today, I want to share 99 quotes that have had the greatest impact on me and how I think about the concept of risk.

I’m a big fan of quotes because they have the greatest signal to noise ratio of nearly any communication. For better or worse, a quote has the power to take a person’s whole life and boil it down to one searing passage for us to remember.

And now I’ll get out of the way and let the words speak for themselves. I hope they have as profound an effect on you as they have on me.

Don’t listen to those who say ‘you taking too big a chance.’ Michelangelo would have painted the Sistine floor, and it would surely be rubbed out by today. Most important, don’t listen when the little voice of fear inside you rears its ugly head and says ‘they all smarter than you out there. They’re more talented, they’re taller, blonder, prettier, luckier, and they have connections.” I firmly believe that if you follow a path that interests you, not to the exclusion of love, sensitivity, and cooperation with others, but with the strength of conviction that you can move others by your own efforts—and do not make success or failure the criteria by which you live—the chances are you’ll be a person worthy of your own respects. – Neil Simon

The fear of death is the most unjustified of all fears, for there’s no risk of accident for someone who’s dead. – Albert Einstein

Unless you choose to do great things with it, it makes no difference how much you are rewarded, or how much power you have. – Oprah Winfrey

No man is worth his salt who is not ready at all times to risk his well-being, to risk his body, to risk his life in a great cause. – Theodore Roosevelt

Only those who will risk going too far can possibly find out how far one can go. – T. S. Eliot

If you are not willing to risk the unusual, you will have to settle for the ordinary. – Jim Rohn

Once we believe in ourselves we can risk curiosity, wonder, spontaneous delight, or any experience that reveals the human spirit. – e. e. cummings

The only way to find true happiness is to risk being completely cut open. – Chuck Palahniuk

It seems to be a law of nature, inflexible and inexorable, that those who will not risk cannot win. – John Paul Jones

You can measure opportunity with the same yardstick that measures the risk involved. They go together. – Earl Nightingale

Life is inherently risky. There is only one big risk you should avoid at all costs, and that is the risk of doing nothing. – Denis Waitley

It is better to risk starving to death then surrender. If you give up on your dreams, what’s left? – Jim Carrey

Decision is a risk rooted in the courage of being free. – Paul Tillich

I have come to believe over and over again that what is most important to me must be spoken, made verbal and shared, even at the risk of having it bruised or misunderstood. – Audre Lorde

The risk of a wrong decision is preferable to the terror of indecision. – Maimonides

It is better by noble boldness to run the risk of being subject to half the evils we anticipate than to remain in cowardly listlessness for fear of what might happen. – Herodotus

If we listened to our intellect, we’d never have a love affair. We’d never have a friendship. We’d never go into business because we’d be too cynical. Well, that’s nonsense. You’ve got to jump off cliffs all the time and build your wings on the way down. – Annie Dillard

There’s something liberating about not pretending. Dare to embarrass yourself. Risk. – Drew Barrymore

You don’t concentrate on risks. You concentrate on results. No risk is too great to prevent the necessary job from getting done. – Chuck Yeager

Every man has the right to risk his own life in order to preserve it. Has it ever been said that a man who throws himself out the window to escape from a fire is guilty of suicide? – Jean-Jacques Rousseau

Creative people who can’t help but explore other mental territories are at greater risk, just as someone who climbs a mountain is more at risk than someone who just walks along a village lane. – R. D. Laing

Anyone who takes himself too seriously always runs the risk of looking ridiculous; anyone who can consistently laugh at himself does not. – Vaclav Havel

Often the difference between a successful man and a failure is not one’s better abilities or ideas, but the courage that one has to bet on his ideaa, to take a calculated risk, and to act. – Maxwell Maltz

There can be no vulnerability without risk. There can be no community without vulnerability. There can be no peace, and ultimately no life, without community. – M. Scott Peck

In battle it is the cowards who run the most risk; bravery is a rampart of defense. – Sallust

Accept that all of us can be hurt, that all of us can and surely will at times fail. Other vulnerabilities, like being embarrassed or risking love, can be terrifying, too. I think we should follow a simple rule: if we can take the worst, take the risk. – Joyce Brothers

To win without risk is to triumph without glory. – Pierre Corneille

You have to leave the city of your comfort and go into the wilderness of your intuition.You can’t get there by bus, only by hard work and risk and by not quite knowing what you’re doing. What you’ll discover will be wonderful. What you’ll discover will be yourself. – Alan Alda

Our lives improve only when we take chances, and the first and most difficult risk we can take is to be honest with ourselves. – Walter Anderson

Creative risk-taking is essential to success in any goal where the stakes are high. Thoughtless risks are destructive, of course, but perhaps even more wasteful is thoughtless caution which prompts inaction and promotes failure to seize opportunity. – Gary Ryan Blair

What I tell these young people is, the world is not as dangerous as the older generation would like you to believe. Anyone I know who has ever taken a risk and lost a job has ended up getting a better one two years later. – Jonathan Kozol

The refusal to rest content—the willingness to risk excess on behalf of one’s obsessions—is what distinguishes artists from entertainers and what makes some artists adventurers on behalf of us all. – John Updike

The principle element in a performance is risk, and if you’re losing interest then by scaring yourself to death the audience will feel it and boy it’ll wake them up. – Leo Kottke

Because if you’re prepared and you know what it takes, it’s not a risk. You just have to figure out how to get there. There is always a way to get there. – Mark Cuban

Risk! Risk anything! Care no more for the opinions of others, for those voices. Do the hardest thing on earth for you. Act for yourself. Face the truth. – Katherine Mansfield

The time to take counsel of your fears is before you make an important battle decision. That’s the time to listen to every fear you can imagine! When you have collected all the facts and fears and made your decision, turn off all your fears and go ahead! – General George S. Patton

You’ve got to keep fighting; you’ve got to risk your life every six months to stay alive. – Elia Kazan

You must accept that you might fail; then, if you do your best and still don’t win, at least you can be satisfied that you’ve tried. If you don’t accept failure as a possibility, you don’t set high goals, you don’t branch out, you don’t try, you don’t take the risk. – Rosalynn Carter

Many a man is praised for his reserve and so-called shyness when he is simply too proud to risk making a fool of himself. – J. B. Priestley

Death is not the biggest fear we have; our biggest fear is taking the risk to be alive—the risk to be alive and express what we really are. – Miguel Angel Ruiz

When you play it too safe, you’re taking the biggest risk of your life. Time is the only wealth we’re given. – Barbara Sher

If my ego was out of whack and I believed I could carry anything off, that would be a stupid risk. But so far there’s been no reason not to try anything. – Kathleen Turner

Everyone has a ‘risk muscle.’ You keep it in shape by trying new things. If you don’t, it atrophies. Make a point of using it at least once a day. – Roger von Oech

You have to be able to risk your identity for a bigger future than the present you are living. – Fernando Flores

I’m of the mind that life is a risk. Every time you leave your house it’s a risk, and I see no reason to go through life with my hands tied behind my back for any reason. I’d be foolish to let something stop me from doing what I love to do. – Thomas Jane

The person who risks nothing does nothing, has nothing, is nothing, and becomes nothing. He may avoid suffering and sorrow, but he simply cannot learn and feel and change and grow and love and live. – Leo F. Buscaglia

Man cannot discover new oceans unless he has the courage to lose sight of the shore. – Andre Gide

It seems to me that people have vast potential. Most people can do extraordinary things if they have the confidence or take the risks. Yet most people don’t. They sit in front of the telly and treat life as if it goes on forever. – Philip Adams

It’s not because things are difficult that we dare not venture. It’s because we dare not venture that they are difficult. – Seneca

He who risks and fails can be forgiven. He who never risks and never fails is a failure in his whole being. – Paul Tillich

It is only by risking our persons from one hour to another that we live at all. – William James

Pitiful is the person who is afraid of taking risks. Perhaps this person will never be disappointed or disillusioned; perhaps she won’t suffer the way people do when they have a dream to follow. But when the person looks back-she will hear her heart – Paulo Coelho

Yes, risk-taking is inherently failure-prone. Otherwise, it would be called sure-thing-taking. – Jim McMahon

People who don’t take risks generally make about two big mistakes a year. People who do take risks generally make about two big mistakes a year. – Peter F. Drucker

If a man isn’t willing to take some risk for his opinions, either his opinions are no good or he’s no good. – Ezra Pound

You must lose a fly to catch a trout. – George Herbert

One hour of life, crowded to the full with glorious action and filled with noble risks, is worth whole years of those mean observances of paltry decorum. – Sir Walter Scott

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

I am always doing that which I cannot do, in order that I may learn how to do it. – Pablo Picasso

Don’t be afraid to take a big step. You can’t cross a chasm in two small jumps. – David Lloyd George

Trust your own instinct. Your mistakes might as well be your own, instead of someone else’s. – Billy Wilder

The dangers of life are infinite, and among them is safety. – Goethe

A man would do nothing if he waited until he could do it so well that no one would find fault with what he has done. – Cardinal Newman

Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did. So throw off the bowlines, sail away from the safe harbor, catch the trade winds in your sails. Explore. Dream. Discover. – Mark Twain

Every society honors its live conformists and its dead troublemakers. – Mignon McLaughlin

Do not be too timid and squeamish about your actions. All life is an experiment. The more experiments you make the better. What if they are a little course, and you may get your coat soiled or torn? What if you do fail, and get fairly rolled in the dirt once or twice. Up again, you shall never be so afraid of a tumble. – Ralph Waldo Emerson

Don’t refuse to go on an occasional wild goose chase; that’s what wild geese are for. – Henry S. Haskins

To dare is to lose one’s footing momentarily. To not dare is to lose oneself. – Soren Kierkegaard

When in doubt, make a fool of yourself. There is a microscopically thin line between being brilliantly creative and acting like the most gigantic idiot on earth. So what the hell, leap. – Cynthia Heimel

Many great ideas have been lost because the people who had them could not stand being laughed at. – Unknown

I believe in getting into hot water; it keeps you clean. – G.K. Chesterton

A ship in harbor is safe, but that is not what ships are for. – John A. Shedd

This nation was built by men who took risks—pioneers who were not afraid of the wilderness, businessmen who were not afraid of failure, scientists who were not afraid of the truth, thinkers who were not afraid of progress, dreamers who were not afraid of action. – Brooks Atkinson

The knowledge of the world is only to be acquired in the world, and not in a closet. – Philip Dormer Stanhope Chesterfield

Keep away from people who belittle your ambitions. Small people always do that, but the really great make you feel that you, too, can become great. – Mark Twain

Two roads diverged in a wood, and I… I took the one less traveled by, and that has made all the difference. – Robert Frost

I guess what I’m trying to say is I don’t think you can measure life in terms of years. I think longevity doesn’t necessarily have anything to do with happiness. I mean happiness comes from facing challenges and going out on a limb and taking risks. If you’re not willing to take a risk for something you really care about, you might as well be dead. – Diane Frolov

To be a good human being is to have a kind of openness to the world—an ability to trust uncertain things beyond your own control—that can lead you to be shattered in very extreme circumstances for which you were not to blame. That says something very important about the condition of the ethical life: that it is based on a trust in the uncertain and on a willingness to be exposed; it’s based on being more like a plant than like a jewel—something rather fragile, but whose very particular beauty is inseparable from that fragility. – Martha Nussbaum

The fishermen know that the sea is dangerous and the storm terrible, but they have never found these dangers sufficient reason for remaining ashore. – Vincent van Gogh

An adventure is only an inconvenience rightly considered. An inconvenience is only an adventure wrongly considered. – G. K. Chesterton

The most important thing to remember is this: to be ready at any moment to give up what you are for what you might become. – W. E. B. Du Bois

The young do not know enough to be prudent, and therefore they attempt the impossible—and achieve it, generation after generation. – Pearl S. Buck

People wish to be settled: only as far as they are unsettled is there any hope for them. – Ralph Waldo Emerson

Whenever I prepare for a journey I prepare as though for death. Should I never return, all is in order. – Katherine Mansfield

Whatever you do, you need courage. Whatever course you decide upon, there is always someone to tell you that you are wrong. There are always difficulties arising that tempt you to believe your critics are right. To map out a course of action and follow it to an end requires some of the same courage that a soldier needs. Peace has its victories, but it takes brave men and women to win them. – Ralph Waldo Emerson

Play the game for more than you can afford to lose… only then will you learn the game. – Winston Churchill

Behold the turtle. He makes progress only when he sticks his neck out. – James B. Conant

When you are in any contest, you should work as if there were—to the very last minute—a chance to lose it. This is battle, this is politics, this is anything. – Dwight D. Eisenhower

Only those who will risk going too far can possibly find out how far they can go. – T. S. Eliot

I dip my pen in the blackest ink, because I am not afraid of falling into my inkpot. – Ralph Waldo Emerson

If you never budge, don’t expect a push. – Malcolm S. Forbes

Without the element of uncertainty—the bringing off of even—the greatest triumph would be dull, routine, and eminently unsatisfying. – J. Paul Getty

It is true that when we take chances, we stand to lose. But it is also true that we will never win anything if we never even enter the game. Lucky people are aware of the possibility of losing, and indeed they may lose often. But since the chances they take are small, the losses tend to be small. By being willing to accept small losses they put themselves in position to make large gains. – Max Gunther

It is better to be boldly decisive and risk being wrong than to agonize at length and be right too late. – Marilyn Moats Kennedy

Risk more than others think is safe. Care more than others think is wise. Dream more than others think is practical. Expect more than others think is possible. – Cadet Maxim

‘How does one become a butterfly?’ she asked pensively. You must want to fly so much that you are willing to give up being a caterpillar. – Trina Paulus

It is not the critic who counts. Not the man who points out how the strong man stumbled or where the doer of deeds could have done 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; 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—at least fails while daring greatly so that his place shall never be with those timid souls who know neither victory nor defeat. – Theodore Roosevelt

Somebody must take a chance. There are monkeys who became men, and the monkeys who didn’t are still jumping around in trees making faces at the monkeys who did. – Lincoln Steffens