150 Quotes About Taking Risks to Conquer Your Fears

I remember standing at the edge of a literal cliff in Acadia National Park a few years ago. My heart was hammering against my ribs, and every instinct I had was screaming at me to stay on the solid, safe path. But there was a view just a few feet lower—on a rocky outcrop that required a bit of a leap—that I knew would be breathtaking. I hesitated for what felt like an hour. When I finally took that jump, the perspective I gained wasn’t just visual; it was mental. I realized that the most beautiful things in my life have always been just on the other side of a “scary” decision.

We all face these moments, though usually they don’t involve actual cliffs. Maybe it’s the risk of starting a new business, the risk of being vulnerable in a relationship, or simply the risk of trying a new hobby where you might fail publicly. I’ve found that when I’m stuck, it’s usually because I’m over-valuing the safety of the status quo and under-valuing the potential of the unknown. That’s why I’ve compiled this collection. These words have been my “espresso shots of wisdom” whenever I’ve needed that extra push to stop overthinking and start doing.

Here are 150 powerful, bite-sized quotes to fuel your courage and help you navigate the rewarding path of risk-taking.

Inspiring Quotes About Taking Risks for Personal Growth

Personal growth is rarely a linear, comfortable process. It’s more like a series of “leaps in the dark,” as Henry Miller once put it. I’ve noticed in my own journey that whenever I feel too comfortable, I’m probably not growing. These quotes remind us that the risk of staying the same is often much greater than the risk of changing. If you’re looking to push your boundaries, our growth mindset quotes for success offer more deep dives into this philosophy.

“Don’t be too timid and squeamish about your actions. All life is an experiment. The more experiments you make the better.”

— Ralph Waldo Emerson

Emerson’s view of life as an experiment takes the pressure off. If it’s just an experiment, you can’t really “fail”—you just gather data.

“The risk to remain tight in a bud was more painful than the risk it took to blossom.”

— Anaïs Nin

This is one of my favorites. It perfectly captures that internal tension when we know we’re meant for more but are afraid to open up.

“I believe that the most important single thing, beyond discipline and creativity, is daring to dare.”

— Maya Angelou

“We cannot grow when we are not willing to risk.”

— Debasish Mridha

“To grow, you must be willing to let your present and future be totally unlike your past.”

— Alan Cohen

“Growth means change, and change involves risk.”

— George Shinn

“All growth is a leap in the dark, a spontaneous unpremeditated act without benefit of experience.”

— Henry Miller

“We don’t grow when things are easy. We grow when we face challenges.”

— Joyce Meyer

“Be brave. Take risks. Nothing can substitute experience.”

— Paulo Coelho

“Life shrinks or expands in proportion to one’s courage.”

— Anaïs Nin

“It takes courage to grow up and become who you really are.”

— E. E. Cummings

“Deep personal growth and healing is the most courageous pursuit there is.”

— Melanie Curtis

“I am always doing that which I cannot do, in order that I may learn how to do it.”

— Pablo Picasso

“If you do what you’ve always done, you’ll get what you’ve always gotten.”

— Tony Robbins

“The only way to find true happiness is to risk being completely cut open.”

— Chuck Palahniuk

“You only do good work when you’re taking risks and pushing yourself.”

— Sally Hawkins

“To truly live, we must be willing to RISK. To be nothing in order to find everything.”

— Mandy Hale

“Everything you’ve ever wanted is on the other side of fear.”

— George Addair

“Comfort is the enemy of progress.”

— P.T. Barnum

“The biggest risk you can take is to do nothing.”

— Denis Waitley

“If you push through that feeling of being scared, really amazing things can happen.”

— Marissa Mayer

“Unless you try to do something beyond what you have already mastered, you will never grow.”

— Ronald E. Osborn

Bold Quotes on Stepping Out of Your Comfort Zone

I used to think my comfort zone was a sanctuary, but I’ve realized it’s more of a cage. Stepping out of it doesn’t mean you have to do something reckless; it just means doing something new. For a deeper look at finding that inner strength, check out our confidence quotes to believe in yourself. For more on the psychology of comfort zones, Psychology Today provides some fascinating insights into why our brains resist change.

“Life begins at the end of your comfort zone.”

— Neale Donald Walsch

This is a classic for a reason. It’s a reminder that the “safe” zone is often where life stalls.

“A ship is safe in harbor, but that’s not what ships are for.”

— William G.T. Shedd

I keep a small model ship on my desk just to remind me of this quote. It’s a call to fulfill our purpose rather than just seeking safety.

“Man cannot discover new oceans unless he has the courage to lose sight of the shore.”

— André Gide

“Do one thing every day that scares you.”

— Eleanor Roosevelt

“Just try new things. Don’t be afraid. Step out of your comfort zones and soar.”

— Michelle Obama

“We tend to be held back from our goals by the simplicity of our comfort zones… but just how comfortable are we?”

— Michelle Ustaszeski

“If you try to guard yourself against every unlikely danger, you’ll never stretch beyond your comfort zone.”

— Diane Conway

“You can’t steal second base and keep your foot on first.”

— Frederick B. Wilcox

“To dare is to lose one’s footing momentarily.”

— Søren Kierkegaard

“The ground beneath you is shifting, and either you get sucked in by holding on to old ways, or you take a giant step forward.”

— Bonnie Hammer

“If you are not willing to risk the unusual, you will have to settle for the ordinary.”

— Jim Rohn

“Leap and the net will appear.”

— John Burroughs

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did.”

— Mark Twain

“Why not go out on a limb? Isn’t that where the fruit is?”

— Frank Scully

“You can’t outwit fate by standing on the sidelines placing little side bets about the outcome of life.”

— Judith McNaught

“If you only take small risks, you are only entitled to a small life.”

— Robin Sharma

“Adventure without risk is Disneyland.”

— Douglas Coupland

“Make the choices that make you nervous. If you make the choice that’s the easy way out, that wasn’t the big vision.”

— Eileen Burbidge

“There’s something liberating about not pretending. Dare to embarrass yourself. Risk.”

— Drew Barrymore

“If we listened to our intellect, we’d never have a love affair. We’d never have a friendship. You’ve got to jump off cliffs.”

— Annie Dillard

“Everybody knows if you are too careful you are so occupied in being careful that you are sure to stumble over something.”

— Gertrude Stein

“The only way out is through.”

— Robert Frost

Motivational Sayings About the Reward of Risk-Taking

We often focus on what we might lose when we take a risk, but we rarely focus on what we stand to gain. In my experience, the rewards aren’t always what I expected—sometimes the reward is just the confidence that I could do it. If you’re navigating a difficult season while taking these leaps, our perseverance quotes for tough times can provide the stamina you need.

“If there is no risk, there is no reward.”

— Christy Raedeke

This is the fundamental law of achievement. You have to put something on the line to get something back.

“To win without risk is to triumph without glory.”

— Pierre Corneille

There’s a specific kind of satisfaction that comes from succeeding when the odds were against you.

“Fortune favors the bold.”

— Latin Proverb

“The reward is in the risk.”

— Rachel Cohn

“When you take risks and just go for it, you tend to be rewarded and see things happen.”

— Megan Berry

“Pearls don’t lie on the seashore. If you want one, you must dive for it.”

— Chinese Proverb

“If you want the most reward you have to take the most risk.”

— Jesse Itzler

“The biggest risk is not taking any risk… the only strategy that is guaranteed to fail is not taking risks.”

— Mark Zuckerberg

“If you risk nothing, then you risk everything.”

— Geena Davis

“Risk: no full life occurs without it.”

— Gina Greenlee

“Only those who play win. Only those who risk win. History favors risk-takers.”

— Iveta Cherneva

“But we also believe in taking risks, because that’s how you move things along.”

— Melinda Gates

“When you take risks and they work out, they lead to new capabilities you never saw before.”

— Tom Soderstrom

“The reward for work well done is the opportunity to do more.”

— Dr. Jonas Salk

“There is freedom waiting for you, On the breezes of the sky… What if I fly?”

— Erin Hanson

“Two roads diverged in a wood … I took the one less travelled by, and that has made all the difference.”

— Robert Frost

“Don’t be afraid to give up the good to go for the great.”

— John D. Rockefeller

“The ultimate measure of a man is… where he stands at times of challenge and controversy.”

— Martin Luther King, Jr.

“Happiness comes from facing challenges and going out on a limb and taking risks.”

— Diane Frolov

“Only those who will risk going too far can possibly find out how far it is possible to go.”

— T.S. Eliot

“Success is not final, failure is not fatal: it is the courage to continue that counts.”

— Winston Churchill

“I needed the push. Once a glass ceiling is broken, it stays broken.”

— Jennifer Granholm

Courageous Risk Quotes for Success and Achievement

In the world of business and achievement, risk is the currency of innovation. Every major success story I’ve studied involves a moment where someone had to “roll the dice.” For entrepreneurs looking to scale their vision, Harvard Business Review often explores the balance between bold action and strategic planning. If you’re in the middle of building something great, our motivational success quotes are a perfect companion to these risk-focused words.

“If you are not willing to risk the unusual, you will have to settle for the ordinary.”

— Jim Rohn

Jim Rohn’s wisdom is always about the trade-offs we make. Ordinary is safe, but the unusual requires a price.

“Entrepreneurs are risk takers, willing to roll the dice with their money or reputation.”

— Victor Kiam

“Business is a risk-reward proposition.”

— Bill Bain

“If you don’t build your dream, someone else will hire you to help them build theirs.”

— Dhirubhai Ambani

“You can’t be successful in business without taking risks. It’s really that simple.”

— Adena Friedman

“Test fast, fail fast, adjust fast.”

— Tom Peters

“In today’s industry, in which change happens at a relentless pace, standing still is not an option.”

— Sanjib Sahoo

“If ROI is that obvious and certain, the idea probably isn’t that risky (or transformational) in the first place.”

— Peter Buonora

“Take the risk, be aggressive, push hard, and set your sights way, way, way farther out than you think you can get.”

— Bryson Koehler

“If you’re not making some notable mistakes along the way, you’re certainly not taking enough career chances.”

— Sallie Krawcheck

“If you’re offered a seat on a rocket ship, don’t ask what seat! Just get on.”

— Sheryl Sandberg

“He who is not courageous enough to take risks will accomplish nothing in life.”

— Muhammad Ali

“Don’t wait. The time will never be just right.”

— Napoleon Hill

“I see working for yourself as a way to have more freedom and control.”

— Gail Gardner

“If something is important enough, even if the odds are against you, you should still do it.”

— Elon Musk

“Turn a perceived risk into an asset.”

— Aaron Patzer

“The only thing worse than starting something and failing is not starting something.”

— Seth Godin

“Statistically, 100 percent of the shots you don’t take, don’t go in.”

— Wayne Gretzky

“I’ve failed over and over and over again in my life. And that is why I succeed.”

— Michael Jordan

“Opportunities, the good ones, they’re messy and confusing. They’re risky.”

— Susan Wojcicki

“It is better to fail in originality than to succeed in imitation.”

— Herman Melville

“The most important single thing… is daring to dare.”

— Maya Angelou

Powerful Words on Overcoming the Fear of Failure

The fear of failure is often what keeps us paralyzed. I’ve found that the best way to overcome it is to change my definition of failure. If I learn something, is it really a failure? Our collection of courage quotes to face your fears provides even more tools for this mental shift. To understand how to dismantle these fears practically, Tony Robbins shares some excellent strategies on his official site.

“Failure is a badge of honor. It means you risked failure.”

— Charlie Kaufman

I love the idea of failure as a “badge.” It means you were in the arena, not just watching from the stands.

“When you take risks you learn that there will be times when you succeed and there will be times when you fail, and both are equally important.”

— Ellen DeGeneres

“Do the one thing you think you cannot do. Fail at it. Try again. Do better the second time.”

— Oprah Winfrey

“Accept that all of us can be hurt, that all of us can—and surely will at times–fail. If we can take the worst, take the risk.”

— Joyce Brothers

“It is hard to fail, but it is worse never to have tried to succeed.”

— Theodore Roosevelt

“Courage is not the absence of fear, but rather the judgement that something else is more important than fear.”

— Ambrose Redmoon

“Courage doesn’t always roar. Sometimes courage is the quiet voice at the end of the day saying, ‘I will try again tomorrow.’”

— Mary Anne Radmacher

“Fear stifles our thinking and actions… Lost opportunities cause erosion of confidence.”

— Charles Stanley

“Courage doesn’t mean you don’t get afraid. Courage means you don’t let fear stop you.”

— Bethany Hamilton

“He who is not everyday conquering some fear has not learned the secret of life.”

— Ralph Waldo Emerson

“The only way to find true happiness is to risk being completely cut open.”

— Chuck Palahniuk

“Living with fear stops us from taking risks, and if you don’t go out on the branch, you’re never going to get the best fruit.”

— Sarah Parish

“It’s important to be willing to make mistakes. The worst thing that can happen is you become memorable.”

— Sara Blakely

“You must accept that you might fail; then, if you do your best and still don’t win, at least you can be satisfied.”

— Rosalynn Carter

“Only those who dare to fail greatly can ever achieve greatly.”

— Robert F. Kennedy

“A lot of times people look at risk and ask, ‘What are the odds that I will succeed?’ A different way to look at risk is to ask, ‘What’s the worst thing that would happen if I failed?’”

— Dave Hitz

“Never let the odds keep you from doing what you know in your heart you were meant to do.”

— H. Jackson Brown, Jr.

“The struggles within yourself—the invisible, inevitable battles… that’s where it’s at.”

— Jesse Owens

“Don’t be afraid to take a big step. You can’t cross a chasm in two small jumps.”

— David Lloyd George

“Pitiful is the person who is afraid of taking risks… But when the person looks back—she will hear her heart.”

— Paulo Coelho

“If you push through that feeling of being scared… really amazing things can happen.”

— Marissa Mayer

“There is no failure except in no longer trying.”

— Elbert Hubbard

Wise Quotes on Calculated Risks and Decision Making

There’s a big difference between being a “risk-taker” and being “reckless.” The best risk-takers I know are actually quite meticulous—they take calculated risks. They gather information, weigh the outcomes, and then move decisively. If you’re currently facing a big decision, our quotes about choices and consequences might help you weigh your options more effectively.

“Take calculated risks – that is quite different from being rash.”

— General George S. Patton

Patton knew that in battle, hesitation was as dangerous as recklessness. The key is in the calculation.

“The risk of a wrong decision is preferable to the terror of indecision.”

— Maimonides

This one hits home for me. I’ve spent far more energy worrying about a decision than it actually took to execute it.

“It is better to be boldly decisive and risk being wrong than to agonize at length and be right too late.”

— Marilyn Moats Kennedy

“The time to take counsel of your fears is before you make an important battle decision… When you have made your decision, turn off all your fears and go ahead!”

— George S. Patton

“If failing is an accepted part of doing business… risk is not perceived as a threat anymore.”

— Guido Laures

“You don’t concentrate on risks; you concentrate on results.”

— Chuck Yeager

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

— John F. Kennedy

“The whole reason for risk is to innovate faster, and you do need failure to do it, but you need to fail in a way that leads to new understanding.”

— Stuart Kippelman

“Data is great. But sometimes, even when you have all the data in the world, if you don’t follow your gut, you won’t discover the true potential.”

— Arianna Huffington

“It is not the manager’s job to prevent risks. It is the manager’s job to make it safe to take them.”

— Ed Catmull

“Yes, risk-taking is inherently failure-prone. Otherwise, it would be called sure-thing-taking.”

— Jim McMahon

“A surplus of effort could overcome a deficit of confidence.”

— Sonia Sotomayor

“Your time is limited, so don’t waste it living someone else’s life.”

— Steve Jobs

“Destiny is no matter of chance. It is a matter of choice.”

— William Jennings Bryan

“Trust the still, small voice that says, ‘this might work and I’ll try it.’”

— Diane Mariechild

“In a world that’s changing really quickly, the only strategy that is guaranteed to fail is not taking risks.”

— Mark Zuckerberg

“If you don’t risk anything, you risk even more.”

— Erica Jong

“Being safe doesn’t mean you won’t be sorry.”

— Katerina Stoykova Klemer

“If I stop to kick every barking dog I am not going to get where I’m going.”

— Jackie Joyner-Kersee

“Everything else is just waiting.”

— Karl Wallenda

“He who is not courageous enough to take risks will accomplish nothing in life.”

— Muhammad Ali

“Don’t be afraid to take a big step. You can’t cross a chasm in two small jumps.”

— David Lloyd George

Uplifting Quotes About Embracing Uncertainty and Change

At the heart of every risk is uncertainty. We don’t know the outcome, and that’s what makes it a risk. But uncertainty is also where the magic happens—it’s the space where anything is possible. If you’re feeling overwhelmed by life’s unknowns, our inspirational quotes to keep you going offer some much-needed light. You can also explore the works of Brené Brown, who has written extensively about the connection between vulnerability, risk, and a wholehearted life.

“Living at risk is jumping off the cliff and building your wings on the way down.”

— Ray Bradbury

This is such a visceral image of faith and improvisation. You don’t need all the answers before you start.

“Love is always a risk—for there is no love without vulnerability.”

— Brené Brown

To love someone is perhaps the greatest risk of all, because you are giving them the power to hurt you.

“To love at all is to be vulnerable.”

— C.S. Lewis

“The only impossible journey is the one you never begin.”

— Tony Robbins

“Life is either a daring adventure or nothing at all.”

— Helen Keller

“Security is mostly a superstition. It does not exist in nature.”

— Helen Keller

“It is only by risking our persons from one hour to another that we live at all.”

— William James

“This is our big chance to see what people think of us. The real us. We have to show em there’s nothing to be afraid of.”

— Lisi Harrison

“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.”

— Martha Nussbaum

“I have come to believe… that what is most important to me must be spoken… even at the risk of having it bruised.”

— Audre Lorde

“When in doubt, make a fool of yourself… So what the hell, leap.”

— Cynthia Heimel

“Life doesn’t always present you with the perfect opportunity at the perfect time.”

— Susan Wojcicki

“There is only one way to avoid criticism: do nothing, say nothing, and be nothing.”

— Aristotle

“To truly live, we must be willing to RISK. To be nothing in order to find everything.”

— Mandy Hale

“You only do good work when you’re taking risks and pushing yourself.”

— Sally Hawkins

“The ground beneath you is shifting… take a giant step forward by taking some risks.”

— Bonnie Hammer

“A life lesson for me is, how do you muster the courage to take on a new risk?”

— Ann Bancroft

“If you don’t go after what you want, you’ll never have it.”

— Nora Roberts

“That’s the risk you take if you change: that people you’ve been involved with won’t like the new you.”

— Lisa Alther

“If we listened to our intellect, we’d never have a love affair… You’ve got to jump off cliffs.”

— Annie Dillard

“Pearls don’t lie on the seashore. If you want one, you must dive for it.”

— Chinese proverb

“Man cannot discover new oceans unless he has the courage to lose sight of the shore.”

— André Gide

I hope these quotes give you the same spark of courage they’ve given me. Remember, the goal isn’t to live a life without risk—it’s to choose the risks that are worth taking. Whether you’re standing at the edge of a literal cliff or a metaphorical one, I’ve found that the view from the other side is always worth the jump. Stop waiting for the perfect moment; it doesn’t exist. Take the risk, make the leap, and trust yourself to build your wings on the way down.