By Jiji Lee

10 Powerful Quotes About Taking Risks


Advice from experts on taking a leap and having success.

Leap and the net shall appear.

Easy, right? 

While this popular quote about taking chances is inspiring, it doesn’t capture all the behind the scenes work that goes into taking a big risk. I think a more fitting quote would be: “Measure the length of the leap, do some practice leaps, get advice from people who’ve already taken a leap, leap.”

When it comes to risk taking, the prevailing sentiment seems to be “just take a chance and have faith that it will work out.” After all, didn’t Bill Gates and Steve Jobs drop out of college to pursue their dreams? And while, yes, they did drop out and go on to find huge success at Microsoft and Apple, what’s missing from this narrative is all the hard work, planning, and preparation that went into taking these risks. 

Rather than just blindly taking a big leap, consider taking calculated risks instead

For example, if you’re unhappy at your day job and want to quit, you might want to  dedicate some time to researching your backup options, reviewing your resume, networking, and brushing up on skills before you take that leap. This way, you’re not “waiting for the net to appear” -- instead, you are creating some of the net yourself.  

Taking a calculated risk isn’t about being overly cautious and delaying success, but rather, having a more measured and thoughtful approach to risk-taking.

Ahead are powerful quotes about risks from some of the world’s most successful and innovative CEOS, artists, editors, and leaders. You’ll learn that hard work and risk go hand in hand, and that you can conquer your fear of failure. You will feel inspired to work towards your big goals and you’ll also feel emboldened to face any challenge and take a big risk. 

Quotes on learning and taking risks

1. Bill Gates, Co-founder, Microsoft and Bill & Melinda Gates Foundation

“Ultimately, no matter how much analysis we do, I have to be comfortable with a lot of uncertainty. We are tackling problems where progress is measured not just in years but often decades—where your end goal doesn’t change, but your path to get there might have to. The trick is to do whatever I can to keep learning and to be open to new and novel ways to bring us a step closer to our goals. That approach has guided every big bet I’ve made in my career from Microsoft to today—including polio.”

2. Morgan Debaun, Founder of the Website Blavity

“It’s the job of startup founders to take risks, push the envelope, and ask things that don’t yet exist. I view any type of decline as a learning opportunity. A ‘no’ is just another step to a ‘yes.’ It’s part of the process and something that should be appreciated and respected”.

3. Oprah Winfrey

“I believe that one of life’s greatest risks is never daring to risk… Do the one thing you think you cannot do. Fail at it. Try again. Do better the second time.”

4. Mark Cuban, Owner of Dallas Mavericks, investor on ABC’s Shark Tank

“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.” 

5. Sarah Blakely, Founder of Spanx 

“My dad would encourage me any time something didn’t go the way I expected it to, or maybe I got embarrassed by a situation, to write down where the hidden gifts were and what I got out of it. I started realizing that in everything there was some amazing nugget that I wouldn’t have wanted to pass up.”

Quotes on overcoming your fear of failure and taking risks 

6. Richard Branson, Founder, the Virgin Group

“If you allow the fear of failure to become a barrier, you’re already putting roadblocks in your way. Entrepreneurs take risks by attempting to change the status quo.”

7. Seth Godin, entrepreneur, blogger

“If you are willing to do something that might not work, you’re closer to being an artist.” 

8. Christene Barberich, Co-founder, Refinery29

“Starting Refinery29 felt like a huge risk. Leaving a steady paycheck for something new and unknown is always scary, whether you’re 22 or 62. I was in my 30s at the time and a lot of my peers were in a much more settled place with relationships, family, property — all the things we’re told as women we need to achieve at that stage of life to feel validated and like we’re on track. But the urge in me to pursue things that give me creative purpose has always been too strong to ignore. This was a chance to do something I loved that could really make a difference in millions of women’s lives. That’s when convention goes out the window and you just have to go for it…no matter how long it takes.”

9. Debbie Millman, Designer and Host of Design Matters podcast

“The only way to alleviate that fear is actually doing the thing you are scared and nervous about over and over until you get better at it. Very few people ever do something the first time and do it perfectly right out of the gate. Being nervous and scared is normal. But the fears will lessen over time as you get more and more comfortable actually doing the thing you are scared of doing.”

10. Michelle Lee, Editor of Allure Magazine

“My risk-taking definitely developed later in my career and it paid off in lots of big ways. Earlier in my career, I should've known that I can do things that are risky and everything's going to be okay.”

"If you are just doing things that are safe, especially in media, if you're trying to just appeal to everyone, you're going to appeal to no one.”