Risk-taking quotes to inspire business leaders

It wasn't too long ago that “risk” was a taboo four-letter word among business leaders – something to be avoided at all costs. But now risk is considered part of the job, especially for IT leaders who face a number of relatively new challenges falling squarely within their purview, from major legacy upgrades, to cloud migrations, to the Internet of Things, to digital transformation. Meanwhile, the ever-present threat of data security breaches and the IT talent crisis only add to the risks and unknowns facing today's CIO.
But risks are a necessary part of moving the business forward, so we wanted to help inspire IT leaders to take those risks with a collection of motivational quotes. And while there is no shortage of risk-taking quotes only a Google search away, our list is unique. The 22 quotes below all come from other IT and business leaders who may have faced some of the same risks, opportunities, and challenges as you.

[ Take a deep dive on digital transformation. See our related article, 10 digital transformation must-reads. ]

We hope these quotes will leave you feeling inspired and ready to conquer the tasks at hand.

On seizing opportunities

• "When you take risks and they work out, they lead to new capabilities you never saw before." – Tom Soderstrom, chief technology and innovation officer, office of the CIO, Jet Propulsion Laboratory
• “Life doesn’t always present you with the perfect opportunity at the perfect time. Opportunities come when you least expect them, or when you’re not ready for them. Rarely are opportunities presented to you in the perfect way, in a nice little box with a yellow bow on top. … Opportunities, the good ones, they’re messy and confusing and hard to recognize. They’re risky. They challenge you.” – Susan Wojcicki, CEO of YouTube

On taking a chance

• “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, founder & EVP of NetApp

• "I always did something I was a little not ready to do. I think that's how you grow. When there's that moment of 'Wow, I'm not really sure I can do this,' and you push through those moments, that's when you have a breakthrough." – Marissa Mayer, president and CEO of Yahoo!
• “At the core of Silicon Valley is a passion for ‘yes.’” – Steven Levy, Wired senior writer, author of Hackers, In the Plex, and other books
• “[The tech] industry is risk-friendly, so it’s better to take the chance or take the lead if you think something might work. Just go for it and really put yourself out there, because it’s an industry that really responds to that. When you take risks and just go for it, you tend to be rewarded and see things happen.” – Megan Berry, VP of product at RebelMouse
• “I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not trying.” – Jeff Bezos, founder and CEO of Amazon

On embracing the unknown

• “The biggest risk is not taking any risk.” – Mark Zuckerberg, chairman, CEO, and co-founder of Facebook
• "In today’s industry, in which change happens at a relentless pace, standing still is not an option. You must take a risk at some point." – Sanjib Sahoo, CIO for Transport—North America, XPO Logistics
• "If ROI is that obvious and certain, the idea probably isn’t that risky (or transformational) in the first place." – Peter Buonora, enterprise architect
• “If you are not in touch with your intuition, you cannot be successful. 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 and be able to recognize critical opportunities.” – Arianna Huffington, co-founder and editor-in-chief of The Huffington Post
• “Make the choices that make you nervous. If you make the choice that’s the easy way out, that wasn’t the big vision or big choice to make.” – Eileen Burbidge, partner of Passion Capital

On smart risk-taking

• "By establishing milestones, gates, and questions along the way, you're ensuring that you're being smart about the risks you're taking. And as hard as it is, you’ve got to be ready to say, “We are stopping." – Ina Kamenz, former CIO of Eli Lilly and Company
• "You have to [take risks] if you’re going to innovate and revolutionize anything with an organization. In fact, your tolerance for risk is directly related to how successful you can be and that tolerance is worth challenging." – Ginna Raahauge, CTO, SVP Strategy & Architecture, Catholic Health Initiatives

On leadership

• “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, co-founder of Pixar Animation Studios, president of Pixar Animation and Disney Animation
• "Entrepreneurship is exactly what failure is. It’s actually a more elegant way of saying it." – Aaron Stibel, CTO, emerging businesses for Dun & Bradstreet
• "Take the risk, be aggressive, push hard, and set your sights way, way, way farther out than you think you can get. Drive your team toward it every day. That way, if you don’t get all the way to that goal line, you’ve at least gone further than you would have had you tried to de-risk the project up front." – Bryson Koehler, chief information and technology officer for The Weather Company
• "If failing is an accepted part of doing business and the blame game is not embedded in the organization, risk is not perceived as a threat anymore. The emphasis is on learning from mistakes to not repeat them rather than being too timid to attempt something for fear of reprisals." – Guido Laures, CTO at Spreadshirt

On learning from mistakes

• “The only thing worse than starting something and failing is not starting something.” – Seth Godin, author, entrepreneur, public speaker
• "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, CIO of Platform Specialty Products Corp.

On changing the world

• "The people who are crazy enough to think they can change the world are the ones who do." – Steve Jobs, former co-founder, chairman, and CEO of Apple Inc.
• “You shouldn’t focus on why you can’t do something, which is what most people do. You should focus on why perhaps you can, and be one of the exceptions.” – Steve Case, co-founder of AOL