Don’t Just Climb the Ladder. Explore the Jungle Gym – CIO

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By Chet Kapoor, Chairman & CEO of Datastax
I have the great privilege of getting to know leaders from the world’s most recognized brands and fastest-growing startups. We share the stories, obstacles, and defining moments that have helped shape our careers.
Each individual’s journey is unique, but there’s a common thread connecting all of these leaders: no one’s path to success has been a straight line. Most of our journeys look more like a zigzag – or maybe even a jungle gym.
You will always face uncertainty and unexpected challenges. This is a fact in work and life. It’s how you deal with these moments that define you. Here are lessons from five world-class leaders that will help you embrace fear and navigate your path to a fulfilling career.
For former Adobe CTO and CPO Abhay Parasnis, the road to becoming a leader at one of the largest software companies in the world was not a direct path. It was a zigzag.
I recently asked Abhay about his journey to building such an impressive career. He described it as “a series of unplanned things that worked out well when I didn’t expect them.” Some of the career decisions he put the most thought into actually ended up being missteps. What has guided him along the way, through both good and bad times, has always been his “deep passion for technology, products, and building new things.”
You might know exactly what your desired career path looks like, or you might be totally winging it. Either way, you will have to face uncertainty. When you’re up against an obstacle or feeling unsure of what “next step” to take, it helps tremendously to have a North Star – a purpose that you keep coming back to. Abhay’s North Star is building new technology and products. Mine is serving enterprises and developers. Yours might be empowering others to be themselves. Make sure to spend time exploring your purpose – beyond just your job title, status, or pay – and let it guide you every step of the way.
When Abhay looked back on his career, he reflected that “it is not just about the choices you make but the relationships you build.” I love this perspective. At the end of the day, you won’t remember the money you made (or lost), the opportunities you won (or missed). You will remember the people you worked with and the customers you served. And it’s through these relationships and connections that you might find the next step or a whole new direction in your journey.
When Elizabeth Hunter started college, she dreamed of becoming the editor-in-chief of Vogue magazine. But two years into her education, she realized she didn’t just want to write about things that other people do. She wanted to actually do things herself. Elizabeth switched her major from journalism to English and after graduating, she took a job as a temporary secretary in a power company’s IT department. She didn’t know it at the time, but this would be the decision that changed the trajectory of her entire career.
Elizabeth’s manager became the first of many mentors that would help guide her on the path to becoming an IT leader at telecom giants AT&T and T-Mobile. And she has never forgotten about him.
“His name is Tom Morgan. I think about it all the time…how he believed in me, saw something that I didn’t see, gave me an opportunity when I had literally no experience,” Elizabeth said.
The best mentors show up in good and bad times and push you to become better in business, leadership, and life. Because of the awesome mentors who helped Elizabeth throughout her career, she has committed to paying it forward – especially to women and other underrepresented minorities in tech. “I think very consciously every day about what I am doing to help others further their careers or whatever it is that they want to develop,” she said.
Similarly, Google Cloud’s Director of Global Healthcare Strategy and Solutions Aashima Gupta told me about the impact of mentors and sponsors in her journey.
“A mentor gives advice on how you can do things better for yourself. Whereas sponsors are people who advocate for you and create opportunities for you. I’ve been very fortunate to have [both] along the way,” she said.
Seek out mentors and sponsors early and often in your career. Even the most accomplished CEOs and leaders benefit from this type of support. Many people you meet will be willing and even eager to help, so don’t be afraid to reach out and ask for an introductory meeting. Still, be discerning in who you choose. Your mentor should share some of your core values or definitions of success, have relevant expertise in the areas you want to grow, and lead with empathy and honesty. Once you’ve found a mentor or sponsor, make sure to nurture the relationship – have frequent check-ins, offer a helping hand, and share gratitude often. It’s a two-way street, after all.
Alana Mayo, President of Orion Pictures, has worked on award-winning films like The Big Short, Selma, and many others. Since childhood, Alana knew she wanted to do some form of visual storytelling – whether via film, television, or theater.
“My whole story is around story. It’s around loving storytelling and wanting to find a way to connect that to a career,” she said.
But even when you have a strong idea of your destination, the path to getting there will have twists and turns. Alana and I talked about one of the defining moments of her journey. Months after she started an exciting new role at Vimeo, the company shifted its strategy away from building a content offering. Alana decided to leave the company and take a short hiatus from work.
“I think I really needed a break. I had been moving at such a fast pace, just chasing this carrot for 10 or 12 years. I had never really sat down, taken a moment to rest and think about what I really wanted to do with my life,” she said.
During her six months off, Alana had a shift in perspective and “found more clarity than ever before.” She realized that something was missing in the legacy entertainment industry: diverse representation, both from the creator and casting point of view. From there, Alana set out with a new goal to tell stories that resonate with ALL types of people and communities, and to reflect the world as it exists.
Alana’s experience tells me that it’s okay to hit pause. Your career is not going to disappear just because you take a step back to recharge and reevaluate where you’re headed. Sometimes, your biggest breakthrough will come from choosing not to do something rather than forcing an opportunity that isn’t there.
Guy Kawasaki is a renowned venture capitalist, New York Times bestselling author, podcaster, and Canva‘s chief evangelist. He got his bachelor’s degree in psychology from Stanford University, which ended up serving him well in his later roles in sales, evangelism, and now podcasting. I asked him why he chose to study psychology. He laughed and said: “It was one of the easiest majors. That’s why I picked it.”
Most of us do not approach work (or life) with a master plan in mind, and many of the steps we take are beautiful accidents that help us become who we are. “I’m 67 years old,” Guy said, “and I think I finally found my true calling.” He was referring to his podcast, Remarkable People, where he interviews exceptional leaders and innovators (think Jane Goodall, Neil deGrasse Tyson, Steve Wozniak, and Kristi Yamaguchi) about how they got to be remarkable.
“In a sense, my whole career has prepared me for this moment. I’ve had decades of experience in startups and large companies. So that gives me the data to ask great questions that my listeners really want the answers to,” Guy said.
Guy is undeniably brilliant, and his success is no accident. But still, he believes that luck has played a part in his success. In his words, “Basically, I’ve come to the conclusion that it’s better to be lucky than smart.”
Maybe Guy is right. Or perhaps, the smartest people know when to take advantage of luck and act on the opportunities that present themselves. Whatever the case, it’s important to take calculated risks. Don’t let the fear of failure get in the way of seizing an awesome opportunity, because sometimes, luck breaks your way.
If there is one thing I’ve learned from these phenomenal leaders, it’s that your career is not about climbing a ladder. It’s about forging your own path – with the help of mentors and sponsors – and overcoming fear to reach your version of success. Uncertainty will always be uncomfortable. But the more you face it head-on, the more confident you will become in your ability to handle challenges, and the closer you’ll get to finding what truly fulfills you.
One more thing: don’t forget to enjoy the journey! When you look back, you won’t remember what was in your bank account or the times you failed. You’ll remember all the amazing people you met and the lessons you learned along the way. Take the time to appreciate that.
Learn more about DataStax here

About Chet Kapoor:
Chet is Chairman and CEO of DataStax. He is a proven leader and innovator in the tech industry with more than 20 years in leadership at innovative software and cloud companies, including Google, IBM, BEA Systems, WebMethods, and NeXT. As Chairman and CEO of Apigee, he led company-wide initiatives to build Apigee into a leading technology provider for digital business. Google (Apigee) is the cross-cloud API management platform that operates in a multi- and hybrid-cloud world. Chet successfully took Apigee public before the company was acquired by Google in 2016. Chet earned his B.S. in engineering from Arizona State University.
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