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How to Grow Your Career by Embracing Risk

It's time to leap into the unknown to find new challenges and fulfillment in your career.

A woman is standing on top of a ledge with a hand reaching out to her.

Steve Cadigan wasn’t actively job-hunting when a friend convinced him to interview for an HR role with a Silicon Valley company focused on helping people build their 

professional networks online. While the employer was fairly well-established, he was nervous about the prospect after experiencing the volatility of the tech world earlier in his career. 

Yet he was also intrigued. After all, this would hardly be the first time he had taken a professional risk. Cadigan began his HR career as a recruiter for a small fashion startup and moved through a diverse series of positions—from generalist at a commercial insurance company to a role specializing in mergers and acquisitions at Cisco, which moved him to Singapore to help run its Asia operations. 

“If you really want to get ahead, you have to sit in as many spots as possible and find your expertise,” he says. “It doesn’t matter whether you start out as a recruiter or a generalist, you can learn from any position.” 

For Cadigan, that included the job he went on to take as vice president of talent for the tech company, which he helped grow from 400 employees to 4,000. During his nearly four years there, the organization also became a household name: LinkedIn.

No Risk, No Reward

Cadigan clearly isn’t afraid of stretch goals—that is, career challenges that “cannot be achieved by incremental or small improvements but require extending oneself to the limit to be actualized,” according to

But he appears to be a rare breed in HR. Based on a survey of 2,187 CEOs and business leaders, leadership consulting firm Zenger Folkman identified establishing stretch goals as the No. 1 competency gap among HR leaders. 

“HR leaders can be overly risk-averse to their own detriment,” says Steven Rice, CHRO of the Bill & Melinda Gates Foundation in Seattle. “Fear drives mediocrity. It’s necessary to take risks to move forward.” 

Rice attributes his own success to his willingness to challenge assumptions and jettison programs and processes that are no longer working. 

A Recipe for Taking Risks

Doing that may be easier for Millennials who are early in their careers than for other generations in the workforce, because younger employees haven’t spent years inside the proverbial box of the traditional workplace. While experience can bring wisdom and versatility to your career portfolio, it is only an advantage if it doesn’t lead to complacency.

Here is advice from Cadigan and others on what’s needed to take big risks: 

Don’t settle for what’s easy. Regardless of where you are in your career, approach each situation and relationship with fresh eyes—and lots of questions.

“We can’t be satisfied with the easy ways of doing things,” says John Hudson, business partner with Slalom Consulting in Chicago. “We have to challenge assumptions. We can’t just make knee-jerk decisions based on what everyone else is doing.”

Remember that growth involves both risk and failure. Don’t be so afraid of making mistakes that you’re unwilling to try something different. It may not feel good in the moment, but failing “can promote a willingness to take risks and foster resilience-enhancing experimentation,” says Sim Sitkin, faculty director of the Center on Leadership and Ethics at Duke University. And those are the things needed to move boldly forward in your career. 

Build a strong support system. “It’s important to build an ecosystem of people you can turn to for advice and who challenge you to move outside your comfort zone,” Cadigan says.

That’s why Zella King recommends creating a “personal boardroom” that functions much like a company’s board of directors, but targeted to your own career trajectory. 

“People say it’s important to have a network. But what does that really mean?” says King, CEO and co-founder of Personal Boardroom in the United Kingdom. “It’s not about random connections with a lot of people. It’s about a few high-quality relationships with people who can help you succeed.” 

She recommends creating a personal boardroom with three categories of contacts:

Informational connections. Contacts who provide knowledge, information and expertise to help you address challenges and solve problems.

Power contacts. People who are in positions of influence who can open new doors for you.

Development associates. Those whose primary function is to help you grow and learn.

Following King’s lead, ask yourself “Who am I surrounding myself with? Do these people have the knowledge, experience and desire to help me grow and succeed?” If not, you should begin to think more carefully about who you ask to join your personal boardroom.

“You can never predict exactly what skills will be needed in the future,” Cadigan says. “So invest the necessary time in nurturing your network and helping your network solve problems so that you can leverage it when you need it.”

Lead the way. The HR function touches everyone in an organization. This gives HR leaders a unique opportunity to become true business partners, team leaders and employee advocates. 

“We want our organization to become a culture of learners, not a culture of knowers, so we try to give our people space to grow and learn, to fail and try new things without retribution,” Hudson says of Slalom Consulting. “Even more than that, we reward people for taking risks.”

Having a culture that promotes meaningful feedback is essential to that process. HR should not only provide a framework for cultivating candor but also help set an example of what that looks like. For instance, at Slalom, leaders are encouraged to share stories that show their vulnerabilities so that their struggles are made visible and others can relate to their challenges.

“If you are trying to build a culture of feedback, an HR leader must lead the way in providing peers and colleagues with direct feedback given with care and the intent to help that person grow,” Hudson says. “Trust is the foundation of performance management and relationships.”

Be brave. It takes courage to become a great leader—and to embrace risk. But it’s a misconception that courageous leaders don’t get scared. They do. But what they also do is leverage their fears to accomplish their goals. “When I’m scared, that’s when I feel most energized and alive,” Cadigan says. Or, as the late psychologist Susan Jeffers wisely advised, “Feel the fear and do it anyway.” 

That’s what Cadigan did. After spending nearly four intense years growing LinkedIn, he was ready for a different adventure. So he recently moved on to co-found ISDI Digital University in San Francisco and start his own consulting firm.

Arlene S. Hirsch is a career counselor and author based in Chicago.

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