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Career advice from a Fortune 500 CEO: ‘Go into places and experiences that make you uncomfortable’

Penny Pennington.
Courtesy Edward Jones/

Penny Pennington, 59, did not always know what she'd do in life. She just knew she wanted to lead.

Now the CEO of financial services Fortune 500 company Edward Jones, Pennington grew up in Nashville, Tennessee, both her parents executives in their fields. Her mother was an energy conservation expert at the Tennessee Valley Authority, and her father worked his way up the corporate ladder at footwear retailer Genesco.

Whatever they were doing, "It was about helping other people and making the world a better place," she says. "They were using the tools of business to do it. But they were doing it across a lot of domains." And that resonated.

Pennington went to the University of Virginia to study finance and ended up working in investment banking for 14 years before getting hired at Edward Jones in the year 2000. Today, the company serves 8 million clients and oversees $1.7 trillion in assets. She became CEO in 2019 and is now one of just 9% of CEOs in the Fortune 500 who are women, according to the Women Business Collaborative.

Here are four pieces of career advice Pennington has for those wanting to find success in their career, whether that's at the top of a trillion-dollar company or not.

Ask yourself, 'Why am I doing what I'm doing?'

As with her parents, Pennington wanted to figure out how to make people's lives better. That, she felt, was her purpose. And it's been the driving force behind her rise to the top.

"I arranged the constellation of my life, my family, my work, my community, my spirituality, to align with my purpose," she says, having realized she could use the tools of finance to do so. "Because that's where my energy comes from. That's where I'll be able to be my best and bring my signature strengths to the table."

She admits it can be hard for others to identify their personal purpose. But, she says, "it's become more tangible for people over the past two or three years because I think we've all been invited to think, what is all this about? Why am I doing what I'm doing? Who am I and what do I want to be?"

Take on the 'experiences that make you uncomfortable'

Throughout her career, Pennington has been presented with numerous opportunities to take on projects and positions she'd never done before. And at times, she hesitated, or even downright said no. But it was through diving into that unknown that she grew.

Becoming a financial advisor for the first time was one such instance. "I had never worked one on one with families before," she says, and she didn't initially have some of the certifications necessary to undertake the role. But she learned along the way and picked up the certifications she needed, and it was doing that role that set her on a course to reach the very top of the company.

"Go into places and experiences that make you uncomfortable," she says, adding that, "that's where the growth comes. That's where the confidence comes."

'Courage does not mean you're fearless'

When it comes to leadership, specifically, Pennington has found that courage is key.

"Courage does not mean you're fearless," she says. "It means that you act in the face of trepidation, ambiguity. But you act based on a North star, based on your own purpose, based on the purpose of the team and what you're trying to accomplish together."

In the case of the pandemic, for example, Pennington had to get on Zoom in front of tens of thousands of Edward Jones' workers to assuage fears and anxiety about the future and the right way to serve clients in that unprecedented time.

"You go into it with recognition that there are a lot of unknowns, that not everything's going to go great," she says. "And in fact, things may fail or go in a direction you did not expect. But you act nonetheless."

'What's going on inside your head and your heart?'

The other critical trait in leadership: compassion, the crux of which is empathy for your reports.

"I need to understand you, what makes you, you?" she says about how she thinks about her employees. "What's going on inside your head and your heart? What are you afraid of? What are you excited about? How have your experiences shaped you? Because only by knowing that can I support you and can we be a really effective team."

Pennington believes every person can make a difference in their organization, regardless of role. It's about, "how courageous are you? How compassionate are you? How patient are you? How invigorated are you by the opportunity that's there?" she says.

Check out:

A 34-year-old entrepreneur and cancer survivor's best career advice: 'Be fearless'

Entrepreneur and TED Talks speaker's best career advice: 'Suck slightly less than everyone else'

'Emily in Paris' actor Ashley Park's career advice: 'You're allowed to dream big'

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