"Discovering the Strength in Being My True Self," by Penny Pennington

In 2000, after 14 years of corporate banking,  Penny Pennington  "jumped off the career cliff" and joined Edward Jones . That jump marked the first of several career inflection points and taught her about the value of authentic leadership, and the power of being her true self at work.

Now Managing Partner at Edward Jones, Pennington spoke to Women Leader 50 members last year about her personal leadership journey. Inspired by that conversation, we followed up with Pennington to capture her written story – in her own words – and share it with the greater leadership community.

Oscar Wilde once famously said, “Be yourself; everyone else is already taken.” It’s one of my favorite quotes, and for very good reason: It’s been proven true time and again in my own life, often in ways that have surprised me.

One notable time was in 2000, the year I joined Edward Jones. Up until that point, I’d been in corporate banking for 14 years, and I learned a lot from that experience. I’m a passionate learner, and becoming knowledgeable about so many different industries in my work was something I enjoyed. And I was on a strong trajectory – the organizations I worked for were happy with the results I was generating.

In time, however, I reached the conclusion that it was a career that simply wasn’t me. The more I looked at the potential professional paths in front of me, the more I realized I wasn’t interested in pursuing them. It didn’t matter that it was me who showed up to work every day. The deals I was doing could have been done very well by plenty of other people. I knew I wasn’t meant to do that kind of work.

In the midst of this career crossroads, I found myself poking around on an employment website late one night and saw a posting about Edward Jones. There were two things that immediately attracted me to the firm: the investment philosophy and the business model.

The investment philosophy was one that I recognized works to grow durable, sustainable wealth for individual investors over time. And the business model really spoke to me. It focused on giving financial advisors and their branch teams the opportunity to build a trusted practice in their local communities. Those financial advisors meet with clients face-to-face and have the support of a large organization as well as their peers in their region. Most importantly, it mattered that they are the ones doing the work – and it matters who they really, authentically are.

At that point, I jumped off the metaphorical career cliff. I walked away from my corporate banking career and became a financial advisor with Edward Jones.

My parents were a bit flummoxed. I was on a good trajectory with fine companies. But I just felt there was no “risk-free” option – I was choosing either the risk of trying something new or the risk of wondering what would have happened if I had. I chose the path that I had not yet traveled, with a commitment to having no “plan B.” I wanted to throw my all into it and live with as few regrets as possible. I knew it would be terrifying at moments – but ultimately, it would be a life that was me, that used the best of me, and taught me more every day.

Surviving vs. Thriving

I became a financial advisor for Edward Jones in January of 2000 in Livonia, Mich., a Detroit suburb. Two months later, the tech bubble burst, and it impacted the auto industry in a big way. Many of my clients back then were feeling the effects of the disruption and uncertainty. As if all that weren’t terrifying enough, in the summer of 2003, I was diagnosed with breast cancer. It would have been easy to feel like things were stacking up against me, and nobody would have blamed me if I had elected to simply survive through that period.

But that’s not what I wanted. I didn’t want to merely survive; I wanted to thrive. I had a strong sense of responsibility to the families I was serving and really getting to know well. I wanted them to have confidence in me, and I wanted to serve them through their own hard times. Something remarkable happened for me as I endured the health journey and served clients at the same time. I realized I had so much more empathy for the struggles of others.

It was tough at times, without a doubt. Candidly, I was terrified that my clients would leave once they found out I was battling cancer. I thought to myself, “Who wants to work with a financial advisor who might die?” But my clients pleasantly surprised me. They stuck with me. I was worried they would leave, and instead, I found out how much they cared about me. And I have to say, that really vaulted my healing journey and gave it some momentum.

That was the mentality I took to my fight with cancer, and I beat it. At the same time, I built my practice in Livonia and I continued to learn every day – about my profession, about my clients, about being a leader in my region, all of it.

I served as a financial advisor for six years, and got to experience a lot along the way, including a leadership development experience at our home office in St. Louis. Not long after that, my predecessor as Managing Partner, Jim Weddle, flew to Detroit and asked me (and my husband) if I’d be willing to move to St. Louis to work in the home office, where I would be helping to oversee training for our new financial advisors. I still remember sitting next to my husband while Jim wrote out the role and the details of the offer. Another incredibly thoughtful thing he took a note of – the ages of my teenage daughters, with a conversation about what this move would mean to them.

It was another key inflection point in my career. Moving to St. Louis would mean turning over my practice to another financial advisor. It would be a very different kind of work than I’d done in my practice. Related, yes, but different. So much of my life would change. And my family’s life would change too.

Once again, I was choosing whether to live with the regrets that might come in trying something very new or live with the regret of wondering what could have been. That’s exactly what I shared with my husband that night. I said, “I’m pretty sure I’ll regret something about this one way or another, but all my instincts are telling me that I need to do this.” I accepted the position. And I was right: It was a lot of change for all of us. But it was clear to me early on that I’d made the right choice. And I think it was clear to my family that I was living out my own purpose and best gifts.

Choosing to Say "Yes" to Things That Terrify Me

Over the next 13 years, I held five roles, and each one was terrifying at first. Each new one was so completely different from the previous one that in some ways it was like I was starting from scratch. But each time someone sponsored me for a new role, or I raised my hand for it, I acknowledged my fears and said yes.

Saying "yes" didn’t come naturally to me. I haven’t always been that person. But I made a conscious decision to become that person and develop my experience so that I would be ready for whatever was coming after that. I’ve made “always say yes” a part of my nature when it comes to opportunity. I recently heard something that has really resonated with me about changing roles, trying on new experiences, and how it feels – in the early going of anything new, consider that you are fully capable, but you might not yet be fully “qualified,” and that’s okay. Play to your capability and grow into the qualification.

My level of comfort with truly being myself in my career wasn’t always easy, either. There were times when I found myself wondering if I should try to tamp down certain parts of me and be someone else. In one memorable instance, I was in a role and found myself, if not conservative, then certainly careful in some of the decisions I was making. After I’d moved on to my next role, the person who inherited my previous position did some really bold things that were more valuable and made more of an impact.

I learned an important lesson from that experience. Over time, I decided to trust my instincts more, to be bolder – and that has helped me create more value along the way. I’ve found it to be more successful and rewarding when I am simply myself and bring who I am into the picture. It’s fair to say that earlier in my career, I was hesitant about fully proclaiming my purpose and my passions.

I’ll share a specific example of what I’m talking about. Several years ago, a very senior role in our organization became open. The person in this role leads the development of our entire field operation – basically all of our branch offices. This happened when I was part of the firm’s leadership team, and as our team tried to determine the best person for this role, I spent some time writing down the things that I felt this person would need to be thinking about in order to carry us into the future. It was strongly worded and succinct.

At our next leadership meeting, I read the letter and shared my strong feelings. And I followed it by saying I’m personally not qualified for the role because, while I had been a financial advisor, I had never been a regional leader or area leader. I felt those were necessary qualifications for the role, and without them, I wouldn’t have enough credibility. I thought my conclusion made good business sense.

That night, I told my husband about the meeting, and about what I had said about not being qualified for the role. And he stopped in his tracks. He said I had just made a tremendous mistake. I had disrespected our family – who had relocated from Detroit to St. Louis so I could pursue more opportunities in the firm – and worse, I had disqualified myself. He told me I needed to fix my mistake, immediately.

In my shock, I realized he was absolutely right. Just because I wasn’t 100% qualified for the role, I had taken myself out of the running for it. So at our next leadership meeting, I told everyone that I had made a mistake, and that I was throwing my hat in the ring for the open position. And my leader at the time, he just looked at me for a long moment. Then he said, “I’m glad you said that, because we all thought you could do this role, too, but it’s not going to work if you’re not all in.” I recently heard something that has really resonated with me about changing roles, trying on new experiences, and how it feels – in the early going of anything new, consider that you are fully capable, but you might not yet be fully “qualified,” and that’s OK. Play to your capability and grow into the qualification.

That was one of those “aha” moments in life and in my career. And it’s a great example of how my life really turned on – got to be technicolor – when I stopped being hesitant about being my full self at work.

Living Boldly

There’s a confidence that comes from being who I am – and those feelings grow as I continue to gain more experience and take on more challenges that initially make me uncomfortable. Pushing my boundaries and learning to be comfortable with being uncomfortable has helped me find my voice and recognize that it was me the firm needed in a given role, not a modified version of me.

I proudly and boldly live out my purpose and that of Edward Jones, which is to partner for positive impact, to improve the lives of our clients and colleagues, and, together, better our communities and society. That ambitious purpose is one that is deeply rooted in helping every client, with every colleague and in every community where we live and work to thrive.

It’s a purpose I’m deeply passionate about. You can’t shut me up or wipe the smile off my face when I’m talking about the better future we can help create for investors, clients, the 52,000 amazing people who work at Edward Jones, and the thousands of communities we serve.

Purpose is the wellspring of our energy and joy – if you ask me, it’s the reason we’re put on this earth, and it’s what can get us through those fear-filled moments. Purpose is something that’s planted in us, and we’re the most successful when we know we’re living into it. It may take some reflection and some life experience to identify your own personal purpose, but it’s there.

There’s a purpose embedded in each of us, and it’s part of what makes us who we are. Once it’s been clearly defined, it’s much more possible to find a place where we can plant ourselves, bloom, and thrive. We should all choose to NOT live with the regret of having never tried.

Oscar Wilde was right.