What happens when you veer from the expected career path and embrace the unexpected turns life offers? Lela Davidson, Chief Operating Officer of Crystal Bridges Museum of American Art and the Momentary, joins Ken and Patti Leith to share her refreshingly honest journey through the professional landscape.

Davidson describes her career as "squiggly" rather than linear—starting as a CPA before moving through media, e-commerce, retail, and advertising before landing at one of America's premier art institutions. Far from seeing these transitions as setbacks, she frames them as opportunities that have culminated in meaningful community impact. Her story challenges us to reconsider how we view career progression and professional identity.

The conversation delves into a crucial leadership evolution that many professionals experience but few articulate so clearly. Davidson shares how she transformed from "being in the bush with a machete, hacking down whatever was in our path" to building sustainable infrastructure for others to succeed. This metaphor brilliantly captures the shift from individual contributor to truly strategic leader.

Throughout the discussion, Davidson offers wisdom on creating genuine feedback cultures, the power of community connections in Northwest Arkansas, and embracing failure as an inevitable part of growth. Her candid advice—"make your plans but don't worry about them too much"—serves as both permission and encouragement for those navigating their own career uncertainties.

Whether you're contemplating a career pivot, stepping into leadership, or simply seeking to build meaningful connections in your community, this conversation offers practical insights delivered with warmth and authenticity. As Davidson reminds us, "The only way you fail is if you stop trying."

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More About this Episode

From CPA to Community Leader: Embracing the Squiggly Career Path with Lela Davidson

Every career has a story, and often, the most meaningful ones don’t follow a straight line. Lela Davidson, the Chief Operating Officer of Crystal Bridges Museum of American Art and the Momentary, is a prime example of what it means to embrace the “squiggly” path and thrive in the process. In a recent conversation on the Four Bars Podcast, Lela opened up about her career journey, her leadership values, and her deep-rooted belief in the power of connection and community.

The Myth of the Straight Path

For many professionals, the early years are shaped by a belief in linear progression. Get the degree. Land the job. Climb the ladder. Stay in your lane. For Lela, however, life had other plans. She began her career as a CPA, an arguably “safe” and technically grounded choice, but soon realized that her interests and strengths extended far beyond balance sheets.

Lela describes her professional journey as a “squiggly career path,” shaped less by a linear plan and more by a willingness to embrace opportunities as they came. With experience spanning finance, media, e-commerce, retail, and advertising, her diverse background uniquely positioned her for leadership at one of the country’s most forward-thinking art institutions.

Her story is a reminder that flexibility and curiosity often outpace rigid planning. “Make your plans, but don’t worry if they change,” she advises. “Be committed, but also willing to let that plan go if something better comes up.”

Letting Curiosity Lead

What’s striking about Lela’s journey is her appetite for challenge. While many professionals are hesitant to leave familiar roles, Lela seems driven by the opposite: a fear of stagnation.

“I think I just get bored easily,” she admits with a laugh. “Once I've mastered something, I'm ready to move on.” This restlessness has led her to take bold leaps, like leaving a global creative agency to join Crystal Bridges, even when the future wasn’t certain. What compelled her? “I knew if someone else got the role, I’d be kicking myself for not trying.”

That willingness to try something new, even when the outcome is uncertain, speaks to a broader truth: growth is rarely comfortable, but it’s always worthwhile.

The Power of Community and Women’s Networks

Throughout her career, one constant has been Lela’s commitment to connection, especially with other women. Her active involvement with organizations like NextUp, which focuses on advancing women in business, has played a significant role in shaping both her personal and professional journey.

Her leadership philosophy is deeply rooted in relationships. Much of her success has been built through the people she’s learned from, collaborated with, and supported along the way. For Lela, community and connection aren't just values; they’re essential drivers of growth and impact.

Evolving as a Leader

Lela’s evolution from individual contributor to executive leader has been shaped by a clear understanding that leadership requires more than strong individual performance. She describes the early stages of leadership as a tricky transition, shifting from doing the work yourself to enabling others to succeed.

In the beginning, she thought of herself as someone clearing a path through the weeds with a machete, removing obstacles for her team. Today, however, she views her role as building infrastructure, creating roads and bridges that make long-term success possible. It’s a shift from short-term problem-solving to establishing systems that sustain growth.

That transition isn’t always intuitive, and she stresses that organizations often don’t adequately prepare people for their first leadership roles. Too often, new managers are expected to figure it out on their own when, in reality, it requires intentional support and development.

She also believes strongly in empowering teams through feedback. While she sees herself as approachable, she recognizes that her role and title can create barriers. Because of that, she makes a deliberate effort to create spaces where people feel safe being honest, even when sharing things she may not want to hear.

Leading with Clarity, Openness, and Intent

One of Lela’s core leadership values is creating clarity and order. She thrives on putting systems in place, learning from one area, and applying those lessons to another. She enjoys growth and sees change as an essential part of it.

Her leadership style is also grounded in openness. She keeps her door open, seeks out feedback to show her team that she is receptive, and makes an effort to get to know people on an individual level. At the same time, she acknowledges the challenge of balancing the needs of individuals with the collective needs of the team. Having not grown up in sports, teamwork wasn’t something she learned early on, but rather something she developed in her professional life. That experience has shaped how she leads today by finding ways to guide both the individual and the group toward shared success.

Learning Through Experience Good and Bad

When reflecting on formative experiences in her leadership journey, Lela doesn’t point to a single defining moment. Instead, she credits the cumulative impact of working with a range of leaders over the years. They weren’t perfect, but that in itself was valuable it showed her that you don’t have to be flawless to be effective.

She explained that studying accounting early on gave her a sense of stability, and she once imagined spending decades in the same organization with the same leadership. Life took her in a different direction, though, and instead she learned from many leaders across different environments. Some taught her by example, while others showed her what she didn’t want to emulate.

For young professionals, she emphasizes the importance of being intentional: master the role you’re in, do your best in the moment, and focus on what you can learn from each experience positive or negative. That mindset, she believes, is what allows each step to prepare you for the next.

Confidence Isn’t Static; It’s Built

Lela is candid about her own journey with confidence. “It’s like lipstick,” she says. “You have to reapply it,” Her advice? Practice being confident, even if it doesn’t come naturally. Be okay with failure. Be okay with looking silly. Be okay with people not liking you. That’s just part of being human.

This mindset allows her to lead from a place of grounded authenticity, always learning, always evolving, and never afraid to admit that she doesn’t have all the answers.

Be Brave, Keep Going

As the episode winds down, Lela leaves listeners with simple but powerful advice. She describes herself as a planner, someone who loves to make plans even if those plans change the very next day. Her guidance is to make plans but not hold on to them too tightly, because life will inevitably shift.

Above all, she reminds listeners that you really can’t fail. The only true failure is stopping. Along the way, there will be setbacks, but those are the very moments that teach the most. Her encouragement is to be brave, keep going, and stay open to the opportunities that appear, even when they don’t match the plan.

Her story shows how a “squiggly” career can lead to growth, resilience, and meaningful connection, and why embracing change can open the door to unexpected success.