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Maggie O’Brien is Managing Director - Co-Head of Chicago at J.P. Morgan Private Bank. She is a Daniel Burnham Fellow member of Leadership Greater Chicago, the region’s premier civic leadership organization. Complementing Maggie’s offer as a corporate and community leader, she is a mom and wife, committed to the love and advancement of her family. This conversation is ‘real’ and ‘raw’, getting deep into the reality of a PROVEN woman leader who navigates her journey with resilience, mindfulness and authenticity.
Maggie never expected to be pulled over on the side of a road for our conversation about female empowerment, but as she puts it - "such is the life we lead." This unplanned moment perfectly captures the reality of being a working woman balancing career ambitions with family responsibilities.
From the earliest days of her finance career, Maggie questioned whether she belonged in the room. At 23, walking into meetings with manufacturing executives, she wondered why they would ever listen to her advice. This vulnerability around confidence, especially for women in male-dominated fields, becomes our central theme. The conversation reveals how women often need significantly more certainty before taking risks compared to their male counterparts - a hesitation that can hold us back from opportunities for growth.
The turning point in Maggie's confidence came after successfully turning around an underperforming team, giving her tangible proof of her capabilities. Yet even successful leaders face setbacks. Her most valuable leadership lesson came from a failed turnaround where feedback revealed she'd been perceived as a "bulldozer" who hadn't taken time to understand the team before implementing changes. This taught her the essential principle that "you've got to get people in the boat with you before you ask them to row."
For women whose confidence has been shaken, Maggie recommends cultivating a personal "cheerleading squad" - trusted friends who genuinely see your value and can remind you of it during difficult times. This becomes increasingly important as leadership positions become more isolated, with positive reinforcement growing scarce.
The parallels between professional confidence and financial empowerment are striking. Women approach money decisions with similar caution, yet 80% will need to manage family finances at some point. For young women entering finance careers today, there's reason for optimism as technological advances make work-life balance more achievable, but representation remains critical - we need to see women who've successfully balanced career advancement with family life to believe it's possible for ourselves.
Listen for practical wisdom on developing self-advocacy, overcoming imposter syndrome, and finding your own power outfit (Maggie's is a hot pink Veronica Beard suit) that helps you own your presence in any room.
Drive, Ambition, Doing, Leading, Creating... all good until we forget about our own self-care. This Village of All-Stars pays it forward with transparency about misses and celebration in winning. We cover many topics and keep it 100. We are Proven Not Perfect™️
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