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What Does Legacy Mean to You? – Cassandra Shepard

High-achieving professional women contemplate leadership in the context of legacy

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The L³ Alliance (Lifestyle, Legacy, and Leading by example) is the women’s group for the Wells International Foundation. Founder & CEO, Dr. Monique Y. Wells, believes it is important for high-achieving professional women to keep the idea of legacy “top of mind” and to observe how doing so influences their impact as leaders. She invites women leaders to reflect on this concept by contributing to the What Does Legacy Mean to You? article series.

Today’s article features Cassandra Shepard—an executive coach and life strategist passionately dedicated to helping professional women thrive in leadership and in life.  Shepard’s life’s work is centered on helping women CEOs, business owners, and family enterprise reach their highest potential and good. Her expertise is based on a track record of success in a wide range of leadership roles in Fortune 500 companies and one of the world’s largest multinational non-profit organizations.

Cassandra Shepard
Trusted Advisor and Business Strategist | Principal at Shepherd+CO LLC

L³ Alliance: What does the word “legacy” mean to you? How does it apply to you right now as a woman who is a leader in your field?

CS: The word ‘‘legacy’’ is often defined as what one leaves behind when they are gone.  For me, however, legacy is an active word.  It’s about how I live TODAY.  It leads me to live a purposeful life right now…a life that will make my 95-year-old self proud.

L³ Alliance: Do you believe there is a relationship between leadership and legacy? If so, describe what the relationship is. If not, explain why not.

CS: There has to be if you intend to have either.  It takes leadership today to live a life that creates a positive legacy in the now and in the future.

Legacy-worthy things typically require courage.  So much of leadership is about courage to go in places that you haven’t been before or to do things you’ve never done before. 

L³ Alliance: How can keeping legacy “top of mind” help you be a better leader?

CS: Often we get so caught up in managing the day-to-day that it’s oh so easy to lose focus on whether those ‘‘dailies’’ are leading to our longer-term goals.  Before you know it, months, if not years, can go by and you find yourself miles away from where you really desired to be and how you wanted to impact the world around you.

Keeping legacy top of mind helps avoid that trap. Legacy serves as the North Star that you can effortlessly adjust your daily compass to.

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