Mari-Anne Chikerema Chiromo’s career path is fluid, but her mission is steadfast: as a single mom, to build a legacy and future opportunity for her son. Mari-Anne and I talk about her identity as a single mom, immigrant, and woman of color and its impact on her career and decision to launch entrepreneurial side hustles.

Cary Lin pivoted from finance and consulting to working with the beauty industry’s biggest female leaders–to finally, taking her place in line as founder and CEO of Common Heir. We talk about the pressure on female founders, biases in venture capital funding, and the power of seeing role models who look like you.

Kristi Andrus left a successful career as a media executive at HBO. She and her husband spent two years traveling and raising their kids. Then, Kristi launched a coaching business. We talk about why entrepreneurship is the best-kept secret for moms and how women can work less but be more.

Allison Whalen left Wall Street to move into the startup tech world. As a new mom she experienced a challenging parental leave, which inspired the founding of Parentaly. We talk about the difficulty of pivoting away from a job you love and how becoming a mom made Allison a better leader.

Leela Srinivasan took a meandering path to her role as Chief Marketing Officer at fintech decacorn Checkout.com—pivoting from receptionist at a newswire service, to salesperson, to banker and consultant, and finally to marketing. We talk about the benefits of a nonlinear career path and how knowing your authentic self will point you in the right direction.

Dr. Melynda Barnes left a coveted career in plastic surgery to take a chance on a health tech startup. Today Melynda is the Chief Medical Officer at Ro Health, a “unicorn” valued at $5B. We talk reactions from friends and family, the pressure of being a role model, and why Melynda knew she had to pivot.

Ellen Rice Chever pivoted her career as a healthcare consultant to become a DEI&A leader and podcast host. I talk with Ellen about the importance of aligning your career with your lived experiences, how being “the only” in the room motivated her pivot, and advice for women and underrepresented groups trying to build their best possible career.

Megan Elizabeth Gray worked for one of the largest law firms in the world. She was intensely driven to become a Partner, but along the way her ambition changed—and Megan left her firm. We discuss how ambition evolves throughout your career, the resources Megan relied on to get clarity, and how you reconcile the values of a working immigrant family with the choice to change one’s path.