Careers, Callings, and Common Threads: Stephanie Interviews her Mom

Stephanie Eidelman, Chair of WCF, joins her mom, Toby Kaulkin, for a conversation about what they have learned from one another as they navigate work, family, and fulfillment. 

Though Stephanie and her mother, Toby, have both had careers spanning decades and industries, they found some common threads in their stories. 

Toby takes us back to her early career in advertising in New York City and shares how she found her calling in constituent services after taking time off to care for her children. Later, after working on Capitol Hill for eight years, she faced a crossroads when she was offered a position as Chuck Schumer's administrative assistant. Despite being a prime candidate for the job, she realized that it would require an intense, 24/7 commitment that would make it difficult to spend time with her family, and she decided it wasn’t for her. 

“Once I decided that, I realized I had no more future on the hill. I didn’t want to go any higher. I didn’t want to stay where I was.”

That’s when an unexpected opportunity presented itself.  

“Fortuitously, the Washington Post published an insert section about a new trade that was suddenly appearing on the horizon.” That trade was financial planning, and Toby immediately knew that it was for her. She and her husband started a financial planning business, which became an exciting new chapter of Toby's career. 

History repeats itself. 

Stephanie faced a similar crossroads in her career. After working at an early internet startup in California, she moved back east to start a family and embrace a life outside of work. She went on to become the CEO of The IA Institute and now enjoys a much more balanced lifestyle that allows her to embrace her strengths at work and enjoy time with her family.

What lessons do we pass on?

As Stephanie’s daughter approaches the start of her career, she asks if her mother has any generational wisdom to share.

“The very best thing a mom can do with a daughter is give them as much self-assurance as possible," Toby said.

Stephanie added that the same is true for leaders of all kinds. The more confidence and self-trust you can instill in someone, the more they are capable of, no matter what path they take.

This idea is at the core of Women in Consumer Finance. Our community is centered around helping women from across financial services build confidence and leadership skills that will help them reach their full potential.

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