E113: Cheryl L. Evans, JD: Lifetime Financial Security (LFS) Program of the Milken Institute’s Finance

Cheryl L. Evans joins host Barbara Bickham from the Milken Institute’s Global Conference to discuss longevity, retirement planning, and the emerging wealth transfer impacting women and future generations. Drawing on her background in securities law and financial education, Cheryl shares actionable insights about financial security, the necessity of lifetime income, and challenges and opportunities for younger generations in today’s economic landscape.

Redefining Retirement: How Financial Security, Longevity, and Wealth Transfer Are Reshaping the Future

The Challenge of Lifetime Financial Security

What does it mean to feel financially secure—not just today, but for the rest of your life? That question sits at the core of Cheryl L. Evans’s work as Director of the Lifetime Financial Security (LFS) Program at the Milken Institute. In a recent episode of the Female VC Lab Podcast, Evans sat down with host Barbara Bickham to unravel the complexities surrounding not just retirement, but the profound shifts in financial wellbeing happening across all generations.

Cheryl Evans’s journey to this field was anything but linear. Trained as a securities lawyer, she spent over a decade at the SEC before pivoting to roles in the CFA Institute and the Chamber of Commerce, blending market expertise with a passion for helping others navigate key life transitions. Her recent work spans beyond traditional retirement, looking at early wealth building and the holistic picture of financial security across the lifespan.

Gen Z, Millennials, and the “Peak 65” Moment

Much of the national conversation about financial security centers around Baby Boomers and their impending retirement. Evans highlights the so-called “peak 65” moment—the years between 2024 and 2027 when record numbers of Boomers turn 65. With 11,200 people on average becoming eligible for retirement every day, issues of longevity and wealth adequacy are drawing intense scrutiny.

However, Evans cautions against overlooking the unique challenges facing younger generations. Gen Z and Millennials contend with a landscape of “headwinds”—sky-high home prices, fears about never affording a house, persistent student loan debt, and a changing job market. As Evans emphasizes, success in navigating these challenges lies in knowledge and adaptability. Her panel at Milken brought together academics, economists, and leaders like Khalil Byrd (Shure) and Sylvia Kwan (Ellevest), shining a light on the tools and strategies younger generations need to thrive.

Retirement Products and Personalization: An Evolving Landscape

The contours of retirement are no longer shaped by the promise of a pension and Social Security alone. With pensions available to far fewer Americans today (down from 60%+ in the 1980s to as low as 8-15% now), Evans’s work focuses on innovative products like guaranteed lifetime income within 401(k) plans—essentially built-in annuities that aim to replicate the stability pensions once offered.

But, as Evans points out, barriers remain. Lawsuits, lack of education around these products, and confusion among both employers and employees hinder widespread adoption. The need for clear, accessible information—and the call to recognize these products as a distinct asset class—is crucial. Retirement, she stresses, is inherently personal: Do you want fixed income, growth opportunity, or the ability to leave a legacy? Experts like Christine Benz (Morningstar) now encourage people to visualize their ideal second act, personalize their plans, and think beyond outdated “rules of thumb.”

The Great Wealth Transfer and Its Ripple Effects

One of the biggest stories in finance is the impending transfer of wealth as Boomers pass on their assets. Evans explains that much of this wealth will flow to women, who statistically outlive men and often step into caregiving roles. This shift could have profound implications for entrepreneurship, philanthropy, and venture capital.

Evans is optimistic that with more women inheriting and controlling capital, we’ll see a rise in female-led startups and VC firms. Her efforts—like launching the Women’s Financial Security Initiative and collaborating with icons like Gloria Steinem—focus on building both knowledge and confidence. “The coolest thing I’ve gotten to do since I’ve been here,” Evans reflects, “is to sit down with Gloria Steinem and discuss women’s confidence and financial security.”

Looking to the Future: A Call to Action

The message is clear: Financial security is not a one-size-fits-all journey. It requires intentional planning, education, and ongoing support. As longevity increases and traditional retirement timelines get stretched, the need for lifelong financial literacy and adaptable products has never been higher.

With the Milken Institute’s new Milken Center for Advancing the American Dream opening soon, Evans and her team are pushing the conversation on a national—and global—scale. The vision? To help every individual, regardless of generation or background, build, retain, and enjoy lifetime financial security.

For those passionate about these issues, Evans remains open and accessible, inviting listeners and readers alike to join the movement for a more secure financial future.