Build Your Own Boat

How do you build a strategic financial plan for entrepreneurship after 40 — one that includes retirement savings, catch-up contributions, and a paid-off house? This episode answers that question through the lived experience of Cindy Morris, founder of The Benson Agency and Women Who Changed the World. Cindy walks through the difference between building a business out of necessity versus building one on purpose, why she interviewed 60–70 women before designing a four-year financial and career plan for herself, and how she budgets, saves, and recovers from a slow revenue year without losing momentum. She also shares why she deliberately practices failure — through an art class and a personal trainer — to build resilience as an entrepreneur, and why publicly and vulnerably sharing her journey on Substack matters to other women considering the leap into midlife entrepreneurship.

Cindy Morris is a nonprofit strategist, capacity-building expert, entrepreneur, and mother of two. She is the founder of The Benson Agency, a national consulting firm that provides behind-the-scenes operational and strategic support to nonprofit organizations, and the founder of Women Who Change the World, an emerging venture that teaches women to build strategic plans for their own lives and careers. Cindy previously served as Chief Advancement Officer at the American Society on Aging, where she worked for three and a half years after the COVID-19 pandemic temporarily closed her consulting practice. Earlier in her career, she held roles with major hospitality brands including Hilton, InterContinental, Four Seasons, American Express Vacations, and Aeroméxico. Cindy writes candidly about money, planning, and vulnerability on her Substack, Women Who Changed the World.

Start by identifying a clear savings target and timeline — for example, a minimum retirement balance and a target date, such as having a home paid off or a set amount saved by a specific age. Build a month-by-month savings tracker, budget for a realistic average rate of return (Cindy uses 6%), and set aside extra income in the months it's available to cover leaner months ahead.

Women who take time out of the workforce to raise children or care for family members often need to contribute above the minimum 401(k) or retirement contribution once they return to earning, since early-career years typically generate lower income and less time to compound savings. Setting a specific savings percentage above the standard minimum, and tracking it monthly, helps close that gap over time.

Reach out directly to your existing professional network and say explicitly that you are available for work. Referrals from people who trust you — even those who have never worked with you directly — can lead to strong anchor clients. Securing even one solid anchor client can be enough to sustain a relaunch in its first year.

Deliberately practicing activities you are not naturally good at — such as an art class or physical training — can build comfort with failure in a lower-stakes setting, which translates into greater resilience when facing setbacks in business, such as a slow revenue year.

A necessity-driven business is typically launched quickly in response to an immediate need, such as income loss or a life transition, with growth taking a back seat to other priorities. A purpose-driven business is built with a defined plan, timeline, and specific goals from the outset, allowing for more intentional growth and investment.

Build Your Own Boat is a podcast series hosted by Janine Vanderburg — award-winning three-time entrepreneur and anti-ageism advocate — featuring women who have launched new entrepreneurial ventures in midlife and beyond. The series is part of a larger storytelling project that includes a Substack publication and a forthcoming book, all built around one goal: changing the narrative about who entrepreneurs are and making women in midlife and beyond visible as builders of wealth, freedom, and possibility.