59. Planning a work optional lifestyle Stephen Daprile

Leo Daprile is joined by Stephen Daprile, President of Gem Young Wealth, to wrap up our special client series on the work-optional lifestyle. After hearing real stories from clients living this stage of life, Leo and Stephen take a step back to discuss what truly goes into building a work-optional future. They explore why retirement planning is never cookie-cutter, why understanding each client’s goals and definition of success matters, and how going deeper into every financial plan makes all the difference. This conversation highlights the philosophy behind the planning — and the commitment to helping clients create freedom, flexibility, and confidence in the next chapter of life. If you want to understand what it really takes to build a work-optional future, this is an episode you won’t want to miss.