On this episode of Simply Money presented by Allworth Financial, Bob and Brian challenge the traditional idea of retirement by asking: what if financial freedom isn’t about quitting work forever, but having the power to choose how you work, when, and with whom? They dive into the growing trend of financial flexibility and how high-net-worth individuals are redefining their retirement goals. From part-time consulting at GE to opening woodshops or working at Costco for healthcare, the conversation covers how purpose, planning, and portfolio management play a role in these transitions. Plus, they explain how to fund this lifestyle shift with smarter income strategies, tax diversification, and tools like the Rule of 55. Later in the show, they explore why clinging to outdated investments might be holding your financial plan back, how to think differently about downsizing your home, and why your future success often comes down to basic math.

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