Living Off a Portfolio: Dividends vs Selling Shares

This book explores the two primary strategies investors use to generate income in retirement or financial independence: living off dividends versus selling shares. It begins by explaining the mechanics, tax implications, and risks of each approach, with particular emphasis on how they support sustainable income over the long term. Readers learn how dividends can offer psychological comfort and predictable cash flow, while selling shares offers flexibility and often better tax efficiency. Real-world examples, data-driven analysis, and investor behavior insights are woven throughout to illustrate how each strategy works in practice.

As the book progresses, it dives into the intricacies of retirement income planning-covering cash flow forecasting, sequence of returns risk, tax-efficient withdrawal strategies, and the emotional factors that influence spending habits. The total return approach, with its focus on overall portfolio growth and strategic withdrawals, is contrasted with dividend-focused methods that rely on recurring income without touching principal. Hybrid strategies are introduced as a practical middle ground, allowing retirees to combine the benefits of both systems while minimizing their respective downsides.

In the final chapters, the book addresses planning for longevity and rising healthcare costs-two of the most critical and underestimated threats to a retirement portfolio. Case studies of real individuals and couples show how different strategies are applied in various life situations. A decision framework helps readers match their risk tolerance, spending style, and emotional preferences to the right income strategy. Ultimately, the book empowers readers to design a retirement income plan that's sustainable, tax-smart, behaviorally aligned, and adaptable for the future.