What would you do if you won the lottery—grab the lump sum, or opt for a guaranteed income stream for life? In this episode, Keith Singer unpacks the unseen math, tax traps, and psychology behind sudden windfalls and pivotal financial decisions most people will face in retirement. Using real-life stories, he reveals how the same dilemmas play out for everyday savers when choosing between lump sums, annuities, or pension buyouts, and why what you don’t know can be the most expensive mistake of all. Discover how to structure income, protect your nest egg, and avoid the pitfalls that even the wealthy often miss.

Prosper with Keith Singer is a weekly radio program heard all over South Florida, featuring Keith Singer and David Friedland of Singer Wealth Advisors, based in Boca Raton. Keith and David take on numerous financial topics and investment opportunities, and how they relate to retirement planning, with special emphasis on proper tax and legacy planning.