On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why retirement today looks nothing like it did for previous generations. From skyrocketing healthcare costs and longer lifespans to new tax law changes and the growing complexity of managing large retirement accounts, they explore how to truly prepare for this new era. They explain why many retirees are still working—not out of necessity, but by choice—and why high-net-worth families need to be especially cautious about rollovers and planning for long-term care. Plus, how psychological hurdles might be the biggest retirement challenge of all.