Deciding when to retire is a big deal. There are a host of things to consider, and trying to get everything dialed in can feel overwhelming. Take a moment to think of someone who you consider to be a successful retiree. What makes them good at retirement? In most cases they have found a way to replace their work identity, fill their time with meaningful tasks, stay connected and relevant, keep mentally fit and physically active, express their spiritual beliefs, and feel financially secure.