Should You Ever Retire? A growing number of Americans are pushing back the age at which they plan to retire. Or deciding not to retire at all. Related Content A Bucket Plan to Go with Your Bucket List Longer, healthier living can put greater stress on retirement assets; the bucket approach may be one answer. When to Self-Insure Choosing to bear the financial burden of an adverse event is called self-insuring. Do you know what that entails? How Much Home Can I Afford? With a few simple inputs you can estimate how much of a mortgage you may be able to obtain.