When to Tap Social Security: The Sometimes Surprising Answer From Online Calculators The conventional wisdom is to wait as long as possible. But that isn’t always the best advice. By Neal Templin Jan. 8, 2021 5:23 pm ET One of the most complicated and consequential decisions in retirement—when to start collecting Social Security—has been transformed by online calculators. The conventional wisdom says that you should wait to claim benefits as long as possible, to maximize your payments. But one size doesn’t fit all, and people’s circumstances are often different than the standard assumptions about expected lifespan and career plans.