Deep Dive AI • Retirement Planning Case Study The Retirement Plan That Treats Health Insurance Like Part of the Math What if early retirement is not just about how much money you have — but about which money you spend, when you spend it, and how much taxable income you create? Disclosure: This article describes our personal retirement-planning scenario for educational purposes. Tax, Medicaid, Medicare and Social Security rules can change. Some links may be affiliate links, which may earn us a commission at no additional cost to you. Most retirement plans begin with one question: How much money do I need to retire? After working through our own numbers, I think that question is incomplete. The question that has become much more important for us is: How much taxable income do we need to create each year — and what does that income do to our health insurance costs? That one question changed the way I think about early retirement. We are not ...

Deep Dive AI · Retirement Lab · 2026 What If Social Security Paid Less Than You Expect? We took the latest 2026 Social Security numbers, translated the projected funding gap into real household dollars, and built interactive tools so you can stress-test your own retirement. Updated October 3, 2026 · Interactive Deep Dive For decades, the Social Security conversation has been framed as a binary question: will the program be there, or won't it? That is the wrong question. Social Security's current financial outlook is more complicated—and much more useful for retirement planning—than either “everything is fine” or “Social Security is disappearing.” The 2026 Trustees Report gives us actual numbers to work with. OASI reserve depletion Q4 2032 Current projection for the retirement and survivors trust fund. ...