Most people think retiring at 55 comes down to a single number. After almost 25 years of doing this, I can tell you it doesn't. I've worked with people who could retire comfortably at 55 — and others, with even more money, who realized they weren't ready. The difference isn't found on an account statement. It's found in a financial plan that accounts for everything that comes after your last paycheck.
In my latest video, I walk through the five boxes I'd want checked before anyone retires early. The first three are financial: whether your income — not your net worth — can actually replace your paycheck; whether your plan can absorb ten years of healthcare costs before Medicare begins at 65; and whether you're taking advantage of what is often the lowest-tax window of your entire life, a rare opportunity for strategies like Roth conversions. The fourth box has nothing to do with money at all. It's purpose — because I've watched financially prepared people struggle in retirement simply because they retired from work without ever deciding what they were retiring to. The fifth is flexibility: a plan that only works when markets cooperate isn't really a plan, it's a hope.
Retiring at 55 isn't about hitting a magic number. It's about being prepared for everything that comes after your last paycheck — the spending, the healthcare, the taxes, the purpose, and the market surprises along the way. Get those five boxes checked, and you'll have a much better chance of enjoying the retirement you've worked so hard to build. If you'd like help thinking through whether early retirement is realistic for you, I'd welcome the conversation.
