Retirement Readiness Quiz

What this quiz actually measures

Most retirement quizzes ask one question in ten different ways: how much have you saved. That number matters, but on its own it is a poor predictor of whether someone's retirement will work. People arrive at 65 with a large balance and no plan for drawing it down, no coverage for the years before Medicare, and no documents in place. Others arrive with a modest balance, a paid-off house, and a plan that holds up fine.

So this one spreads its ten questions across the dimensions that independently determine the outcome: your savings rate, whether you hold a dedicated retirement account, your emergency reserve, healthcare coverage, whether you know your actual number, your debt position, your income sources in retirement, your investment approach, your estate documents, and your own confidence. Each answer scores 0 to 3, and the total lands you in one of four bands out of 30.

• 0–9, Early Stage. The foundation is still being built, and the highest-value moves are the simple ones: an emergency fund and an open retirement account, funded at whatever level is sustainable.
• 10–18, Building Momentum. The building blocks exist. What is usually missing is consistency: automatic contributions, an annual review, and a target you are actually aiming at.
• 19–24, On Track. Solid habits across most dimensions, with specific gaps. Healthcare planning and estate documents are where otherwise well-prepared people almost always fall short.
• 25–30, Well Prepared. The work now is maintenance: keeping the plan current as life changes, and revisiting the drawdown and tax sequence rather than the accumulation strategy.

Are you ready to retire? Two different questions

There is a financial version of this question and an emotional one, and they do not resolve at the same time. The quiz above answers the financial version. The emotional version is worth naming separately, because it is the one that catches people off guard.

Work supplies more than income. It supplies structure, a reason to leave the house, a set of relationships that mostly do not survive the transition, and for many people a substantial part of how they answer the question of who they are. Retirees who struggle in the first two years are rarely the ones who ran out of money. They are the ones who had a spreadsheet and no answer to what Tuesday looks like.

A useful test: describe an ordinary Wednesday in your third year of retirement, in specifics, without using the words travel, golf, or relax. If that is difficult, it is worth as much attention as the savings rate, and it is more easily fixed before you retire than after.

The four gaps that show up most often

The pre-Medicare healthcare gap

Anyone retiring before 65 needs a plan for coverage in the interim, and it is frequently the largest unbudgeted expense in an early retirement. The options (a marketplace plan, COBRA, a spouse's employer plan) differ enormously in cost, and marketplace subsidies are income-tested, which interacts directly with how you draw down accounts in those years.

No drawdown sequence

Knowing your total is not the same as knowing which account you spend from first. The order you draw from taxable, tax-deferred, and Roth accounts changes your lifetime tax bill materially, and the low-income years right after retiring are also the best window for Roth conversions. Both decisions have to be made together.

Social Security claimed by default

Claiming at 62 because that is when the option appears is the single most common irreversible mistake in retirement. The difference between the earliest and latest claiming ages is roughly 77% in monthly benefit, and for married couples the decision affects a survivor benefit that may run for decades.

Estate documents that were never finished

A will, powers of attorney for finances and healthcare, and current beneficiary designations. Beneficiary designations in particular override whatever the will says, and they are the thing most likely to be years out of date: still naming a former spouse, or an estate rather than a person.

What to do with a low score

Treat the lowest-scoring dimension as the whole task and ignore the rest for now. Readiness is not an average. It fails at its weakest point, and there is no return on optimizing an investment strategy while an emergency fund is empty or a power of attorney does not exist. Fix one dimension, retake the quiz, and move to the next.