Are You Ready for Retirement?

Here’s why that’s harder to answer than it sounds.

by Cam Marston

Ask someone if they’re financially ready for retirement, and most can give you a real answer — a number, a date, a plan reviewed more than once. Ask the same person if they’re ready for retirement in a broader sense, and the conversation usually gets quiet. It’s not that people don’t care about the answer. It’s that almost no one has been asked the question in a way they know how to answer.

That gap is one of the more interesting — and overlooked — issues I’ve come across in years of studying how people navigate work and life transitions.

A Well-Funded Plan Isn’t the Same as a Well-Prepared Life

Financial planning has had a five-decade head start. There are calculators for withdrawal rates, software for tax-efficient distributions and professionals trained to stress-test a portfolio against market downturns, inflation and longevity risk. By the time most people retire, they’ve run the numbers more than once.

But a portfolio doesn’t tell you what your Tuesday will look like. It doesn’t tell you whether you’ll feel needed, whether your friendships will hold up once the office disappears or whether you’ll stay active without a commute or a step-count nudging you along. Those questions sit outside the spreadsheet — and for a long time, they’ve sat outside retirement planning entirely.

That’s starting to change, and for good reason. A growing body of research — including long-running studies out of Harvard, Boston College’s Center for Retirement Research and national health surveys — points to the same conclusion from different directions: The non-financial dimensions of retirement are at least as predictive of how well someone adjusts as the financial ones and, in some cases, more so.

The Dimensions Nobody Puts on a Checklist

When I look at what separates people who thrive in retirement from those who struggle, a few themes show up again and again.

Structure and Routine

Work imposes a schedule whether we love it or not. Mornings have a shape. Afternoons have a rhythm. When that scaffolding disappears all at once, some people fill the space easily — and others find that unstructured time, in large quantities, is surprisingly hard to manage. The people who navigate this best tend to have thought about their daily rhythm before the structure of work disappeared, not after.

Social Connection

For a large share of working adults, the workplace is a primary source of regular social contact — not just close friendships, but the dozens of small daily interactions that, cumulatively, matter more than people realize. When that ends, those connections don’t automatically transfer elsewhere. Without some intention, social circles can quietly shrink, and isolation can creep in long before anyone would describe themselves as “lonely.”

Physical Activity and Health Habits

Even sedentary jobs build in movement — the walk to a meeting, the trip to the parking garage, the errand squeezed into a lunch break. Retirement removes much of that incidental activity, and without a plan to replace it, activity levels can drop in ways that show up gradually, on a timeline of months and years rather than days.

A Reason to Get Up

This doesn’t have to mean a grand “purpose” in the philosophical sense. It can be as simple as something to look forward to — a project, a commitment, a person who’s counting on you. But “I’ll figure it out” is rarely a strong enough plan to carry someone through three decades of mornings.

Why Awareness Beats Surprise

None of these factors are fixed, and none of them require a major life overhaul to address. The challenge is timing: Most people don’t think seriously about routine, social connection, activity levels or day-to-day fulfillment until those things have already changed — at which point rebuilding them takes more effort than maintaining them would have.

This is the same logic that underlies financial planning. Nobody waits until the year they retire to start saving. The earlier someone identifies a gap, the more options they have to close it — whether that means building new social connections gradually, testing out volunteer or part-time roles before fully stepping away or simply having an honest conversation with a spouse about what the next chapter actually looks like day to day.

A Tool for a Conversation That Often Doesn’t Happen

This is the thinking behind PHASE Into Retirement™, an assessment I helped develop that looks at five areas — Purpose, Health, Activities, Social life and Everyday life — and gives people a clearer picture of where they’re already in good shape and where a little attention now could prevent a harder adjustment later. It’s not a test with a passing score; it’s more like a readiness check — the kind that’s common before a major trip or a big project — applied to a transition most people only go through once.

For anyone within a few years of retirement — or anyone helping a spouse, parent or close friend think through what’s next — a tool like this can open up a conversation that’s easy to put off simply because no one quite knows how to start it. It reframes retirement readiness the same way people already think about other major decisions: with eyes open, ahead of time, rather than figuring it out in real time.

The Bigger Picture

Retirement is one of the few major life transitions that arrive with no training, no onboarding and often very little advance thought beyond the financial side. That’s not because the non-financial side doesn’t matter — it’s because, until recently, there hasn’t been an easy way to think about it systematically.

That’s changing. And for anyone within a handful of years of retirement, the best time to start asking these questions isn’t after the transition happens. It’s now, while there’s still time to do something about the answers.

Cam Marston is co-founder of PurposeNext and co-creator of PHASE Into Retirement™, a research-backed assessment that helps people evaluate their readiness for retirement across five key dimensions — Purpose, Health, Activities, Social life and Everyday life. Drawing on decades of research into life and workplace transitions, Marston helps individuals and organizations think proactively about what comes next. Learn more at PhaseIntoRetirement.com.