Sunday Night Test: How to Practice Retirement Before You’re There

You know that feeling on Sunday night, when the weekend is gone and Monday is loading? Most people I talk to in their late fifties say that feeling has changed. It used to be dread. Now it’s something quieter. Like the volume’s been turned down on something they thought they’d have figured out by now. It’s no longer just about work. Sometimes it’s a resignation, a giving in to the inevitable. And under it all, still wondering about retirement. But wouldn’t it be great if you could figure out how to practice retirement before you even got there?

If you’re somewhere between 55 and 64, the retirement conversation has probably narrowed to one question: do I have enough money? It’s the loudest question, so it crowds out the other one. The one most pre-retirees don’t realize they’re avoiding until they’re three months in and pacing the kitchen at ten in the morning.

What are you actually going to do with the rest of your life?

That’s the question the Sunday Night Test is built for. It’s free, it’s straightforward, it doesn’t require a spreadsheet, and you can run it tonight. I mean, why wait until Sunday night?

The test, in one sentence

If Monday morning you didn’t have to go to work, ever again, what would you actually do? Not for one Monday. For the next ten thousand of them.

Most people get through about three days of answers before they stall. Sleep in. Catch up on the yard. Take that trip you’ve been putting off. Read the stack of books on the nightstand. Maybe golf. After that, the list goes thin. And the silence under the silence starts to show.

That silence is the data. That’s what the test is really measuring.

Why “what would you do?” is the wrong place to start

Here’s the trap. When we ask ourselves what we’d do without work, we tend to think in terms of activities. Things we’d cross off. But activities aren’t the structure of a life. They’re decorations. The structure is something else: a reason to get up, a sense of being needed somewhere, a rhythm of belonging, a problem worth solving.

Work has been doing all of that for you, quietly, for decades. The paycheck was the obvious part. The rest was the part you didn’t notice until it stopped.

So the better Sunday night question isn’t “what would I do?” It’s “what would I miss?” If you can answer that honestly, you’ll know what you’re actually retiring from. Which tells you what you need to retire toward.

My own version of the test (and how badly I failed it)

I’ll be straight with you. The first time I tried this on myself, I came up empty. I had a vague answer about traveling more and writing something. That was the whole list. I’m a guy who’d spent decades being highly scheduled and highly responsible, and when I subtracted all of that, what was left was a daydream and a question mark.

That was a hard night. But it was useful. Because the alternative was finding all of that out at 65, in real time, with no off-ramp.

What I’ve learned since is that the answers don’t show up by sitting still and thinking harder. They show up by doing. By treating the next five years as a runway, not a holding pattern. Try the thing. Volunteer for the thing. Take the small online course. Talk to the people who already do the thing. The Sunday Night Test isn’t a thought experiment. It’s an invitation to start practicing.

How to actually run it (a small ritual that works)

Here’s the version I’d recommend if you want to try it for real. It takes about twenty minutes, once a week, for a month.

On a Sunday night, get a notebook. Not your phone. Write down the answer to two questions. Use a pen and actually write it down.

First: if I didn’t have to work tomorrow, what would I do with the day? Be specific. Down to the hour. Not “travel” but “sit at the kitchen table with coffee until 9, walk for an hour, then…” Notice when you run out of road.

Second: what would I miss if I never went back? Don’t filter. The honest answers are usually the smallest ones. The chatter at the coffee machine. Knowing your opinion matters in the meeting. The feeling of finishing a hard week.

Do this four Sundays in a row. By the fourth one, patterns start showing up. Some are warning signs. Some are seeds. Both are useful.

What the test usually surfaces

After running this with friends, family, and a lot of readers, a few things show up over and over.

A lot of pre-retirees discover they don’t actually want to stop working. They want to stop this work. There’s a difference, and it’s a big one. If that’s you, retirement isn’t your finish line. A pivot is.

Others discover the opposite. They want a slower life, but they’ve never built the muscle for it. They’ve spent forty years optimizing for output, and now the idea of an unscheduled afternoon makes them itch. That’s worth knowing. It means slowness is a skill they need to start practicing, not a reward they’ll automatically enjoy.

And a few discover something harder. They realize their identity has been almost entirely built on the job. Which means the Sunday Night Test isn’t just about what to do. It’s about who they’re going to be. That’s a longer project. The good news is, five years is enough time to start it.

The point isn’t to have the answer. It’s to start asking.

Here’s what I want you to take from this. You don’t need to crack the code by next Sunday. You need to stop pretending the question doesn’t exist. The pre-retirees who land softly are the ones who started rehearsing five years out. The ones who land hard are usually the ones who assumed the answers would just arrive on schedule, the way the pension does.

They don’t. You have to go find them. And the search is more interesting than the panic, I promise.

If any of this is rattling around for you, the books I’ve written are about exactly this kind of pre-retirement honesty, including the financial side most people are quietly afraid to look at. The Retirement Lie is a 5 dollar download on the site if you want a place to start. Let me know what you think.