The Tuesday Morning Test
Ask anyone what their biggest worry about retirement is, and they’ll almost certainly say: "Can I afford it?"
After nearly thirty years as a Chartered Financial Planner, I've come to believe that there is an equally important question:
"What are you actually going to do next Tuesday morning?"
And I don't mean your leaving do, or that massive celebratory cruise, or hosting Christmas for the grandkids. I mean a totally ordinary, quiet Tuesday in mid-October. Because once the novelty wears off and the celebrations are over, retirement is mostly made up of ordinary days.
A former Managing Director once told me about a question he always asked employees as they retired. After the usual speeches and thank-yous, he’d ask them what they were doing next.
Nearly everyone said the same thing: “Oh, I've got some DIY to do,” “The garden needs sorting,” or “I'm painting the spare room.”
Then he'd hit them with: “And what about when you finish those?”
Most of the time, he just got blank stares. They had planned the first fortnight perfectly, but they hadn't thought about the thirty years after that. That story has stayed with me because I still see versions of it today.
Planning Money Is Easier Than Planning Life
Let's face it: planning your money is much easier than planning your life.
We spend decades obsessing over pensions, ISAs, tax, and cashflow forecasts. But almost nobody stops to think about what they’ll actually do with their time.
Your job gives you a lot more than just a paycheque. It gives you a routine, people to talk to, a challenge, friends, and a reason to get out of bed. Take that away overnight, the transition can be much harder than people expect. Retirement isn’t the finish line—it’s a totally blank slate.
The 21 Boxes
I often get my clients to try a simple exercise. Picture next week as 21 blank boxes: seven mornings, seven afternoons, and seven evenings. Now, try filling them.
Who are you seeing? What is challenging you? What are you actually looking forward to?
You can explore the full 21 Boxes exercise and download the accompanying template in the 100 Tomorrow Collection.
Now imagine doing that for thirty years. If you retire at 65 and live to 95, that’s over 32,000 boxes. A couple of holidays and a regular round of golf each week still leave thousands of ordinary Tuesday mornings to fill. Those are the boxes that matter.
The Happiest Retirees I Meet
One thing I've noticed over the years is that my retired clients are often harder to book a meeting with than my working clients.
Their diaries are absolutely packed—golf, volunteering, walking groups, lunch with mates, grandkid duty, learning something new, travelling. They always tell me, “I don't know how I ever found time to work.”
Look at what those people did. They didn't just stop working. They replaced it with something they actually care about. They retired to something, not just away from something.
Money Can Buy Freedom...
In my book, I wrote something that pretty much sums up my entire philosophy:
Money can buy you freedom from work, but it can't give you a reason to get out of bed on a Tuesday morning.
Good financial planning isn't simply about making sure your money lasts. It's about creating the freedom to build a life you genuinely enjoy living.
One Question Worth Asking
If you had to retire in six months, could you describe your next Tuesday? Specifically—not just "relaxing."
Who are you meeting? What are you learning? What's going to make you smile?
If you can picture your next Tuesday with excitement rather than uncertainty, you're probably much closer to being ready for retirement than you think.
Because the real goal isn't simply to retire.
It's to build a life you don't want to take a holiday from.
Try the exercise:
Download the free 21 Boxes template from the 100 Tomorrow Collection and sketch out what an ordinary week in retirement might look like.
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