Think about one of your favourite holidays.
How much of the enjoyment actually happened while you were away?
There was probably plenty of pleasure beforehand. Choosing where to go, looking at photographs, planning what you might do and imagining yourself sitting somewhere warm with a glass of wine.
Then there are the memories afterwards. The photographs on your phone. The restaurant you discovered. The beautiful view. The stories that get better each time you tell them.
Both anticipation and memory have an advantage: they edit out the annoying bits.
The holiday itself is different.
The bed isn’t as comfortable as your own. The family in the next room are noisy. You wonder whether you’ll make the airport transfer. The restaurant isn’t quite as good as you expected. And somewhere in the background is the thought, “I hope everything is all right at home.” You can be having a wonderful holiday while simultaneously being irritated that the shower has no water pressure.
That doesn’t mean it isn’t a wonderful holiday. It means you’re experiencing the real thing rather than the edited version created by anticipation or memory.
I believe retirement can be remarkably similar.
The retirement we imagine
For many people, retirement is something they look forward to for years. Work may have become less enjoyable. Sunday evenings have lost some of their appeal. The commute feels increasingly pointless.
Retirement represents freedom. You imagine slower mornings, holidays outside the school holidays, time with grandchildren, golf, walking, gardening or simply deciding what you want to do each day.
Financial planning can reinforce this sense of anticipation. We talk about your retirement date. We calculate whether you have enough. We consider pensions, investments and how much you might spend. Eventually, your financial plan may show that work has become optional. It can feel as though you’re approaching a finishing line.
But retirement isn’t a finishing line. It’s life.
And life still comes with noisy neighbours and disappointing showers.
When the cookie jar is suddenly full
This reminds me of something I’ve written about before in A Jar Full of Cookies.
Imagine that you love cookies, but you only get one occasionally. You really look forward to it.
Now imagine having an enormous jar of them sitting in front of you every day. You can have one whenever you like.
Strangely, some of the pleasure disappears.
Free time during your working life can be like that cookie. A free afternoon is precious because it is scarce. A lie in on Saturday feels wonderful. Playing golf on a Tuesday afternoon sounds like an enormous luxury.
Then you retire. Suddenly, the jar is full.
You can play golf tomorrow. You can have a lie in on Wednesday. Thursday afternoon is free too.
The thing you spent years wanting hasn’t necessarily changed. Your relationship with it has.
Scarcity makes things feel special. Abundance makes them normal.
This doesn’t mean retirement is disappointing. It means that even something wonderful eventually becomes humdrum.
The danger of trying to retire properly
Once retirement becomes normal, another problem can appear: you may start wondering whether you’re making enough of it.
I’ve written about this before in It’s Your Retirement, You Don’t Need to Feel Guilty.
A client felt she ought to be doing more with her retirement. Perhaps she should join a book club, learn a language or spend more time gardening. These weren’t necessarily things she desperately wanted to do. They were things she thought retired people were supposed to do.
Retirement can come with a surprisingly long list of expectations.
- You should travel.
- You should have hobbies.
- You should exercise.
- You should volunteer.
- You should see your grandchildren.
- You should make the most of every day.
That’s quite a lot of pressure for a stage of life we spent decades imagining as freedom.
Eventually, my client reached a much simpler conclusion. If she wanted to do something, she would. If she didn’t, she wouldn’t.
There is considerable freedom in that thought.
Ordinary days are allowed
Perhaps one of the problems is that we compare an ordinary Wednesday in retirement with the retirement we imagined at 55.
That’s an unfair comparison. The imagined version contained the highlights; it didn’t include waiting for the plumber, going to the dentist or spending half an hour looking for your glasses.
It probably didn’t include worrying about your children either. Real retirement does.
There may also be days when you miss aspects of work. Not necessarily the meetings or deadlines, but the structure, friendships, purpose or sense of being useful. That doesn’t mean you’ve made a mistake; not every day needs to be memorable.
If retirement lasts 25 or 30 years, most days inevitably won’t be. That’s true of every good life.
Then we edit it all over again
Now imagine yourself at 85, looking back at your 60s.
What will you remember?
- Will you remember the morning the washing machine broke?
- Will you remember worrying because your investments had fallen that week?
- Will you remember the argument about where to park at the National Trust property?
Probably not.
You’ll remember different things.
- The month you spent in Spain.
- Taking your granddaughter to school.
- Long summer evenings in the garden.
- Walking along the coast together.
- You might remember having coffee on a Tuesday morning and realising there was nowhere else you needed to be.
The little frustrations that occupied your thoughts at the time gradually disappear from the story. Just as they do with holidays.
We anticipate retirement fondly, experience it imperfectly and may eventually remember it fondly again. There is something useful in recognising that while you’re still in the middle of it.
Money can provide freedom, but not fulfilment
This also highlights an important distinction in financial planning. A good financial plan can help you understand whether you have enough. It can show whether you can retire earlier than expected. It can give you confidence to travel more, help your family or spend money on things you value.
That matters enormously.
Financial security can remove many worries. But a spreadsheet cannot make you enjoy Wednesday afternoon.
Money provides choices. What you do with those choices is the more interesting part of retirement planning.
- What gives your week some structure?
- Who do you want to spend time with?
- What makes you feel useful?
- What are you curious about?
- And what makes an ordinary week feel like a good one?
There aren’t necessarily right answers; they may change as you move through retirement.
Enjoy the bit in the middle
There is nothing wrong with looking forward to retirement; anticipation is part of the pleasure. And hopefully, many years from now, looking back on your retirement will provide another kind of pleasure.
But don’t overlook the bit in between.
The cookie jar is full now. You don’t have to eat every cookie, and you don’t have to feel guilty because someone else thinks you should be enjoying a different flavour.
Retirement won’t feel wonderful every day; there will be worries, frustrations, family concerns, bad weather and afternoons when you don’t know what to do with yourself.
There will also be spontaneous lunches, trips away, time with people you love and mornings when you realise you don’t have to be anywhere.
Perhaps a successful retirement isn’t one where every day feels special. Perhaps it’s one where you have the freedom to live mostly on your own terms, imperfections included.
And every so often, amid all those wonderfully ordinary days, you stop and think:
This is good. And I’m glad I’m here to enjoy it.






