Our trip to Vancouver Island this September was built around one thing: seeing bears in the wild. Before we booked a single night, we had to answer the question every traveller starts with. It turns out to be exactly the same question you face when you’re deciding when to retire. When do you go?
The window was wide, roughly April to early October. Go in spring and you see the bears emerging with their newborn cubs. Go in September and you catch the salmon run, with the bears down at the rivers to meet it. In between sit July and August, peak season, when the crowds are biggest and everything costs the most.
We didn’t need or want the summer. We chose September. The weather’s generally kinder in Canada at that time of year, and the salmon run sounded the more exciting of the two. It also leaves us a perfectly good excuse to go back one spring.
Travellers call those in-between weeks shoulder season. Plenty of people never consider it, simply because they’ve always gone in August and it’s never occurred to them there’s a choice.
I’ll be honest about the privilege in that. We could pick our dates because I’m my own boss, and I know most people don’t get that kind of freedom over their calendar until they retire. Which is what makes the next bit so odd. Retirement is when you finally get to choose your own dates, and yet the very first one, the retirement date itself, is so often the one nobody really chooses at all.
The first date you finally get to choose is so often the one nobody really chooses at all.
Retirement has a peak season too
In travel, peak season is peak because it’s obvious. School holidays, bank holidays, the weeks everyone else is using. Very few people sit down and decide August suits them best. It’s just when you go.
Retirement has its own version. The round-number birthday. State Pension age. The end of the school year. The age you mentioned to a colleague ten years ago that has somehow become the plan.
The official figures reflect it. The latest government statistics put the average age people leave work at 65.8 for men and 65.1 for women, both sitting just below a State Pension age of 66.
None of those dates is wrong. But a date you inherited isn’t the same as a date you chose, and it’s worth knowing which one you’ve got.
Four months for a summer
One client of mine had always planned to retire on her 61st birthday, in September. It was the classic birthday date. It sounded right, and nobody had ever questioned it, including her.
We’d talked about her retirement on and off for a few years, and in that final year we really refined the detail: the timing, and what she actually wanted to do with the first stretch of it. As we ran the numbers against the life she was picturing, a September finish started to look like a strange choice. She’d be stepping into her new life just as the evenings drew in and the clocks went back.
So she left in June instead. It cost her around four months’ net pay. What she got in return was a whole summer, the first of her retirement, spent living it rather than waiting for it.
The way we saw it, it was better to have the time now than a bit of extra money to use in twenty or thirty years’ time.
Search online for the best month to retire and most of what you’ll find is about tax: finish near the end of March and start the new tax year clean. That part’s real, and I do raise it. If someone’s planning to finish in May, I’ll often suggest the end of March as an idea worth looking at. But it’s a detail to weigh, not the thing that decides. Notice what that advice is choosing for. Nobody’s asking which month you’d most like to wake up free.
Shoulder season doesn’t always mean early
It would be easy to read that and think shoulder season simply means going sooner. It doesn’t. It means going when it suits you, and sometimes that’s later than planned.
Another client always intended to retire at 55. When 55 arrived, he wasn’t quite ready. Financially he was, comfortably. But he enjoyed his work and he liked being busy, and stopping just because the date had come round didn’t feel right.
So rather than fix a new date, he looked at it again each year. At 58 the answer changed. The work environment had shifted, he had plenty lined up to keep him busy, and he knew. He retired happy, and sure it was the right time.
The money was never his question. Readiness was.
Shoulder season doesn’t mean going early. It means going when it suits you
The one-more-year trap
Teachers know a particular version of this. Almost every teacher I work with wants to finish at the end of a school year, and that’s completely understandable. You want to see your own classes through. There’s something right about closing a chapter at the end of a chapter.
The pull that concerns me more is the next one: the feeling that one more year will make a real difference to the pension.
When we sit down with someone’s actual figures, the extra year usually adds less to the pension than they expected. The bigger number on the table tends to be the year’s salary itself. That changes the shape of the decision. It stops being “stay for a better pension” and becomes something closer to “work another year for another year’s pay”.
Sometimes that’s absolutely the right call. Everyone’s figures are different, and yours are worth seeing properly before you decide. But I often ask one question, gently: is it really what you want?
Because the cost isn’t only financial. It’s a year of knowing you could go and choosing to stay, carrying the weight of a job you’re ready to leave, for an upside that may well turn out to be small. That’s what golden handcuffs look like in real life. They’re rarely locked. They just never quite come off.
Golden handcuffs are rarely locked. They just never quite come off.
Waiting for the perfect week
There’s one more trap, and it’s the quietest. Some people never pick peak or shoulder. They keep checking prices, waiting for the perfect week, and the booking never quite happens.
In retirement it sounds like “next year, probably”, said every year. Waiting for the markets to settle, for the mortgage to finish, for work to calm down. Waiting for the right time slowly becomes the plan, and the window you were waiting for quietly closes.
That’s different from my client who reviewed his date each year. He looked again on purpose, with a real question in front of him. Drifting is the opposite: not quite looking at all. It’s the missing deadline I wrote about last month. Without a reminder, a date that drifts isn’t a decision. It’s a default.
Finding your own season
So how do you find your shoulder season? Knowing when to retire doesn’t come from a formula. It comes from a few honest questions.
- Where did my date come from? Did I choose it, or did it arrive by default?
- What would going a little sooner actually cost, in months of pay rather than vague worry, and what would I gain?
- What would staying a little longer really give me, and is that gain real or just familiar?
- Which season do I want to start my new life in?
- Am I ready, or just able?
There’s no answer that fits everyone, and that’s rather the point. The right date is the one you picked on purpose, with your own figures in front of you and your own life in mind. It’s the thinking behind this whole series, which started with the two-week holiday that lasts thirty years.
Back to the bears
We could have gone to Canada in August. We’d still have seen bears, and we’d have had a lovely time. But September was ours, chosen for our own reasons, and the trip was better for it.
If you’re approaching retirement, you get that choice too, perhaps for the first time in your working life. It would be a shame to spend it on a date you never really chose.
So when would you go, if nobody else’s calendar came into it?
If you’d like help working out your own timing, a discovery call costs nothing and there’s no agenda attached to it. Or if you’d rather have a bit of this thinking arrive every couple of weeks, the newsletter is the easiest way in. I’m here when you’re ready.
Next month in this series: have you packed enough spending money?
Paul
