Retirement Planning

When to Retire: Finding the Sweet Spot

When to retire isn’t just something abstract on the horizon if you are 50+ it’s something you want to understand and explore before it becomes a reality balancing the five big levers.

Chris Harris

01 Oct 2025 — 5 min read

Walking the dog on sunny days - an ideal retirement for many

If you’re in your fifties, sixties and sometimes seventies, the question of when to retire isn’t just something abstract on the horizon—it’s a topic that creeps into conversations over Sunday lunch, pops up in financial planning ads, and sometimes keeps you awake at three in the morning.

On my recent “mates” trip to Berlin there were six of us all in our 50’s discussing it and thinking about what the reality would be of calling it a day at work, it was a thought-provoking reflection for all of us.

This topic has been portrayed in all sorts of ways, from the blissful cottage life in Escape to the Country to the restless reinventions in Richard Osman’s Thursday Murder Club books. But real life is always more nuanced as were our discussions in Berlin, so I took a mental note to investigate more and try to find a practical way to look at the challenge.

To make sense of it, I like to think of the decision as balancing five big levers: Money/Wealth, Health, Lifestyle, Personal Goals, and Family Impact. Each one pulls us in a slightly different direction, and the art is finding your own “optimum point” between the mid-50s and late 70s.

1. Money and Wealth – The Practical Anchor

Let’s be honest: money underpins it all. The Beatles sang that money can’t buy you love, but as the Flying Lizards sang, your love won’t pay my bills, money is needed for heating bills, and the occasional trip to wherever gives you joy. When considering retirement, you need to look not just at your pension pot, but at how your outgoings might change. Do you still have a mortgage? Will the children need help with house deposits or university fees?

When I first looked at this I built a base model of my desired lifestyle for the broad decades in excel, I looked at the first few years if retirement probably involving a lot of travelling (hopefully) and then as the years pass fewer long-haul trips with a shift toward short-haul and eventually to UK based long weekends. This was heavily influenced by work I had done in the 1990’s for Saga group, analysing the purchase and engagement of their customer lifecycle from 55 to dormancy.

In my personal assessment, I anticipated my expenditure to reduce in my 80’s to be about 60% of what I predicted spending in my mid-60’s. To work this out, the total expenditure over my life expectancy (87 years) was X which I then divided by the number of years between expected retirement and life expectancy to obtain an average (100), and then factored in the lifestyle I wanted in each period of five years. The result was a heavily front loading of expense followed by tapering off. Financial planners will advise including provision for inflation but for me understanding that I could have the lifestyle I wanted and it was obtainable much quicker than I thought was a revelation (and yes I still have a mortgage to clear!).

A practical toolkit here is to run two scenarios: one where you stop earning at, say, 65, and another where you continue to 70. Compare not just the total pension fund needed, but what your monthly income looks like after tax, adjusting for inflation. If retiring earlier means scraping by, that’s a reality check. On the flip side, if working longer simply piles up wealth you’ll never realistically use, then what’s the point?

My big learning point here is that the Taxman cometh, with the triple lock pension formulae in the UK likely to result in state pensioners having to pay tax on their state pension due to the long term holding of the basic tax threshold – this is a very important factor affecting my decision.

2. Health – The Unpredictable Joker

Health is the biggest wild card. Mick Jagger may still strutting around a stage as a septuagenarian, but for most of us we are probably not built for a three-hour gig followed by a world tour in our 70’s. You can’t predict everything, but you can stack the odds in your favour by paying attention to lifestyle now—diet, exercise, regular check-ups.

When weighing retirement, ask yourself: what is the likelihood of being healthy enough to do the things you dream of in your 60s versus your 70s? If your ambitions involve trekking through Machu Picchu or cycling across France, earlier might be wiser. If, however, your pleasures are more sedate—gardening, reading, gentle travel—then later retirement could still give you ample years to enjoy them.

3. Lifestyle – What Do You Actually Want to Do?

We often assume retirement equals a life of leisure. But as many people find, the novelty of lie-ins and weekday golf can fade. Remember the characters in The Good Life, reinventing suburban living? Lifestyle questions boil down to: what excites you when you no longer have the Monday morning alarm?

A simple toolkit here is to list three or four activities you genuinely want to spend more time on. If you can’t name them, maybe you’re not ready to retire. Equally, if you already have projects, hobbies, or even part-time work you’re itching to explore, then earlier retirement can be a ticket to freedom.

4. Personal Goals – Beyond the Job Title

This one is highly individual. For some, career is identity—walking away feels like losing your role in life. For others, the job has always been a means to an end. Think of it like Doctor Who: regeneration into the next phase of life.

Set down a few goals for yourself: Do you want to write that novel, volunteer, or perhaps mentor younger people in your field? Retiring earlier may create space for these ambitions. Working longer might delay them indefinitely.

5. Family Impact – The Wider Circle

Retirement doesn’t just affect you—it ripples through your family. Will your partner still be working while you’re suddenly free all day? Are grandchildren in the picture, and do you want to be the available grandparent or the one still stuck in meetings? There’s also the question of inheritance: retiring later may bolster what you leave behind, but retiring earlier might create shared experiences that no money can replace.

A practical test here: talk openly with family. Their expectations might surprise you. Some may crave more time together, others may fear you underfoot all day!

The Vector Between Earlier and Later

So, what’s the optimum point? In truth, it’s less of a fixed age and more of a vector, a balance between financial security, health trajectory, desired lifestyle, personal ambitions, and family dynamics. The key is not to default into later simply out of fear, nor to leap too early out of frustration.

Think of it like the final episode of a good series—whether you bow out like Fawlty Towers at its peak or keep going like EastEnders, the timing matters. Ideally, you want to leave the working stage while you’re still energetic enough to enjoy Act Two of your life, but secure enough not to fret about the bills.

For me, the sweet spot seems somewhere in the early to mid-60s, with flexibility to adjust. The best advice? Keep the levers under review, revisit them regularly, and remember: retirement isn’t an ending, it’s a remix.

One-Page Analytical Toolkit:

When to Retire?

1. Money/Wealth

Run early vs late retirement income scenarios (60 vs 70).
Check affordability of mortgage, dependants, and lifestyle.
Ask: Do I have “enough”, or am I chasing “more” I’ll never spend?

2. Health

Assess current fitness and family health history.
Match retirement age to energy-intensive dreams (travel, sport) vs gentler pursuits.
Ask: Will I be fit enough later to do what I want?

3. Lifestyle