It might seem logical to start any conversation about retirement with how much do I need? It’s a natural question, and the maths matters, but it rarely tells you whether that future is one you’d truly enjoy living. As financial planners, we believe the more useful conversation sits just beside it: not just “will the money last”, but “will the years feel worth having“.
In January we spoke with Justin King, Registered Life Planner® and top UK adviser, and author of The Nine Accelerators: Rethinking Retirement . The conversation left us with six questions worth sitting with, whether retirement is still ahead of you or you’re well into it.
As Justin put it:
“Everyone starts from the position of ‘Have I got enough?’… but actually there are many more questions that need answering.”
1. What would a purposeless retirement look like?
It’s a strange question, but often an easier one to answer than “what would a great retirement look like?” The answer is different for everyone.
For some it might be,
- Isolation
- Losing a sense of routine
Drifting from the people who matter.
Whatever it looks like for you, seeing it clearly tends to reveal the shape of what you’d rather have instead.
Still working towards retirement? Sit with this before you set a retirement date, while there’s still room to shape things.
Already retired? Revisit it now, in case any of those things have quietly crept in. A good retirement isn’t decided once and left alone. It’s worth checking on.
2. Is your health part of the plan?
We often see health getting less attention than wealth in a retirement plan, even though a good retirement depends on both. We think health deserves the same priority as the numbers: one pays for the years, the other is what lets you enjoy them.
What counts as “enough” varies hugely from person to person.
- Someone might need very little to feel secure.
Someone else might need a great deal more.
The difference tends to be the life someone’s chosen, not the size of the bank balance.
Still working towards retirement? If the plan shows the money lasting thirty years, ask what needs to be true of your health for those years to feel like a gift.
Already retired? Ask the same question now, honestly, and give it the same care as any figure in the plan. It’s not too late to put health back on equal footing with wealth.
3. What are you retiring towards?
In our experience, the people who find retirement hardest are often the ones who’ve not go something to go to. Retire to something, not away from work. Once you’re no longer the person your job title described, the question becomes who you are instead.
Justin highlighted an example from the episode: a client of his who’d never become a nurse, because of family commitments, later found fulfilment through hospice volunteering, reconnecting with an old ambition.
Still working towards retirement? Write down two or three things you’d genuinely look forward to on a Tuesday morning.
Already retired? If that “something” hasn’t shown up yet, or has quietly faded, it’s never too late to ask what you’d add now. That client found hers years into retirement, not before it.
4. Is your plan built to last as long as you do?
A good plan has to work for as long as life goes on, and that’s often longer than people expect. If you’re planning alongside a partner, it’s worth building in that you may need the plan to last for different lengths of time for each of you. Either way, thirty years or more is long enough that “will the money last” and “is this a life worth living” become two separate questions.
Still working towards retirement? Build the plan around a longer life than you expect, not just the average.
Already retired? Revisit it now, with the benefit of knowing more than you did at the outset. The right answer at sixty five isn’t always the answer at seventy five, and a plan can still be adjusted.
5. What if you needed more support, later on?
It’s a sensitive question, and not an easy one to sit with, which may be why it tends to get left until later. Thinking ahead about care preferences and who would make decisions on your behalf, while you’re able to talk it through clearly and calmly, brings more peace of mind than putting it off.
This isn’t something we can advise on directly. The legal structures, care preferences and contingency plans involved sit outside financial advice. But we can point you towards people who specialise in this, whether that’s a solicitor or a later life care adviser, so the right conversation happens with the right person.
Still working towards retirement? Raise it alongside your wider planning, rather than leaving it as a separate conversation for another day.
Already retired? If this hasn’t been discussed yet, now, while there’s clarity and time, is a good moment. It’s a conversation worth having at any age.
6. Has the conversation happened more than once?
A conversation with a partner, or with us, helps more than any of this sitting quietly in your own head. It doesn’t need to be perfect. It needs to happen, and then happen again.
Still working towards retirement? Have it well before you set a retirement date, while there’s still room to shape things.
Already retired? Have it anyway. It matters just as much years in as it did before you left work, arguably more, once circumstances have had time to change.
Where this fits into your plan
These aren’t questions with a single right answer, and none of them are meant to be answered alone. Contact us if any of this sits with you, whatever stage of retirement you’re at. That’s the kind of conversation a WealthSpan™ plan is built around: the numbers, and the life they’re meant to support.
The full conversation with Justin King is on the Purposeful Wealth Podcast: The Nine Accelerators: Rethinking Retirement Click the links below to listen for yourself.
Risk warnings
This article is intended for general guidance only and should not be considered financial or investment advice. Where we’ve touched on health, care, or legal matters, these are shared for context only and sit outside financial advice. Any decisions should be made solely in consultation with a qualified and regulated adviser or, where relevant, a solicitor.
Wells Gibson is authorised and regulated by the Financial Conduct Authority (Firm Reference Number 731027).



