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Retirement has long been sold as the ultimate reward: decades of work followed by freedom, leisure and a well-earned rest. But what if that promise is not just outdated, but actively harmful?
As more people chase early retirement and dream of escaping work altogether, Lyndsey Simpson, founder of 55/Redefined and author of The Age Rebellion, is on what she describes as ‘a mission to retire the word retirement’.
It’s quite a turnaround from a woman who, back in 2018, had her own dreams of retiring at 50. At the time, 41-year-old Simpson had already spent nearly a decade working at Barclays and was leading a large recruitment and HR business.
When a contact got in touch asking for help locating experienced bankers from the 1990s to advise on a regulatory review, she turned to her old network.
‘I still had some of my old contacts from my Barclays days, so I rang them up to see if I could coax them out of retirement,’ she explains. ‘These were people who could afford to have a comfortable time, but every person I spoke to said: “Retirement was the worst decision I ever made.”’
These conversations changed everything for Simpson, not only regarding her own retirement plans, but also her perspective on work in general.
‘I realised that what most people needed in the second half of their life was a sabbatical,’ she says, rather than to ‘check out of life for the next 50 years.’ In her view, retirement is ‘a trap, not a dream’.
Retirement has long been sold as the ultimate reward. But what if that promise is not just outdated, but actively harmful?
Lyndsey Simpson, author of The Age Rebellion: Supercharge The Second Half Of Your Life, is on ‘a mission to retire the word retirement’
Life expectancy has extended a lot since the idea of retirement came about. ‘It’s flipped from being something that was designed a century ago for people with three years of life expectancy, to being this 40-year gig that people are targeting as if it’s the end game,’ says Simpson.
Despite living decades longer, we’re still clinging to a model built for much shorter lifespans, says Simpson, and the results can be disastrous.
‘Literally thousands of people are sleepwalking off of a cliff into retirement,’ she says. ‘Or actually, sometimes they’re not even sleepwalking. They’re being pushed off the cliff.’
She says there is lots of research showing how staying in work helps you live longer, including one study that found delaying retirement can improve survival rates by 11 per cent.
A separate Austrian study from 2020 found that for men, retiring just one year earlier is associated with a 5.5 per cent increase in the risk of premature death.
‘Study after study shows that if you don’t replace work with a really meaningful structure, then actually what happens is you shrink,’ Simpson says.
Of course, for many people retirement doesn’t feel bleak at first – there may even be an initial burst of freedom. ‘There’s generally the little honeymoon period; the first six to 12 to 18 months,’ Simpson says.
While for some the picture remains joyful, others find that after this initial stage of glorious freedom, a grimmer reality sets in.
‘Eighteen months post-retirement, for many people, the world starts to crash down,’ says Simpson.
The problem is not simply retirement itself, but the absence of purpose and connection that work once provided. The structure that once defined daily life disappears, but if nothing has been consciously built to replace it, you can start to drift. Work provides more than income. It offers routine, identity, social interaction and a sense of contribution. ‘We need to feel needed,’ she says, ‘We love routine as humans.’
As such, Simpson’s view is that even if you are set on retirement, you need to do it with a plan in place. Rather than simply ‘going cold turkey’ it’s about having a clear idea of your ongoing purpose and plans.
For those who do step away from traditional careers, the key is intentionality. ‘Design your life, design your week, design your month, design your year with purpose and intention,’ she advises. That might mean volunteering, learning new skills, caring for others, or pursuing long-delayed ambitions. What matters is not the label of ‘retired’, but the presence of meaning.
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‘We’re fooling ourselves if we think that we can just have decades long of holiday,’ says Simpson. Rather than simply drifting into retirement, she encourages people to actively design what comes next.
And if you are desperate to give up work, says Simpson, it could also be worth thinking about whether you need to change role, rather than simply leaving the workforce altogether. Later-life career change is something Simpson is hugely keen on, even if she accepts ‘It’s going to be really bloody difficult.’
To identify where to shift your efforts, she advises you think about ‘What is it that the world needs? What is it that the world is prepared to pay you for? What are you good at?’
With longer lifespans, she envisions a world in which continuous reinvention is possible for all of us. ‘We’re going to be reskilling, having sabbaticals, taking time into it, taking time out of work.’ She also wants to dispel the ‘association that work equals bad and retirement equals good.’
‘We’ve made it a competitive sport: “if I can retire at 58, I’ve won at life”’ Simpson says. Instead, ‘We have to rip up the script and get rid of this focus on retirement.’ It’s a mission Simpson has thrown herself into with such conviction that you certainly feel she won’t be giving that up any time soon.
