Carrie Bradshaw hit the nail on the head in a 2003 episode of _Sex And The City_when she recounted the many times she had celebrated the life choices of a particular friend – via an engagement party, a wedding and three baby showers. ‘If you’re single, after graduation there isn’t one occasion where people celebrate you,’ she said, exasperated. ‘Hallmark doesn’t make a “Congratulations, you didn’t marry the wrong guy” card.’
Two decades on, some milestones still seem to count more than others. The accepted wisdom is that life should follow this route: get a career, buy a home, get married, have children. If we don’t achieve all of those things in our twenties and thirties – whether by choice or accident – it can be very unnerving. I know this, because I’ve watched almost everyone I know get married and have babies, while I have not.
I’m now 41. I’ve never yearned to be a mum, but I still remember the strange months, during the pandemic, when the possibility of it not happening started to feel more certain. For years as a young woman, you can see in the distance a fork in the road, beyond which lie two completely different lives – then suddenly, the fork is behind you and there’s no going back. The road you will not travel would have taken you through exhaustion, 3am cuddles, school plays and late-night drives to collect teenagers from parties. The other will take you... well, where will it take you?
For me, the future looked so blank that I briefly experienced a kind of vertigo. What would replace the family life around which other people had arranged themselves? I wondered if I would struggle to fill the hours and decades without that structure and responsibility. Would I feel worthless in middle age, with no children depending on me? Would my life be trivial compared to those of my friends, and would I be racked with regret?
So much of this is an illusion, because of course, nobody knows what the future holds or what they will regret, and I now see as many midlife crises among my parent friends as among the rest of us. However rewarding marriage or kids might be, they don’t make life easier or less fraught with pain or uncertainty.
In her excellent memoir, Dinner For One, American writer Sutanya Dacres recounts how she fell in love with a Frenchman, moved to Paris to marry him, then divorced at 33. ‘I thought I ticked all the boxes, but it was a really unhappy marriage,’ she says now. ‘Hitting those milestones doesn’t necessarily bring happiness.’
At 39, she’s unsure of what the future holds. ‘What’s helped a lot in decreasing my anxiety is realising just how many opportuni- ties I have, to live for myself and not be responsible for anyone yet,’ she says. ‘Not having the boxes checked has left a lot of room in my life for different kinds of magic.’
For my friend Lucy, it was increasingly apparent in her thirties that being single suited her better than dating. She worried that she would come to regret this but, instead, at the age of 47 she is more content than ever. ‘I remind myself that I was making decisions the whole time and those decisions have led me here,’ she says. ‘I just didn’t realise I was making them.’
Looking back, my situation is also the result of me never having prioritised parenthood. Since the pandemic wobble subsided, I have grown confident and excited about the path I find myself on. My middle age will likely contain many of the elements of everybody else’s, including caring for older family members, but if I’m not parenting, I can devote more to the things that have always been important to me: writing, learn- ing and spending time with the people I love.
When I do have moments of sadness, nothing lifts and inspires me like the friend- ship of other women who’ve gone off-piste. My wise friend Anna, 42, reminds me that we make our own milestones. ‘My life isn’t exactly how I thought it would be – I’m liv- ing in a city that I don’t think I’ll stay in and I’ve returned to being a student – but I have more freedom to make decisions,’ she says. ‘My next milestones will be finishing my MBA and deciding where to live next.’
Throw yourself wholeheartedly into whatever is meaningful to you and you might also be surprised by how others celebrate it. I published my first book recently and was overwhelmed by support. ‘This book is your baby,’ said my mother, buying multiple copies as gifts. ‘It’s my grandchild and I want to show everybody.’
Hattie Crisell is the author of ‘In Writing: Conversations On Inspiration, Perspiration And Creative Desperation’
Additional reporting by Alice Hall
‘I never thought I would take the leap to leave the city'
By Camilla Collins, 37
When I was 29, I realised that my life was not on a traditional trajectory. My relationship ended, the dating scene was harder than I thought and I was working for myself, not in a traditional 9-5. While friends were all settling down, I knew I needed a change of scene. I had a lovely house and I lived in a great area in London, but it was full of families.
During Covid, I started spending more time in the countryside, taking advantage of the empty lockdown roads to drive out of London and walk my dogs. I grew up in London and the countryside had never appealed to me, but I found myself falling in love with nature, more space and the slower pace of life. The turning point came two years ago when I booked an Airbnb in the Cotswolds and didn’t want to come home.
When I got back to London, I felt like I didn’t belong there any more. I immediately started looking for houses and, three months later, I had packed up my London life and swapped it for a beautiful Grade-II listed property in a small village called Box (just outside of Bath).
The move has caused me to drift from some of my friends, but this has been more of a natural process as we’ve fallen out of alignment and I no longer feel the need to pretend we’re still similar. There’s something so freeing about letting go of other people’s expectations and my own of myself – I never thought I’d leave the city but I’m so happy where I am now and love the idea that nothing is as fixed as I thought it had to be.
’I’m a young widow figuring out who I am again.'
By Isabella Day, 51
When I met Ford, the love of my life, I never dreamed I’d be widowed 10 years later. We were both goldsmiths and I came across him on YouTube when I was 40. He was British but living in South Africa and I admired his techniques, so I wrote to him.
When he returned to the UK, I studied with him and we fell in love. We both had children from previous relationships, so we decided to focus on our careers. I used to be a cinematographer, so I made films for his YouTube channel and combined that with my goldsmithing business. He was recognised in his field and in demand. But Ford had an immune disease and used a wheelchair.
When he died in 2023, I was completely lost. We were such a close couple – in business and in our life goals – that I didn’t have a plan for myself. I had to start the process of finding out who I was again, and what I wanted – and I’m still figuring it out. I grieved the family milestones we would have celebrated together: my son passed his GCSEs and went on to do A-levels; Ford’s youngest son went back to college.
In those final months of his life, instead of worrying about the things people thought we should be doing – saving for a pension, buying a house – we focused on the time we had, such as sitting and watching the birds together. We called these moments ‘tiny delights’ – and I will always be grateful for them. His passing has emphasised for me how society’s expectations don’t matter.
‘There's joy and freedom in not having kids - but also sadness'
By Charlotte Holmes, 36
I never really wanted children. Growing up, I don’t ever recall having that maternal pull people describe. When I got married at 31, my now ex-husband and I both knew we didn’t want children – however, it was often the first question people would ask us. I donated my eggs twice and still the questions came: ‘Do you still not want kids?’
There’s been a lot of movement and change in the past five years of my life, the age where society assumes women should be preparing for motherhood. Instead, in my ‘having kids’ decade
I moved to India and became a yoga teacher in an Ashram in the Himalayas – something I’ve loved and would never have done if I’d gone down the traditional route of having a family.
But as much as there’s joy, freedom and acceptance in my decision, there’s also grief. Every time a friend messages me to say they’re pregnant, I get a wave of sadness that I’m never going to mother my own child – even though I know it’s the right decision for me. I know my grandmother might have been sad for me. All I know is that my life without children makes me happy and fulfilled. Being a mother is an amazing thing, but so is stepping into the role of an aunt and godmother.
‘I built my dream career in my fifties'
By Kay Thomas, 58
When I used to think about turning 60, I imagined I’d be kicking back with a retirement plan. But I’m actually just entering the next phase of my life. I’ve retrained to be a counsellor and I’m starting from scratch in a new industry after life didn’t pan out the way I expected it to.
I got married later than my friends, at 36, and I had my son at 37, then twins at 40. Working as a writer, I found it difficult to juggle my career with three young children, so I took a break. At the time, lots of publications were closing and people were being made redundant. When I came back, everything was digital and the salaries had fallen. I was getting older and I didn’t feel like it was the right space for me any more.
So, aged 53, I decided to start over and retrain as a counsellor. I’m 58 now, and when I meet friends for coffee, they’re working three days a week, looking at their pensions, or taking on casual jobs with less stress. I’m at the other end of the spectrum in a totally new industry. Sometimes I’m working six days a week just to build my business and fit everything in.
When I was younger, I spent so much time panicking about life milestones. I remember turning 30, still being single and living at home with my parents. Now, I’m two years away from 60 and, while others are winding down, I’m doing the exact opposite. And I’ve realised, none of it matters; we can make up the order ourselves. I’m enjoying learning new things every day and there’s no way I’m ready to stop any time soon. I love that life doesn’t have to follow a predictable pattern.