People pleasing in midlife: are you choosing your life or managing everyone's reactions?

This conversation started with a realisation Heidi Cullip and I kept circling: we are so deeply conditioned, at pretty much every step of our lives, to follow a path somebody else drew. Go to uni, get a job, buy a house, have a family, climb the ladder. Heidi is a marketing director who recently set up The Second Half, a Substack and community about what the second half of our lives and careers could look like if they felt more real and more authentic. She is also, like me, a recovering people pleaser.

Fear of being judged: the hidden rules we all follow

Heidi's wobble came in her late 30s. At 34 she'd taken a year off to travel, a life-changing experience, and people thought she was crazy. Then she came back and went straight into a very similar job to the one she'd left, because that's what you do. She'd had her year off. She should be grateful. Surprise, surprise, she quickly felt uncomfortable again, and it took another four or five years before she did anything about it.

When she told friends, family and colleagues she wasn't happy, the response was: this is just how it is. There was something really uncomfortable for people about the fact that she wasn't comfortable. So where do the shoulds come from? Heidi thinks most of it is implicit. We're all living inside a structure, and people don't even know they're enforcing it any more. Our words are littered with judgements we've never examined. But once you start asking why something isn't normal, nobody has an answer, and after that people often become quite supportive.

Making decisions without everyone's approval

I've been thinking about this a lot: are we, as women, actually making conscious decisions, or are we managing reactions to our choices? I made a conscious decision to have one baby. One and done. The scrutiny has been endless, and never ill-intentioned: he'll be so lonely, what happens when you're old and grey, that's really selfish, you should definitely have two.

I wobbled. I went down a spiral of internet studies, and found that science shows only children are no worse off than children with siblings. But the wobble was the wake-up call. Was I really going to make decisions about my own life based on other people's reactions? And it wasn't just my child choices. I was doing it with my career, with how much I was willing to share, with how much I'd push back.

Childfree by choice: "what about now?"

Heidi told her mum when she was 12 that she didn't want children, and she never changed her mind. That hasn't stopped people asking her whole life: what about now? Surely? Even when she got married at 39, it was, well, now you're getting married. As she says, what has that got to do with it?

It's none of anyone's business whether someone decides to have children or not, or why they don't have any. But I've always been fiercely proud of it. It was a conscious decision I made, and I'm happy to talk to you about how sure I am of that decision.

The judgement of what a woman should be doing with her time is so constricting. And when you actually look at the women in your life, they've all made different choices: no kids, one kid, five kids. Who cares? Do what makes you happy.

Being kind without being a people pleaser

I care deeply about what people think of me. I've been the nice girl, the palatable one, the one who doesn't rock the boat, and I've started to wonder how much of my life has been underpinned by being as likeable as possible. Heidi's the same. She was raised to be amenable, acquiescent, supportive, and there are studies showing girls mask their true feelings from a very young age. Girls are bossy; boys are strong-willed.

At work, her people pleasing meant being the person who was really easy to work with, and over time that hurt her more than anyone else: the workload grew, and she watched people get ahead of her because they could put a foot down and say no. But she's careful not to throw the good out with the bad. Being easy to work with is a skill. Oiling the wheels, communicating well, being someone people like working with: those are genuinely good things. The line is when it starts encroaching on your own happiness or your own success.

I've been trying to reframe it for myself. I'm kind, but I don't necessarily have to be nice. Nice feels like dropping my boundaries and rolling over. Kindness can come with integrity. Heidi took that further:

Sometimes the kindest thing to do is have a difficult conversation. Sometimes the kindest thing, for yourself and for the other person, is to stand there and say, I can't do this any more.

Feeling guilty for choosing yourself

People tell Heidi that when they want to make a big change, a career shift, a pay cut to do something they love, it feels very selfish, especially when a partner, children or ageing parents depend on them. Her answer is that you don't need to be everything to everyone all the time, because that isn't kindness to yourself either. Moving forward with kindness, while keeping your integrity close to your heart, is allowed.

That guilt is part of what she's building The Second Half around. She'd worked 20 years for a career that no longer brought her joy, and felt the disappointment of arriving somewhere that didn't hit the notes she'd expected. So she started having coffee with women in her network who had made a midlife change, to hear how they'd done it and what their lives were like now. The eye-opener wasn't just that they'd done it. It was how happy they were. Now she interviews them for a How I Did It series: a teacher who became a travel consultant, a senior events producer who became a calligrapher. Everyone, at some point in mid-career or their mid-30s, starts to feel things are a little bit weird.

She's also honest that being able to say "I'm not happy, I want to change" is a privileged position. Plenty of people, for financial reasons or otherwise, just have to get on. But for those of us who can ask the question, the old dream, work hard, retire at 60, then enjoy yourself, isn't a future we can rely on any more. People are looking to live more authentic lives now rather than wait for a utopia that might not turn up.

Finding joy in midlife: enjoying hobbies without being good at them

Here's the bit that surprised me most. When work feels forced, we assume work is the thing that has to change. Heidi disagrees. If you can find something outside work that lifts you up, everything else starts to feel better. For her it's calligraphy: two hours of slow, mindful practice where she can't think about anything else. At the end of it, she's not very good, and it doesn't matter. No one's going to mark it, no one's going to see it, and she goes back to work the next day with a clearer head. She thinks it makes her better at her job: more creative, with a clearer mind.

I am the cautionary tale here. I took up painting and pottery, and my first thought was: I can make money out of this. A new revenue stream. Then I was diabolical at both and felt genuinely disappointed. Somewhere along the way I lost my silliness, my fun, the head-back laugh where your chest is open and free. I can't remember the last time I laughed like that.

Heidi's mum joined a tap-dancing class in her 60s, something she'd always wanted to do. She's not very good, God love her, and she couldn't care less. She's having the time of her life and opened up a whole new community of friends, all because she was brave enough to say: I don't care if I'm any good at this, I just want to do it. Children are the same. They come home saying look what I did, and nobody marks it out of 10 or books a development chat about next week. So why do we do that to ourselves?

Changing your life without changing everything

So where does change actually start? Heidi's answer is the reframe. First, understand yourself: what is actually making you unhappy or unsatisfied? That's hard, and it can take a long time. Then look objectively at your position. Do you really want to throw the baby out with the bathwater, stick a hand grenade in your life and run away to a hut in the hills? Or can you make some small tweaks?

A lot of people go straight to, I need to change everything. When actually you only need to change one or two things, and things will get better straight away.

Start with the small tweaks and see if they help. It's easier and far more sustainable than blowing everything up. And if, a year down the line, you decide the hand grenade is right, at least you know you're doing it for the right reasons. There's no shame in saying you went down a path that doesn't make you happy. As Heidi put it, there's no shame in turning around, or getting a shovel and creating a new path.

And the fear of what everyone will think? She loves a raised eyebrow, these days. We're group animals, wired to worry what the group thinks. But 99 times out of 100, the group doesn't think anything. We give far too much importance to other people's opinions, and most of the time, when someone does react badly, it's jealousy: they wish they were doing the thing you're doing. What matters is what you think, and what your closest inner circle thinks. Everyone else is just Sarah or Bob down the road.

Read Heidi's stories and interviews about second careers, second chances and fulfilment at The Second Half.