How I broke up with society’s shoulds in my 30s and starting entertaining the coulds

Once you learn about “the shoulds”, you start to see them everywhere. I first came across it in my therapist’s office. “Why do you keep saying you should act that way?”, she asked. “Who’s saying that?”. And it’s true: in your 30s you do tend to hear the word – whether internally or from others – almost everywhere. 

Should statements are blacklisted in popular talking therapy. According to popular psychology, shoulds often come from external sources – from childhood, cultural or religious pressures – rather than reflecting your truest desires. Instead, they can be rooted in guilt, shame, panic or inadequacy; a perception that what you’re currently doing isn’t enough.

Hidden narratives had been undermining my life choices

I should go to that party. I should go to the gym. I should have a more creative job. I should be on the property ladder. These statements often feature in the voice in our heads. Sometimes we also hear them said out loud from those around us, like our newly single friend reluctantly signing up to that dating app – I should get back out there. 

Since entering my 30s, I’ve noticed certain shoulds calling to me more urgently (get married, have kids, be successful, be better with money), intermingling with the existing ones (be well-travelled, look after my health, be a good friend and committed family member). 

Yet it wasn’t until I understood the concept that I realised how much these hidden rules and narratives had been undermining my confidence in my own life choices.

Asking this one simple question streamlined my decision-making

For instance, I’d berate myself for my lack of broodiness when friends shared baby pictures on WhatsApp, rather than accepting the way I instinctively felt. Or feeling FOMO for turning down a group skiing holiday, even though I’ve never wanted to ski. 

I started to ask myself a simple question: “Am I agreeing to this because I want to – or because I think I should?”. It quickly streamlined my decision-making.

Over time, this judgement factored into everything I did. For instance, how I approached my dating life (did I actually have a good rapport with this person, or were they just “good on paper?”). Also, whether I took on certain work opportunities (was this actually a smart career move or was I just people-pleasing?). Ironically, it was because of this that I actually quit talking therapy, realising it was a costly experiment that I felt I should be exploring.

I asked myself how could my life look?

Not all shoulds are bad of course – they’re imperative to paying the bills, or being a dutiful family member – but what helped was making sure I identified where they were coming from in the first place, rather than saying yes without knowing why. 

I felt increasingly comfortable with the choices I did make, having exorcised the undermining voice in my head telling me to do otherwise. 

Liberated from some pressures, I asked myself a different question: “How could my life look? What could I do?” The possibilities are, of course, endless. But I paid attention to the things that sparked my curiosity, like learning Spanish because I like it or falling in love with yoga rather than the more punishing cardio I felt I should do.

My schedule isn’t dictated by the wrong things anymore

It left me open to opportunities that came my way, like a month-long fling with someone I met randomly who was soon to move to Berlin. It was the first time in years I’d dated with a completely carefree attitude and no expectation of commitment, and it taught me a valuable lesson about enjoying getting to know someone in the present. 

My schedule isn’t dictated by the wrong things anymore. I fill my weeks with stuff I actually want to do – quality time with family, enriching activities, people whose company I value. 

No longer do I endure second dates with the air of a soldier going to war, or feel guilty about flaking on arrangements or events I’d agreed to without truly wanting to be there.

I launched my newsletter ‘The Shoulds’ around this very concept

In March, I’m relocating to Lisbon for a couple of months to focus on a creative project. It’s a decision I’m taking in spite of the biggest should on my mind: whether to find a partner, settle down and build a stable life in London – the same trajectory many of my close friends are on right now. It’s not necessarily that I don’t want that trajectory someday, but I’d rather do it out of choice than a fear of falling behind. 

Three months ago, I launched a newsletter around this very concept, titled (you guessed it) The Shoulds. Every week, I explore a common theme, like breaking up or productivity guilt, and break down the shoulds attached to it.

The newsletter now has thousands of subscribers – typically readers in their 30s and 40s – and that community has taught me just how universally this sense of external pressure is felt.

A life guided by shoulds is rarely one we’ve chosen for ourself

Every week, I read comments and emails from people who’ve felt restricted by the life they think they ought to be living, always at the expense of the one they’d like to be experiencing now. 

It’s through founding this online community (which also contains discussion threads and virtual meet-ups) that I’m working to change that.

Because whatever your vantage point, a life lived guided solely by the shoulds is rarely the one we’ve chosen for ourself – or one that will give us a long-term sense of satisfaction and purpose. Proactively making decisions based on what we want – rather than what we should want – is a great place to start. 

SOLO columnist Francesca Specter is writer of The Shoulds – an online, reader-funded publication, exploring the hidden rules that shape our lives. 

She’s also the author of Alonement – a Times book of the year 2021 – and host of an award-nominated podcast of the same name.

Images: courtesy of Francesca Specter