Why we are haunted by the choices we didn’t make

Seven years ago, I was a burned-out journalist in my late 20s who considered leaving the industry. I didn’t think seriously about what I wanted except to escape, but having studied only media, I figured the solution was to pursue a master’s in a different discipline. 

I spent months applying for a two-year Master in Public Policy programme, went through the whole process and got offered a spot.

Much like Sylvia Plath’s famous fig tree metaphor, I saw the paths that branched out in front of me, at least for the next two years. Accepting the offer would mean I’d diversify my skills.

But I would also be sacrificing the chance to pick up new skills in my industry – as well as predictable career progression.

In the end, familiarity – and a little fear of the unknown – won out. I realised I wanted to leave my job more than I wanted to go back to school.

Looking back today, that episode feels like a side quest I’d embarked on for fun. I have built a fulfilling career, found lifelong mentors and gained new perspectives I probably wouldn’t have otherwise. The future I was so worried about mostly worked out.

Yet, I still occasionally think about the kind of career younger Grace who took the other path might have carved out, and whether our paths would have eventually converged.

And judging from my social media feed, I’m not alone in wondering what could’ve been – or imagining what could still be.

The illusion of the ‘right’ choice

Since late 2025, a particular online sentiment among mostly women in their mid-30s seems to suggest there is something larger at play.

These women tend to be high-achieving, having climbed the corporate ladder effectively for the past decade, but for some reason they now feel deeply discontented. 

It has been described on Instagram and TikTok as “the great millennial career crisis”. It is driven by a specific disillusionment: This is what success feels like? That’s it? 

This existential questioning seems to have hit many who had precisely built a successful career, whatever it may be. We look back at pivotal moments in our lives when we made conscious, life-altering decisions to stick to the tried-and-tested and wonder: Did we make the right choice then?

It seems we ask this largely because we grow up believing that the right choice would undoubtedly come with contentment. And it seems too, as we get older and our pathways feel increasingly fixed, that we wonder more about whether the path not taken was as “wrong” as we initially thought it was. 

Whether I was considering taking the polytechnic route after secondary school or taking a pay cut to work in a start-up, I was constantly asked: How do you know this will work out? 

I didn’t know, of course, and this fear of uncertainty – and therefore making a choice we end up regretting – can prompt us to play it safe. 

No matter how much research we do before making a decision, however, we will never know that it will “work out” for sure. Because certainty doesn’t exist. 

But if we assume that it does, when a choice doesn’t work out, we may instinctively blame others – like family or society – for pushing us into the “wrong” choice, when it could have been down to us not truly knowing our needs and wants in the first place. 

Having made many more choices since, and seeing friends and family make their own, I now understand that the question “how do you know?” may be well intentioned, simply encouraging us to pause to consider the alternative path. 

But if we haven’t taken the time to understand ourselves, it might trigger an outsized fear that we could make the “wrong” choice.

In fact, there is rarely a “right” choice, if ever. We hear stories of people who land their dream job only to hate it, and others who regret leaving their corporate 9-to-5 role to become an entrepreneur.

There is only a choice – the one we make – and the life that unfolds, seldom in a straight line.

When we didn’t own our decisions

To be clear, the path untaken might not be objectively “right”, or necessarily be optimised for ultimate happiness. Rather, it is more likely to be simply the path that we end up idealising because we made the choice that we thought we should want – regardless of whether we actually truly wanted it.

A Reddit thread from a year ago highlights this dilemma. The 26-year-old poster says he has first-class honours, a high salary, a steady relationship with a partner he hopes to marry, and a close group of friends: Accomplishments, he knows, he is incredibly fortunate to have. 

Yet, he admits: “I feel so empty inside.” He feels like he’s been living up to a standard that others have set for him, rather than being himself, and that he’s struggling to cope with the realisation that this is going to be his life.

Among the hundreds of comments, one stands out: “Because you achieved Singaporean success, not your success.”

The post resonated. But contrary to popular assumption, I think what we mourn in these instances isn’t our life now, nor the other that was possible. It’s that we lacked the courage to make a choice based on how well we knew ourselves and what we wanted.

Perhaps we made a decision out of fear of failure or judgment. Perhaps we wanted to appease a parent, a boss or even our own ego. Or we made it for reasons that felt necessary at the time, like prioritising stability over passion or safety over instinct. 

But to move ahead, we have to own the decisions we made, whatever the reasons behind them. 

We often ruminate over the “what ifs” when we catch glimpses of an alternative path we could have taken. In these moments, the possibility of upending our current trajectory can feel particularly seductive. 

But no matter how much we beat ourselves up, we can’t reopen a closed door or give ourselves the exact life we believe we’d have if we’d chosen differently. We made our choice then, with the information we had then, as the person we were then. 

The unlived life will always be unlived – and fully accepting that is the first step to fully living this one.

We may always wonder about the paths not taken. But when we recognise that we are chiefly responsible for our own lives and the choices we make, no matter the reasons for our decisions, it gives us the courage to trust ourselves enough to step off a path that’s no longer serving us. 

That way, no matter how often we might need to pivot, we can – through both minor and significant efforts – do it over and again until we find the life that truly fits.