Professional Regret: Why is it so Prominent, How Can You Avoid it, and What Can You do if You Have it

It’s the sliding doors moment you look back on and think, “what if?” Or it could be less definitive. Rather than an obvious fork in the road where you chose to go one way not the other, it might just be a more generalised sense of dissatisfaction, that lingering feeling that in another life things might have gone a different way. It’s regret, and for many people it’s unavoidable – in life and in work.

A Harvard Business Review study1 of more than 300 US-based workers and their colleagues found that just 6% of those surveyed reported never or almost never thinking about other professional paths they could have taken. 21% reported pondering other paths often or almost always. In other words, professional regret is ubiquitous. And, unsurprisingly, it can have a negative effect.

The aforementioned study also found – through self-evaluations and input from colleagues – that “workers who felt somewhat stuck in the past were more likely to be distracted and to daydream while at work, took more breaks and days off, were less engaged with their colleagues, and were more likely to search for other jobs.” It’s not necessarily that these people weren’t happy with their current lives; in fact, many of them reported that they were. But contentment with what you have doesn’t necessarily preclude one from having dreams of what might have been.

The age of dissatisfaction

Experiencing regret is natural. There’s a reason this year’s Best Picture winner at the Oscars (Everything Everywhere All At Once2) as well as modern culture’s monolithic blockbuster franchise (the Marvel Cinematic Universe) are both focused on the theory of the multiverse – other dimensions in which the films’ protagonists can interact with different iterations of themselves and witness how their lives would have turned out if they hadn’t done X or had done Y. Audiences connect because it chimes with their own internal questioning. What if I’d kept up the painting? What if I’d married the blonde? What if I’d had the confidence to really pursue my dream? We could ponder forever on the endless lives we might have lived and the better people we could have been. Except it gets us nowhere.

The concept of professional regret is nothing new, but aspects of modern culture serve to exacerbate the problem. The world has simultaneously got bigger and smaller. Bigger, in that the professional options available to people now are wide-ranging in a way it would have been impossible for our ancestors to imagine. A few centuries ago, your career was predetermined. It was what your family did and had time for time eternal (if you were a man, that is; if you were a woman it was unlikely you’d be allowed a career at all.) Diverging from this path was rare. In the modern worksphere, however, not only are the occupants more diverse but the jobs themselves are too. Children are raised under the clichéd auspice that they can be anything they want to be. The benefits are obvious, with even the most niche of interests often catered for in the professional market, provided you know where to look. But the downsides are becoming increasingly apparent too. Choice overload is stifling and leaves people feeling trapped. If you’re a student with a broad range of interests, how do you know if you want to pursue photography or science, move into politics, start your own business or pack it all in to open a beach bar in Tulum? Being able to do everything makes it increasingly easy to do nothing.

The world is getting smaller in that it’s more connected. Digitalization of the social and professional spheres have led to work and social practices that are sometimes unrecognisable compared with even relatively recent history. Practices of the 1990s are starting to earn their stripes as relics of a previous century.

Social media has had the most obvious impact – on professional regret, especially. Being able to witness the lives of celebrities or successful friends play out in real time on your phone is the masochist’s lifeblood. It is the actualisation of how you tell yourself the other half lives. From the discomfort of your sofa, you get to compare your reality to other people’s highlight reels, and tell yourself that if you’d played your cards right, it could, instead, have been you in the newsfeed, boasting to the jealous masses or cashing some indiscreet check for that sweet #Ad money. Social media and choice overload, paired with more the traditional shackles of work-life balance, financial considerations and good old-fashioned imposter syndrome, have led to a collective malaise, where even relative high-flyers spend their days obsessing over the lives of those one rung higher on the ladder and bemoaning their own shortcomings. Marlon Brando’s iconic words of defeat from On the Waterfront3 now pour from the lips of each and every middle-management yuppie and should-have-been-a-singer CEO across the land: “I could’ve been somebody.

It won’t surprise you to learn that dedicating your actual life to lamenting an imaginary one is not a recommended route to happiness or success. But given our propensity to yearn for greener grass, how do we better manage such thoughts so that we’re not derailed by them, or indeed are able to channel them into something useful?

Managing existing regret

There are a variety of techniques you can use to counteract professional regret. Some involve processing the thoughts in a different way, such as through mindfulness – accepting that the thoughts are thoughts and nothing more, and returning to the present before you spiral off and tumble down the rabbit hole. Alternatively, you could shift your perspective, adopting a more positive approach. Our thought patterns are not fixed; our brains can be trained and altered until we’re able to wield them more effectively. Try reframing negative ideas, such as replacing “should haves” with positive “what ifs”4. Rather than hitting the brick wall of “I should have never chosen this career”, you can say “what if I chose this because I was once passionate about it and I simply need to relocate what it was that drew me here in the first place?” Or “what if I took the skills I’ve gathered in this role and applied them to something I’m more invested in?” There are endless options, but turning dead end negatives into positives that offer options is a good place to start.

Another useful solution is crafting5. Crafting involves adapting your work role based on your existing skills and passions. In other words, rather than leaving your job for some other career that might suit your skillsets, adjust your role so that you’re utilising the many facets you bring to the table. Are you a budding writer stuck in a job that’s pure numbers? Offer to write a regular blog for your company. Are you a people person whose only interactions are with computers? Ask if you can get involved in client calls or join internal meetings. If you have something to offer, it will quickly become apparent, and you’ll not only feel more valued but like you’re being properly utilised rather than hiding your light under a bushel.

If you’re in a management position, it’s important to be on the lookout for hidden skills your team might possess. Maybe you’re looking to make an in-house corporate video and discover that rather than hiring a third party agency for twice the price, you have a co-worker who has spent his weekends shooting and editing short films for years and is looking to make more use of these skills in his day-to-day life. You never know what other lives lurk beneath your colleagues’ corporate veneers.

Mitigating future regret

Forbes6 cites a study from the journal Emotion7 which found that humans are most inclined to regret things associated with opportunities. Meanwhile a separate study8 found that 78% of people wish they’d taken more career risks. If you’re in the fortunate position now where you’ve been offered a grand opportunity and are considering taking a big leap but have trepidation, it’s worth thinking about your future self. Are you the type to spend the rest of your life wondering what might have been if you’d accepted? If so, wouldn’t it be worth finding out, or at least exploring the option thoroughly so that, should you turn it down, you can take comfort in knowing that you gave it due consideration? Trying something new is a scary prospect. But weighed against the possibility of a lifetime of regret, its fangs might lose a bit of their bite.

Which is not to say, of course, that the risk will pay off or that there won’t also be the other regret – what if I’d stayed? But even if it all goes wrong, rather than dwelling on what could have been, focus on what you can do now. Get up, dust yourself down, and go again. The Japanese have a name for this level of resilience: Nana korobi ya ok9i. It translates to “seven falls, eight getting up.” It’s the old Rocky Balboa motivational treatise: “It ain’t about how hard you hit, it’s about how hard you can get hit and keep moving forward.”10 If it’s good enough for Sylvester Stallone…

If your professional regret boils down to the fact that you really are in the wrong career, it can be tempting to start thinking that it’s all too late, especially if you are of an older generation, but that simply isn’t true. Experience is experience, even if it’s in a different field, and many of the traits we associate with getting older – caring less of what others think, having a better idea of your own mind and less fear of failure – are all positives.

Don’t fret about regret

Professional regret is commonplace. It’s human nature to ruminate on the roads not taken and the advent of social media has only served to pour fuel on an already raging fire. With the right perspective, however, and through crafting and personalising existing work habits, it’s possible to make your current role more satisfying and temper some of those multiversal ponderings. If you’re truly dissatisfied, it’s never too late to make changes. But first, give a fair assessment to your reality. You may come to find that the real grass beneath your feet is greener than you thought, and certainly offers a more solid standing than its fictional counterpart on the other side.7