Chess grandmaster and author Jonathan Rowson on dignified regret

In a world awash with stories of success and failure, we seem remarkably incurious about how it feels to experience both at the same time.

Two thirds of competitors on Olympic podiums gave the best part of their lives to get painfully close to Gold. Writers of exquisite prose take decades to master their craft but fall short of prize longlists. In almost any human endeavour the exceptional performers receive lavish attention, while an army of the frustrated excellent fade into the distance.

Few successful people are resolutely fulfilled. More often, success is laced with failure, but we appear to have few cultural resources to explore that state of mind.

I am a three-time British Chess Champion (2004-6) and a chess Grandmaster, which is the highest formal international title obtainable other than World Champion. There are about 1500 Grandmasters and my highest world ranking was 139 in 2005, when I was twenty-eight. I stopped competing seriously around 2008 while becoming a father, and built a career outside of chess.

Life has been kind.

But I did not fulfil my chess potential. And it still hurts to think that. I cannot shake off the notion that I could have climbed higher in the status charts; perhaps even the world top fifty, and rarely does a day go by when I don’t briefly think about that unlived life.

There were limits though. I always knew I could not go all the way to the summit. In my games against world champions and their contenders my inferiority was palpable; they had consistently better and quicker judgment, and more fundamentally, none of my doubts about playing chess as a worthwhile way of life.

So my regret is suffused with relief. I might have climbed a little higher, yes, but I could so easily have squandered my life as a hungry ghost, hostage by 32 pieces and 64 squares forever.

Yet I find that my regret does not want to go away. Perhaps we need some regret in our psyches to keep hubris at bay, and to act as an essential adhesive in our fragile self-creation process. The story of who we are does not ring true without at least a little pain at the thought of who we might have been instead.

If we are not careful, however, the associated feelings of envy and inferiority can curdle into a kind of shame. When our identity is wrapped up in being the best we can be at one particular thing, knowing that others are unambiguously better can contaminate the soul. One cultural reference point for this kind of experience is the composer Salieri, who drove himself insane through his envy of Mozart.

I strongly believe the emotional equilibrium we need to cultivate is successful underachievement – the hard-earned experience of dignified regret and acceptable inferiority combined with a forgiving conviction that we make the most of our potential in the full context of our life.

Successful underachievement is not about settling for mediocrity, but pursuing a wiser path to excellence. Our underachievement becomes successful whenever we put achievement and the striving it engenders into some larger perspective beyond winning and losing without disavowing the value of competition.

The Zen saying that ‘eighty percent is perfect’ captures this notion. To strive for perfection in one particular thing is admirable, but to accept the imperfection inherent in our striving nature is more admirable still.

The taste of paradox in that expansion of perspective is challenging in a culture shaped by the competitive tenor of politics, economics and sport reporting; where winning seems to be what life is all about. In that context, it is easier to downplay the importance of goals or to imagine they might yet be achieved than it is to accept what is more often the whole truth: yes, my goals mattered, and yes I only partly succeeded, so it is true that I failed.

That realisation, however, is a deeper kind of success. It is only because we are capable of living as if our success and failure really matter that we can enjoy achievement. But a growing awareness of the nature and purpose of that ‘as if’ phenomenon is precisely what allows us to see competitive achievement for what it is – a true fiction.

Rather than explain our underachieving away, we are better advised to ease into the discomfort of it, and look it squarely in the eye with an increasingly knowing smile. Only after we have done all we can to satisfy the ego’s craving for validation are we justified in turning the pain of our inevitable failure into a justified insurgency against the sovereignty of the ego.

The way out of ego pain is to see what we are experiencing from more profound vantage points. It is possible to stop being our regret and instead adopt it as something we have that is uniquely our own. Successful underachievement relies on making peace with what is troublesome, and the kind of deep mutual understanding we can only have with former enemies.

I think the idea of successful underachievement matters. I don’t know how else to make sense of succeeding while failing without lying to ourselves. We need to make peace with ourselves as beings blessed to strive and condemned to fail. As Francis Spufford puts it: ‘We are a work in progress. We will always be a work in progress. We will always fail, and it will always matter.’

Jonathan Rowson is the author of The Moves that Matter: A Chess Grandmaster on the Game of Life, published by Bloomsbury. He tweets @Jonathan_Rowson