It's time to rethink boredom, procrastination and regret

The Guardian

15-02-2025

We all procrastinate, but most conventional advice for conquering it doesn't work, at least not for me, beyond chores like cleaning the kitchen or going to the gym or getting my tax return in on time. It certainly doesn't work for the kind of procrastination that has obstructed my best life: swerving that relationship I craved; postponing for years a book on the philosophy of love that I yearned to write before finally putting pen to paper; failing to pursue the hobby – piano playing – to which I've been devoted since childhood, while my piano sat in a corner, closed and silent.
It's no use being told by self-help books to formulate my top priorities when I already have core goals that define who I am or want to become. Or to be urged to break up tasks into bite-sized steps, with a deadline for each step, because how does that work when it's a relationship or a vocation that I'm avoiding? Conventional advice says I should forgive myself my paralysis rather than beating myself up about it but, soothing as this is, it doesn't magically give me either the focus or the energy I need to fulfil those prized goals. I can remove external distractions, especially online access, but what am I to do about distractions inside my head: fantasising, say, about a holiday or a romance as an escape from the task in hand?
When the philosopher Augustine (354–430 AD) begged God to grant him 'chastity and self-control, but not yet,' he, too, wouldn't have been helped by, say, Cal Newport's core recommendations in Slow Productivity: 'Do fewer things', 'Work at a natural pace', and 'Obsess over quality'. Augustine knew exactly what his top priority was: to abandon sensual pleasures for a life of total devotion to God. His problem wasn't doing too many things, a manic work schedule or poor quality. Rather it was that he couldn't unleash his inner motivation to live his best life. And so he was putting it off, helped by procrastination's crucial illusions: that deferral is always temporary and that nothing decisive will be lost by it.
When it comes to avoiding, resisting, even sabotaging our highest priorities, we need a very different approach to conquering procrastination. First off, let's realise that a priority's very significance – it is our ticket to a meaningful life and self-esteem – can paralyse and overwhelm us. So why not imaginatively lower its stakes and think of it instead as our favoured displacement activity, there to sneak off and have fun with while we sideline everything else?
Then let's reimagine our priority not as grim slavery to a maximally successful life, as if we're machines to be optimised for efficient productivity, but rather as play. By play I mean an explorative, joyful mindset by which to loosen those paralysed cogs of our mind, releasing it from servitude to the managerial dullness of the to-do list mentality and allowing it to move nimbly. Play is a way of becoming open to new ways forward, new ideas, surprise. It's entirely consistent with clear goals, tight focus, hard work and ambition. Which is surely why, historically, the spirit of play has catalysed so many innovations, from 9th-century Baghdad, where far-sighted engineering breakthroughs were developed that, centuries later, fuelled the west's industrial revolutions, right up to today's digital and AI revolutions. It's why corporations such as Google and Nvidia cultivate an environment of free-wheeling exploration. When dull, dutiful routine is bogging us down, the spirit of play can be just what's needed to break the logjam.
But if neither the spirit of play nor lowering the stakes of our priorities suffices, then it's time to harness the creative power of regret and boredom – two emotions abundantly created by procrastination and often, wrongly, seen as entirely negative. Yes, they can further paralyse us procrastinators, corroding our self-esteem and wasting our one shot at living. But sometimes the message they're sending us isn't to try again and try harder. Rather it's that our ambitions are unsuited to us, even when they're strongly held. Or that how we're pursuing them is unthinking and ossified by routine. Or that we're not yet ready for them; for it can be perilous to come too early to, say, our vocation or an important relationship. In other words, regret and boredom can turn procrastination into a blessing: a rebellion against stale priorities and soulless routines; a life-giving refusal, arising deep within us, to go on as before.
The 19th-century philosopher Søren Kierkegaard describes how regret fuelled, but was eventually key to resolving, the greatest dilemma of his life: whether or not to marry Regine Olsen, whom he loved. One of history's great amorous procrastinators, Kierkegaard discovered he would regret it if he married Regine and regret it if he didn't. No sooner had she accepted his proposal, after a three-year courtship, than he panicked. Gradually, however, his regret afforded him deeper insight into who he was, propelling him to the wrenching decision to forgo the woman he loved for his vocation as a writer – a vocation he came to believe was incompatible with the duties and responsibilities of marriage. He learned how regret's clarifying pain – its tremendous power to make vivid to the mind's eye what is lost by pursuing one life priority over another – can impel us to choose and then to live our choice authentically and to the full.
What, however, if we successfully choose a course in life, or accomplish a long-cherished priority, yet we soon feel empty, unfulfilled? We're besieged by that fatal little question, 'So what?' – fatal for procrastination because it leeches all motivation, as the great Russian writer Leo Tolstoy discovered at age 50, already world-famous and with timeless novels like Anna Karenina and War and Peace under his belt. 'Well, fine,' the question whispered to him, 'so you will be more famous than Gogol, Pushkin, Shakespeare, Molière, more famous than all the writers in the world, and so what?' In the face of inevitable death, Tolstoy agonised, what is the greatest success worth?
If that question can paralyse a driven superachiever like Tolstoy, it can paralyse any of us. How then can we recover our motivation?
To start with, by abandoning our expectation of stable fulfilment. The reality is that fulfilment – like most pleasure – is temporary. Our memory is remarkably poor at retaining the experience of it. Nor can we ever know – as the 'So what?' question assumes we can – what exactly our achievements add up to or how and whether they'll endure. Like Tolstoy, none of us can sum the net value of the meanings, delights, fulfilled desires and other outcomes we've secured on just one of our top priorities, say being a writer, a parent or a charity worker. Let alone across all of our top priorities.We can't even know to what extent we've fulfilled our potential, because the very idea that we each have a fixed potential waiting to be fulfilled (or, even if we do, that we could know when we've attained it) is probably an illusion.
What really matters are the delights of the journey. Shakespeare's Cressida surely expresses this when she says: 'Things won are done; joy's soul lies in the doing'; as does a remark attributed to Confucius: 'Roads are made for journeys, not destinations.' A well-lived life is one where we richly employ our energies and talents in the activity of pursuing those ends we most cherish.
What then of death annulling all our achievements, which was at the heart of Tolstoy's paralysing nightmare? How do we stop that thought from miring us in procrastination? The answer, ironically, is by diving deeper into death's reality. Here we need to learn from the experience of so many of the incurably ill who, alongside fearful uncertainty, discover thrillingly fresh vitality, clarity of purpose and joy in life, whether in its most routine moments or its largest priorities. These brave people teach us that nothing can commit us more powerfully and meaningfully to the people and projects we love than truly experiencing ourselves as mortal.
But this requires us to go far beyond 'mere acceptance that we'll eventually die', transience, or the shocking brevity of even a long lifespan – acceptance that remains too abstract to motivate us more than sporadically. Instead we need to attain a deep awareness that death can arrive at any moment. To achieve this awareness, those of us who have no experience of a terrible diagnosis will need to use that most powerful of all motivators: our imagination. For the most vivid possible relationship to our mortality is the key to rediscovering the living force of our hopes and commitments, and so to conquering procrastination.
High time, therefore, for me to get back to the piano. To reimagine it as my favoured displacement activity. To enjoy it as disciplined, goal-driven free play. To learn from my boredom with my own playing. To delight in the beauty of sound right now. And above all, to realise that life could be over in just a minute.
Jump! A New Philosophy for Conquering Procrastination by Simon May is published by Basic Books at £16.99 on 25 February. Buy a copy for £15.29 from guardianbookshop.com