One problem with trying to improve your life is that, all too often, the improvements you’re attempting have little to do with your life. That’s especially obvious when, say, you seek to emulate the extreme fitness routine of a high-profile influencer, overlooking the fact that he or she has a team of assistants to free up all the time it requires. But following the advice of the average self-help book is unlikely to work much better: no matter how wise or sincere its author, it’s vanishingly unlikely they’ve ever met you. Even when a plan for change seems to arise independently, from inside your own mind, it usually takes the form of a fantasy about the person you think you ought to be, or would like to be, into which you then try to squeeze the person you actually are – for a few days, anyway, until the struggle becomes so frustrating that you give up in despair.

This is where the questions in this series come into their own. They’re asked by people with expertise in the fields of relationships, career, health, home organisation and more. But they can be answered only by the person who possesses by far the most detailed understanding of what might genuinely make a difference in your life, which is you.

The notion that questions might be more powerful tools for self-transformation than off-the-shelf advice implies a specific view of human psychology: that most of the time, somewhere deep down, we already know what we want or need. Maybe that’s why books and articles that merely rattle through the ingredients of a happy life – close relationships, time spent in nature, plenty of physical movement, etc – so frequently seem to fall flat. Nobody really needs telling that these things matter. The issue is how to address the unique set of hang-ups, character traits and personal circumstances that always seem to stop you putting them into practice. And the trouble is that the answers usually lie outside consciousness: the conscious part of the mind, as the Jungian therapist and writer James Hollis puts it, “is at best a thin wafer floating on an iridescent sea”. But the right question can dredge that wisdom up to the surface. Your answers to the questions that follow might surprise you; perhaps you’ll conclude that you don’t need to reduce the clutter at home, or that your marriage is healthier than you’d realised. The fact that it’s even possible to surprise yourself like this proves the point: there’s some wisdom you know, but that you don’t necessarily know that you know.

Sometimes, a good question works by conjuring a parallel universe, permitting you temporarily to change the rules by which you engage with reality. This is the value of classic self-help prompts such as, “What would you do if money were no object?” or, “What would you do if you weren’t afraid?” The point isn’t that money won’t ever not be an object, or that you’ll succeed in abolishing all fear. It’s that by setting these buzzing anxieties aside for a moment, you get to hear other parts of yourself. If you discover that in the absence of financial worries you’d write songs all day, that’s critical data – not because you should give up the day job (that could be the case, though it probably isn’t) but because if you can find even 20 minutes a day for songwriting, you’ll be amazed at how much more enriching life becomes.

A related sort of question helps us bypass the misleading or superficial factors on which we tend to focus when deciding how to spend our time. Confronted by a significant life choice, I’ve long relied on a question Hollis recommends: is the path I’m on, or the path I’m proposing to take, one that enlarges or diminishes me? It’s frequently impossible to say which of two options is the “best” or “right” one, or even which is more likely to lead to happiness. But it’s often surprisingly easy to know, on an intuitive level, which is the path of “enlargement” or psychological growth. For different people, or at different stages of life, the very same external action – moving to another city, say, or beginning to look for a new job – could be an act of courage (which is enlarging) or an act of avoidance (which is diminishing). Hollis’s question can help you determine which is true for you.

Ultimately, the purpose of any good question like this is to redirect your attention away from escapist fantasies and back to the reality before you – which is the only place, after all, where real change could ever actually occur. I love the Zen Buddhist and chef Edward Espé Brown’s favourite question for prompting deeper engagement with the world: “What have we here?” This embodies the attitude of the person opening the kitchen cupboard at 6pm on a weekday, to see what they might rustle up for dinner. But it’s an attitude worth taking to pretty much all of life. Suppose you’d like to exercise more in 2025. All right: what have we here? A daily school run; a packed work schedule; perhaps a longstanding and seemingly intractable difficulty in getting up early. So maybe four 90-minute trips to the gym aren’t the place to begin. What about a brisk walk, dailyish? It’s tempting to dismiss this as taking the easy option, but it isn’t. Frittering your time away on daydreams of the perfect workout routine is the easy option. Facing the reality you’re in, and asking what you could start doing today, is the bold and empowering one.

Something similar is true, incidentally, when it comes to the longing many of us feel to do more about the multiple crises engulfing the world. Doom-scrolling through global climate data or news of international conflicts might feel like doing something, superficially, but we all know it doesn’t count. Instead, look at your reality, which extends far beyond your phone. What have we here? A local group that could use your volunteering, possibly; a sum of money you could afford to donate; a flair for graphic design, or organising events, or anything else that might be the beginning of something real.

In other words, the right question meets you where you are – which includes not just your external surroundings but your internal moods and emotions, too. Conventional approaches to self-change often involve attempting to suppress what you’re feeling, so as to stick at all costs to a plan. But how’s that working out for you so far? In her essay Learning to Work, the linguist and feminist scholar Virginia Valian describes being unable to make progress on her PhD thesis, thanks to paralysing anxiety, until she began asking herself how much time she’d truly be willing to give it each day. Three hours? “The very thought gave me an anxiety attack.” Two hours? One? Still impossible. Moving ever downwards, she eventually reached her point of willingness: 15 minutes. “A nice solid amount of time, an amount of time I knew I could live through every day.” People laughed at how little it was, but all that mattered was that it worked, and that later she could gradually increase it: she was up and running again. Frankly, even a single minute a day of actual work, never mind 15, would have counted for more than all the hypothetical hours she might have told herself she ought to be working.

And the questions need never stop. In a famous 1903 letter, the Austrian poet Rainer Maria Rilke urges a protege of his to “be patient toward all that is unsolved in your heart and to try to love the questions themselves like locked rooms and like books that are written in a very foreign tongue … The point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.” His words capture the sense that asking questions is a way of living, complete in itself – not merely a preliminary step before you finally get life figured out. History records no instance of anyone ever getting life finally figured out, so it’s probably best not to stake your happiness on achieving that yourself. All you need is the next question, then the next, and the next …

Meditations for Mortals: Four Weeks to Embrace Your Limitations and Make Time for What Counts by Oliver Burkeman is published by Bodley Head. To support the Guardian and Observer, order your copy at guardianbookshop.com. Delivery charges may apply.