Before diving in this week, I’m delighted to let you know that the paperback edition of MEDITATIONS FOR MORTALS is out in the UK next Thursday, with a beautifully reworked cover and also… ads on the London Underground! (So I guess I’m going to be spending some time loitering around the Tube.) As you may know, pre-orders make a huge difference to a book’s success, so you’d have my immense gratitude if you decide to pre-order from wherever you buy books, or from Waterstones, Amazon, Bookshop.org or another retailer here. Readers of the Imperfectionist can also get 25% off tickets for the launch event I’m doing with Tim Harford and Intelligence Squared next Tuesday in London by clicking here. Thank you so much for your support – Oliver

Be a disappointment

The older I get, the more convinced I become that it’s a critical life-skill – at least if you’re roughly the sort of person I am – to get better at disappointing other people.

I don’t just mean you should go easier on yourself when you catch yourself feeling bad for falling short of others’ expectations (although you should do that, too). I mean that it’s worth deliberately and consciously practicing disappointing others, letting the associated feelings sink into your bones, and generally spending time hanging out in the space of ‘being a disappointment’.

For example, you might set the intention to disappoint at least one person, in some real way, over the next 24 hours. Try it! You’ll probably hate it. But maybe you’ll also find, as I have, that the more comfortable you get with the risk of disappointing, the better things go on all fronts: the more vibrantly alive you feel; the more meaningfully productive you get; and the more engaged you become in your roles as partner, parent, friend, citizen of a world heading to hell in a handcart, and all the rest.

You’re especially likely to benefit if you belong to the category of people psychologists call “insecure overachievers”. (At book festivals and other events, it’s always fun to see people’s eyes widen in recognition when I use that phrase.) That is to say you’re the sort who works hard, gets stuff done, and impresses others with your achievements – but that to some degree, for whatever combination of reasons to do with upbringing, culture or DNA, you do it all because you feel that otherwise you won’t quite have earned your right to exist on the planet.

Accomplishments that ought to be a source of delight – good grades, promotions, professional success – can feel ironically oppressive to insecure overachievers, because once you’ve meta standard like that, it becomes the new minimum standard you’ve got to meet, next time, in order to carry on feeling adequate.

If any of this resonates, I have two main pieces of advice. One is to watch the gut-punchingly perceptive Disney movie Encanto, which was written for you – but that’s a topic for another newsletter. The other is to get better at disappointing people. And one main way to do that, of course, is to say no: to decline things, to politely refuse what’s demanded of you, or sometimes not to engage at all. And then to discover, time and again, a) that you can handle the feeling that someone might be judging you negatively, without it completely destroying your life and b) that most of the time, they weren’t making any negative judgments anyway.

It can help here to remember the concept the psychotherapist Alfred Adler called “the separation of tasks”, which features centrally in the recent bestseller The Courage to Be Disliked (though the idea crops up in multiple traditions under other names). The essence of it is that there are a few tasks in life – in work, relationships and community – which are truly yours. Then there are all the other tasks, which belong to other people. And essentially all of life’s problems arise from trying to do other people’s tasks for them, or trying to get them to do yours.

Deciding whether or not to be pleased or disappointed by something you’ve done, or failed to do, is an archetypal case of someone else’s task. It’s never your job to spare someone the experience of disappointment, provided that the action that triggers it is, in other ways, the right one to take.

It’s probably worth saying that none of this has anything to do with behaving selfishly or with high-handed disregard for others. If you’re a moderately well-adjusted person, the goals you’re pursuing will in some sense be about making the world a better place; and the kind of person you’re seeking to be, in your various roles, will presumably be a generally compassionate and helpful one. It’s just that to do all this freely, enjoyably and well demands that your actions not be dictated by the fear of everyone else’s judgments.

Full disclosure: I still don’t find this particularly easy. From time to time, for example, I get into an absurd tangle with my email that unfolds as follows: first, I get behind on my messages; then, I start worrying that people in my professional circles are getting impatient with me for not replying to their messages; then I begin avoiding my inbox for long stretches, because I fear discovering that someone has indeed become frustrated by my silence. Whereupon the whole thing spirals – because if there’s one way to maximise the chances of someone actually getting cross at your not replying to an email, it’s avoiding email in the first place. And so, in a horrible irony, the more I’m guided by fear, the more justified the fear becomes.

Life goes much more smoothly, for me and everyone else, when I can tolerate the risk of disappointment, check my messages, and say no when appropriate. Or perhaps even read an email and file it away unanswered: that’s OK too, in some contexts! The point is simply not to avoid, for fear of letting someone down, doing whatever needs to be done then moving on.

(Although please let’s not get into some twisted email-related psychodrama here, where you refrain from replying to this newsletter because you don’t want me to feel bad for not having the bandwidth to write back. Being willing to risk your disappointment is my task. No need for you to try to handle it for me!)

From one angle, all this is just a useful mindset for protecting your time and getting better at saying no. But there’s something more profound to it as well. Disappointment feels close to the core of what it means to confront the truth about human limitation. After all, it’s because our time and attention are limited that we can’t please everyone. And the ceaseless sacrifice of alternative possibilities demanded by our finitude is nothing if not disappointing.

And so the more I’m willing to experience disappointment, and to risk disappointing others, the more I’m really here, feeling the full poignancy of my situation. Accepting the place of disappointment in life means falling back down to earth; and falling back down to earth is never going to be entirely pleasant. But it also puts you back in the only place where you can stand on solid ground, put one foot in front of the other, and actually get on with the things you care about the most.