Unnamed Document

May 22, 2025

Highlights

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’.


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.


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.


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.


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.