A few days ago, we had some questions about "idiot compassion," and how to tell it from real helpfulness. Idiot compassion is a useful phrase, but I think it's important to point out its limitations. It can be seen as a synonym for "niceness," or as "enabling." We like this idea in the West--I think we like thinking that Buddhist practice is not only making us more compassionate, but also smarter at being compassionate. The phrase "idiot compassion" was coined by Chogyam Trungpa Rinpoche in the late 20th century. It's not found in the traditional Buddhist writings, and it's not really a central part of Buddhist teaching. If you're worried about it, fretting over whether an action is idiot compassion or not, don't. Buddha never said, "Thou shalt never practice idiot compassion."
In Trungpa Rinpoche's use of the word, it was often connected to over-analyzing acts of compassion, or as Trungpa put it, "a highly conceptualized idea that you want to do good." Idiot compassion comes from thinking too much and second-guessing your instincts about the way to help people. Someone who's failing a class asks you to help cheat on an exam, and your instinct is not to cheat--but then you get a concept of being seen as helpful and likeable, and the would-be cheater is begging, and you give in. It isn't helpful.
But I think we're also lacking in real compassion. I replied to the original question with an example about my six-year-old niece, who wanted help blowing up a balloon. If I over-analyzed it, I might stop to think whether balloon-blowing was the best use of resources, that maybe a more compassionate outcome would be had if we put the time, energy and money that would have gone to the balloon and put it into her college fund. But in her world, a balloon was important. It was exactly what she wanted. And by helping her with the balloon, I showed her that what is important to her is important to me. I am on her side.
Maybe it's wise sometimes to give dignity and worth to others, especially if they haven't been given much of it. Sometimes if a beggar asks you for money, even if you know the money will be spent on cheap liquor, you might say, "What's important to you is important to me. If booze is what you want, then booze is what I want you to have. I'm giving you the power to make that choice."
It becomes idiot compassion when we institutionalize it, and do it without mindfulness. If one day, your child wants a chocolate bar for breakfast, you might say with kindness, "Just this once, a special treat for you." But if you allow it day after day, it's not good for them, and not compassionate. That's the idiot compassion that Trungpa was talking about.
Through practice, we develop wisdom, and wisdom helps us make good choices. Until then, I'd say just work on being more compassionate. If you're still an idiot, just work on being a compassionate idiot. That's the best start.