You may have seen the Tao of Pooh and the Te of Piglet, but have you thought about the Selflessness of Eeyore?

Eeyore is most famous for being depressed. If there is something wrong with the situation, he’ll find it. And Ralph Wright (the first actor to play him for Disney) gave him that constant mournful singsong speaking voice.  When Piglet wishes him, “Good morning!” Eeyore replies, “Well, I suppose it is…for some.” To a large extent he makes his own bad luck. He makes a house out of sticks ready to fall down, and when it does, he makes the exact same rickety structure again. As Winnie the Pooh put it in the recent Christopher Robbin movie, “What a gloomy, rainy, day! Pity Eeyore isn’t here to enjoy it!”

And yet Eeyore is also one of the most giving creatures in the Hundred Acre Wood.

When Eeyore loses his tail, Pooh, of course, helpfully offers to search for it. They get to Owl’s house, which is sporting a new bell for visitors to announce themselves. Owl had to show off the bell-rope, which he had just found. The bell-rope, “Looks familiar…” If it weren’t for Pooh, Owl would still have that new bell rope yet. At least in the Disney version, Pooh had to argue Eeyore into taking it back!

Eeyore doesn’t expect anything from the universe but misfortune, and so when someone else needs something, he asks like naturally they deserve it more.

He is selfless.

Rav Shimon Shkop is not a fan of selfless giving, as he writes at length in the introduction to Shaarei Yosher (see Widen Your Tent pg 50-54 for the text with translation, and chapter 4 for analysis, discussion and extrapolation).

Hashem’s holiness, which Rav Shimon defines as a commitment and consecration to provide benefit for others, is indeed Selfless. But Hashem has no needs. We are not like that. The verse says “Qedoshim tihyu ki Qadosh Ani, Ani Hashem — Be holy for I Am Holy; I Am Hashem”. Which the medrash explains that while we are supposed to emulate Hashem’s Holiness, at the end over everything, “Ani Hashem” — Hashem’s Holiness will be qualitatively “above” ours.

Chapter 4 of Widen Your Tent explores these idea in more depth.

We need self-love and self interest in order to be motivated to produce. It is because, as the sages put it, “a person prefers one kav (a measure) of his own making than 9 kav of others'” that we are driven to make. So that if giving starts with self-love, in the end we have more to give.

This is why, Rav Shimon explains, Hillel describes the law of empathy in the negative, “What you loathe, don’t do to others”. Because in the positive, it’s appropriate and healthy to give to oneself. Similarly we follow Rabbi Aqiva’s ruling that if you own a canteen of water that is only enough to keep one person alive, you are not obligated to share it with another.

“Ve’ahavta lereiakha kamokha — Love your friend like yourself.” We don’t give out of selflessness, but out of Chessed / Lovingkingdness. That self-love is grown so that it includes others. As discussed in the next part of Rav Shimon’s introduction (and ch. 5 of Widen Your Tent), this is how it’s easier to give to my wife than a stranger, to sacrifice for my own children more than others, and can be generous out of love. The whole measure of a human soul is how many people are included when they say the word “I”.

Eeyore isn’t giving out of Chessed / Lovingkindness, a desire to share his own happiness with the people (and animals) he feels connected to. He is putting himself last. He is perpetually gloomy and expecting the worst. And he consequently has less to share with them.

Don’t be Eeyore. Love yourself, And then, “love your neighbor like yourself.”