We philanthropists have it hard. For having decided we love humankind, we are forever burdened by the question, "how much?"

--Gordon Sherman (my father)

I live torn between two devotions. First and earliest, I’m a philanthropist, meaning literally that I love humans (phil=love; anthropos=humans).  And of all humans, I love myself most compulsively (Sorry, I can’t help it — I tingle most vividly when I’m pleasured, not when you are, and sting most piercingly when I’m cut, not when you are.)  

As a philanthropist, I like to keep myself happy, encouraged, enthusiastic about being me among us, which entails me staying loved by other humans, or at least the ones who love me back.  I give philanthropically of myself, because I genuinely love people and because I love myself when I do.  

But I’m also a philosopher, literally a lover of wisdom (phil=love; sophy=wisdom).  What is wisdom?  It’s facing as squarely as one can into reality as it really is, regardless of whether it makes me and us happy, encouraged, and enthusiastic, and keeps me loved by other humans.

Affectionate people are my daily bread and butter, and I pray to them that they give me this day my daily dose. So of course, I’m inclined to say what pleases others, to form mutual admiration in societies, to bite my tongue about anything that would bite the hands that feed me the affirmation I crave. 

Still, I can’t afford to veer too far from wise assessment of reality, or it will ruin me.  Too much wishful thinking of the sort that merely keeps me cheery and cheers the people I love, will fly me blind into brick walls.  Indeed, too much people-sparing positivity ultimately hurts humankind.

So you see my predicament.

How do I handle it?

I check Facebook too often, but drag myself back by the collar to disciplined solitary research. Little by little and never completely, I learn to live with the disappointment that comes of losing friends who feel discouraged by my best guesses at wisdom. I end up with friends who are like-torn between philanthropy and philosophy.  I cultivate a loving community of those who especially strain to keep their philosophy growing, despite the disappointments that reality checks bring.

I make slow and incomplete peace with the ends of friendships with people who seem only philanthropic; the positivity police who, it seems, would sacrifice wisdom entirely to protect their tenuous love for themselves and the company that keeps them.  

I keep alive my curiosity about whether I’m just a cranky curmudgeon, because some people are, and there’s no reason I couldn’t be. People who claim they’re “just being honest” when they take down their fellow humans, as though we wouldn’t also be motivated to lift ourselves up by putting other’s down, seek self-affirmation by other-disaffirmation. But I don’t believe it every time someone accuses me of doing that, because accusing those who disappoint of “just trying to disappoint” would be the first line of defense for the positivity police.  

I look for the sweet spot overlaps, the insights where philanthropy and philosophy converge on what’s both kind and true, affirming and honest, encouraging and realistic.  But I try to take care about the order in which I find such insights, not starting with my hopes and looking for tru-ish rationales that might support them.  Rather I’d want to start with best guesses at truth and try to find what’s encouraging and useful about them.  

And I think a lot about the tension I live with, that I think we all should live with, between saying what’s locally affirming and saying what’s truer and therefore more likely to help us in the long run.

I watch with interest two opposing kinds of paradoxical strategists, those who argue unrealistically that people just want you to be real, and those who argue realistically that people just want you to sell them on wishful thinking. They’re both right. And both wrong. 

And I meditate on the paradoxical realism of unrealism, the real need for optimal illusion. Realistically humans need each other and therefore, honestly and wisely we have to be sparing with each other. But not too sparing. 

This article was in part inspired by Rebecca Goldstein's book, Plato at the Googleplex which revives my admiration for the loving, arduous pursuit of wisdom as exhibited by Socrates, even at the cost of his own life.  

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