Question:

Especially on the upper-echelon levels (Magnum). It seems that all these photographers are perpetually dissatisfied (in a pessimistic, bad way).

Certainly happiness isn't the end of life, but it is a good stimulus for our photographic progress. Some thoughts:

The first thought:

I say social media. Practical via negativa thought:

Do numbers exist for the sake of humans, or do humans exist for the sake of numbers?

The algorithm don't have the answers. An algorithm is simply an equation in which a (often very nerdy) individual creates weights to say:

For example on social media, to get more likes and followers is the apex. It goes to the American attitude:

But is this true? No. Otherwise McDonalds would be the #1 Restaurant in the world. Or a Honda Accord is probably the 'best' car. But what do we desire?

Certainly we first strive to impress ourselves, then others (a small group of others). For example, when I did a Magnum Workshop with David Alan Harvey and Constantine Manos, I will never forget:

To me this was worth 100000x more than getting a trillion likes on Instagram or Social Media.

So the question:

It seems we only want to impress our equals. This is why I don't really care for the critical feedback of my street photos from non-street photographers. Similarly speaking, better to impress 1 Magnum Photographer than 1 billion random people online.

It is a lie to say that we don't care what others think about our artwork (photos). Rather, we want to figure out who are the few people we are trying to impress.

What is happiness? It is a sense that we are progressing and advancing. For example, who is happier?

The fall hurts 1000x more than the come-up. This is where the notion 'ASAP' (always strive and prosper) is good. And the notion 'Stay hungry, stay foolish'.

Once you lose your appetite for growth and progression, then what? Nothing.