Have you ever been passionate about something, and yet satisfied with yourself in that pursuit?

I don’t think that “deep dissatisfaction” is a driver; rather, people learn because of interest and curiosity.

And expertise arises from continued curiosity about a subject. Indeed, a deep satisfaction from learning a little and wanting to to know a little more makes one continue studying a subject.

Passion, expertise, and self satisfaction are all different.

I am a cyclist, and through the nineties I was quite passionate about it. And I knew I would never be a racer, and that I would never even be the strongest on club rides. Yet I was quite satisfied with my ability and my stamina. And I did have quite a bit of expertise on cycling, enough to advise people on what kind of bike to buy, getting in shape for long distance rides, how to be safe while riding.

I’ve had similar passion and expertise in a number of areas. And I have been satisfied too!

It’s not that “each goal is never enough,” Achieving a goal is a bit of a high, and the person wants that high again.

And the question discounts anything to do with humility. Consider Derek Jeter. He is as passionate as anyone, definitely has expertise, and I would say for the most part he has had great satisfaction. But he is retiring, not because he is satisfied, but because he is humble enough to know it is time to go, that his body can’t do what it did ten years ago.

For the most part I agree with @zenvelo. But at times it’s a little different. With music, I still want to learn. There’s so much I can’t do on the piano that I want to learn to do despite already having a good amount of experience. Yes: It’s curiosity and interest. But I’m not achieving it to get the high that comes with a successful pursuit, I’m working towards it to get the high of being able to play, say, smooth jazz.
I’m an amateur. I do it because it’s fun and I’m always satisfied. This isn’t the case for everything I’m passionate about, though.

I agree with @zenvelo
My passion arises from curiosity and a love of knowledge seeking and creative pursuits.
I am very self accepting and what I do, I do for fun and creative stimulation minus feeling competitive with myself or others. Whatever we do should be motivated by joy not neurotic competitiveness. When we are truly in alignment with ourselves what we do shows up very naturally without contrivance and an egoic need to compete with self or others.

@dxs I have never been satisfied with my musical ability. I probably never will be either.

Bill Gates stepped back from all-consuming passion.

I don’t think “angst” is the human condition. There are unlimited motivators, and as many endings.

“Perfection”, to me, is a better descriptive than “deep dissatisfaction”. The ability to draw the line between “Goal realized” and “Endless second guessing”. An expert painter finishes a wall, an expert painter finishes the house, an expert painter finishes the Guggenheim, an expert painter finishes the Mona Lisa. They all know when to quit, and they all move on.

Dissatisfaction happens when ego gets involved. Here’s how that typically works:

I want to become, say, a skilled potter. I’ve seen skilled potters work, and the process fascinates me. I also love the product: beautiful ceramics. I take up pottery because I imagine being a skilled potter myself and I like the way that feels. I also like the idea of others admiring my pots and appreciating the skill that went into them. I throw myself into the craft not just because I enjoy the process and love beautiful pots, but because there’s potential for enhancing my self-image and garnering admiration. Those are powerful motivators, so I’m passionate (oh, and I also don’t overtly acknowledge this ego aspect of my passion, because it’s a little unsavory).

I get through the initial mucking-about stages of learning the craft, trying and often failing, sustained by the promise of future mastery and its ego perks. Now I’m producing decent, serviceable pots. But when I compare these to what I see more advanced potters produce, I can’t like them. And it’s not so much that there’s a problem with my pots; it’s more that they’re not admirable. They don’t reflect any glory on me, so I prefer to disown them and keep trying for something more praiseworthy.

I’ve observed this process first-hand many times, and it’s true that this can eventually lead to something that looks kind of like mastery. Only that’s not what mastery really is. To get from there to mastery, the ego aspect has to go. There’s no room in mastery for ego.

The Japanese understand this better than we do. It’s why they place great value on work that shows no evidence of ego indulgence. The master doesn’t see himself as a Master (much less relish the role) but more as a midwife, facilitating the fulfillment of potential inherent in materials and processes. Ego involvement only corrupts what should be a quite natural “becoming”.