Hmm, it sounds little like you're looking to understandably come to terms with how your life has played out. I guess we all do that.

But my issue is that you've never had a wildly successful run in your career, and that if you do, that this framing might change completely.

I was in a similar boat, jumping around jobs, and then found a mission driven 'dream job' before being disillusioned with it's imperfections, and shortly thereafter realizing that it wasn't a dream job at all. So I left and went into another industry, this time focused on the rat race.

It's changed me, and the way I view things and myself, for the better I don't know, but I certainly see that the way I viewed my dream job was largely a way to justify it's shortcomings. Im about to swap to yet another role which pays $160k more than my "dream job" and finally I can take a second to consider what the "dream job" really is if it exists in even a momentary stasis.

My dream job was to teach btw, and have seen so many people demoralized. I hope you stay the course and find further fulfillment, but I would bet on the contrary in the long run.