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This is what I see with people who are uninspired - they think they're going to fix that problem by doing a careful search of what might inspire them. Then, once they find it, they'll take lots of action.

Nope. That's backwards.

[...]

I decide to try a really good crack at painting... and... well, it wasn't for me.

What?

Well, I learned that to be a decent painter, you need to know how to draw, and I just don't like drawing very much.

Ah, don't get me wrong, I like and respect people who can draw a lot. I just don't really get any pleasure or inspiration out of working with pencils, and the fine level of detail of it.

But both of these outcomes only emerged from action - I had this vague thought that maybe I want to be a painter, but I was never really excited about it until I did it, and then I saw a couple sparks of inspiration and passion starting to grow. But when I investigated what the training would be like and started learning how to draw, it didn't really resonate with me. There's lots of things I enjoy and think are worth pursuing, but the time I'd have to put in to learn how to draw and paint, I didn't think would be worth putting in.

And I think that's how you discover passions. Take a crack at it once and see if you like it at all. Then start studying and improving your craft, and see if you like that too.

Writing did resonate with me with me when I started, but more importantly, I also enjoyed the process of improving my craft and skill at writing.

In business and life-in-general, I love taking a really complex problem, defining it, figuring out what the real objectives are, brainstorming through a number of paths that could get there, spec'ing out a campaign, implementing the campaign, and reviewing the results. I like taking the hazy and undefined, and turning it into the experimental, and turning the experimental into the concrete.

Well, that's pretty much the definition of a strategist...

But what little kid says, "When I grow up, I want to take hazy problems, define the problem and desired outcomes, experiment to see if a proposed solution gets the desired outcome, and implement it" - well, nobody thinks like that. I only discovered it by applying myself, working on different stuff. I love when I read a book on something like knightly orders in the 1100's, and it gives me an idea for something a business can do in 2011 to grow.

But who would've guessed they'd be passionate about that sort of thing without diving in? Nobody.

So that's the first thing I think about passion - it doesn't come from sitting and thinking about it, it comes from diving in and getting dirty.

What OP needs is mechanisms for generating the desire to pursue some good goal. Off the top of my head, both travel and psychedelics seem to have nontrivial rates of inducing new goals/dreams.

That's all true, but I think that the problem for the OP is generating goals/dreams that fit inside the constraints of his life. Once you have your own family and kids the range of (non-drastic) things that you can do narrows considerably. Things like going off to live on a Polynesian island for a while, or, say, deciding to become a starving artist and create ART in capital letters -- all these become... problematic.