He's in his forties, like me, is rather intelligent (so maybe not like me, who's to say... 
, a bit of a sci-fi/fantasy nerd (a bit like me), and is perpetually on the edge of being dead broke.
He seems to be a typical straight guy in terms of the usual basic reaction to attractive women, but seem so have no interest at all in any sort of relationship.
He's a thin guy, not much for grooming, and smokes, so he carries that funk around with him most of the time.
He accepts people 'spotting him' for a meal when out with the guys and is grateful, but any hint of 'that means you pay me back' gets a little awkward, so those of us who do spot him know that we're picking up the tab and leave it at that.
I'm in a board gaming group of a bunch of 40-ish guys who get together every few weeks for plenty of BS around a table that will feature a few of the latest games to be found among the 'board game hobbyist culture' (try www.boardgamegeek.com for a glimpse of what I'm talking about.) And if the particular friend I refer to ever wins a game, we all try to pretend it's not a major event... He learns rules, can plan ahead, but just doesn't seem interested in winning.
He's not emotionally stunted, so far as anyone can discern. His closest friend, (they go back all the way to grade school) a guy who has made plenty of money in IT through his life, is very politically liberal (except that he's a gun nut and is totally up-front about the irony), has a healthy, well balanced family that he's utterly devoted to, in all the right ways, and recently chucked the IT life to become a H.S. physics teacher (which took a lot of ambition), is convinced that he just plain lacks the basic machinery for initiative.
He's a pleasant person with a healthy sense of humor. And, although we talk a little bit about the jobs he tends to hold down for about 6 months before he 'loses' them and goes through a few months of rapidly depleting reserves before he has absolutely no choice but to track down another job, I know there's no point suggesting strategies for a more stable income-type life. It could be the best advice ever given on the subject and it'd be lost on him.
And as for 'ego,' he does seem to display signs of faux-indignation when someone ribs him, but I've never seen him take actual umbrage to anything said about him. Of course, he doesn't get treated in a way that would elicit that by his friends, but, of course, guys sometimes take things just a bit past the edge, and he's practically immune. It would be like... I don't know, repeatedly kicking a puppy (I don't kick puppies!, just looking for a comparison) that yips happily as you start breaking bones and cause internal injuries. And so you realize that, not only is there no reason in the world to kick the puppy, the psychological harm you would cause to yourself doing such a thing would cause you to stop way faster than any response from the puppy.
And for all that, I'd gladly include him in any sort of 'guy's night' activity. If he gets into real money trouble, I'm among the guys who would (have a couple of times) contribute to the bailout.
And so one thing I've learned about people over the years is that not everyone possesses the essential attributes necessary to 'better themselves' (financially speaking), make or execute long-term goals, or, really, just plain accomplish stuff. Some people are just along for the ride, wherever it takes them.
When I see some asshole bitching about how 'welfare queens' are milking the system, I know one thing - 'miking the system' in the way that they're talking about takes a lot of work for minimal return. And when the target is a homeless panhandler, who apparently only needs people to stop 'enabling' her/him so that there'll be no choice but to get a job, I think (for the very few who aren't crippled by serious psychological or psychiatric problems) that, for the people who really just aren't driven to even modest ambition, the cost among those of us who do have such drives to enable them to have at least a rudimentary level of basic needs met is so minimal that there's no point in talking about disincentives to work, etc.
The other thing I've learned is that ambition and ego often go together, but not always. I know I'd sacrifice my life for any member of my family if it was necessary to save them from serious harm or death. And I've comforted myself a little bit by thinking through that sort of thing hypothetically, the comfort coming from the recognition that hesitation based on concern for my own safety wouldn't be a factor at all. Of course, the probability of doing something like that is minimal in the extreme, but if it happened, my ego wouldn't be involved. It would be an act driven solely by my valuation of someone else's well-being at a higher level than my own. If I, and certainly many parents, grandparents, uncles and aunts, etc., would act almost instinctively based on that comparison of value, how many other things that we do, which don't require such a sacrifice, are also driven by valuation of the well-being of others sometimes at a higher level of ourselves. It happens in war, it must also happen in peacetime and in all sorts of ways.
If you read all of this... I'm really sorry 
Time to get back to work - shouldn't abuse the fact that I'm the IT director of my employer's company...
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