Most people read such articles and come away aspiring to be more like the person described in it. What Jack Dorsey has done is amazing. It shows what's possible when someone is really driven.<p>I worry about how Jack feels. Is this a happy, content guy? It's certainly possible, but I thought I'd offer a slightly different perspective, based on the work I've done with people like this.<p>The impression from the outside is that they are on top of the world. The private story is often very different. Usually there is a huge drive at play in order to compensate for something else that is lacking inside.<p>You can look at it this way: One would get the impression that this person is extremely content because he is starting the biggest companies, driving a BMW, wearing the latest and best Prada clothes and Rolex watches. The implication is that by having, doing, and being the best, that person feels best internally. But if you needed all that in order to feel good, then the other 99.999% of the world would have to feel absolutely miserable. This is where the logic of the implication breaks down, because that is simply not the case.<p>The other way to see it is that one success is never enough. Neither are two. Or three, or four. The sense of having 'arrived' (finally being satisfied, approved of, secure) never comes. Even if the current endeavor becomes the biggest success, as soon as it's checked off, so to speak, a big sense of disappointment will follow, which will re-create the need to prove it again. So here too, it becomes clear that the external successes have almost nothing to do with how the person feels.