Well first thing I would look at in this context is the temperament. I follow Zoller somewhat here.
ASC - cold and wet
Moon - cold and dry
Mars - hot and dry
Jupiter - wet
H - 1 (but I do note Mars and the Sun's close influence of the ASC)
C - 2
W - 2
D - 2
His is a tough one as Mars aspects the ASC and is lord of the Moon and Fortune. Strictly following the table would suggest Phelgmatic/Melancholic but I would think there would be a lot of Choler there due to Mars, and to a lesser extent, the Sun. I'm not sure what to label this guy but Mars does dominate his chart.
Looking to the Rank of Fame, Mars bodyguards for both Luminaries, aspecting the degrees following the Moon and preceeding the Sun whie being angular with both luminaries angular and in masculine signs. It is recommended to look to the bodyguard's local determination and rulerships as well as its nature to see how it will manifest its aid. Mars with Jupiter is a good case for the military or something equally as adventurous, while the Sun in the 1st as almuten of the 10th suggests leadership or fame, or at least some recognition by powerful people. The Sect Light elevated and in the 10th suggest prominence too.
For his career, Mars seems an obvious choice since he is responsible for most of the important points in the chart. Mercury in the ASC and trine the MC also suggests he is important though he is under the beams, I don't know if that inhibits him in any way from performing this role. I'd say his career was Mars predominantly with Mercury and Jupiter assisting. According to Masha'allah in The book of Aristotle this would show:
...supplies fiery work: for he constructs arms, is engaged in controversies, burns for sexual intercourse with women, tames monkeys or cures wounds, or persists in lies...But Jupiter regarding them furnishes leaders of wars, engages in controversies, and indulges in lies. PN1, Dykes, p168
So I'm definitely seeing the military here, maybe even a high leadership role due to the lights being so effective. Mars is in a human sign which only emphasises that rather than a construction or engineering job, or even taming monkeys! Though the leadership part is hard to say without knowing where he began in life.
As for one of the main points asked about, I wouldn't say that there would neccessarily be a distinct signature of being successful in two different careers in life, some people just seem to turn to gold whatever they touch and looking to this guy's luminaries and its attendant, I'd say he is one of them. I don't see any signs of a fall as the dispositors of the luminaries are placed really well. As for many careers, I confess I have no idea how to look for that. Maybe all thos planets aspecting the MC? Anyway, I don't see any other planet being as dominant as Mars is here.
So to sum up: I'd think a Martial career involving humans and one which he achieved some level of recognition for. I just noticed his Moon/Mars/Jupiter combo is quite similar to Bill Gates' Moon/Mars/Mercury combo, I'd think Jupiter would stop him from being known for his aggressive and shady actions but maybe not since he is out-of-sect. The part of the Masha'allah quote suggesting lies ismaking me second-guess myself. Gates' combination does lack a benefic regard though, so I could be just drawing conclusions that aren't there.
One other thing, I can't remember where I read this (or even if I did, maybe I dreamed it) but I think Mars in the 4th can show a person who moves from place-to-place or at elast from the country of birth. Just another thing to throw out there.