But the point he is making is that there will be just as many WITH the aptitude, inclination, luck or ability that won't be as successful as those with the same amount of aptitude, inclination, luck or ability, because.....life.
It is a hard subject for people to argue over as it is going to be extremely rare for someone who is successful to admit that it was due to luck or that they didn't work all that hard for it. To look at this objectively is an extremely hard thing to do.
I'd say Taleb is/was fairly successful and is currently making a career out of pretty much putting forward this argument.
I've noticed a few posters seem to think that anyone realising chance pays a significant factor in our lives hasn't benefited from it themselves. I earn more than the OP and like the OP has described with his career progression there have been certain events out of my control that have helped immensely.. from starting off in the right team, getting exposure to the right projects, chance meeting with a senior manager in the pub leading to me being able to get a move to another team I wanted to and bypass HR etc..
I've got a very smart friend who ostensibly had the same job title as me, has a 1st class degree, masters, speaks several languages... unknown to this friend they didn't get placed in the job they initially wanted and were moved to another department not due to lack of ability but because one manager noticed the language skills and so put them in a different client facing role... their team was badly run, department not as well respected or compensated... friend had a much different experience over a few years then quit to pursue something else. That friend is as capable or more so than me but simply had, as a result of chance, an experience that was completely different to mine and suffered a huge opportunity cost over the few years they were they. That dept is now run by someone else who carries a lot of weight in the company, is gaining more prominence and would actually be a good place to start these days.
I feel I've got to re-emphasize that yes hard work, skills (both soft and tangible) etc.. are generally necessary to increase our chances of success... you can say that a hard working person who knuckles down and studies is pretty likely to do OK in life... but chance is massively underestimated and the illusion of control seems to be something plenty of people fall victim to.
I'd go as far as to say chance is the biggest factor when you look at the tail end of sucess - people who've got to the top of a company say... plenty of smart people work at X big bank... the guy who gets to C level or senior MD level isn't just the smart guy with the skills (obviously those are necessary, he's competing against smart skilled people) - but he's they guy who happened to get placed in the right department at the time he started, who's asset class happened to be doing better than some others, who had the right sort of manager initially, maybe had people ahead of him leave at the right time in his career which allowed for quicker progression than usual. Obviously you'd need to be very good and get noticed etc.. but of the pool of thousands of smart people working at these places the idea that the best candidate will rise to the top just doesn't work... it might well be one of the top % but there needs to be a bit of luck involved to to get ahead of the competition and that luck element is hugely significant.
Frankly in business even more so... certain key decisions/risks that shape the whole business could go either way.... there are only going to be so many big ones and the sample is likely small enough that chance plays a huge role. At the tail end of this distribution are the events that payed off way way over expectation... no one necessarily has an ev in the many millions when initially taking a risk with a small company... getting a result in the many millions can largely be down to chance... you might well have made a +ev decision, done all the right things, worked hard... but when you get unexpected disproportionate payoffs they can be down to external factors, being in the right place at the right time etc... Frankly someone like Alan Sugar could quite easily be running a successful estate agents with a few of his own buy to let properties on the side had chance events taken a different course.
