Bill Clinton left the White House with millions of dollars in legal bills. He also had to deal with the personal emotional deflation of not being the U.S. president. But, he did land on his feet financially - and emotionally.
In THE NEW REPUBLIC, Alec MacGillis analyzes Clinton's resilience. Here you can read that. His ace in the hole seems to be his ability to bring people together.
Maybe X needs an introduction to Y. Maybe X needs to be at the party Y is at to observe the moves made. Maybe X needs funding and has to be able to tap into a lot of Ys to find it - eventually.
Because of this strength, Clinton has been able to prevent his weaknesses from undermining his ability to earn a buck. The takeaway is clear: Leveraging strengths and the weaknesses seem to be less of a factor in success or failure.