I personally don't think that she will ever work again. She'll be a board filler at a bunch of places I'm sure, but probably not CEO again. We'll see though.
Why would anyone?
That's what I don't get about these people. I'm not saying they should retire, but they can still keep their professional connections and a semblance of "work" life by sitting on various boards or doing non-profit stuff, and not actually have to deal with the humongous stresses of C-level work.
I mean let's be honest: $186M is enough to last Marrissa's descendants forever and ever. If I were in her position, I would figure out a way to make my exit. It's not like she's the founder of Yahoo so there won't be any emotional or moral attachment.
If I had that kind of money I don't think I would still be able to put a value on my time.
The thing is, the reason you think this way is the same reason why you won't be as successful as her. Because by the time you make your 1MM, you won't take these big risks any more.
Money was clearly not the issue. She was at Google very early and ended up VP. Clearly she didn't need the money.
If you define success as "has money" then yeah, probably. But that's okay, I don't need nearly as much money as MM. Money, after all, has significant marginal utility. The difference between having $10M and $50M is not that much, unless you have extremely expensive hobbies.
For example, let's assume she couldn't become CEO of something near the level of Yahoo again (which I think she still could possibly, although perhaps slim). I still bet you at the lower end that there would be plenty of 5MM-25MM/year revenue companies that would love for her to be CEO, if not for the press and connections she brings to the table. At that level it becomes whether she wants to accept a salary that she probably would make off the interest of her net worth alone.