Re: options (finance)
JB,
The key factor you will need to determine is whether you fall in love with it. If one of the reasons you're looking at options/finance is "because the hours aren't bad", stick with poker. Options, and other trading/investing in general, requires inordinate amounts of independent studying to actually be able to think independetly from the rest of the "participants".
So you are basically looking for the same "feeling" that I assume you experienced in the beginning with poker. As in wow, I wanna do this 24/7, and even if I had 1 billion $$ already. Otherwise, just look for something else that gives you that same feeling -- there are many opportunities in finance outside of options trading that are just as independetly-minded and lucrative, but perhaps more abstract than mathematical(unlike options) -- such as global macro. Then there's also VCs and entrepreneurship. While poker and chess relate significantly to all of the above, it is probably impossible to pick a random poker pro and determine which one he will fall in love with / is most inclined towards. For example, a lot of poker players WOULD NOT make good options traders b.c. they hate math and excel in poker while eschewing math almost completely.
Your "plan" sounds feasible except that in the initial stage, I'd focus more on knowledge accumulation than on paper / small portfolio results -- because those will be largely irrelevant when it comes to actual big money results. Its like showing someone your .25/.50 NL stats to apply for a chance at 200/400. The ease with which you command the fundamentals / history is what will really matter, and it will easily show in a 1-hour conversation with any expert you wanna work with b.c. all you need to pick up are the "tricks" that still work in the current time (thus not yet published), and combine them with knowledge to generate new tricks and insights that will hopefully be 1 step ahead of the everyone else.
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