Part II (for technical reasons
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You gotta ask yourself those questions and those:
* What is my business plan and how saturated is the market? For poker: Which variant I´m gonna focus on (as Nsavov perfectly described)? How good is the traffic in this variant, how many donkeys are there and thus: How profitable is this variant?
* How much starting money do I have and how can I make a living during the start-up-period? How can I make a living during start-up when I don´t win/earn enough money yet?
* How important is a regular salary to me? How important are regular working times for me? Am I ready to work more than regular?
* How can I find starting money/investors/stakers?
* What are my skills? What can I do best and where are my weak spots? How can I integrate this into the current "market"? How well can I "sell my products"? In poker: variants.
* How am I gonna plan my working time, how am I gonna plan my work-life-balance?
* What could be an alternative if I find out that this is not the right thing for me? Whan am I gonna do then?
* How is my daily schedule gonna look like?
* Do I need social contacts at work or am I the type of person who loves to work alone?
* How am I gonna handle the responsibility? How am I gonna plan my paper work (accounting, taxes, calculations.....bla bla)?
* How can I handle times with no earning/winning: financially and mentally? In poker: downswings!!!
* What are my plans for the future like: next 5 or 10 years?
..............
This is just a little checklist from my experience as self-employer/freelancer ----> same goes for poker pros ..... ♠_thumbsup:
Many poker players come with the attitude: "Work/school sucks, I´m gonna be a poker pro, I wanna be independent and earn a lot of money" This attitude is very very wrong!!!
Beeing a poker pro or self-employed has nothing to do with this attitude, you gotta love what you do, you gotta love the responsibility, you gotta LOVE to be self-employed and you gotta be ready to work very hard for it, otherwise you will go under, quicker than "Titanic". 
Many people think "Aw, nice, I can do with my time what I want, I´m independent in time" ---> NO WAY! I gotta be there for my clients even though it´s Saturday, Sunday or vacation. You have to play at times when the most donkeys are at the tables, when you make the most profit. If you get staked, you gotta be there for your backer, you gotta report, you gotta play as much as required! So, no "tralala free time whenever I want".