W-2 Exit strategy

[Stephanie Cortez]

I am considering the possibility of leaving my W-2 job by Dec. I am in the beginning stages of planning what this will look like and if it is possible. Fears that come up for me are 1. Medical insurance 2. Taxes 3. Security 4. Emergency life situations. I am curious to know more about other folks journey into entrepreneurship. 

What factors did you consider before leaving and how much did you have in reserves, if any? 

What suggestions/feedback would you offer someone who is considering leaving their W-2? 

Also, medical insurance, how does that work as an entrepreneur? Is it astronomically expensive? 

Is there a best way to align your business LLC vs S-corp that makes the most sense for tax purposes?