Nate,
For me, it required a leap of faith. I was a stockbroker making good money each month and when I told some people that I was resigning to trade, I can't explain all the variety of things I was told... I had built a strong book of business and was just going to walk away. It's kind of like putting in your time trading, getting successful and then leave.
But for me, it was something that I wanted/had to do. I wanted out of corp. America and wanted to own my own biz. I've always loved the markets so being a private trader was a logical step.
And of course, this has/is a tough biz to crack into. It took me longer than I thought. I mean, how hard could this be, right?
I think you'll read 2 schools of thought on this topic:
1) If you are going to get wet, you mind as well jump into the deep end and see if you can swim.
2) Put your tiny toe in the water and see if it hurts. If so, get out!
My belief is that if you are ready (or as ready as you think you will ever be), you jump and don't look back. And I mean jump. You either treat this is a full-time biz or treat it as a part-time hobby. NOTHING will replace 'face time' - time in front of the computer and charts in REAL TIME. It's way to easy to look at past charts and just see all the $$$ you would have made.
Now, I am not saying you take your life savings and place some large trades day one. I am saying that a full-time biz requires work before 9am, during RTH, and after 4pm. It means you live and breathe your biz. It means you pay no attention to the naysayers out there. It means you give it your all and don't look back.
To me, the absolute worst thing a person can do is always wonder 'what if....' Life is way to short to be wondering what if.