downtickboy:
As a guy who abruptly left a lucrative career in computer programming to become a full-time daytrader, I can offer you this sage advice:
DO WHAT YOU LOVE AND THE MONEY WILL FOLLOW.
Yes, it's a bit worn out--that saying, but it's totally true. I used to believe that the money was what made it worthwhile for me to continue working in the IT departments of large companies, but I finally realized that no amount of money (not even in the millions) could make me do a job I hate, day in and day out.
Now, here's the practical advice: what I did in order to transition over to trading can be your way back to the "real job" path: consulting. The first thing I did when I quit my full-time job was start a little consulting corporation to do pretty much the same thing as I had done as an employee, but with these significant, happy advantages:
1) no boss!
2) flexible schedule
3) higher hourly rate
You'll be able to add one advantage to the list if you start out as a consultant: 4) Building a resume without having to convince a manager to hire you as an full-time employee.
One would think that it would be harder to convince a hiring manager to hire you at a higher hourly rate with a resume as thin as yours may seem to be, but the funny thing is that NO ONE EVER ASKED TO SEE MY RESUME WHEN I WAS A CONSULTANT. The decision to hire me was always made on two factors: 1) word-of-mouth recommendations, and 2) in-person interviews. I have no trouble getting consulting work in programming thanks to a network of happy clients.
So, you might be wondering: "how am I going to build a network of happy clients when I don't have years and years of experience to consult with?" Well, I've found that successful consulting has very little to do with technical expertise in your professed area of consulting. It almost entirely depends on achieving customer satisfaction.
Sure, customer satisfaction depends to some degree on your ability to get the job done, but it really comes down to listening to what the customer REALLY wants and delivering it. For example: most clients of mine aren't actually looking for a computer whiz. They are really looking for a short-term, results-oriented project manager. The actual work might be 10% computer programming and 90% making the right phone calls and lining up the right resources.
Translation: they actually want entrepreneurial skills on-demand, and since traders are usually entrepreneurial in nature, this will come easily to you. Now, here's the benefit to you: while you are actually using the entrepreneurial skills you already have, you are able to write down something more useful to you on your resume: "completed XYZ project worth $$$ dollars," making you look like you have the technical skills portion of your profession.
Eventually, you'll be able to snag a job based on these credentials; either you'll already have gained the requisite technical abilities via your consulting, schooling, or independent studying, or you'll be able to learn on-the-job with your new position. (The trick is of course to aim a bit lower, where your resume full of expert consulting experience will make you a shoe-in but you'll get a chance to pick up the skills you need to advance to higher positions later.)
Good luck. The ability to switch back and forth between self-employment and employee is a fantastically-useful one. Still, these are not abilities that lead one to PASSIVE income. You should consider the advice of other responders to invest your money so that it works for you. Personally, I plan on buying a few laundromats or automated businesses so that I can trade for fun and not for income.
