Contract flying can be a great life - I've done it for a while but am going back to a good full time gig. There is a HUGE difference between doing 'some contract flying on the days off' and being a 'full time Independant Contract Pilot' - being a full time contract pilot can be very, very hard. First thing is to be taken seriously you generally need to have a significant amount of experience in the aircraft you're flying with appropriate ratings, etc..
To give you a glimpse of the economics involved - on the Challenger 604 I was charging $850 a day for domestic trips and $950 a day for international trips. Some months are obviously better than others but let's assume you work an average of 15 'billable' days(which would be very hard to average) a month at $850 a day - that's $12,750 a month for a total gross of $153,000 a year - not bad huh?? Now subtract an easy $35,000(minimum) for Flight Safety training - Challenger recurrent is expensive, plus add money for travel and lodging, plus a trip to Intl Procedures recurrent - now you're down to $118,000 - still not bad right? Knock off another 20G's for various taxes. Don't forgot to put in some health care costs because you'll have to buy your own insurance - add in money for standard business expenses(because being an ICP is very much a 'real business' with advertising costs, etc).......at the end of the day you may end up with $75,000 of that original $153,000 - still not bad for a year of working 15 days a month but $75,000 for a Challenger Captain is only average or below average pay - most corporate flight departments would pay more.
People think that being a contract pilot gives you ultimate control over your life(schedule wise) but that's not really true. You have to be prepared to go anywhere when the phone rings. Sure you can turn down any trips you want BUT do that too often and operators will quit calling you and you'll find it hard to fill schedule.
Contract flying can be fun and many people enjoy doing it but being a contract pilot as your primary job can be tough going - you have to work very very ahrd to be successful.
Jason