I frequently fantasize about ditching my healthcare desk job, buying a truck and trying to carve out a living in some form of trucking but every time I run the numbers- or more importantly, every time I quiz someone who's doing it or has done it- I get the same conclusion:
By the time you pay for insurance, fuel, permits, truck & maintenance, at the end of the year what's left over is pretty sad. I even exchanged PMs with a forum member who used to do it and he echoed exactly that, which is why he moved onto a different career.
I know some are very successful at it, but it seems that unless a guy has a line on great-paying, consistent freight situation it's a ton of time away from the family for very very modest income.