I'm currently 100% self-employed, working on two businesses: one in IT consulting for individuals and companies, and one in news aggregation and publishing (whi

I'm currently 100% self-employed, working on two businesses: one in IT consulting for individuals and companies, and one in news aggregation and publishing (which has been suffering lately but is about to get a shot in the arm again). First, the bad stuff that I don't like: I haven't had a real vacation in quite a while; any money that I make has to go back into the business, so I'm perpetually poor; I work long hours and most days of the week; I am on the front-lines, dealing with the frustrations that various technologies bring to the people trying to use them. So it's not all roses, but I do still prefer it to a regular job. For one thing, if I make a stupid decision -- and I often do! -- I can clean it up. My businesses are limited only by what I'm willing to achieve. I have done some pretty good things for my clients, and that's rewarding by itself. The one advice-y lesson I've learned so far: GET HELP. I was struggling with the consulting business, and then Leslie (my girlfriend) started helping out, and it's made a tremendous difference. Now my billing is mostly on time, there's someone that knows what my expenses and revenues look like, and she's running around behind me keeping my head screwed on straight. :-) Additionally I've hired a tech (twice), and it's valuable getting someone else's point of view and experience involved, so long as you're willing to give them some pretty clear rules at the beginning and then get out of their way.