After working in law enforcement for 28 years, I decided to 'retire' to be my own boss as I 'had' to be better than what I had.
Since that time my wife and I have owned a Bed & Breakfast until the IRS audit determined we weren't making enough money for their standards (they tied us up for 18 months and wound up owing us over $11,000).
I've been a private investigator for attornies, a bail bondsman, transportation driver for disabled vets, and a part time grounds keeper at a sporting clays facility.
The freedom is nice, but has a price; No Paid Vacation, No Paid Holidays, No Paid Sick Leave, No help on Medical Insurance, Emergency expenses can drain a savings rapidly.
On the plus side, I can work as many hours as I need to make sure the job is done right without having to answer for overtime, I don't have to get approval for an extra weeks vacation, I can combine business with pleasure, my Ethics Standards are my own with out worrying about being investigated by the FBI, the News Media, or my superiors. If I choose to rely on a man's word and a handshake, I only have to answer to myself. I don't have to have any agreement going through a legal review board.
The fact that I have a nominal pension and social security helps, but doesn't cover the above by any stretch, so it takes financial discipline to enjoy being self employed.