Self Employed???
I'll share a few thoughts with you. Your biggest expense will be your health care. Maybe not so important at 39 years old but with a wife and family you can't afford to live without it. As far as dealing with people that's going to happen no matter what you do. You may have a co-worker or boss you don't care for but being self employed and working with customers can be more trying than you think. You should look at the future and seriously consider all of your daily living expenses. Write everything down you spend for the month and the year and figure at least $2000/mo for family health insurance including dental. Don't forget to include the same amount that you and your present employer pay in to the fed for your Social Security. Arrive at a total figure and see if you can match that even with your wifes job included.
If you're satisfied that the dollars match and you can get by you probably could make it. If you're going to start a business don't forget start up costs and figure on not taking a profit for at least the first few years. The number one cause of small business failure is undercapitalization. The best tool you can buy for your business is a good accountant. dan