There are definitely times in life where working by choice as a contractor makes more emotional and financial sense. Sometimes you just don’t want to be “all-in” at a company but still contributing and making a good salary.

If you have a spouse to provide benefits and hire an accountant to setup things properly, you can make very good money as a contractor. Even better if you can work part time for several with a high rate and juggle them around - then you start outsourcing some labor, and before you know it you have a consulting business.