I don't think it was that easy for G.K. Chesterton to be self-employed. He seems to have had a difficult time with money-handling, book-keeping, record-keeping and such. He procrastinated his deadlines and never became rich. Although Frances didn't have to go to work, they had a gardener and a housekeeper and a cook, and so he obviously made an adequate living.
Today, in America, a person who is self-employed, and whether it's someone who is a sole proprietor or someone who has up to 100 employees (all considered by the government to be a "small" business), the endless paperwork can seem overwhelming. One might even think there might be a consipiracy to discourage small business.
Being one's own boss comes at a price. The price is keeping up with all of the government regulations, the paperwork, paying the taxes, (fees, fines, licenses and so forth are basically still taxes), and managing the headaches. But the upside is you are your own man (in the old fashioned sense of the word). Your own boss. The maker of your own fate. With God's help, of course.
Are you self-employed like Chesterton? What do you like about it? What don't you like about it?