how much work you need to feel good about it is not the same for everyone. in 30 years as as a smalltime house painter, I cannot think of a year when I didn't have at least a month to two months of work lined up before we were able to get started outside. I'd estimate would account for roughly 20% of annual sales. 20+ years ago I employed two crews, had a partner. today, I'm fine with a months work for me working by myself. I can get nearly any painting job I look at if I want it bad enough and I'm willing to settle for less money for the sake of staying busy or making "something", but I seldom do that today because I don't care if I'm balls to the walls busy for 7 months any longer. my career as a full time house painter is going to end in a few more years. I simply do not have to make as much money as I once did to meet my financial goals because we are debt free, aside from recent land purchase. If you are good at your work and treat people right, you will always have some work to do, but that isn't necessarily enough. you have to earn a living AND make a profit to run a successful business. I do less today to earn a living than I ever have. business working for me, not me working for the business any longer. I have the luxury of a solid reputation and tons of repeat business, but that has taken me over 30 years with my nose to the grindstone minding all the details of my work and business affairs to achieve. self-employment ain't for pussies or people lacking confidence. gotta take risks to get the rewards. some people are cut out for it, some are not. being good with you hands does not mean you can be successful at running your own business. lots of supremely talented tradesmen fail miserably at running their own business. only one way to find out if you can do it.