Thomas Watson sang the high praises of contentment in his book The Art of Divine Contentment, recently republished by Soli Deo Gloria Publications. He wrote that he didn’t know of any ornament in religion “that doth more bespangle a Christian, or glitter in the eye of God and man, than this of contentment.”  
Watson defined contentment as “a sweet temper of spirit, whereby a Christian carries himself in an equal poise in every condition.” True contentment is a gift from above and is only found in those who have been born of the Spirit. “It is a fruit that grows not in the garden of philosophy, but is of heavenly birth.”  
Contentment exists and flows from the heart.  It “lies within a man; not in the bark, but the root.” This is why difficult circumstances may not destroy a Christian’s contentment. “A bee may sting through the skin, but it cannot sting to the heart: outward afflictions cannot sting to a Christian’s heart, where contentment lies.” This is also why outward prosperity doesn’t necessarily produce contentment. “A drop or two of vinegar will sour a whole glass of wine.  Let a man have the affluence and confluence of worldly comforts, a drop or two of discontent will embitter and poison all.” 
How do you know if you are content?  Here are four diagnostic questions based upon Watson’s book. 1) Do you silently, willingly receive God’s providential dealings with you or do you complain and grumble?  Watson carefully distinguished between a holy complaint and a discontented complaint. In the former “we complain to God,” and in the latter “we complain of God.” 2) Do you thank God in every situation? Phil. 4:6; 1 Thess. 5:18. 3) Do you rejoice always? Phil. 4:4. 4) Do you ever use sinful means to get out of your troubled situation?
Watson had much to say about learning and pursuing contentment. The heart of the matter is the matter of the heart since contentment lies in the heart.  Thus, “the way for a man to be contented, is not by raising his estate higher, but by bringing his heart lower.” And “the way to be comfortable, is not by having our barns filled, but our minds quiet.”
In typical Puritan fashion, Watson provided 18 rules for attaining “holy contentment.” The first is to advance faith and the last is to be much in prayer. In between, he said that we should often compare our condition. Specifically, he said that we should make a five-fold comparison. First, let us compare our condition with what we deserve. “If we have not what we desire, we have more than we deserve.” Second, let us compare our condition with others. When we do so we will see some have it better than us and some have it worse than us. Many of the saints listed in Hebrews 11 had to endure much more than we do today. Third, let us compare our condition with Christ’s upon earth. Fourth, let us compare our condition with what it was once. Fifth, let us compare our condition with what it shall be shortly.  
Watson’s book is very readable and contains a wealth of material on this important subject. He is one of, if not, the most quotable puritan. This book is not only worth reading for the subject matter, but it is also worth reading, especially for teachers and preachers, to learn how to illustrate truth with vivid word pictures. In this regard, I highly recommend Expository Preaching with Word Pictures: With Illustrations from the Sermons of Thomas Watson by Jack Hughes.