Jesse reflects on learning to relax about spending money, especially on the "black box" line items -- unspecified purchases from Amazon that don't fit neatly into any other category, or purchases that he simply doesn't want to look up and re-categorize. Part of learning to relax about these expenditures is realizing that as long as you are achieving your primary goals -- funding an emergency fund, saving for retirement, saving for a house perhaps -- then it doesn't really matter what happens to the rest of your money. It's another way of looking at the big picture.   Sign up for a free 34-day trial of YNAB at www.youneedabudget.com