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.
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Helping Savers Spend
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Ask Jesse: Heady Books and Final Settlement, Among Other Things
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Your Biggest Single Expense
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Ask Jesse: Lavish Praise and Woodchip Gardening (Sort Of)
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Looking In the Mirror
Money Is Not a Tool
Dire Straits, or Rolling In It, It's All the Same
Ask Jesse: How to Plan with a Reluctant Partner, and Some Successes
A Sample of Interesting, Joyful Spending
YNABers Share Their New Years Resolutions
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