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Is it normal to think of money in different “contexts”?
The psychology around money is the subject of a lifetime of study.  Your observations are not uncommon.  The market daily fluctuation is out of our control. Hopefully, by the time the 1% volatility impacts you by say $1,000, you'll have grown accustomed to it, so when the 1% is then $10,000, you won't lose sleep. The difference between the $1000 up/down and the $3 sandwich is simple - one is in your control, the other isn't.  When you're out, you need to try to cut down on the math, it will only bring you unhappiness. You're paying for the socializing and can't let the individual items on the check bother you. I'm at the point in my life when I prefer a more expensive restaurant meal that I can't make at home to a moderate one that I'd make myself. For me, that logic works, and it's not keeping us home. Funny how my own sense of value for the dollar pushes me to a more expensive experience, but one that I'll enjoy.  By the way - eBay has done an amazing thing, it's created a market for you to sell your stuff, but it's also pulled everyone's collection of junk out for sale. Books I thought might be worth selling go for $1-$2 plus shipping. It's not worth my time or effort, and I need to just break the emotional ties to 'stuff.' I box them up and bring them to the library for their sale. If that picture frame isn't antique, throw it out or have a yard sale.  This may be right on track to your question or a complete tangent....