Story time: At the age of 89, my grandfather was dying. Had entered hospice and his kidneys were failing. Death was expected in the next few days ... maybe a week at most. Over his life, he had bought two farms in the mid-west and they were now worth ~$2million+. 5 Adult children don't want the farms, and everyone agrees the farm & land will be sold upon inheritance. Grandfather also has one house lot in Arkansas. At one point, he thought he might build a house and retire there, but didn't. Purchased 20 year ago for $3,000.
Grandfather is at death's door. Grandfather + Adult children + family lawyer are all working together to legally reduce probate/inheritance taxes. This means that some adult children are buying some of assets from grandfather (I don't know the specifics). My father talks to grandfather: "Your lawyer says it will be better if I buy the Arkansas lot from you." Here's a check for $2,500 [more than the open market value; this lot is in a proposed planning community that flopped]. Grandfather response, "Well, I've got more than that in it."
I think about that moment all the time. He died 2 days later. But in that moment, he was worth $2 million+ (and likely had $50k in his checking account), but he wanted his son to pay him at least $500 more for an empty lot ... that if they hadn't done this, the same son would inherit this lot upon his death.
Without question, his frugality and entrepreneur mindset was what allowed him to amass a huge net worth for a kid who chopped wood for 6 days a week during the Great Depression. But he could never escape that mindset. He would never have thought to order the steak instead of the cheapest burger at a restaurant. He would travel, but it would always be bare bones & 3rd class. In fact, another famous story was about him not being able to go on a trip and leave a few eggs behind, so he put them in his carry-on bag (where they promptly cracked).
He's a perfect example of being stuck in a mindset that got him there has now outlived its usefulness. So I push myself to think about when should money be traded for experiences. What is the value of this dollar now compared to what it may have been different 5, 10, or 40 years ago?? What's the point of accumulating resources if we don't use them to enrich our lives instead of some green pieces of paper or a certain number on a bank account screen?