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Recently retired Ross and Penny have an estate planning challenge. They've accumulated a comfortable net worth, with a good portion of it in liquid investments. They plan to leave everything to their three adult children, but they also want to help them financially right now. The problem is that all of their children have a different relationship with money than Ross and Penny. In a nutshell, the parents are savers and the children spenders. If they give large sums of money, Ross and Penny would want their children to use the cash to improve their financial lives. Would they do that?

Like many young adults, Lindsay took what her parents had to say with a grain of salt when it came to money. A new college graduate with an entry-level job, she was more interested in spending her paycheques than saving them. Saving was for later, she thought. Life was for living. When her father raised an eyebrow or offered advice, she brushed him off.

Then came the financial collapse of 2008. Lindsay lost her job and moved back into her parents' basement, regretting immediately almost every dollar she had blown.