Our advice columnists have heard it all over the years—so we’re diving into the Pay Dirt archives to share classic letters with our readers. Submit your own questions about money here . (It’s anonymous!)

Dear Pay Dirt,

My parents passed away when my sister and I were teenagers, and we are now both in our late 40s. They left us enough money to finish college plus about $100,000 each. I used those funds very frugally early in life and saved most of it for retirement. My sister burned through everything quickly and has repeatedly gone through boom/bust cycles.

We earn about the same amount, but my family is much more comfortable and has saved a lot more for retirement because of choices we each made. We like to vacation with her family, but inevitably I pay for things in the moment

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