Life is about choices and we all are on the path led by our choices. It's not easy to talk about life regrets in general because we are/were in quite different situations. To make this thread easier, we just focus on the regrets in finances. I believe many of them can be lessons to learn from. I'll start first. Over a decade ago, I was living in a mega city of my country. At the time, the city was already a metropolitan place where you can meet all people over the world. Of course, the land was scarce and the price of housing was pretty high, nomal people could not afford to buy an apartment, let alone a house. However, one friend of mine was taking to a suburban area for an apartment, super nice but the neighborhood was not fully developed yet. The total cost of that departemtn was about $100,000. Well, I did not have that much money at that time but if I borrowed some from my parents and it was not a problem. Maybe because I was too young and did not get along with my parents at the time, I did not ask for that so I refused the offer and let go of that apartment. A few years later, the suburban area became part of the CBD and the housing price was going up insanely. Today, that apartment I missed is worth at least $1.2 million. Oh my... I hate myself for not buying that apartment every time I think about it.