Hrmph… In my closet right now sits a backpack specifically designed for surfing. There’s a separate compartment for a wetsuit. There’s a small pocket for surf fins. There’s a plastic-lined pocket for surf wax. The metal adjustments for the backpack straps are padded with neoprene so that when you’re carrying a surfboard under your arm, the metal won’t scratch or ding the board. It’s an awesome backpack for surfers. I’m told. I’ve never used it. I bought it on one of those daily flash deal websites a while back. I’ve been meaning to list it on Craigslist for a long time now. Yup. I regret purchasing that. This is a good question to ask yourself. And the follow-up questions I found with it are equally important: “Why do you regret purchasing it? What was your mood when you purchased it? Can you implement strategies to avoid making the same mistake again?” Continue reading What was the last item you regretted purchasing? →

Did you get a weekly allowance? Were you paid for doing regular chores around the house? Did you borrow from an older sibling? Did you just ask and receive money whenever you wanted? Did you start hustling from an early age – shoveling driveways for neighbors in the wintertime? Early experiences of getting money have a way of permeating into later life. (Side story: When I was in 4th grade, a very crafty 5th-grader named Alex photocopied a Nintendo magazine that listed ALL of the Mortal Kombat II finishing moves. He peddled these black and white photocopied packets on the playground for $10 bucks a piece. I bought one and didn’t regret for a single second. (Why would I? It was Mortal Kombat II!) Looking back at it now, Alex must have made over $200 that quarter! At least. And he was 10 years old! I should look him up. Dude’s probably a billionaire. Or in jail…) Continue reading How did you get money as a kid? →

And how did your parents spend and save money? In many ways, the attitudes we have about money come directly from our upbringings. Reflecting on these questions helps you make sense of yourself and your own finances. Asking these questions of others helps you, in turn, understand them better. Just this weekend, Emily and I got into a really interesting conversation with three other friends. All of us were fortunate enough to go to college. And all of us were doubly fortunate to have significant financial help from family in order to make college possible. But our respective families had very different attitudes and approaches to money. Some expected their kids to work during college. Others did not. Some made sure that their kids knew the exact monthly costs of financing higher education. Other parents adopted the view that excelling in school was the child’s job while paying for it was the parents’ responsibility. It was fascinating to see the differences. Continue reading Was money discussed openly in your family growing up? →