Help! I'm afraid poor money management runs in my family
When families provide financial help, sometimes they keep their adult children from fully growing up.
When I was a kid, my parents weren't careful with money and would sometimes get behind with their bills. Things would get very tense and there would be a lot of arguing, and the situation would be resolved by borrowing money from my grandparents (with the understanding that it would never really be repaid). Afterward we'd have a period of belt-tightening, but then eventually the cycle would repeat. As a child this bothered me so much and I swore I'd do better, but as an adult I find myself in a similar situation. I get behind, I don’t know what to do and I go to my parents, who are more stable now since my sister and I are out of the house. I make a great salary and should have money for all my needs but I carry an open bag and it trickles out until it's gone. I am mortified that my three daughters are learning this same lesson from me. How can I turn this around for my children, and for me?
Getting financial help from one's family is not a bad thing in and of itself. In fact, the idea that each generation should be financially separate and autonomous is a relatively modern, middle-class Western concept. Throughout history and around the world, money has flowed from parents to children (and then eventually reverses, when grown children assume financial caretaking for elderly parents) in a mutually understood, culturally bound dynamic. This practice helps to stabilize families in conditions where it's difficult for young people to launch without receiving a familial leg up. It also establishes and maintains bonds between family members, since it's harder to really separate when someone constantly owes someone something.
Your family's pattern sounds incredibly beneficial in terms of economic stability (if help from grandma and grandpa keeps the lights on and food on the table, let's be grateful), yet it's not the fluid-but-equitable, culturally bound dynamic outlined above.
The situation you describe has more of a flavor of rescue than assistance, giving the impression of one generation who stumbles and the other who picks them up. So the relationships that are established and reinforced ("you are the one who messes up, I am the one who bails you out") create a disincentive for growth. As well-intentioned as their help certainly is, it might actually make it more difficult for the younger adults to reach full maturity and self-sufficiency.
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While your family's pattern may have something to do with relationships between generations, I feel it's unfair to overlook the very real financial burden faced by families raising young children. You say that after you and your sister left the house that your parents were stable enough to provide assistance to you and your girls, so I wouldn't spend more energy on exploring this than it deserves. The more important question is: What does financial maturity mean for you?
Since you mention that your income should be sufficient for your needs, I would begin by tracking all of your spending when you're in "open bag" mode. Take a month to simply pay attention and learn to be conscious with money, but don't worry about changing your spending behavior or trying to balance your budget just yet. By simply being conscious with money you can identify the potential changes that will be most realistic, achievable and effective. The next month, take what you learned from your tracking and come up with a first draft of a balanced monthly spending plan. Each month moving forward, take time to troubleshoot any challenges that came up during the previous month and start to integrate irregular and periodic expenses into your plan. Eventually, by focusing on sustainable effort and deliberate change, you will achieve financial maturity.
What will be interesting to see is if you get any push-back from your parents once you no longer need to be financially rescued. If you feel like they are giving you subtle digs or undermining your progress outright, don't jump to blame them. Your family has used money to maintain relationships for generations, and your folks may feel confused and adrift when you start to break old patterns. Try to give them something positive to contribute, like depositing money in your daughters' 529 accounts or springing for an extended family vacation that allows them to give but does not disrupt your new adult boundaries.