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    Home»Money»Why Letting My Kids Fail Was the Best Parenting Lesson I Ever Learned
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    Why Letting My Kids Fail Was the Best Parenting Lesson I Ever Learned

    Press RoomBy Press RoomNovember 9, 2025No Comments4 Mins Read
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    The first time I was called to the principal’s office was to discuss some questionable artwork my oldest son had created in 3rd grade.

    The principal expressed his concern that the picture of bloody, beheaded snowmen was a warning sign. It wasn’t. In fact, my son and his classmate had drawn the snowmen after watching a particularly graphic, but PG cartoon on TV. Given that he now makes a living as an artist, perhaps more than a red flag, this was a preview of the talent he would use to craft a very lucrative career.

    It wasn’t until years later that I realized I might not need to be so involved in their messes.

    There are always messes to clean up

    I am the mother of five — four boys and a girl. Given the size of my family, there have been plenty of messes to clean up. There was a fist fight on the walk home from school one afternoon. There were a couple of shoplifting episodes, such as when my 2-year-old son, who was 2 years old and unbeknownst to me, grabbed some candy from a lower shelf in the grocery store. He didn’t get caught, and I didn’t discover it until we got home. And then there was the day the police showed up at the door to inform me that my sons had shot a BB into a neighbor’s screen door. My response was, “Not my children. They would never do such a thing!”

    But it was my children. Somehow, they’d procured a BB gun and hid it in the loft of our garage. As they huddled in the rafters, they goaded each other into taking a shot, which did, indeed, damage the screen door of the house behind ours. It took a while, but they did sheepishly admit to their crime. It was a collective confession. I’m not sure which one took the actual shot. I was surprised that they did not receive a harsher reprimand from the police officer, and I was too stunned to do anything more than take the gun away.

    Their messes don’t reflect on my parenting skills

    No parent wants to deal with a child’s transgressions, no matter how minor. Each time mine got caught, it truly felt like a reflection of my parenting skills. However, there comes a day when we are no longer responsible for the actions of our children. For me, it happened when they each left for college.

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    I know many parents continue to oversee their child’s activities even after they’ve moved into a dorm, but I chose not to. I was done with stressing over their exams and worrying about whether they were eating well and getting enough sleep. I never asked for access to their grades, something many parents who are paying tuition feel entitled to do. I certainly did not request that they give me the password to their email accounts so I could read the messages they were receiving.

    My lack of knowledge does not mean that they were not engaging in questionable behavior in college. In fact, I’m pretty sure they all did. I am aware of at least one incident involving one of my sons. The details are murky, but it involved the overconsumption of alcohol.

    He only told me because we were talking about my teen years and the impact my mother’s alcoholism had on me. In response, he let me know he’d been “written up.” This led to a deeper conversation during which I told him, “I can’t help you if you don’t tell me what happened.”

    He replied, “You need to let me make my own mistakes.”

    That response hit me like a ton of bricks. I was amazed at his willingness to take responsibility for his actions. The college did not impose any severe consequences on him. He graduated on time with no blemishes on his transcript, but I think I’m the one who has learned the greater lesson.

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