Why I Allow My Son to “Win” in Parenting

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My eldest child is a master negotiator. From the moment he uttered his first word, he’s been challenging me about bedtime, extra screen time, and the number of chocolate chip cookies he can indulge in. What I’ve come to realize is that, beyond wanting that extra episode of his favorite show or that additional cookie, his desire to “win” is what drives him most.

As adults, we often look back on childhood with a sense of nostalgia, forgetting how powerless we felt at times. It can be frustrating to have our decisions made for us, chores enforced, and meals predetermined—especially for an intelligent and slightly rebellious kid like mine. Rather than stifling his need for autonomy, I decided to let him win—not every time (I’ll never let him have that eighth cookie), but often enough that he’s developed a strong self-identity and impressive negotiation skills. Now that he’s nearly 12, I grant him even more power over his environment. He’s savvy enough to grasp that poor decisions often come with their own consequences.

Here are eight instances from this week where I allowed my son to “win”:

  1. Breakfast Battles: I usually insist he eats breakfast, but this week I chose to let it slide. He returned home from school miserable and hungry, leading him to prepare a bowl of cereal the following morning without prompting.
  2. Rainy Day Choices: Even though it was pouring, I didn’t insist he wear a jacket or take an umbrella. He ended up drenched, and I had to suppress my laughter.
  3. Homework First or Games First?: I allowed him to play video games after school instead of tackling his homework right away. He lost track of time and stayed up late to finish his assignments, which, as you can imagine, led to a chorus of “I told you so” in my head.
  4. The Remote-Control Helicopter: I let him spend his own $40 on a poorly reviewed remote-control helicopter. It broke within an hour, and while my heart went out to him, I resisted the urge to return his money.
  5. Room Cleanup: I didn’t make him clean his room, resulting in the loss of a library book, two favorite pairs of pants, and some cash. When he finally found the books, he had to use his own money to pay the overdue fees.
  6. Chores Left Undone: I skipped insisting on chores like taking out the trash. Dinner consisted of peanut butter and jelly sandwiches served on napkins next to an overflowing garbage can. I savored my takeout sushi with a hint of satisfaction.
  7. Dog Gate Incident: He hung on the dog gate despite my warnings, and naturally, it broke. The dog had a field day chewing up his cherished baseball cards, and I bit my tongue to resist lecturing him.
  8. Bus Stop Hugs: I didn’t force him to hug me in front of his friends on the first day of school. Although it brought a tear to my eye, seeing him wave from the back of the bus made my heart swell.

Ultimately, our children won’t be with us forever. While raising them to be compliant might make our lives easier in the short term, teaching them about the natural consequences of their choices equips them for the future. I admit there are still moments when I lay down the law (that eighth cookie will never be his!). However, I strive to let him win whenever possible—even when I know that victory might lead to a lesson learned the hard way.

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Summary

In my parenting journey, I’ve found that allowing my son to “win” in certain situations fosters his independence and builds essential life skills. By stepping back occasionally, I not only teach him about consequences but also help him develop a stronger sense of self. While I maintain boundaries, I recognize the importance of letting him experience the results of his decisions.


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