Why I Allow My Son to Have His Way

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My eldest boy is a master negotiator. Ever since he uttered his first word, he has engaged me in debates about bedtime, how many extra TV shows he can watch, and, of course, the number of chocolate chip cookies he’s allowed.

What I’ve come to understand is that, beyond wanting that extra episode of his favorite show or that seventh cookie, it’s the thrill of winning that truly matters to him.

As adults, we often look back on childhood with a sense of nostalgia. We forget, however, how powerless we felt at times. For a capable and somewhat rebellious child like my son, having every aspect of his day dictated must be incredibly frustrating.

Instead of stifling his desire to have a say in his choices, I’ve opted to let him win—though not all the time (the eighth cookie will never be his!). I’ve found that by allowing him some victories, he’s built a robust sense of self and honed his negotiation skills. Now that he’s approaching 12, I grant him even more autonomy. He’s mature enough to grasp that poor decisions often come with consequences. As time passes, I find myself leaning less on punishments and more on the satisfaction of seeing him learn.

Here are eight instances where I allowed him to “win” this week:

  1. I didn’t force him to eat breakfast. This has been a long-standing battle. This week, I decided to let it go. He returned from school hungry and unhappy, but the next day he made his own cereal without a word.
  2. I let him go outside without a jacket or umbrella, despite the pouring rain. He got soaked, and while I wanted to chuckle, I held back.
  3. I allowed him to play video games after school before starting on his homework. He lost track of time, stayed up late finishing his assignments, and the next day, he opted to do his homework right after school. My head was filled with all those “I told you so” thoughts.
  4. I let him spend his own $40 on a flimsy remote-control helicopter with bad reviews. It broke within an hour, and while I felt for him, I resisted the urge to give him his money back.
  5. I didn’t insist he clean his room. He ended up losing a library book, two favorite pairs of pants, and $3. When he finally found the library books, he had to use the $3 he discovered in his lost pants to pay a late fee.
  6. I skipped making him do his chores—taking out the garbage and washing the dishes. I didn’t do them either. For dinner, he had peanut butter and jelly sandwiches on napkins next to an overflowing trash can. I savored my takeout sushi with a quiet smile.
  7. I let him hang on the dog gate, despite my many warnings that it would break. It did, and the dog chewed up five of his prized baseball cards. I had to bite my tongue to avoid lecturing him.
  8. I didn’t make him hug me in front of his friends at the bus stop on the first day of school. I didn’t smirk then; instead, I wiped away a few tears. However, when he waved at me from the “cool section” on the bus, my heart did a little victory dance.

The reality is, our children won’t be with us forever. While raising obedient kids might make parenting easier in the short term, teaching them to understand the natural consequences of their choices will serve them well throughout their lives. Yes, there are still moments when I lay down the law (that eighth cookie will remain off-limits!). However, I strive to let him win whenever possible—even when those victories lead to losses down the road.

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Summary: Allowing children to experience the consequences of their choices fosters independence and decision-making skills. By letting my son “win” in various situations, I encourage his growth and self-awareness, even when I know it might lead to disappointment later on.