Why I Allow My Son to Succeed

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My eldest child, Oliver, has a remarkable talent for negotiation. From the moment he uttered his first word, he has been debating with me about bedtime, the number of extra television episodes he can watch, and his allowance of chocolate chip cookies.

What I’ve discovered is that, more than indulging in an additional episode of his favorite show or snagging that seventh cookie, what Oliver craves most is a sense of victory.

As adults, we often idealize childhood, forgetting the limited autonomy we experienced. It can be quite frustrating to have one’s schedule dictated—bedtimes, chores, meals—especially for a bright and slightly rebellious child like Oliver.

Rather than stifle his desire for control, I often allow him to “win.” Of course, I draw the line sometimes (he will never have that eighth cookie!), but frequently enough to help him cultivate self-confidence and develop impressive negotiation skills. Now that he’s nearing 12, I grant him even more agency in his life. He is mature enough to grasp that poor decisions can lead to natural consequences. As time passes, I find myself employing fewer punishments and more subtle smiles of understanding.

Here are eight instances from this week where I allowed Oliver to triumph:

  1. I didn’t insist he eat breakfast. This has been an ongoing struggle, with him claiming a lack of time or hunger. Typically, I would enforce a meal, but this week, I simply let it go. He returned from school feeling hungry and miserable, and the next day, he prepared his own cereal without prompting.
  2. I allowed him to skip wearing a jacket or taking an umbrella, despite the pouring rain. He ended up soaked, and I managed to suppress any laughter.
  3. I permitted him to play computer games after school instead of completing his homework first. He lost track of time and stayed up too late finishing assignments. The next day, he opted to do his homework right away, and I felt the familiar “I told you so” thoughts echoing in my mind.
  4. I approved his purchase of a cheap remote-controlled helicopter with his own $40, even after we both read the negative reviews. It broke within an hour, leaving both of us disappointed, but I refrained from giving him back his money.
  5. I chose not to enforce cleaning his room. He misplaced a library book, two favorite pairs of pants, and $3. Eventually, he found the library books but had to use his discovered money to cover late fees.
  6. I didn’t require him to take out the garbage or complete the dishes. Neither of us did it. That night, he ended up with peanut butter and jelly sandwiches on napkins next to a very smelly garbage can while I savored sushi, suppressing my grin.
  7. I allowed him to hang on a dog gate I’ve repeatedly warned him against, resulting in its breakage. The dog then chewed up five of his beloved baseball cards. I had to bite my lip to refrain from lecturing him.
  8. I didn’t force him to hug me at the bus stop on his first day of school, a moment I felt bittersweet about. However, when he waved from the bus’s “cool section,” my heart felt a little lighter.

Ultimately, our children won’t be with us forever. While raising them to be obedient may ease our daily lives, teaching them about the natural consequences of their choices will serve them well throughout life. I acknowledge that I still enforce rules—there will never be an eighth cookie! But I strive to let him win when possible, even if those victories may lead to lessons learned the hard way.

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Summary:

Allowing children the opportunity to make their own choices, even if it leads to mistakes, helps them develop crucial life skills. Parenting is about finding the balance between guiding them and letting them experience the natural consequences of their decisions.

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