I Should Have Let My Son Fail Sooner and He Agrees

“The one thing I wish my mom had done was let me fail.”

Hearing those words from my son, a high school senior, was very jarring. He told me about a conversation with a friend’s moms. His friend’s younger brother was struggling with many of the same things my son had struggled with in early high school – mental health, connecting socially, performing below his academic capacity and being combative at home.

(I was afraid to let my son fail. Shutterstock Monkey Business Images)

I’m not sure exactly how this conversation started, but at some point, he shared that he wished that when he was struggling, I had let him fail.

My son wished that I had let him fail

He had turned things around for himself in 12th grade. He was doing much better academically, engaging in class discussions at school, willingly seeking out extra help and making new friends. He seemed happier and was generally more pleasant at home.

We talked about the many factors that contributed to his turnaround, and he articulated that they centered around diagnoses of ADHD and Celiac Disease, which helped explain many of his challenges, general maturing, and learning about intrinsic motivation.

The more effort, the more success

He was growing up and able to see life through a less adolescent lens. He was thinking about university, what he wanted to study and what he needed to do to get there. He observed other kids in his grade and saw traits he admired and some he did not.

His hard work was paying off, and with that came an understanding that it is worth putting in the effort and that when he did, he more often than not succeeded.

Although he had ‘upped his game’ in grade 12, he wondered if he would have done so sooner if I had let him fail and truly experience the full force of dealing with the consequences of not handing assignments in on time, flunking tests, getting kicked off the team for not showing up to practices, and getting detentions for being late for school. He thought that he may have been better off if I had allowed him to feel the impact of his choices, sit in his discomfort and use those negative experiences as learning opportunities.

My son had to find his internal drive

He recently told me that he now knows the importance of being personally motivated to do the work, to put in the time and to understand the importance of due dates. All of those lessons, for him, were best learned the hard way – not by me getting involved, micro-managing him and keeping him afloat when he needed to sink. Experiencing failure allowed him to find the internal drive to succeed and begin taking back control of his own life.

Holy smokes. Talk about blunt and honest feedback. I’ve heard the expression, ‘Our children are our greatest teachers.’ I was getting ‘schooled’ by my child, and rightly so.

Our conversation gave me a lot to think about and forced me to confront my own role in his struggle. As parents, we all hear that letting our children fail is essential. It sounds so easy in theory, but it is so hard in reality. That was my experience.

My friend taught me a lesson in parenting

For too often, I had made sure (sometimes with lots of yelling) he was on time for school and sports practices, reminded (pestered) him to study for tests, and even helped him (much more than I’m proud of admit) make sure his assignments were done and handed in on time.

I’m guilty of doing all these things and much more. Our conversation forced me to confront why I had felt the need to take all of those actions to prevent him from failing.

I shared with him that I felt his mental health was so fragile that if I let him fail he would hurt himself or worse. He said he understood and that, in those circumstances, I did what I thought was best. However, he responded that until he experienced the pain of his choices, it was hard to make any changes to prevent that pain from coming back. At a very vulnerable time, he understood what was happening around him and to him.

Another reason I intervened was for my own ego

Another, far less altruistic reason why I almost always intervened was because I didn’t want his struggles to reflect poorly on me. Although hard to admit, it’s the truth. At the height of his struggles, I worked in a non-teaching role at the school he attended.

I can recognize now that I was unable to balance being a successful and respected professional and the mother of a student who was flailing. I thought my professional reputation was at odds with my ability to parent my child.

I made his struggles about me and how I needed my colleagues to see me – someone who had it together, could do it all and effortlessly balance being a high-achieving, perfect, full-time working mother. I was more successful in my work role than in my parenting role, which was devastating. But, as I desperately tried to prevent him from failing, I was ultimately failing him.

I should have listened to my son when he told me to back off

My son and I have spoken honestly about this. I have apologized and been forgiven for not supporting him in the way I should have. Instead of making it all about me, I should have listened to him when he told me to back off.

He is one of my greatest and most important teachers. He challenges me to broaden my perspective, and helps me understand that there are opportunities to learn and grow in every situation, good and bad. He calls me out on my BS, and even though I don’t always appreciate it in the moment, I always appreciate his honesty, love and care.

My son is an amazing young man

He is an amazing young man. Among his many accomplishments, he is currently studying computer science and physics at university. He’s so excited to tell me about the various courses he’s taking, the problems he is solving, the friends he’s hanging out with, the clubs he’s involved in, and the strategies he’s using to keep on top of his schoolwork. He’s achieving academically.

I was recently on FaceTime with him while he described how he took apart a robot in his Robotics courses, cleaned it, reset the wheels, replaced the motor, rebalanced it, and reassembled it for optimal function. Every parent wants their kids to be happy and excited about what they are involved in. That recent conversation is the polar opposite of what it used to be like when we talked about school.

My son is succeeding on his own terms

He’s succeeding now because of his efforts, and on his terms. When he fails, he’s able to learn from what didn’t go as planned. He’s developed strategies and routines that work for him. He truly has come a long way, all on his own, with none of my meddling, micro-managing, nagging and unsolicited advice.

Failing helped him find his way. I wish I’d let him fail sooner, but parenting is a lifelong learning process, and I still have a lot to learn.

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About Jill Cannon

Jill Cannon is 53-year-old and a married, working mother of 2 young men. She writes about her personal experiences as a woman, wife, mum, daughter, sister and friend. She values relationships, and seeks out meaning, beauty, connection and humor in her daily interactions. She is a proud member of Generation X, part of the Sandwich Generation, and her kids think she’s the most cringey, uncool person they know.

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