I Almost Bailed Him Out: 5 Reasons I Let My Son Fail

Years ago, I saw an interview with Sara Blakely where she praised her dad for framing failure as a good thing. When she was growing up, her dad would often ask, “What did you fail at this week?” He wanted to hear how she’d taken a risk or attempted something bold. Blakely says this positive relationship with failure propelled her to found Spanx—and become one of the world’s youngest self-made female billionaires.

teen boy
You have to let your teens fail sometimes. (Photo credit: Tonya Rodriguez)

Embracing failure and parenting with tough love

If you’re thinking Ms. Blakely’s dad was a genius, that kids these days need to skin their elbows and rub some dirt on it, then you might be a Gen X parent too. Yeah, my husband and I probably gave our kids way too much attention (to make up for our own latchkey childhoods), but we tried our best to balance it out with tough love.

When one of our kids, 16 at the time, texted during his first shift at a fast-food job, “Please can I come home? This is horrible. I hate it” we said no. Every emotional fiber of my being wanted to swoop in and save my baby, but I texted back through tear-filled eyes, “You got this, bud. I promise it’ll get better.” And it did.

Protecting teens from failure is not the way to make them resilient

He learned the ropes and even got promoted to shift leader a few months later. Nothing makes a teenager’s confidence soar like being put in charge. We believe that coddling our kids, trying to protect them from every failure or setback, is not the way to raise strong, capable humans.

And then Covid. No one wants to go back there, but can we all just agree that that year (or two, or three, depending on where you live) threw us for a loop? During that era, I became more concerned with my kids’ feelings than ever before. My youngest, a high-school freshman in 2020, was especially impacted. The disruptions to his social life, sports, and school routine took a toll. Tough love just seemed…too much at times. So we eased up.

After more than a year of rolling with the pandemic punches—the failing grades started showing up. I panicked. I nagged, threatened, grounded, yelled, begged, encouraged, tried virtual school again, sent him back to in-person school again—all the things—for months. Nothing worked.

His dad talked to him man to man, took away his phone, forced him to go to tutorials. No use. At the end of his sophomore year, our once straight-A student came to us with the facts: “I’m so far behind in Pre-Cal there’s no way I can pass.”

We aren’t comfortable with failure, so we try to shield our kids from it

My husband was quiet and angry. I was sad. Disappointed. Worried. Mostly worried about how a failing grade on his final transcript would impact his future, but also about his mental health.

And I’ll admit, I was worried about his reputation, my reputation. What will people think, that he’s a dud, that I’m a bad parent?

Judge me, but I’m just saying the quiet part out loud. I’m not proud of it. I’d love to be above it, enlightened beyond my own ego, so in harmony with the universe that peace and wisdom prevail in the face of all challenges. The fact is, I often fall into the trap of viewing my kids as a reflection of me, as an extension of myself. And then I get all tangled up in the fallacy.

We parents often fall into the trap of seeing our teens as a reflection of us

If we’re honest, THAT’S probably why most parents shield our kids from failure—because our own ego can’t take the hit. And because we, as parents, literally feel what our kids feel. We aren’t comfortable with failure, so we do everything in our power to shelter them from it, from the discomfort, the shame of…what, not living up to our standards? Not reflecting back to us what we want to see in ourselves? Oof.

Needless to say, I really didn’t want to accept that failing grade. The protective mommy in me really wanted to get my baby out of it. Before I accused his teacher of being unfair, though, or complained to the administrators that it was their policies that had hampered his learning environment, I asked my son: “Did you learn 70% of the material? Do you think you put in enough effort to pass?” He shook his head. “No.”

Sometimes we simply deserve to fail

There it was. My kid deserved to fail. No emailing. No bargaining. No more fighting. It was time to just take the L and move on. And can I just tell you…it turned out to be a good thing, in so many ways.

There are a lot of reasons I’m glad we didn’t bail him out of that jam, but here are my top five.

5 reasons I’m glad we let our son fail

1. He came through it just fine

He suffered through the disappointment and feelings of regret, self-doubt, and embarrassment—and lived to tell about it. It did not harm him in any physical or permanent way. He’s perfectly fine.

It was a mistake—proof of what happens if you avoid a problem for too long—but nothing he couldn’t survive. In an age where social media and self-centeredness can amplify problems, making all of us—especially teenagers—feel like our issues are much bigger than they really are, this perspective can be powerful.

(I don’t mean to make light of mental health struggles. If you truly believe that failing a class would put your child’s life in danger, then please get professional help.Suicide is the third leading cause of death among people 15-24.

2. I came out okay also

Letting him fail that class was something I dreaded, but once it actually happened, I realized that it wasn’t so bad. There was really no shame at all. It just … was.

3. It led him down the right path—for him

Repeat after me: I am not my child. My child is not me. It’s his life, not mine. I had to remind myself often. The failing grade on his transcript put my target school—the one I had in mind for him since birth—out of reach. This forced me to shift my expectations from what I wanted to what was right for him.

And it worked out poetically. He had to settle for conditional acceptance to his first-choice university, but he took it like a champ. It meant he would have to prove himself at another university for a year, and then if he did well, he would be guaranteed acceptance as a transfer student to his dream school the following fall. Fair enough.

4. He got himself together

Failing doesn’t feel good—and it’s not supposed to. In my son’s words, “It didn’t sit right.”

Suffering the consequences of failure unlocked something in him we hadn’t seen in a while—determination in the classroom. He retook Pre-Calc the following year and got an A, just to prove to himself that he could.

He finished high school strong, earned a 4.0 his first semester of college, and is on pace to transfer to his target university this fall. My favorite part: When he calls home every Sunday, I can hear the fascination and excitement in his voice as he recounts lectures, wrestles with new perspectives, or poses philosophical what-ifs for us to debate.

5. He admitted we were right

Parents can nag, warn, and threaten until we’re sick of hearing our own voice, but some kids still have to touch the stove to believe it’s hot. If, after burning their metaphorical finger, your kid learns from their mistake, count it as a win. If they actually concede that their parents were right, admit that you did in fact know what you were talking about, and agree to maybe listen next time you offer advice…consider that a parenting gold medal.

Final thoughts: Not easy but worth it

A friend of mine, one of the most brilliant women I know, is a sage, an educated world traveler who’s done and seen it all—and is the mother of three phenomenal teenagers. Even this beacon of wisdom struggles with letting her kids fail. There could be a flashing neon sign overhead reading, “Let them learn this one the hard way,” and she’d still be inclined to help fix it—for all the reasons in this article and then some.

It’s not easy to let our kids faceplant. But let’s embrace the heartache. As parents, isn’t suffering part of the job? Think of it as another sacrifice we’re willing to make for the betterment of our kids.

Let’s be willing to suspend our own ego, untangle our identity from theirs, grant our teens autonomy, and power through the pain of watching them struggle. When it’s over, we can then bask in their glorious pride as they emerge stronger, wiser, and better for it on the other side.

More Great Reading:

She Wrote the Book on Letting Kids Fail But Forgot Her Best Advice When Her Son Applied to College

About Tonya Rodriguez

Tonya Rodriguez is an insatiably curious old soul trapped in the body of a neurotic suburban mom. She loves irreverent comedy, red wine, her husband, and two grown kids. Longhorn football makes her happy, and then sad. She works hard, runs for fun, reads a lot, listens to podcasts about politics and murder, and is currently transitioning from a career in marketing to...You can find her on LinkedIn, Facebook and Instagram.

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