“Success does not consist in never making mistakes but in never making the same one a second time.”

— George Bernard Shaw

When I was 13 years old, my friend and I sneaked out of my house after dark to meet boys at the baseball field. We walked to and from that field arm in arm, our words whipping over each other, braiding our friendship tightly.

When we got back to my house, our hair and our clothes and our shoes were soaked from the rain. We opened the door, still laughing and talking, and looked away from each other, straight into my father’s eyes.

We all stood still for a heartbeat, water dripping to the floor between my friend and me in the seemingly slow motion that happens when you know you’ve done something wrong and your parents are silent about it. Finally, he asked, “What were you doing?”

My dad, tall and serious with a Russian accent that would silence my future husband mid-sentence, was giving me a lifeline.

I could have told the truth. I could have said we went outside. We were on a walk. We were doing something — anything — that could have resulted in two soaked-from-head-to-toe girls. But, no. I didn’t think of any of these ideas.

“We did each other’s hair,” is what I (weakly) said.

My dad’s eyes flashed, assessing all the ways he knew I was lying, starting, of course, with the front door we had just walked through.

My parents had never sat me down to discuss the dangers of sneaking out after dark and of not letting anyone know where I was. They assumed, with good reason, that I knew better. I was a good kid with nice friends. I was polite to grown-ups and respectful of teachers. And yet, here I was, caught in the act and forcing my parents to have the “no sneaking out” discussion with me the next day.

While I definitely believe in and strive to live by Shaw’s words above, I know from unfortunate experience that we make some mistakes several times before we learn the lessons from them.

And, most importantly, I know that we need to directly teach our children the most vital lessons, rather than assume that they’ll be understood.

The same is true with social media. Although days of sneaking out without having phones in hand are long gone, muddling through being a kid, and being a parent, is still pretty much the same.

What’s different is the addition of technology and social media.

When my son was 2, he walked up to a screen and swiped it. When my daughter was 5, she started a DVD via the Xbox for me. And when my oldest daughter was 10, she knew how to pin on Pinterest and asked questions like, “Are you posting that?”

Our kids are savvy and incredibly lucky to have these amazing tools at their tiny fingertips. I don’t begrudge them this and think it would be a disservice to not let them be online.

I believe this is true for two reasons:

The first is that having an online presence is the reality of the time we live in, and they’ll need to be social-media-savvy for current school and future work opportunities.

And the second reason, the one that’s more focused on the present moment, is that social media is one way kids are connecting with one another. And taking away an opportunity for connecting and relationship-forming isn’t our job as parents. Teaching our kids how to do this responsibly and kindly is.

So it’s that “tiny fingertips” part that I want to home in on: They’re still kids. And even though they’ve grown up with technology as a part of their daily lives, they will make mistakes while using it.

This means that we need to have direct conversations with our kids about the kinds of comments that are okay to make. It’s showing them an appropriate comment and an inappropriate one and having the discussion with them about what makes one okay and the other not.

When we were young and a friend did something that bothered us, we went about our lives, going to sports practice, having dinner with our family, doing our homework, and then — if we had time and still remembered — we called our friend (or sometimes, someone else) to tell them what had happened and why we were upset.

Kids today have a phone tucked inside their thumb-holed sleeves, and if someone bothers them or they’re in a bad mood or their feelings are hurt or their hormones are high, they can text, comment or message their angst instantly without taking the time to cool down.

This can be costly for even the kindest of kids. I shudder when thinking about the decisions I’d make and the words I’d blurt if I didn’t use a thoughts-to-actions filter. Our kids are definitely still developing the skills of taking deep breaths and thinking through their actions, but the availability and immediacy of technology makes it difficult for them to practice.

We need to teach them to take a breath before they post online, just like we teach them to take a breath before they talk back to us, a teacher, a coach or a friend. We need to teach them that not every status needs to be commented on. That not every thought needs to be shared. That not every event needs to be documented. We need to teach them that it’s okay to walk away sometimes, and how to step into and out of a situation as necessary.

And we need to teach them how to come back from the missteps they will take, and how to apologize.

Just like even the nicest of kids will make mistakes, even the savviest of parents won’t be able to keep tabs on everything their kids do on (and off) line. Texts can be deleted. Search histories can be cleared.

We can’t assume that because we check their phones we don’t need to teach our kids how to act kindly online. We can’t — and shouldn’t — parent like we’ll always be there to catch them, because in reality we won’t. Instead, we can teach them how to maneuver kindly online on their own.

Once we taught our kids how to walk, we could trust them to know how to walk anywhere (within reason). We could exhale our worries away. This teaching works in the exact same way.

This is why I advocate for letting our kids be online a little bit younger than most people think I would. The exact right time will be different for each family, but it’s definitely when they begin to show an interest and when their friends begin using social media — and before they have “teen” at the end of their age. Starting these tricky conversations with our kids when they’re a little bit younger means that they’re a little bit more open to our parenting opinions. At a certain point the meaningfulness scale will edge away from us and toward their friends. The right time to teach online kindness is while it’s still tipping in our favor.

Galit Breen is the author of Kindness Wins, a simple, no-nonsense guide to teaching our kids how to be kind online, and head of communications for VProudTV, a troll-free conversation space for women. She blogs at These Little Waves and tweets at @GalitBreen.

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