Live & Learn

Live and Learn: Why Our Teens Need Real-Life Reps

We say things like “live and learn” or “F around and find out!.” Sometimes it comes with a little hint of “I told you so…” 

But when you strip it down to the truth, it’s simple:

We literally learn by living.

And that’s where things get complicated for this generation.

Phones aren’t going anywhere. They’re woven into school, friendships, sports, social lives — everything. It’s not our fault that our teens grew up in a digital world… but it’s also not not our fault. Many of us handed them the device. And now we sometimes feel stuck — like it’s too late.

It’s not too late.

If phones are here to stay (and I assume they are), then it’s our job to teach our teens how to have a phone and how to access the real world.

“Touch grass” is the new slang. And honestly? They need to.

Not because phones are evil.

But because confidence is built through experience — not observation, and certainly not by the “back in my day” stories we can’t help but tell. 

Decision-Making Is a Skill — And Skills Require Reps

You might think:

“I can’t trust them to do that. I can’t even trust them to take out the trash.”

But trust isn’t something they magically wake up with at 18.

We teach them to trust themselves.

And then we test it.

We give them space to try.

We give them room to get it wrong.

We let them feel the natural consequences.

That’s how self-trust is built.

I grew up in Quincy, right outside Boston.I started taking the T aka the subway the summer going in to 6th grade- with friends of course. My parents gave me one simple direction:

“Just don’t get on the Ashmont train.”

That was their way of reminding me to take the correct outbound train.

I assure you — you only need to get on the wrong train once.

There I was, calling from a pay phone:

“Hi Mom… I’m in Ashmont. Can you pick me up?”

My mom or dad… I can’t even recall:

“No. Get back on the train to JFK, switch over to Braintree on the platform… and pay again because you got off to call me.”

Harsh? Maybe for today’s standards.

Effective? Absolutely.

That was the last time I got on the wrong train.

I learned because I lived it.

No tracking app.

No life360.

No step-by-step rescue.

Just a mistake.

A natural consequence.

A correction.

And growth.

I say, “you only get on the wrong train once” a lot.  People probably smile and feign a laugh and wonder what the hell I'm talking about, that’s my version of “LIVE & LEARN!”

The More We Step In, The Less They Step Up

Every teen is different. Every sibling is different.

Just like we didn’t buy our kid a bike — or a car — and say, “Figure it out,” we shouldn’t throw them into decisions they’re not ready for.

But here’s the tension:

The more we over-function…

The more we step in…

The more we take charge…

The more distance we create.

And the less they learn to trust themselves.

We say “practice makes perfect.” Perfect is a stretch — but you absolutely get better at anything the more you do it.

Decision-making is no different.

Teens become good decision-makers by making decisions.

“But 18-Year-Olds Aren’t Like We Were…”

You’re right. They’re not.

There are so many differences — and yes, phones are one of them.

But another huge difference?

We don’t give them the independence we had.

Maybe because we remember what we were doing at that age.

Maybe because technology makes us feel like we should track them at all times.

Maybe because it feels safer to control the outcome.

But whether you like it or not — 18 is approaching.

Or maybe it’s already here.

At 18 they are NOT as mature as we were, and I was not as mature at 18 as my own parents were. My dad was taking the T into the Red Sox game at 9 years old with his brother and the neighborhood boys… I didn’t take the train till 6th grade! 

We can’t give them the exact same freedoms we had. Partly because today, a group of 9 & 10-year-olds alone on a train might raise eyebrows with Child Protective Services. But mostly because the world they’re growing up in moves faster than the one we — and our parents — knew.

It’s our job to slow it down.

And that is the tightrope we walk as parents: when we slow the world down for them, we sometimes slow their climb into adulthood too. There isn’t a perfect timeline to follow, but if you know that 18 is approaching- think of that as the deadline. They will be off at college or in the workforce, you want them to be confident in their decision and problem solving skills. They can still “need” us but:

Our job shifts.

We  are not a crutch.

We are a support.

How to Start Giving Them More Decision Reps

If you want to build independence without chaos, start small.

Conversation Starters to Give Them More Ownership

• “What do you think is the best way to handle this?”

• “If you were me, what would you do?”

• “What’s your plan?”

• “What are the pros and cons?”

• “What do you think the consequence might be?”

• “How confident do you feel about that choice?”

• What’s the worst case scenario, and what’s your plan for that?
  
  

Let them think.

Let them wrestle.

Let them own it.

Catch Them Making Good Decisions

We are quick to correct mistakes.

We’re slower to highlight growth.

Boost their confidence by naming what you see:

• “I noticed you handled that really maturely.”
  
  

• “You thought that through — I’m proud of you.”
  
  

• “That was responsible.”
  
  

• “You fixed that without being asked. That says a lot about you.”
  
  

Confidence grows where it’s acknowledged.

When They Mess Up (Because They Will)

Remember- No one is batting 1000.

When they inevitably screw something up:

Do not belittle.

Do not shame.

Do not rescue immediately.

Instead:

• “What did you learn?”
  
  

• “What would you do differently next time?”
  
  

• “How can you make it right?”
  
  

• “What’s the plan moving forward?”
  
  

It’s not about the mistake.

It’s about taking responsibility and being  accountable and not getting on the wrong train again 😉 

That’s adulthood.

The Goal

The goal isn’t perfectly behaved kids.

The goal is confident humans.

Humans who trust themselves.

Humans who can recover from mistakes.

Humans who know how to function in the real world — not just online.

We build that by allowing them to live.

Not recklessly.

Not carelessly.

But intentionally.

They don’t learn resilience from watching us handle everything.

They learn it from handling things themselves.

Live and learn isn’t a negative phrase.

It’s the blueprint.

Your Friend,

Caitlin