The Rocky Road of Teen Self-Esteem

Self-esteem is one of the most powerful protective factors our teens can have. When teens feel good about who they are, they’re more likely to show prosocial behaviors, do better in school, take healthy risks, and bounce back from setbacks without letting one disappointment spiral into something bigger.

But even the most confident teens — and adults — have pockets where they struggle. Maybe it’s after not making a team, a breakup, bombing a test, getting passed over for a job, or for seniors, the rollercoaster of college acceptances and rejections. Rejection makes us question everything — our ability, our choices, even our identity.

Rejection sucks.

As adults, rejection still stings, but we have perspective. We’ve lived through years of setbacks: the job we didn’t get, the offer that didn’t get accepted, the invitation we didn’t receive. We know it’s not the end of the world, and in most cases those setbacks led to something even better.

Our teens don’t have that perspective yet. To them, rejection feels absolute. Add in the imaginary audience — the belief that everyone is watching and judging them — and the sting becomes magnified. This imaginary audience explains so much of their behavior: why they want to quit or not try something new, why tiny embarrassments feel catastrophic, and, of course, why we are so embarrassing to them.

Before we dive into strategies to help boost their confidence, we need to remember something important:

Everyone Has Places They Feel More or Less Confident

Confidence is not a personality trait — it’s a skill set. And it looks different depending on the situation.

I’m completely comfortable speaking in front of a room full of teens or adults… but I wasn’t always.

I still vividly remember giving my speech for class president sophomore year of high school. I sounded like the Micro Machines man — talking so fast that even I couldn’t keep up. I wanted nothing more than to get the hell away from that podium.

Flash forward to senior year:

I’m standing on our  graduation stage giving a speech to my entire class, their families, my teachers, and the mayor. People probably thought, “Wow, she’s so brave! I could never do that.”

But I wasn’t feeling brave. I was feeling like I wanted to die.

What people didn’t see was the process:

Coming in to school everyday, even though the Seniors were out, to work through my speech with one of my many amazing English teachers, Mr. Cotto 🤍

Standing in my bedroom mirror, repeating my speech over and over and over. 

Calling my grandmother to continue to  practice as she yelled, “SLOW DOWN, CAITLIN!” through the phone. 

Her voice echoed in my head the entire time I stood on that stage.

People saw an 18-year-old delivering a confident speech.

What they didn’t see was the time, effort, and energy it took to not screw it up.

And this is where perspective matters.

Our teens compare themselves constantly — especially with social media — to everyone around them. They see others’ strengths and compare that  to their own weaknesses. Adults do this, too. We look at someone else’s highlight reel without seeing their setbacks, struggles, or rejections.

Confidence grows from doing.

I didn’t start out as a strong public speaker — I became one by doing it over and over. I ended up double-majoring in management and communication in college. Public speaking classes were required, I was in heaven, I got to talk to my classmates and get a grade for it! For some of my classmates coming to class was like their own episode of Fear Factor! Week after week they stood in front of our class with their legs tapping and talking a mile a minute, just like me sophomore year in high school.  But, everyone got better. Because the more we do anything the better we get at it and the more confident we are doing it.

But, put me in a salon with a client, in a police uniform, in a phlebotomist’s office, or anything involving finance? WATCH. ME. QUIVER.

We all have our strengths and our weaknesses.

And knowing them — without comparing our weaknesses to someone else’s strengths — is half the battle.

Our teens learn this not because we lecture them, but because we model it. I was lucky to have people who believed in me, gave me perspective, and let me vent. I grew up knowing that even if I messed up, my parents would help turn that failure into resilience.

This is what our teens need from us.

So How Do We Actually Boost Our Teen’s Self-Esteem?

Here are the strategies that matter most — the ones backed by experience, research, and what we know about teen development:

1. Praise the Process, Not the Outcome

Don’t just tell them they’re amazing — highlight how they worked.

Confidence comes from effort, not perfection.

Try saying:

“You kept showing up even though it was hard.”

“I’m impressed by how much effort you put into that.”

“You bounced back today.”

You aren’t giving them vague compliments, you are being specific and praising the effort. You’re teaching them that effort matters more than outcome. We can’t control every outcomes, we can always control our effort. 

2. Normalize Setbacks — Loudly and Often

Teens think everyone else is thriving while they’re failing quietly. Sharing your own (age-appropriate) rejections gives them the gift of connection and perspective. 

And here’s the part that is so hard for us as parents:

It’s painful to watch our teens struggle. Our instinct is to either love-bomb them with every reason they’re amazing or to rush in and fix the situation for them. But they don’t need us to fight their battles or convince them they’re perfect.

What they really need is to know is:

We’re in their corner
We’re listening
We can help them process the feelings and when they’re ready, we’ll help them take the next step

Our calm, steady presence supports confidence more deeply than any pep talk ever could.

Setbacks don’t define them.

Setbacks shape them.

3. Encourage Low-Stakes New Experiences

Confidence grows through action. Small risks =big resilience.

Encourage them to try:

A new club

A part-time job

A new sport or hobby

A class that sparks curiosity

Volunteering

The goal isn’t to be the best at everything — it’s to be ok with trying different things. 

4. Give Them Real Autonomy

When teens have a say in their lives, their self-esteem strengthens.

As Mel Robbin’s would say: “Let Them…”
Make decisions little and big.
Have input in family plans.
Manage conflicts.

Teens learn through experience, so we need to allow them experiences. Yes it can be painful to watch or listen as they are figuring things out. It’s hard not to interject or jump in to ‘fix it’ mode and when we do, they hear and feel, “I don’t trust you- you can’t do it!”  They need the time and the space to figure it out and when they do, they get the dopamine that comes with it. They get hooked and they want more autonomy. It isn’t scary, it’s empowering. 

The message is: “I trust you — and you can trust yourself.”

5. Build Their Support System

Your teen needs more than just you.

Coaches, teachers, mentors, older cousins, bosses — these adults reinforce their worth and give perspective you can’t always provide.

A strong support system = a strong sense of self.

6. Catch the Negative Self-Talk Spiral Early

Teens catastrophize like it’s their part-time job.

Gently challenge the story, not the feeling.

Try:

“I hear you — this is disappointing.”

“Let’s look at the facts, not the feelings.”

“What would you say to a friend who felt this way?”

This builds emotional regulation and perspective.

7. Make Your Relationship Their Safe Place

Above all, the most powerful way to build a teen’s self-esteem is to create a home where they feel unconditionally valued.

Not for grades.

Not for performance.

Not for behavior.

But for who they are.

This is the foundation everything else is built on.

In the End…

Our teens don’t need us to remove every obstacle.

They need us to walk beside them, help them make sense of the setbacks, and remind them that confidence isn’t built from perfection — it’s built from courage, effort, perspective, and connection.

They need us to model trying, failing, getting up, laughing it off, and trying again.

They need us to show them that self-esteem isn’t something you’re born with — it’s something you build, slowly and imperfectly, over time.

And most of all, they need to know this:

There is nothing they can fail at that will make us love them any less — and nothing they can achieve that will make us love them more.

Safety and Self Esteem are two peas in a pod, just like you and your teen. 

Your friend,

Caitlin

P.S. I should add, as confident as I am in front of the crowd, my Achilles heel is talking about anything that’s tied to my emotions. I am immediately Linda Richman aka Mike Myers- SNL- Coffee Talk- VERKLEMPT!!