This past weekend I went to my 5 high school reunion and it's time to debrief...

I wasn't originally gonna go, last minute decided why not, and through many gin and tonics, I made a lot of realizations about where I am now and how much I've actually grown up in 5 years. This episode and that reunion are a reminder to me that we’re all just tryna figure it out.

What I Learned at My 5-Year High School Reunion: Why Everyone's Finally on the Same Playing Field

Originally shared on the Guyset podcast - a guy's guide to what should be talked about

Going Back to High School (But Make It 2024)

I wasn't going to attend my five-year high school reunion. Honestly, I figured I'd stayed in touch with the people I wanted to keep in touch with - which, let's be real, was literally two people. But something made me change my mind: the realization that there were probably missed connections and friendships that had simply faded due to distance and time, not by choice.

So I went. And what I discovered completely shifted how I think about growing up, comparison, and confidence.

The Conversation Loop

If you've been to a reunion, you know the drill. The conversations were remarkably similar with almost everyone:

• "How are you?"

• "What are you up to now?"

• "Where are you living?"

• "What's your job?"

With closer friends, I pushed past these surface-level questions to get into the real stuff: relationships, family, what's actually going on in their lives. And here's what struck me most - everyone was doing pretty much okay.

The Great Equalizer

This was the biggest revelation: we're all on the same playing field now. In high school, it felt like some people had it all figured out while others (myself included) were just trying to survive. There were the "cool kids" with seemingly endless social plans, relationships, and confidence, while I was content hanging out with the same three people every weekend.

But five years later? That hierarchy has completely dissolved.

Now we're all either:

• Working or job searching

• Living in a new city or back home

• In relationships, dating, or single

• Happy with where we're at or striving for more

• Struggling or thriving

The artificial social structure of high school has given way to real life, where everyone's navigating the same basic challenges of early adulthood.

Why Everyone Seemed So Much Nicer

One of the most surprising things was how genuinely nice everyone was - much nicer than I remembered from high school. People were willing to share openly about how they were doing, and there wasn't that underlying current of drama and judgment that permeated our teenage years.

I think it comes down to this: people are more comfortable in themselves now. We've all had five years to figure out who we are outside of the high school social ecosystem.

The Confidence I Never Had

Looking back, my biggest insecurities in high school were my weight and acne. I was so self-conscious about these things that I dreaded leaving the house on bad skin days. I remember going on Accutane and looking like the Joker from The Dark Knight because my lips were so chapped from the medication.

These insecurities, combined with feeling socially "behind" others, made high school a challenging time. But standing in that reunion venue, I realized I'd found something I desperately wanted back then: confidence in myself.

What Changed in Five Years

The difference isn't just maturity - it's genuine self-discovery. In the five years since graduation, I've:

• Learned about my mental and physical health

• Developed relationships and learned about myself through them

• Found what I'm passionate about (clearly, since I'm podcasting about it)

• Gained confidence I never thought possible

High school me would never have imagined doing something like hosting a podcast where I talk openly about feelings and vulnerabilities. Back then, my biggest worry was what people thought of me.

The Comparison Trap

In high school, I compared everything: looks, grades, athletic ability, social status. I dreaded mile run day in PE because I was worried about being slower than everyone else. Looking back, it seems silly, but at the time, what people thought of me felt like the most important thing in the world.

The difference now? Comparison is still a thing (we're human), but we have much more control over it. We're not trapped in hallways surrounded by the same few hundred people every day. We can turn off social media, choose our environments, and focus on our own paths.

Why High School Was So Hard (And Why It Gets Better)

High school is this weird, formative time where you're still figuring out who you are, but you're constantly surrounded by the same people and forced into situations where you're being evaluated and compared. You spend so much time trying to be something you're not instead of discovering who you actually are.

After high school, you get the chance to:

• Reinvent yourself

• Follow your actual interests and passions

• Meet people who share your values

• Spend time alone and learn about yourself

• Live independently for the first time

For Anyone Still in High School

If you're currently in high school and somehow reading this: it genuinely gets so much better. You'll get to follow the things you actually love instead of trying to fit into predetermined molds. You'll find your people - the ones who appreciate you for who you actually are.

I loved English class, reading, and writing, but I spent so much time wishing I was good at math like my friends. Why? Because I was trying to be someone I wasn't. Now I get to do what I love (talking and sharing ideas) for work and passion.

The Level Playing Field

The most liberating realization was that the artificial advantages some people seemed to have in high school don't matter anymore. The "cool kids" might have seemed like they had life figured out, but now we're all facing the same fundamental questions:

• What do we want to do with our careers?

• Where do we want to live?

• What kind of relationships do we want?

• How do we want to spend our time?

Nobody has a head start on figuring out adult life. We're all learning as we go.

The 10-Year Question

Will I go to the 10-year reunion? Honestly, I don't know. Part of me hopes I'll be too busy with exciting projects to attend. But if I'm free, I'll probably go again to see how much further we've all come.

The Bigger Picture

This reunion was a reminder that the things that felt so important in high school - social hierarchies, who was dating whom, who had the coolest plans - ultimately don't matter. What matters is becoming comfortable with who you are and pursuing what genuinely interests you.

Theodore Roosevelt said, "Comparison is the thief of joy," and I wish I'd internalized that quote earlier. While we can't completely eliminate comparison from our lives, we now have the power to control how much we engage with it.

Key Takeaways

1. Everyone's figuring it out: The people who seemed to have it all together in high school are facing the same life questions as everyone else

2. Confidence comes from self-knowledge: The more you understand and accept yourself, the less you need external validation

3. The playing field levels out: Post-high school, we're all dealing with similar challenges and opportunities

4. Growth takes time: Five years might seem like nothing, but it's enough time for significant personal development

5. High school social dynamics don't predict adult success: The "cool kids" aren't necessarily thriving more than anyone else

A Final Thought

If you're struggling with confidence or feeling behind others, remember that everyone's on their own timeline. The person you're comparing yourself to is probably comparing themselves to someone else. Focus on your own growth, pursue what genuinely interests you, and trust that you're exactly where you need to be.

High school might have been hard, but you're not that same person anymore. You've grown, learned, and developed in ways you couldn't have imagined back then. And that's something worth celebrating.

Josh shares more insights about personal growth, confidence, and navigating your twenties on the Guyset podcast. New episodes drop every Tuesday with honest conversations about what really matters in your twenties.

Reflecting on your own growth? Think about who you were five years ago versus who you are now. You might be surprised by how much you've changed for the better.

What My 5-Year High School Reunion Taught Me About Growing Up (And Why Everyone's More Chill Now)

Honest reflections on how much you actually change in your twenties—and why high school comparisons don't matter anymore

Five years ago, I graduated high school feeling behind, insecure, and constantly comparing myself to the "cool kids" who seemed to have everything figured out. Last weekend, I went to my five-year reunion expecting awkward small talk and flashbacks to teenage drama.

Instead, I discovered something unexpected: we're all finally on the same playing field.

Here's what I learned about growing up, letting go of high school insecurities, and why your twenties are when life actually begins.

Why I Almost Didn't Go (And Why I'm Glad I Did)

My initial thinking: "I've stayed close with the people I want to stay close with—literally two people. Why do I need to see people I haven't talked to in five years?"

What changed my mind: The realization that some friendships just fell away due to distance and time, not because we didn't like each other. College scattered everyone, and there might be connections worth rekindling.

The mindset that made all the difference: Going in with nothing to lose. I already had the friendships I valued most. Anyone else was just a potential bonus connection.

The Conversations: What Everyone Actually Talks About

The standard reunion script:

• How are you?

• What are you up to now?

• Where are you living?

• What's your job?

• Any relationships?

The deeper conversations (with people I was actually close to):

• What's really going on in your life?

• How's your family?

• Are you happy with where you're at?

The surprising discovery: When you're having these conversations for two hours straight, it's hard to maintain a fake persona. You get to the real stuff pretty quickly.

The Biggest Revelation: Everyone's Just Figuring It Out

What I expected: Some people thriving, others struggling, clear winners and losers in the "life game."

What I found: Everyone's doing okay, just in different ways. Some have girlfriends, others are single. Some moved to big cities, others stayed local. Some love their jobs, others are still searching.

The key insight: We're all just trying to figure it out, and that's completely normal.

Why High School Social Hierarchies Don't Matter Anymore

The High School Reality:

• Felt like some people had it "all together"

• Constant comparison was unavoidable (you're literally surrounded by the same people every day)

• Social status felt permanent and defining

• Insecurities were magnified by daily exposure to your "competition"

The Post-College Reality:

• The playing field is level again

• We all face similar choices: job or no job, relationship or single, new city or hometown, happy or still searching

• You can turn off the comparison (unlike high school where you couldn't escape it)

• Everyone gets a fresh start to find what actually matters to them

How Much You Actually Change in Five Years

The most important realization: I've grown up significantly, and it's not just about "maturing"—it's about becoming comfortable with who I actually am.

What's Different Now:

1. My priorities have completely shifted from what mattered in high school

2. I'm way more confident in myself than I ever was around these people

3. I care less about what others think (evidenced by having a podcast where I'm vulnerable every week)

4. I know myself better after five years of learning about relationships, mental health, and personal interests

The High School vs. Now Comparison:

High School Josh:

• Constantly worried about what people thought

• Compared everything: looks, grades, athletic ability, social status

• Tried to be good at things I wasn't passionate about (like math)

• Major insecurities: weight and acne

• Dreaded things like mile runs because of judgment from others

Post-College Josh:

• Pursuing what I actually love (writing, talking, connecting with people)

• Less concerned with others' opinions

• More confident in my own path

• Comfortable being vulnerable publicly

The Transition Nobody Talks About: High School to College

Why this transition is huge:

• You go from the same few hundred people to a world of new faces

• Complete opportunity to reinvent yourself

• First time living on your own

• Chance to explore actual interests rather than just trying to fit in

• Freedom to develop relationships based on genuine compatibility

Why we don't discuss it enough: We're always talking about the college-to-real-life transition, but the high school-to-college shift is equally transformative and deserves more recognition.

What I Wish I Could Tell High School Me

The Insecurities That Seemed Permanent:

• Acne so bad I hated leaving the house (even went on Accutane and looked "like the Joker")

• Weight issues that made me constantly compare myself to others

• Academic struggles in subjects I wasn't passionate about

• Social anxiety about fitting in with the "cool" crowd

The Reality Check:

None of that matters now. The things that felt like the end of the world in high school are barely footnotes in my adult life.

For Anyone Currently in High School:

It genuinely gets way better. You get to:

• Follow what you actually love instead of trying to fit a mold

• Find your real passions and hone in on them

• Surround yourself with people who appreciate the real you

• Build confidence based on genuine accomplishments and growth

Why Everyone Was So Much Nicer

The high school environment naturally breeds comparison, drama, and insecurity because:

• You're surrounded by the same people with no escape

• Everyone's figuring out their identity in a pressure cooker

• Social hierarchies feel permanent and important

• Teenage brains aren't fully developed (literally)

Five years later:

• People are more comfortable with themselves

• Less need to put others down to feel better

• Real-world perspective on what actually matters

• Emotional maturity that comes with experience

The Power of Perspective: Why Comparison Hurts Less Now

Theodore Roosevelt was right: "Comparison is the thief of joy."

High School Comparison:

• Unavoidable (same people, same environment daily)

• High stakes (felt like your entire social worth)

• Limited escape (couldn't just log off or change environments)

Adult Comparison:

• More controllable (you can choose your environment and inputs)

• Broader perspective (you realize everyone's struggling with something)

• Multiple metrics for success (not just grades and popularity)

What This Means for Your Twenties

The Level Playing Field Advantage:

Now that we're all out of the structured environment of school, everyone has similar opportunities to:

• Excel in their chosen field

• Find their passion and purpose

• Build meaningful relationships

• Create the life they actually want

• Reinvent themselves based on who they really are

The Growth Mindset:

Your twenties are when you actually get to become yourself. High school was just preparation—now you get to:

• Choose your own adventure

• Surround yourself with people who appreciate the real you

• Focus on what genuinely interests you

• Build confidence through real accomplishments

Practical Takeaways for Anyone Feeling Behind

If You're Currently Struggling with Comparison:

1. Remember everyone's figuring it out (even the people who seem to have it together)

2. Focus on your own growth rather than others' highlight reels

3. Seek environments where you can be authentically yourself

4. Give yourself credit for how much you've already grown

If You're Considering Your Own Reunion:

• Go with realistic expectations (it's mostly catching up, not life-changing drama)

• Approach it with curiosity rather than anxiety

• Remember you have nothing to prove to anyone

• Use it as a reflection opportunity to see how much you've grown

The Bottom Line: You're Exactly Where You Need to Be

The most important lesson: The people who seemed to have everything figured out in high school were just as confused as everyone else—they were just better at hiding it or happened to thrive in that particular environment.

Your path is your own. The timeline that matters isn't the one set by high school social hierarchies or college expectations—it's the one that aligns with your actual values, interests, and goals.

The relief of perspective: Realizing that everyone's just doing their best with what they have, and that the things that felt so important in high school really don't matter in the grand scheme of building a fulfilling adult life.

Looking Forward: The 10-Year Question

Will I go to the 10-year reunion? Honestly, I hope I'm too busy building something I'm passionate about to make it. But if not, I'll probably go and have another chance to reflect on growth and change.

The bigger question: What kind of person do you want to be by your next major life milestone? Not based on others' expectations, but based on your own values and goals.

Final Thoughts: Embracing the Journey

Your twenties are when you finally get to discover who you are outside of the constraints and comparisons of school. The people who seemed ahead in high school aren't necessarily ahead now—and the people who felt behind might be exactly where they need to be to build something amazing.

Give yourself credit for how far you've come. Five years might not seem like a long time, but it's long enough to completely transform your understanding of yourself and what matters to you.

And remember: the best parts of your story are still being written.

About Guyset

This post is based on an episode from Guyset: A Guy's Guide to What Should Be Talked About - a weekly podcast for guys in their twenties navigating life's transitions and discoveries. New episodes drop every Tuesday.

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• Email: josh@guyset.com

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