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#64 - Dear Freshman

Aug 20, 2024

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This is the episode I wish I heard before I went to college.

College starts again this week so I thought this was the perfect time to reflect on my first semester of freshman year. I talk about 3 of the defining moments from my freshman year (one about roommates, one about friend groups, and one about fraternities) and what I learned from each of them.

This is for anyone starting college but also for anyone who is old enough to reflect on the mistakes they made freshman year... so everyone. This one's special.

Dear College Freshman: The Cringe, The Mistakes, and Why It's All Worth It

What nobody tells you about first semester—and why those embarrassing moments will shape your entire college experience

Starting college is terrifying, exhilarating, and completely overwhelming. You're thrown into this new world with thousands of strangers, expected to make "friends for life," and somehow figure out who you want to be—all while navigating dining halls, dorm rooms, and Thursday night parties.

Josh from Guyset recently reflected on his freshman year, seven years later, and realized something important: those cringe-worthy moments you're desperately trying to forget? They're actually the experiences that taught him the most about life.

The Truth About Freshman Year That Nobody Mentions

Here's what nobody tells you about starting college: it's the first time in your life you're truly on your own. Sure, there's orientation week and dining halls and class schedules, but everything else? That's up to you.

"You get to make the decisions of who you wanna hang out with and what friendships you want to continue making," Josh explains. "Everything else is on your accord."

The pressure is real:

Hoping people will like you
Wanting to make friends for life
Expecting to find your people immediately
Thinking every decision is permanent

The reality is different:

Not everyone will like you (and that's okay)
Some friendships will fade (and that's normal)
You'll make mistakes (and that's expected)
You'll cringe at your past self (and that means you've grown)

Three Lessons from the Freshman Year Trenches

1. Your Roommate Doesn't Have to Be Your Best Friend (But Be Kind Anyway)

Josh got lucky with his freshman roommate—a mutual friend who became one of his closest friends. But even that relationship hit a major bump.

What happened: They got into a "shitty fight" mid-semester over something Josh now describes as "so, so dumb."

What he learned:

You don't have to be best friends with your roommate, but you must be civil and kind
That tiny room is your shared space—keep the energy calm and pleasant
Deal with issues head-on instead of bottling them up
Learn to forgive quickly and move on

Josh's advice: "Try your best not to let the little things get to you when living with somebody. If you bottle the way you're feeling up, then you're just holding a stone in your hand and squeezing tighter and tighter and the other person doesn't even know how you feel."

2. It's Okay to Leave Friend Groups That Don't Feel Right

A few weeks into college, Josh found himself in a friend group that felt "too cool for school" while he felt like "the farthest thing from too cool for anybody."

The dilemma: Stay with people who don't feel like "his people" or risk being alone with no backup plan.

What he did: Made the scary decision to not go out with them one night, even though he had no other plans.

The result: He ended up hanging out with people on his hall who became really good friends throughout the year.

The lesson: "When one door closes, another one opens pretty quickly without you having to look so hard for it."

Key insight: Some friendships fade during freshman year, and that's completely normal. "The ones who are supposed to stay will stay, and the ones who are supposed to come back will also come back."

3. Rejection Is Redirection (Even When It Feels Devastating)

Josh's most painful freshman year experience involved not getting into the fraternity all his friends were rushing.

The setup: You got into parties by receiving a text from the rush chair. If you were on the list, you were basically in. If not...

What happened: Josh waited by his phone for the text that never came. His friends all got invited; he didn't.

How it felt: "As sad as that sounds and embarrassing as that sounds, it was dreadful. Rejection fucking sucks."

The aftermath: Josh was convinced he'd ruined his entire college experience and would lose all his friends.

The plot twist: This rejection led him to join a different fraternity where he met some of his best friends today.

The revelation: "Had I not been rejected, I would have had an incredibly different experience. I would have ended up surrounded by people who did not want to be surrounded by me."

The Questions That Change Everything

After his fraternity rejection, Josh started asking himself different questions:

"Do I even like them?"
"Why would I want to spend time with people who do not want to spend time with me?"
"Why get anxious and upset about learning such helpful news?"

The realization: When someone rejects you, they're telling you they don't want to spend time around you. So why would you want to spend time around them?

Why Freshman Year Feels So Intense

Every decision in freshman year feels earth-shattering because:

You're making choices about who you want to become
You think everything needs to be permanent
You're terrified of missing out or making the wrong choice
You have no experience to put things in perspective

Josh's insight: "Some friendships fade over the course of first semester freshman year and I think that's okay. I think that friends and people come into your life for a reason at some point and you're friends for that person for as long as you're supposed to be."

What Nobody Tells You About the Cringe

Seven years later, Josh looks back at his freshman year behavior with "such a distaste for how I acted." But here's the important part: he doesn't avoid thinking about it.

Why examining the cringe matters: "If you don't ever look back at the times that make you wince or cringe at the way you behaved or the way you acted, then I don't see how you can really grow from those experiences."

The growth mindset:

You aren't your worst mistake
You don't have to stay that person
Looking back with growth, not just regret, is how you learn
Recognizing how far you've come is part of the process

The Real Freshman Year Survival Guide

Based on Josh's experiences and hindsight, here's what actually matters:

Do These Things:

Be kind and civil to your roommate (even if you're not best friends)
Leave situations that don't feel right (trusting your gut is important)
Deal with conflicts head-on instead of bottling up feelings
Accept that some friendships will fade (and that's normal)
Learn from rejection instead of just being devastated by it

Remember These Truths:

Not everyone will like you (and you won't like everyone either)
Mistakes are guaranteed (you're navigating this for the first time)
People come into your life for specific reasons (to teach you something about yourself)
Your cringe moments will become your growth moments (in a few years)
Rejection often redirects you to better opportunities

Ask Yourself:

Do I like the person I'm becoming around these people?
Do I actually enjoy spending time with them?
Am I trying too hard to fit in somewhere I don't belong?
What is this experience teaching me about myself?

The Long View

Josh's main message is this: "You are almost guaranteed to fuck up in the first couple months of college... and you're expected to because what else do you know?"

The permission you need:

It's okay to make mistakes
It's okay to behave in ways you'll later cringe at
It's okay to lose friendships that weren't meant to last
It's okay to get rejected from things you thought you wanted

The promise that makes it worthwhile: "I can guarantee you will learn what to do and you will grow from the mistakes."

For Current Freshmen

If you're in the middle of freshman year right now:

Trust the process - You can't see the lessons while you're living them
Don't put so much pressure on every decision being permanent
Be authentic rather than trying to make everyone like you
Stay open to unexpected friendships and opportunities
Remember that everyone else is figuring it out too

For Everyone Else

If you're past freshman year (or college entirely):

Look back with compassion for your younger self
Extract the lessons from your cringe moments
Appreciate the growth that came from difficult experiences
Share your wisdom with people just starting their journey

The Bottom Line

Freshman year isn't about avoiding mistakes—it's about making them, learning from them, and becoming the person you're supposed to be. Those embarrassing moments you want to forget? They're actually the experiences that will teach you the most about resilience, authenticity, and finding your real people.

Remember: You're not just in college to get good grades. You're there to figure out who you are, what you value, and how you want to show up in the world.

The friends who are meant to stay will stay. The opportunities that are right for you will find you. And all those cringe-worthy moments? They're just proof that you're brave enough to try, fail, learn, and try again.

Starting college soon or want to share this wisdom? Send this to any incoming freshman in your life. Sometimes the best advice comes from someone who's been there, made the mistakes, and lived to tell about it.

Struggling with college transitions or freshman year challenges? Remember that everyone feels overwhelmed sometimes—it's all part of the process of becoming who you're meant to be.

Want more honest conversations about college and life transitions? Listen to Josh's complete freshman year reflection on the Guyset podcast, available on Spotify, Apple Podcasts, and wherever you listen to podcasts.

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