#103 - What They Don't Tell You About Life After College
May 20, 2025
Graduating this year? Already in your twenties and feeling lost? This episode is your brutally honest guide to navigating life after college when everything feels contradictory and confusing.
I break down the impossible expectations placed on twenty-somethings: You're supposed to save money AND travel, take risks AND stay stable, find your purpose AND stick with your first job for two years. Sound contradictory? That's because it is.
In this episode, you'll learn:
Why feeling lost in your twenties is completely normal (and necessary)
The "connect the dots" philosophy that will change how you view uncertainty
How your twenties are like building muscle - through breakdown comes strength
Why the only constant in your twenties is change (and how to embrace it)
How to find magic in the mundane when life feels repetitive
The superpower our generation has that previous ones didn't
Whether you're job hunting, dealing with rejection, questioning your path, or just trying to figure out what the hell you're doing - this episode will make you feel less alone and more equipped to handle whatever comes next.
If you're graduating this year or already stumbling through your twenties wondering what the hell you're supposed to be doing, this one's for you. Because here's what no one tells you about life after college: the contradictions will drive you insane, and that's completely normal.
The Contradiction Trap: Welcome to Your Twenties
After college, you'll be pulled in a thousand different directions. Everyone has expectations for you—including yourself. You'll wake up one day feeling like you have it all together: the date went well, your boss praised your work, you made dinner and felt proud of it. You accomplished everything on your checklist and went to bed feeling good.
The next day? Everything falls apart. She ghosts you. You forgot that important work task. You spend all your time anxious and scrolling on your phone, overthinking every text you send. You isolate yourself from friends and family, push off your goals, and go to bed wishing today was more like yesterday.
And it's only Wednesday.
The Impossible Expectations Game
Here's the catch-22 of your twenties that nobody prepared you for:
You're told this is the time to:
Figure it all out and create your life
Start saving money AND travel the world
Make memories with friends AND focus on yourself
Take risks AND stay in your first job for at least two years
Find your purpose AND don't job-hop
Build your career AND maintain work-life balance
Sound impossible? That's because it is.
The "Connect the Dots" Philosophy
Steve Jobs once talked about connecting the dots in his Stanford graduation speech. He shared how taking a calligraphy class seemed pointless at the time, but later inspired the beautiful fonts we use on computers today. The lesson? What you're doing may not make sense right now, but looking back, it will all connect.
That random internship, that side project you're passionate about, that skill you're developing "just because"—they're all dots waiting to be connected. Trust the process, even when you can't see the bigger picture.
Your Twenties Are Like Building Muscle
Think about how muscle growth works: you break down muscle fibers through resistance training, creating microscopic damage that repairs stronger than before. Your twenties work the same way.
This time in your life will be filled with:
Rejection and redirection
Uncertainty and doubt
Disappointment and loss
Inconsistency and change
But here's the thing—all those moments of "damage" lead to repair. Through rejection, you discover what's meant for you. Through uncertainty, you find your direction. Through disappointment, you build resilience.
Finding Magic in the Mundane
One of the most important lessons? You have to find magic in the mundane. Even when you start to figure things out, there will still be moments of boredom, anxiety, and confusion. Not every day is supposed to be magical.
Start from where you are, with what you know, with the tools you currently have. Maybe that's good enough.
The Only Constant Is Change
In your twenties, you'll experience conflicting feelings about everything:
You're not doing enough vs. you're doing too much
Content with your situation vs. anxious about the future
Confident in your friendships vs. missing how close you used to be
Happy with your job vs. wanting something more meaningful
Your plans will fall through. You'll get rejected. You'll feel lost and insecure one day, confident and strong the next. You'll reinvent yourself year after year, even without realizing it.
Use Your Generation's Superpower
Unlike previous generations, you have an incredible advantage: the ability to connect, share, and ask for help instantly. Don't keep everything bottled up. Ask people in your life for advice. Tell them how you're feeling. Ask for help.
Especially for the guys reading this—don't shove all that stress and confusion down. It will come up in ways you don't want it to.
You Already Have the Tools
You left college with tools you collected over four years—how to handle situations, what to say when, how to problem-solve. Now you just need to figure out how to apply these tools to new experiences.
Using them all at once won't work. You'll have to figure out what works when and how much pressure to apply. But you already have what you need.
The Bottom Line
I'm not telling you this to scare you about what's ahead. I'm telling you so you feel less alone when these things happen. So you know someone else has stood exactly where you're standing today and made it through.
The person reading this? You're ready for it. You have the tools. You just need to figure out when and how to use them. People have been navigating their twenties for generations—you're not the first, and you won't be the last.
Tomorrow is Wednesday. Choose to wake up hopeful. Sometimes positivity isn't a feeling—it's a choice.
This post was inspired by Episode 101 of Guyset, a guy's guide to what should be talked about. For more insights on navigating your twenties, relationships, career advice, and everything else guys should be talking about, listen to the full podcast and check out more content at guyset.com.
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See you guys next Tuesday.
