Life lessons I wish I knew slapped me in the face harder than that time I tripped on a sidewalk in downtown Austin last week, phone flying, coffee splattering, strangers staring. I’m sitting here in a creaky wooden chair at this hole-in-the-wall diner, the kind with sticky menus and a jukebox that’s probably broken since the 90s, scribbling this on a napkin because, well, my laptop’s dead again. My 20s? Man, they were a chaotic blur of bad decisions, late-night tacos, and thinking I had it all figured out. Spoiler: I didn’t. I’m in my 30s now, in the US, reflecting on those life lessons I wish I knew back then, and I’m gonna spill the tea—raw, unfiltered, and maybe a little embarrassing.
Like, seriously, why didn’t anyone tell me how much I’d regret certain choices? Or maybe they did, and I was too stubborn to listen. Anyway, here’s my take—flawed, human, and straight from the heart of someone who’s still figuring it out.
Why Life Lessons I Wish I Knew Matter Now
Back in my 20s, I thought I was invincible. I’d stay up till 3 a.m. in my tiny Chicago apartment, chugging energy drinks, convinced I was “hustling.” I once spent my last $50 on a neon-colored thrift store jacket because it “vibed” with my soul. Cringe, right? That jacket’s probably in a landfill now, and so is the confidence I had that I’d “make it” without a plan. The life lessons I wish I knew would’ve saved me from that mess—or at least softened the blow.
Here’s what I’ve learned, sitting here with diner coffee that tastes like regret: your 20s are a weird mix of freedom and pressure. You’re told to chase dreams, but nobody mentions the fine print—like, how do you even know what your dreams are? I wish I’d slowed down, breathed, and realized mistakes are just data points.

Lesson 1: Stop Chasing “Perfect”
Perfection? It’s a scam. I spent years obsessing over getting everything right—my job, my relationships, even my Instagram aesthetic (yep, guilty). I remember crying in a Target parking lot in Ohio because I didn’t get that “dream job” I thought would define me. Spoiler: It wouldn’t have. The life lesson I wish I knew? Good enough is better than perfect. Chasing flawless just leaves you exhausted and broke.
- Tip: Start small. Mess up, laugh it off, move on.
- Example: I once rewrote a work email 17 times. Seventeen! It still sucked. Nobody cared.
- Why it matters: Perfectionism steals time you could spend living.
Outbound link: Read more about letting go of perfectionism at Psychology Today’s article on self-acceptance.
Lesson 2: Money Isn’t Just for Tacos
Okay, I love tacos, but I wish I’d saved more in my 20s instead of blowing every paycheck on late-night food runs or concert tickets. I’m in this diner right now, staring at a $7 coffee I shouldn’t have bought, and it’s like my 20s self is haunting me. Life lessons I wish I knew include budgeting—like, actually sticking to one. I once “invested” in a $200 blender because I saw a smoothie influencer on X. Never used it. Still in its box somewhere.
- Tip: Save 10% of every paycheck, even if it’s $10. Future you will thank you.
- Mistake: I ignored my student loans, thinking they’d magically disappear. They didn’t.
- Surprise: Learning to budget gave me more freedom, not less.

Outbound link: Check out NerdWallet’s guide to budgeting for beginners.
Life Lessons I Wish I Knew About Relationships
Relationships in my 20s were like trying to herd cats while riding a unicycle. I’d fall for people who were obviously wrong for me—like that guy who “borrowed” my car and returned it with a half-eaten burrito on the seat. Why didn’t I see the red flags? The life lesson I wish I knew: you can’t fix people, and you don’t have to stay in toxic situations. I learned this the hard way in a Seattle coffee shop, breaking up with someone while it poured rain outside, my sneakers soaked, my heart heavier than the clouds.
- Tip: Set boundaries early. It’s not mean; it’s self-respect.
- Embarrassing moment: I once stayed in a relationship because I didn’t want to “waste” the concert tickets we’d bought. Dumb.
- Reflection: Loneliness is better than drama. Trust me.
Outbound link: Learn about healthy boundaries at Verywell Mind.
Lesson 3: Failure Is Just Feedback
I used to think failing meant I was a failure. Like when I bombed a presentation at my first “real” job in Denver—sweaty palms, stuttering, the works. I hid in the bathroom afterward, convinced I’d be fired. Spoiler: I wasn’t. The life lesson I wish I knew? Failure’s just data. It’s not your identity. Now, I’m sitting here in this diner, laughing at how I used to take every L so personally.
- Tip: Write down what went wrong, then move on. It’s not that deep.
- Example: That presentation? My boss gave me feedback, and I got better.
- Surprise: Failing taught me more than succeeding ever did.

Wrapping Up This Chaotic Chat on Life Lessons I Wish I Knew
So, yeah, my 20s were a hot mess, but they taught me life lessons I wish I knew back then—stuff I’m still unpacking while sipping overpriced coffee in this diner, the neon “Open” sign flickering outside. I’m not perfect (far from it), and I’m still learning, but I hope my rambles help you dodge some of the dumb stuff I did. Got a life lesson you wish you knew? Drop it in the comments or hit me up on X—I’m all ears. Well, mostly. My phone’s at 3%, so I gotta wrap this up.