When I think about my twenties, it’s a strange mix of nostalgia and a slight cringe. That decade is such a whirlwind—full of firsts, failures, friendships, flings, and figuring life out on the fly. It’s not surprising to me that there are certain things looking back that I hated about my 20s.
At the time, it felt like I was constantly trying to catch up—trying to be the “adult” I thought I should already be. Now, looking back with a little more clarity (and a lot more grace), there are a handful of things I really didn’t love about that season of life.
A Different View On Life In My 20s
If you’re in the thick of your twenties right now, know this: it’s okay to feel lost. It’s okay to not have it all figured out. And it’s definitely okay to look back one day and think, “Wow, I really hated that.” So here are nine things I hated about my twenties in retrospect—and what I learned from each of them.
1. Feeling Like I Had to Have It All Figured Out By 25 – Most Hated About My 20s
At 22, I genuinely believed I needed to be married, climbing the corporate ladder, financially stable, and living in a Pinterest-worthy apartment by 25. Spoiler: I was still living with roommates, switching jobs every year, and eating cereal for dinner three nights a week.
The pressure to have my entire life mapped out so early was exhausting—and totally unrealistic. Your twenties are not a deadline; they’re a draft. Looking back, I wish I had relaxed more and trusted that growth isn’t linear. Life unfolds in its own messy, beautiful way.
2. Working Jobs That Didn’t Light Me Up (But Felt “Safe”)
Like so many twenty-somethings, I took jobs for the paycheck or because they looked good on paper. I stayed in roles that drained me because I thought it was what “responsible adults” did. I was afraid to start over or try something unconventional—even when I was miserable.
In hindsight, playing it safe often cost me more than taking a risk ever would have. The jobs I truly loved didn’t show up until I stopped settling and started listening to my gut. Stability is important, but so is your sanity.
3. Believing Hustle Culture Was the Only Way to Succeed (An Easy Thing to Hate About My 20s)
I wore burnout like a badge of honor. I believed the only way to be taken seriously was to always be busy, to always be grinding. If I wasn’t staying late or juggling three side projects, I felt like I was falling behind.
The truth? Constant hustle drained my creativity and joy. Slowing down didn’t make me lazy—it made me intentional. I wish I had known that rest is not a reward for productivity—it’s a necessary part of success.
4. Trying to Be Who Everyone Expected Me to Be
I spent way too much time shape-shifting in my twenties. I wanted to be the “cool” girl at work, the agreeable girlfriend, the daughter who never disappointed. But, I swallowed my opinions, downplayed my dreams, and molded myself into whoever I thought the room needed me to be.
It took years to realize that being liked isn’t nearly as fulfilling as being known. People-pleasing is a slow form of self-erasure. If I could go back, I’d remind myself that authenticity is way more magnetic than perfection.
5. Romanticizing the Wrong Relationships is Something I Hated About My 20s
Oof. This one still stings. I look back at some of the relationships I stayed in and think, “Girl, what were you doing?” But I know what I was doing—I was holding onto potential. I was projecting the version of the relationship I wanted to exist instead of facing what was actually happening.
I ignored red flags, overextended myself emotionally, and convinced myself I could “fix it” if I just tried harder. Looking back, I wish I had walked away sooner and prioritized my peace over the fantasy.
6. Comparing My Timeline to Everyone Else’s
There’s something about your twenties that makes you hyper-aware of everyone else’s milestones. She’s getting engaged. He’s buying a house. They’re having a baby. Meanwhile, I was just trying to figure out how to pay my student loans and not cry on my lunch break.
Comparison stole a lot of joy from me during that decade. It made me doubt my own journey and rush decisions I wasn’t ready for. Now I know that life isn’t a race—it’s a road trip. And no two routes look the same.
7. Living in Survival Mode Instead of Intentionality – A HUGE Thing I’ve Hated About My 20s
I spent much of my twenties reacting instead of responding. I said yes out of obligation. I scrambled to make ends meet. I let fear dictate my choices. My mindset was “just get through it,” not “how do I want to build this life?”
I didn’t realize how much power I actually had—to say no, to pause, to change directions. Survival mode made me miss so many opportunities to live intentionally. I wish I had believed I was allowed to be the architect of my own life—even if it wasn’t picture-perfect.
8. Neglecting My Mental Health Because I Thought I Was “Too Young” to Struggle
For a long time, I thought anxiety and burnout were just part of being in my twenties. I brushed off signs of depression. I thought, “Everyone’s overwhelmed—this is normal.” I didn’t seek help because I thought I had to “tough it out.”
But ignoring my mental health only made things worse. Looking back, I wish I had taken my feelings seriously sooner. Therapy isn’t a last resort; it’s an act of self-respect. Asking for help isn’t weak—it’s brave.
9. Not Celebrating How Far I’d Come Made Me Hate My Twenties
I was so focused on what was next that I rarely stopped to appreciate how far I’d already come. I didn’t celebrate small wins. And I brushed off compliments. I told myself it wasn’t enough yet—I wasn’t enough yet.
But the truth is, I was growing in ways I couldn’t always see. I was doing the best I could with what I had—and that deserved acknowledgment. If I could go back, I’d throw myself a little party every time I took a step forward, even if it was tiny.
Final Thoughts: Giving My Twenties Grace
I could beat myself up over these things (and believe me, I have), but I’ve also come to appreciate what they taught me. My twenties were messy, beautiful, confusing, thrilling, and full of growth. They were mine.
If you’re in your twenties now and this post hits home, just know—you’re not alone. So many of us are quietly struggling with the same things behind curated Instagram stories and LinkedIn updates.
Give yourself permission to grow at your own pace.
Give yourself grace for the lessons you’re still learning.
And most of all, don’t be afraid to rewrite the story as you go.
You don’t have to love every moment of your twenties. But I promise—one day, you’ll look back and be proud of how far you’ve come.
About the Author
Anna is a twenty-something living in the south. She's passionate about family, crafting, and continuing her education beyond her college degree.