The 1990s. A time of cassette tapes, landline phones, dial-up internet, and questionable fashion trends.
A time when I thought I had life figured out, despite having zero actual life skills.
A time when I believed I was an adult but was actually an unsupervised child with a paycheck.
And through it all, The Cynic Upstairs was there—watching, sighing, and trying (with increasing frustration) to keep me from ruining my own life.
This is the story of how, in my 20s, I went from arguing with him, ignoring him, and trying to shut him up—to occasionally, just occasionally, listening to him.
1. The 20s Begin – The ‘I Am an Adult Now’ Delusion
Me (first day of my first job): “Ah, adulthood! A steady salary, independence, control over my life! I’m finally free!”
The Cynic Upstairs: “Oh, buddy. You are about to get financially and emotionally destroyed. Can’t wait.”
Me: “Come on, how hard can it be? I’ve got money now! I can do whatever I want!”
The Cynic Upstairs: “Okay. Let’s play a game. It’s called How Long Before You’re Broke? My guess? Two weeks.“
2. The Great Financial Disaster – Salary? What Salary?
First paycheck arrives.
Me: “I AM RICH! Drinks on me, everyone!”
The Cynic Upstairs: “And so it begins…“
Day 1: Fancy dinner, new shoes, expensive cologne because ‘corporate life.’
Day 5: Bought a walkman and an absurd number of cassette tapes.
Day 10: Somehow agreed to lend money to a friend (who will never return it).
Day 15: Checked bank balance. Immediate regret.
Me: “Wait. WHERE DID MY MONEY GO?!”
The Cynic Upstairs: “Oh, look! Your first financial crisis. And it only took half a month.“
3. The Career Confusion – What Am I Even Doing?
Back in the 90s, careers weren’t about ‘following your passion.’
They were about getting a stable job and sticking to it.
Me: “I think I want to do something exciting! Maybe advertising? Maybe media? Maybe… I should switch jobs?”
The Cynic Upstairs: “You’ve worked here for THREE MONTHS. Can you chill?”
Job Switch #1: Thought I’d find my dream job. Ended up doing data entry.
Job Switch #2: Thought I’d get a raise. Got a longer commute.
Job Switch #3: Thought I’d finally be respected. Got a boss who thought sarcasm was leadership.
Me: “WHAT AM I DOING WITH MY LIFE?!”
The Cynic Upstairs: “Ah, yes. The classic ‘What am I doing with my life’ phase! Buckle up, it’s going to last a while.”
4. The Relationship Struggles – The Cynic Watches in Horror
My love life in the 90s was just… a mess.
No social media. No dating apps. Just real-life awkwardness.
Me (before the date): “I think she’s the one! I can feel it!”
The Cynic Upstairs: “Oh, this is going to be painful to watch.”
Date 1: Talked too much about music. She liked poetry.
Date 2: Tried to impress her by quoting philosophy. Got confused mid-sentence.
Date 3: Borrowed a romantic line from a movie. Sounded creepy instead.
After one particularly bad breakup—
Me: “I will NEVER fall in love again!”
The Cynic Upstairs: “Oh, please. You’ll be in love again next week.”
I wasn’t. It took two weeks.
5. The ‘I Can Fix My Life’ Phase (Spoiler: I Could Not)
At some point in my 20s, I tried to become a better person.
- Started going to the gym. Went twice.
- Tried meditation. Fell asleep.
- Woke up early. Once.
- Made a budget. Broke it immediately.
Me: “This time, I will change!”
The Cynic Upstairs: “This is adorable. Call me when you fail.”
By now, I had stopped ignoring him.
Instead, I was arguing with him daily.
6. The Quarter-Life Crisis Hits Hard
One fine day, existential dread kicked in.
Me: “WHAT AM I DOING WITH MY LIFE?!”
The Cynic Upstairs: “Oh, we’re finally here! The classic ‘What am I doing with my life’ phase. Welcome!”
- My friends were getting married. I was still confused about dating.
- Some were buying houses. I was barely affording rent.
- Some had careers figured out. I still didn’t know what I wanted.
Me: “Am I behind in life? Am I failing?!”
The Cynic Upstairs: “Statistically? Yes. But let’s pretend otherwise.”
7. The Cynic Starts Winning (Sometimes)
By my late 20s, I had lost enough battles to start considering his advice.
Me: “I should invest in something! Maybe get a fixed deposit?”
The Cynic Upstairs: “Oh, look at you! A financial decision that doesn’t involve being broke by the 15th! I’m so proud!”
Me: “I think I should stay in one job for more than six months.”
The Cynic Upstairs: “YES! Growth! We love to see it!”
For the first time, he wasn’t just annoying background noise.
I wasn’t fully obeying him yet, but I was listening.
Final Thoughts
My 20s were a beautiful disaster.
I, as always, made dumb choices. The Cynic Upstairs? He tried to stop me, failed a lot, but occasionally won small battles.
And now? The 30s are coming.
Where the real adulting struggle begins.
Up next: The 30s—where The Cynic Upstairs starts taking full control.
Stay tuned. (And may The Cynic Upstairs forgive my past self.)