Why Gen Z Is Breaking Every Rule About Success—And Winning

Let me tell you how I accidentally ended up at a networking brunch in 2025 wearing a blazer, carrying printed resumes, and asking people where the fax machine was.

Spoiler alert: there was no fax machine. There was, however, a barista who offered me a turmeric oat latte and a Gen Z girl named Sasha who made $20,000 a month from a meme account and called me "sir."

Let’s rewind.

Monday: I Wake Up and Choose Delusion

After reading one too many motivational tweets that sounded suspiciously like they were written by ChatGPT on a Red Bull binge (“Wake up at 4AM, grind, become a legend”), I decided to try something radical: live for one week according to every traditional rule of success my parents, teachers, and overly enthusiastic LinkedIn influencers drilled into me.

You know the drill:

• Wake up early
• Dress for the job you want
• Work harder than everyone else
• Network like your life depends on it
• Chase promotions like they’re Pokémon

It was time to boomer up. I even printed a schedule. On paper. With bullet points.

Tuesday: LinkedIn Warrior Mode

I posted on LinkedIn.

"Excited to share that I'm entering a new phase of professional growth. Open to synergistic opportunities in dynamic, fast-paced environments. #grind #careergoals"

I stared at it for a while. Nothing happened. No job offers. Not even a like from my Aunt Shireen who congratulates people for finishing jury duty.

Meanwhile, Sasha (turmeric latte girl) messaged me on Instagram:

"Yo, I just got a brand deal to rate weird microwaves from the 90s. Got 10K for it. You should try it."

I wanted to cry. But I had a webinar on maximizing workplace ROI.

Wednesday: My Job Interview Looks Like a Performance Review

Wearing my finest (and only) suit, I showed up at a WeWork space where I'd scheduled a mock interview with a career coach.

She looked confused.

"Wait, you came in person? We usually do these on Zoom."

"I thought face-to-face builds stronger rapport," I said, sweating through three layers of polyester confidence.

"That’s cute," she replied.

Halfway through, she stopped me.

"You keep saying you're a 'hard worker.' That’s cool, but companies are looking for people who know how to not burn out. Do you know Excel?"

"Like, formulas and pivot tables?"

"No. Like, aesthetics. Can you make a spreadsheet look cute for TikTok?"

I excused myself to the restroom. Googled "cute Excel aesthetic." Cried a little.

Thursday: The Rise of Chaos Productivity

I asked Sasha how she organizes her workday. She sent me a meme of a raccoon holding a phone in a bathtub.

"Honestly," she voice-noted, "I do like two hours of stuff and then nap. And somehow I make more than I ever did when I tried doing 9-to-5."

I didn't understand it.

"Do you have a five-year plan?"

"Yeah," she said. "I plan to vibe."

That day I tried the Gen Z method: no plan, no real structure. Just vibes. I created a TikTok showing myself attempting to microwave a frozen lasagna with motivational quotes dubbed over it. It got 43,000 views.

A recruiter messaged me:

"Loved your energy. Ever thought of being a brand ambassador for weird kitchen products?"

This was not in my bullet journal.

Friday: Hustle Burnout vs. Balance Bragging

By Friday, my back hurt from carrying the weight of every outdated success model I’d tried to follow. I had sent out 39 resumes. Not one reply. My LinkedIn activity was off the charts, but my soul was in decline.

Meanwhile, Sasha posted a TikTok from Bali with the caption:

"Did 30 minutes of Canva work, now vibing with coconuts."

I felt personally attacked.

That night, I asked her, half-joking, "Do you guys just get lucky or is this, like, your version of professionalism?"

"Nah," she replied. "We just stopped pretending that burnout is a badge of honor. We monetize what we’re good at, even if it’s weird. Success isn’t one path anymore."

Saturday: The Revelation

I walked to a nearby park. No headphones. No productivity podcast. Just me and the overwhelming realization that everything I thought I knew about success might be… outdated?

Boomers had job security. Millennials had student debt and unpaid internships. Gen Z? They have creator funds, affiliate links, and side hustles that somehow involve Dungeons & Dragons and crochet.

They don’t chase promotions. They chase algorithms.

They don’t kill themselves for jobs. They build niche audiences and go viral for peeling fruit in oddly satisfying ways.

They’re not lazy. They’re allergic to fake hustle.

Sunday: I Join the Dark Side

I deleted the bullet journal. I archived my LinkedIn selfie. I started an Instagram called @BoomerTriesThings where I review TikTok hacks with deadpan commentary.

First video: "Trying the Gen Z 'sleep until you’re funny' method."

It got 12,000 views. Not viral, but it beat my resume.

Final Thoughts from a Former Hustle Addict

Gen Z is redefining success in a way that horrifies career counselors but delights burnt-out millennials like me. They value authenticity over polish, rest over stress, and creativity over conformity.

And here's the kicker: it works.

So if you see me sipping a coconut, posting memes for money, and using "vibe check" unironically—know that I didn’t give up. I just evolved.

Turns out, success doesn’t wear a tie. It wears Crocs and monetizes chaos.

And somehow, that's winning.