5 Signs You Shoulda Quit the Tech Grind YEARS Ago

Ever feel like you're living in the tech job twilight zone? One minute you’re daydreaming about quitting, selling everything, and disappearing into the mountains. The next? You’re convincing yourself, “Eh… it’s not that bad.” Yeah—I’ve been there.

→ Find Out If You're Ready To Go Solo in Tech

For years. I spent nearly a decade gaslighting myself out of leaving corporate life, ignoring burnout, and pretending I was just “in a rough patch.” But after coaching over 120 devs since going solo, I’ve learned this: most of us know we’re done. We’re just too skilled at lying to ourselves.

So in this episode, I’m calling it out: Here are 5 signs you shoulda quit years ago—and 5 actions you can take right now to start your escape plan. No fluff. No "just follow your passion" nonsense. Just hard-earned lessons from someone who's been in your shoes—and walked out the other side.

We’ll discuss:

• Why being too good at your job is actually a trap
• How apathy about tech might be a deeper signal
• The sneaky way your side projects are trying to tell you something
• What your unused vacation days really mean
• And why your coworkers’ loyalty is starting to feel cult-like

You can also watch this episode on YouTube. 

Chapter markers / timelinks:

(0:00) Introduction
(1:41) 1. 5 Signs You Should Have Quit Working in Tech Years Ago
(1:53) 1.1 You're Too Good At Your Job
(2:49) 1.2 You Stopped Caring About the Tech Stack
(3:50) 1.3 Your Side Gigs are Your Real Job
(5:01) 1.4 You're Hoarding Vacation Days
(6:10) 1.5 You Get Annoyed By Other People's Loyalty
(8:00) 2. 5 Immediate Actions to Start Breaking Free
(8:25) 2.1 Quit Caring About Your Next Performance Review
(9:45) 2.2 Sell Some Old Tech Gear
(10:45) 2.3 Reclaim an Hour From Your Job
(12:17) 2.4 Pitch a Fake Client Proposal
(13:58) 2.5 Burn One Bridge of Responsibility
(16:30) Tech Solopreneur Readiness Scorecard

Visit me at thrivingtechnologist.com