DiscoverOff the VPNWhen asking ‘why?’ gets you fired
When asking ‘why?’ gets you fired

When asking ‘why?’ gets you fired

Update: 2025-06-04
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Description

Avery lands a senior role at, let’s just call the company Seat Snag, with a big paycheck and high expectations. But when his questions about company processes start raising eyebrows, ish hits the fan.


What seemed like a normal transition turns into a clash of cultures. Avery’s quest for clarity turns into frustration, and while he was encouraged to switch teams, doing so only made it worse. Finally, when customer complaints surface online, Avery goes into detective mode, and that’s where the cracks really start to show. 


Want to ask us something or share your own work drama? Hit us up at jellyfish.co/offthevpn. And don’t worry—we’ll keep it Off the VPN.

Highlights:

  • The Curious Cat: When being curious actually harms your tenure
  • Culture Meets Crash Test Dummy: Being an outlier in the company norms
  • Making Headlines: Bad publicity is still publicity, right!? 

Jump into the conversation:
(00:00 ) Avery joins Seat Snag

(05:16 ) The side project becomes the main gig

(07:00 ) In search of needed documentation

(10:12 ) Avery’s constant questions start to raise flags

(13:49 ) Data team mystery

(15:40 ) CEO’s demo surprise

(21:12 ) Avery takes it to social media 

(24:10 ) The aftermath and new opportunities


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When asking ‘why?’ gets you fired

When asking ‘why?’ gets you fired

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