Lily’s onboarding plan? Hit the ground running. Bart’s plan? Monitor her calendar like it’s a live-action thriller. From week one, it’s all tension, mixed signals, and a staff engineer just trying to do her job.
This episode follows the slow-motion implosion of a tech team where one EM’s insecurities create a ripple effect of firings, confusion, and eventually, some pretty unconventional tactics from leadership. There’s a spy, some corporate melodrama, and a reminder that being good at your job can really tick off the wrong people.
Got a question you’d like answered on the show? Drop us a line at
jellyfish.co/offthevpn. And don’t worry! We promise to keep it Off the VPN.
Highlights:- Spy Games: When leadership plants someone on your team just to confirm your EM is the problem
- Calendar Chaos: Lily tries to onboard, Bart tries to control every meeting she has
- Skip-Level SOS: Why going around your manager might’ve saved this entire mess earlier
Jump into the conversation:
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00:00) Intro
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00:13) Bruises, burnout, and beach dreams
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01:46) Lil Instinct lands the job, kinda
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03:11) Bart shows up weird from day one
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04:53) Trusting your gut when it’s sus
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07:11) New gig, same mess, calendar police
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09:30) Bart micromanages like it’s his hobby
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13:52) Being helpful somehow makes it worse
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18:52) Should’ve gone skip-level yesterday
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26:36) Surprise! The new guy was a spy
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29:45) Bart’s gone and finally, peace returns
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34:38) Tech trauma is real, but so is recovery
What is Off the VPN?
Is bringing up your software engineering salary a dating red flag? How do you strike a balance between career ambition and incendiary burnout? Is it ever okay to hold your code hostage in escrow? Navigating a career in tech raises a lot of tricky questions that aren’t exactly appropriate for the daily stand-up. So let’s take this off the VPN.
In this new podcast from Jellyfish, work besties Jasmine and Allison scour the internet to find the real questions engineers and developers are whispering over drinks and posting about anonymously. Together, they’ll tackle the most troubling of inquiries with authenticity, humor, and absolutely no holding back.