Off the VPN

Is passion really a must to succeed in the tech world?

Grace, a coding apprentice, gets called out for not being “passionate enough” about her work. But what does “passionate enough” look like and is that really what matters most in tech?

In this episode, we challenge this stereotype and explore how your skills, not your obsession, should define your success. If you’ve ever felt like passion alone doesn’t cut it, this one’s for you.

Got a tech tale of your own or some workplace drama? Hit us up at jellyfish.co/offthevpn. And don’t worry - we’ll keep it Off the VPN.

Highlights:

• Passion vs. Performance: Why passion isn’t always the key to tech success
• The “Code Nerd” Stereotype: Breaking free from the narrow mold in tech
• Balancing Passion: How to stay true to yourself while thriving in your career

Jump into the conversation:
(00:00) Intro

(02:29) Do you need passion to succeed in tech?

(03:35) Grace’s apprenticeship journey: balancing school and work

(05:06) Not “passionate enough” about coding

(05:38) Trying to prove herself at work

(08:57) Being procedural VS. creative

(10:46) The inappropriate comparison to a male coworker

(14:17) The “passion engineer” stereotype and its impact on career

What happens when our most senior engineer stops writing code altogether and lets AI handle everything? Well, you can expect projects and productivity to go out the window. 

Meet Simon, who is about 30+ years into the game and fully convinced that AI will fully replace the developer. From trying to build a model that could replace the whole team, to refusing to touch a pull request without an AI agent, his workflow has gone from experimental to whack.

If you’ve ever worked with someone who is blindly chasing after shiny new tech at the expense of deadlines, quality, and team morale, then this one will feel eerily familiar. 

Got a tech tale of your own or some workplace drama? Hit us up at jellyfish.co/offthevpn. And don’t worry - we’ll keep it Off the VPN.

Highlights:

• Full AI Adoption: What happens when “prompt-only” coding takes over
• Leadership Lessons: Why avoiding the hard but real conversations make problems worse
• Team Impact: How one person’s workflow can ripple across an entire organization

Jump into the conversation:
(00:00) Intro

(02:24) Loving shiny new tools after 30 years of experience
(05:15) Ambitious AI side project with zero business fit
(06:12) Only coding through AI prompts, no edits
(08:45) Slower work, more bugs, mounting frustration
(13:09) How managers should address extreme AI adoption
(23:39) Head of engineering crashes standup, chaos follows
(25:48) Telling a new  junior they’ll soon be jobless

Imagine sibling rivalry at its finest, but now dip it into tech.

Meet Julian and Ava, two Ivy League computer science students with very different career paths. One’s endlessly stacking internships at Amazon, Google, and other big names, while the other’s soaking up Europe, partying, and living her best life.

When they both go after the same job… turmoil starts to enter. 

Ever faced some serious competition from a sibling when it comes landing your dream job? This one’s for you.

Got a tech tale of your own or some workplace drama? Hit us up at jellyfish.co/offthevpn. And don’t worry - we’ll keep it Off the VPN.

Highlights:

• Tech Career Hustle: When family and ambition collide
• Sibling Showdown: Can you both win in tech?
• Job Hunt Drama: How far will you go to land that offer?

Jump into the conversation:
(00:00) Intro
(06:13) Different paths: internships vs. living your best life
(10:18) Should you follow the tech grind or just chill?
(12:15) The Google dilemma - who gets in first?
(13:39) When parents take your sibling’s side
(15:51) How hard work pays off in tech interviews
(19:20) The entitlement of expecting career handouts

A date so bad, it felt like a work meeting? Yeah, that happened.

Meet Rochelle, who thought she was going on a quirky first date with a software engineer - until an 8-minute voice memo, an unhinged rant about remote work, and a very questionable boss threat turned everything upside down. 

If you’ve ever tried to date in tech and found yourself knee-deep in awkward convos and glaring red flags, you'll totally get this one.

Got a tech tale of your own or some workplace drama? Hit us up at jellyfish.co/offthevpn. And don’t worry - we’ll keep it Off the VPN.

Highlights:

• Tech-Savvy Dating: When your date asks you to give a presentation on your first date
• Remote Work Woes: How far is too far when it comes to job complaints?
• Red Flag Radar: Recognizing the signs...before they send you an 8-minute voice memo.

Jump into the conversation:
(00:00) Intro

(02:03) Quirky date idea that’s almost too much

(04:08) Complaining about remote work on a first date

(07:20) The eight-minute voice memo and hidden recording

(10:02) When venting about work goes too far

(14:15) How the tech bubble affects dating expectations

(16:27) Rochelle’s final move 

(21:31) Final reflections about this tech love story

Ever looked at a pull request and thought…welp. 

Meet Raj, a tech lead just trying to do his job, until his team is buried under an avalanche of AI-generated chaos. We’re talking 10,000-line PRs, hallucinated services, broken tests, and a very real security scare. All in the name of speed?

This episode is for anyone who has watched AI tools get tossed into engineering orgs with zero training, no guardrails, and that faster is always better.

Come on, we’re better than “just add AI.”

Got a tech tale of your own or some workplace drama? Hit us up at jellyfish.co/offthevpn. And don’t worry—we’ll keep it Off the VPN.

David, a junior engineer at a fintech company, is instantly zapped into a project that quickly becomes a memorable early dev experience (both technically and interpersonally). He’s tasked with building a feature alone after his senior engineer gets sidetracked, and unfortunately for him, his junior experience does not meet the high expectations, to put it lightly.

What starts as an exciting opportunity turns into a rough ride. David is under pressure to deliver a critical feature with little guidance, and as his timeline gets tighter, the stakes grow higher. When the feature crashes during testing, it sparks a public reprimand that no one saw coming. The worst part? No one steps in to defend him, and the senior engineer stays silent.

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 Pressure Cooker: How being thrown into the deep end feels
• Silent Treatment: The consequences of no backup when things go wrong
• Career Lessons: How public failure can shape your future

Jump into the conversation:
(00:00) Pushing a junior engineer into the deep end

(06:44) Junior engineers and unrealistic timelines

(09:28) Optimism vs. reality in engineering

(11:42) Performance issues emerge in staging

(13:10) David’s public criticism in the meeting

(16:02) No intervention when David is called out

(21:43) David’s recovery and new opportunities

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

Sometimes getting random DMs in your online community doesn’t always work out like you want it to.  

Picture this, you're Aubrey, a cybersecurity pro thriving in a fast-paced tech scene. Everything’s going smoothly until you try to do a nice thing - offering some extra tickets to a local disco costume party. Sounds harmless, right…right!? 

Enter Ted: a seemingly well-meaning but totally clueless guy who doesn’t quite get the boundaries. What starts as a small gesture develops into a series of awkward DMs, boundary-pushing, and what we’d call very awkward exchanges, oof!

Got a tech tale of your own or some workplace drama? Hit us up at jellyfish.co/offthevpn. And don’t worry—we’ll keep it Off the VPN.

Highlights:

• Ted Doesn’t Get the Memo: You gotta read the room yo! 
• Aubrey Goes CSI: It all starts with the phone number
• Community Vigilance: Moderators, we love you, thanks for keeping communities safe!

Jump into the conversation:
(00:00) Intro
(03:47) Aubrey’s generous ticket giveaway
(07:02) Ted’s unsolicited messages start flooding in
(09:10) Boundaries set, but Ted doesn’t get the hint
(12:55) Crossing over the cybersecurity line
(17:02) When online turns real
(20:52) Aubrey plays CSI on Ted
(25:40) Community moderators step in
(28:09) The moral of the story: Privacy, people

Imagine you’re our good friend Logan (aka the Wolverine) and work is steady – yay!  When all of a sudden a “low priority” side project made it to the CEO’s radar…bummer. 

Chaos begins, stress rises, deadlines shift, and communication has flown out the window. What was once a simple task is now a ticking time bomb. With a small team and virtually no additional resources, Logan’s feeling the summer heat early. As icing on the cake, throw in an MIA manager while the CEO presses for a demo that isn’t even ready.

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:

• Low prio is High Prio: When “no rush” actually  means “drop everything now”
• Communication Void: Weekly updates on Slack with nothing but a thumbs up
• CEO Curveballs: The art of war in urgent demands from the Big Boss 

Jump into the conversation:
(00:00) Intro

(01:47) A nightmare on techstreet

(03:33) Logan: solo support and side quests

(05:16) The “side project” that’s not side

(10:12) Priorities lost in translation

(13:49) Professor X wants the integration

(15:40) CEO’s surprise: where’s the demo button?

(18:58) New deadline, instant chaos, Logan’s dread

(21:12) Panic mode: calling all hands

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:
(00:00) Intro
(00:13) Bruises, burnout, and beach dreams
(01:46) Lil Instinct lands the job, kinda
(03:11) Bart shows up weird from day one
(04:53) Trusting your gut when it’s sus
(07:11) New gig, same mess, calendar police
(09:30) Bart micromanages like it’s his hobby
(13:52) Being helpful somehow makes it worse
(18:52) Should’ve gone skip-level yesterday
(26:36) Surprise! The new guy was a spy
(29:45) Bart’s gone and finally, peace returns
(34:38) Tech trauma is real, but so is recovery