UX dread, software jokes, hard-earned hindsight.
Retro Time treats software work as both craft and absurd workplace theater. Its episodes move between casual banter, UX parables, AI speculation, enterprise-software frustration, and practical reflection on how teams actually build things.
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Retro Time is a software podcast about what happens after the clean diagram meets the actual workplace. It has the shape of a technology show, but its real subject is the human mess around product design and development. Some episodes unfold as casual, joking conversations between Jeremy and Derek about enterprise software, remote work, career levels, AI, automation, and the practical difficulty of getting teams to care. Others are full scripted stories that turn UX problems into campfire horror. A hidden button becomes an infinite usability test. A stakeholder becomes a demon. Dark patterns become witches singing about confusing consent, forced continuity, and misleading choices. A prototype becomes a cursed object that feeds on obsession and perfectionism. The show’s register is loose and comic, but the concerns underneath are serious. Bad software locks people out, wastes attention, distorts incentives, and scales failure faster than teams can explain it. Retro Time is especially sharp when it connects technical systems to ordinary behavior: hallway chatter lost in remote work, overleveled roles created by hiring bands, AI hype compared with older platform shifts, and automation that can make weak processes fail faster. It also has a taste for bits, strange asides, and deliberately ragged banter. That informality keeps the show from feeling like a panel discussion or a lecture. Even the fictional episodes are built around recognizable product anxieties: executive deadlines, unclear controls, impossible stakeholders, confusing information architecture, and teams trying to save a design without losing their minds. The result is part software retrospective, part UX satire, part workplace therapy session. It works best for people who have been inside product meetings long enough to recognize the joke before the punchline arrives.
Made for: Best for software developers, designers, product managers, UX researchers, and tech workers who enjoy candid shop talk with a comic edge. It also suits listeners interested in how tools, teams, incentives, and interface choices shape everyday work.
What sets it apart: Retro Time stands out by mixing ordinary software-career conversation with scripted genre pieces that turn UX failures into horror stories. Its humor is messy and conversational, but the takeaways stay grounded in real product work.
The Retro Time Podcast is all about retrospectives. Join your hosts, Derek Seibert and Jeremy Miller, as they talk about software — from product design to software development to the soft skills you need to make it in the industry. Using their long careers to kick off the conversation, they’ll drop a few nuggets of wisdom each episode… 96.7% guaranteed.
A senior title can be a trap; Jeremy and Derek help you name the awkward math behind it.
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Short reviews from the PlayNext desk, based on the episodes we processed.
Retro Time connects remote work's missing social cues to the empathy that helps teams build better software.
Retro Time's first episode of 2024 frames enterprise software as a social problem as much as a technical one. Jeremy and Derek open with a one-ply toilet paper joke, then move into what remote work can blur: hallway conversations, desk-side clues, and the small discoveries that…
A firelit UX mystery about an unfinished interface that seems to answer from beyond the screen.
The episode sends a Pinnacle Sys Labs retreat in Smellwell Forest into eerie UX folklore, as designers trade firelight stories and the legend of Ethan's cursed prototype starts to take shape.
A senior title can open a door, then make the room harder to leave.
A senior title can look like progress until the work around it starts to narrow instead of widen. Jeremy and Derek trace how a higher salary ask can push someone into a compensation band and title that sit above their actual experience, creating pressure once the role has to be…
A loose AI discussion finds its clearest shape in the history of technology moving from privilege to platform.
Retro Time's second part gives the AI rollout question a useful historical frame: who gets new technology first, and what has to happen before it becomes ordinary.
A loose, thoughtful conversation about incremental software, automation, and fragile systems moving too fast.
Retro Time treats software failure less as a technical mishap than as a question of responsibility. It moves from Derek's years with rigid government requirements documents to Goiko's case for incremental development and impact mapping, then lets automation, Amazon's…
Armenia-centered analysis for a volatile region.
Retro Time's A Thin Line: The Rough Reality of Enterprise Software turns a one-ply toilet-paper joke into a critique of enterprise software, because the people who pay for the tool are not the ones who use it.
A Pinnacle Sys Labs retreat in Smellwell Forest turns into a ghost story about Ethan, a designer who vanished after an unfinished prototype.
Jeremy and Derek introduce “over-leveled” workers as employees promoted into senior titles before they can perform senior-level work.
Retro Time hosts Derek and Jeremy discuss ChatGPT as a writing, debate, summarization, and software-development tool, including GPT-3.5 and GPT-4 performance on the bar exam.
Retro Time Podcast hosts Jeremy and Derek interview Goiko, who is introduced as a writer of multiple books, a conference speaker, and the author of Human vs.
Retro Time // A Software Podcast uses newspapers, restaurants, and software systems to explain network effects as the relationship among platforms, producers, and consumers.
Jeremy and Derek of Retro Time // A Software Podcast examine why teams remain trapped in a status-quo bubble even when members know that 15,000-step processes and broken production releases are unnecessary.
Retro Time // A Software Podcast examines who software teams serve, beginning with Jeremy's household rule that partners should serve the house rather than repeatedly covering each other's unfinished tasks.
Jeremy and Derek examine why a software system grew into more than 50 services after repeated partial fixes, abandoned architectural strategies, and pressure to prioritize speed over quality.
Jeremy and Derek use Montgomery Scott's “miracle worker” advice in Star Trek: The Next Generation to examine why visible crisis recovery receives more recognition than quiet prevention.
Jeremy and Derek of Retro Time // A Software Podcast use Jeremy's failed LG smart dishwasher and simpler Bosch replacement to frame a discussion of software complexity.
Retro Time // A Software Podcast presents Jeremy’s argument that networking should continue after landing a software, UX, or product role because internal relationships improve work and career options.
Retro Time interviews Uncle Bob Martin about the 2001 Agile Manifesto meeting at Snowbird, Utah, where 17 software consultants debated how to unify Extreme Programming, Scrum, FDD, and related methods.
Jesper Boehm, author of Real Life Agile, Priming Kanban, and Level Up Agile with Toyota Kata, explains why 16 years of Agile work have not ended recurring method wars.
Neil Thompson tells Jeremy and Derek of Retro Time // A Software Podcast how failed presentations as a product development engineer led him to Toastmasters and to creating Teach the Geek to Speak.
Retro Time // A Software Podcast interviews Tom Greever, author of Articulating Design Decisions, about explaining UX work to stakeholders and business partners.
Jeremy and Derek examine employee attrition through the example of Tim Bone, a fictional sysadmin whose scheduled jobs and system knowledge exist mainly in his head.
The hosts discuss the Russia-Ukraine war and its personal impact on the tech community, drawing parallels to historical events.
The hosts discuss a listener-suggested topic about what it's like being new on a software team and how to help new members integrate.