Discussing Stupid: A byte-sized podcast on stupid UX

About Discussing Stupid: A byte-sized podcast on stupid UX

Discussing Stupid returns to the airwaves to transform digital facepalms into teachable moments—all in the time it takes to enjoy your coffee break! Sponsored by High Monkey, this podcast dives into ‘stupid’ practices across websites and Microsoft collaboration tools, among other digital realms. Our "byte-sized" bi-weekly episodes are packed with expert insights and a healthy dose of humor. Discussions focus on five key areas: Business Process & Collaboration, UX/IA, Inclusive Design, Content & Search, and Performance & SEO. Join us and let’s start making the digital world a bit less stupid, one episode at a time. Visit our website at https://www.discussingstupid.com

Publisher

High Monkey

Category

business · technology

Language

en

Explicit

No

First episode

11 Apr 2018

Latest episode

6 Oct 2026

Latest episodes

53 episodes in the feed.

1. 

   6 Oct 2026

   S4E1 - The new WCAG 2.2 rules you're already breaking (part 1)

   WCAG 2.1 became 2.2, and most people building websites still have not looked at what actually changed. Seth Moline, High Monkey's accessibility specialist, joins Virgil and Cole to go through the new success criteria one at a time and explain what each one asks for, who it helps, and what it costs to build. Part 1 covers three of them. 3.2.6 Consistent Help (Level A), which says your support options need to stay in the same place across your site instead of vanishing the moment someone enters checkout. 3.3.7 Redundant Entry (Level A), which says stop making people re-enter information you already have. And 2.4.11 Focus Not Obscured, Minimum (Level AA), which says the field someone tabs to should not be sitting behind a sticky header or a chat bubble. If you just recognized your own site in any of those, that is sort of the point. Almost none of this is new thinking. These are UX practices people have advocated for years, now written down as standards with teeth. Good UX and good accessibility keep turning out to be the same thing, which is either reassuring or uncomfortable depending on how your last redesign went. What surprised us was the gap between how simple these sound and what they take to fix. Maintaining form state across five screens, auditing every third-party checkout tool, changing the architecture of systems owned by different teams with different permissions. Easy to explain in a sentence, expensive to repair in a codebase. There was too much here for one episode, so this is a two-parter. Part 2 drops October 20 and takes on 2.5.7 Dragging Movements, 2.5.8 Target Size, 3.3.8 Accessible Authentication, and the AAA criteria, including the one Virgil keeps calling the biggest on the list. One note: this episode is audio only. We had a recording issue, and Virgil explains it himself in the first minute. Video returns in part 2. (0:00) - Intro (4:37) - 3.2.6 Consistent Help (A) (9:27) - 3.3.7 Redundant Entry (A) (18:05) - 2.4.11 Focus Not Obscured, Minimum (AA) (23:51) - Closing thoughts Key Episode Links What's New in WCAG 2.2 (W3C): https://www.w3.org/WAI/standards-guidelines/wcag/new-in-22 (https://www.w3.org/WAI/standards-guidelines/wcag/new-in-22) Understanding 3.2.6 Consistent Help: https://www.w3.org/WAI/WCAG22/Understanding/consistent-help (https://www.w3.org/WAI/WCAG22/Understanding/consistent-help) Understanding 3.3.7 Redundant Entry: https://www.w3.org/WAI/WCAG22/Understanding/redundant-entry (https://www.w3.org/WAI/WCAG22/Understanding/redundant-entry) Understanding 2.4.11 Focus Not Obscured (Minimum): https://www.w3.org/WAI/WCAG22/Understanding/focus-not-obscured-minimum (https://www.w3.org/WAI/WCAG22/Understanding/focus-not-obscured-minimum) Full WCAG 2.2 specification: https://www.w3.org/TR/WCAG22/ (https://www.w3.org/TR/WCAG22/) Subscribe for email updates on our website: https://www.discussingstupid.com/ (https://links.discussingstupid.com/home) Watch us on YouTube: https://www.youtube.com/@discussingstupid (https://links.discussingstupid.com/youtube) Listen on Apple Podcasts, Spotify, or Soundcloud: https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024 (https://links.discussingstupid.com/applepodcasts) https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0 (https://links.discussingstupid.com/spotify) https://soundcloud.com/discussing-stupid (https://links.discussingstupid.com/soundcloud) Check Us Out on Socials: https://www.linkedin.com/company/discussing-stupid (https://links.discussingstupid.com/linkedin) https://www.instagram.com/discussingstupid/ (https://links.discussingstupid.com/instagram) https://www.facebook.com/discussingstupid (https://links.discussingstupid.com/facebook) https://x.com/DiscussStupid (https://links.discussingstupid.com/twitter)

2. 

   15 Sept 2026

   Season 4: The Teaser

   Welcome to Season 4 of Discussing Stupid! This podcast has always been about the same thing: the bad habits, lazy defaults, and inherited decisions that make digital work harder than it needs to be. Season 3 narrowed in on AI for a full run of episodes. This season we're back to the whole field. That means accessibility, user experience, content, search, design, and the way organizations actually make decisions about all of it. Some episodes will be about things that have been broken for fifteen years and nobody has bothered to fix. Others will be about brand new mistakes people are making with very new tools. AI is still in the mix, but it's one topic among many instead of the whole map. The format isn't changing - two people who do this work for a living, talking through what's going wrong and what to do instead. No theory for its own sake and absolutely no pretending there's a clean answer when there isn't one. We've got a decent list of topics for this season going, but we'd love to hear what's driving you nuts as well in the digital world. Drop a comment on YouTube, hit us up on social, or use the contact form at highmonkey.com/podcast. Also, in this trailer you'll hear a preview of our new theme music, written and produced by Cole. Episode 1 drops October 6! (0:00) - Welcome to Season 4 (0:26) - Setting the Season 4 scene (2:07) - Send us your topics (2:29) - Original music for Season 4 (3:32) - Music sneak peek (4:09) - Brought to you by High Monkey (4:20) - We have a video version (4:50) - Season 4 starts October 6 Subscribe for email updates on our website: https://www.discussingstupid.com/ (https://links.discussingstupid.com/home) Watch us on YouTube: https://www.youtube.com/@discussingstupid (https://links.discussingstupid.com/youtube) Listen on Apple Podcasts, Spotify, or Soundcloud: https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024 (https://links.discussingstupid.com/applepodcasts) https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0 (https://links.discussingstupid.com/spotify) https://soundcloud.com/discussing-stupid (https://links.discussingstupid.com/soundcloud) Check Us Out on Socials: https://www.linkedin.com/company/discussing-stupid (https://links.discussingstupid.com/linkedin) https://www.instagram.com/discussingstupid/ (https://links.discussingstupid.com/instagram) https://www.facebook.com/discussingstupid (https://links.discussingstupid.com/facebook) https://x.com/DiscussStupid (https://links.discussingstupid.com/twitter)

3. 

   16 Jun 2026

   S3E18 - Intentional AI: Series takeaways - the real reason AI isn't working for you

   Season 3 of the Intentional AI series started with a simple premise: AI is a powerful tool, but the way it gets marketed and the way most people actually use it are two very different things. Eighteen episodes later, that premise has held up. In this finale, Virgil and Cole take stock of what the season actually taught them. Not the hype, not the headlines - what they observed firsthand through testing, building, and paying attention to how AI performs when real work is on the line. A big part of this episode centers on a real-world example: Virgil's experience building an internal business application using an AI low-code tool called Zite. What made it work wasn't the tool. It was the month of planning that happened before a single line of code was written - database diagrams, stakeholder conversations, process mapping, all of it done before AI touched anything. The app ended up replacing four SaaS systems. That kind of result doesn't come from letting AI lead. It comes from knowing exactly what you need before you ask AI for help. The flip side of that shows up in a small but telling moment: a teenager at the gym using AI to generate a workout plan. It probably gave him something reasonable. But here's the problem - he won't know whether it worked for three to six months, and he likely has no framework to evaluate it either way. That's the same trap organizations fall into when they hand big process decisions to AI without the expertise to judge the output. Cole frames it simply: AI is a mirror. Whatever you bring to it, it reflects back. Strong process knowledge, clear goals, and domain expertise get amplified. Gaps and blind spots get amplified too. The tool doesn't know the difference. Virgil runs through where AI held up the most across the season - SEO, analytics, research, coding, wireframes - and where it didn't, including original content, image generation, video, and design. Eighteen episodes in, the picture is a lot clearer than when we started. Previously in the Intentional AI series: Episode 1: Intentional AI and the Content Lifecycle Episode 2: Maximizing AI for Research and Analysis Episode 3: Smarter Content Creation with AI Episode 4: The role of AI in content management Episode 5: How much can you trust AI for accessibility Episode 6: You’re asking AI to solve the wrong problems for SEO, GEO, and AEO Episode 7: Why AI can make your content personalization worse Episode 8: The real value of AI wireframes is NOT the wireframes Episode 9: Just because AI can create images doesn't mean you should use them Episode 10: The Super Bowl didn't sell AI, it exposed it Episode 11: AI video rewards planning, not your ideas Episode 12: AI might struggle with creativity, but coding isn't creative Episode 13.1: What the rise of conversational search means for your website Episode 14: AI agents are only as good as your workflow Episode 15: AI can't fix your social media if you have nothing to say Episode 16: The most important operation in analytics - understanding your "why?" Episode 17: How to get better results from AI prompts That's a wrap on Season 3. Thanks for coming along for the ride - see you in Season 4! For more conversations about AI, design, and digital strategy, visit https://www.highmonkey.com/podcast (https://www.highmonkey.com/podcast) and subscribe on your favorite podcast platform. (0:00) - Intro (1:15) - Season 3 milestone: 2,000 listeners (2:06) - Why we started this series (3:09) - The AI backlash: justified or not? (6:33) - Virgil's AI-built internal app (7:29) - AI is only as powerful as the person using it (9:56) - AI at the gym! (13:00) - The workout is a microcosm of how AI gets misused (15:24) - AI's real value: saving time (16:42) - Plan first, build second (21:04) - Security: the thing low-code builders miss (24:59) - AI is a mirror: it reflects what you bring to it (25:32) - Where we would use AI (28:07) - Cheers to Season 3 + what's next (28:48) - Outro Subscribe for email updates on our website: https://www.discussingstupid.com/ (https://links.discussingstupid.com/home) Watch us on YouTube: https://www.youtube.com/@discussingstupid (https://links.discussingstupid.com/youtube) Listen on Apple Podcasts, Spotify, or Soundcloud: https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024 (https://links.discussingstupid.com/applepodcasts) https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0 (https://links.discussingstupid.com/spotify) https://soundcloud.com/discussing-stupid (https://links.discussingstupid.com/soundcloud) Check Us Out on Socials: https://www.linkedin.com/company/discussing-stupid (https://links.discussingstupid.com/linkedin) https://www.instagram.com/discussingstupid/ (https://links.discussingstupid.com/instagram) https://www.facebook.com/discussingstupid (https://links.discussingstupid.com/facebook) https://x.com/DiscussStupid (https://links.discussingstupid.com/twitter)

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

4,175

Score snapshot 15 Sept 2025

Spotify

5.0 / 5

2 ratings

Podcast Authority Score: 63 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

82

Social presence

90

YouTube

65

Engagement

0

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