How good software
goes bad

Every app starts simple. Then come the features, the metrics, the stakeholders, the quarterly goals. Here are five products that launched calm and slowly became anxious — told through their interfaces over time.

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iTunes

2001 → 2019 (R.I.P.)
From jukebox to everything store to... four separate apps.
2001

A jukebox. That's it.

iTunes 1.0 played music. It had a library, a search bar, and playback controls. Apple called it "the world's best and easiest to use jukebox software." It was 8 MB.
Such Great Heights
The Postal Service
◀◀   ▶   ▶▶
2008

Music + Movies + TV + Podcasts + Apps + Ringtones

The iTunes Store launched. Then video. Then podcasts. Then the App Store. Then Genius recommendations. The sidebar grew. The tabs multiplied. It was still usable — but the mission had expanded enormously.
Songs Albums Artists Genres
1 Such Great Heights — The Postal Service
2 Maps — Yeah Yeah Yeahs
3 Seven Nation Army — The White Stripes
4 Float On — Modest Mouse
5 Mr. Brightside — The Killers
2015

The Everything App

iTunes 12 managed your music library, the iTunes Store, Apple Music streaming, movie purchases, TV show subscriptions, podcast subscriptions, audiobooks, iPhone backups, iPhone app management, and ringtones. It was 400 MB. People hated it. Apple knew.
Try Apple Music Free for 3 Months! Start Trial →
NEW: Spatial Audio • Lossless • Listen Now
For You
Browse
Radio
New
Charts
Genres
2019

Apple kills iTunes. Replaces it with three calm apps.

Music. Podcasts. TV. Each does one thing. The lesson: sometimes the only way to make software calm again is to break it apart and start over. Apple essentially admitted that iTunes had become untenable.

The pattern

Success invites scope creep. iTunes didn't get bloated because Apple was incompetent — it got bloated because it was successful. Every new feature had a business case. It took 18 years and a complete product reset to get back to "one app, one job."


S

Skype

2003 → present (barely)
The app that invented video calling, then forgot why people used it.
2003

Call anyone in the world. For free.

Skype's original interface was breathtakingly simple: a contacts list, a search bar, and a call button. It did voice calls over the internet when that was genuinely revolutionary. 100 million downloads in two years.
Alex Chen
Hey, are you free for a call?
Yeah, calling you now!
Type a message...
2011

Microsoft acquires Skype for $8.5 billion.

The integration begins. Skype becomes a platform for Microsoft's enterprise ambitions. Features start arriving that no one asked for: Facebook integration, group video, screen sharing, file transfer, Skype WiFi, Skype To Go numbers.
2017

The Snapchat pivot

Microsoft completely redesigns Skype to chase Snapchat. Stories. Reactions. "Highlights." A colorful UI aimed at teenagers — used primarily by adults calling their parents abroad. The backlash is immediate and savage.
ChatsCallsHighlightsCapture
NEW: Express yourself with Mojis, Stickers & Reactions!
You
AC
JD
MK
LS
Alex Chen
Sent a Moji
3
Mom
Can you hear me?
1
Skype Bot
Try our new features!
2020

Zoom happens.

A pandemic hits. The world needs video calling — the thing Skype literally invented. They choose Zoom instead. Zoom's pitch: click a link, join a call. No account, no stories, no Mojis, no Highlights. Zoom goes from 10M to 300M daily users in three months. Skype's market share collapses.

The pattern

Skype had a 17-year head start on Zoom. It lost because it forgot its job. Users wanted to call people. Microsoft gave them Stories, Mojis, and a Snapchat clone. Zoom gave them a link that worked. Calm won.


E

Evernote

2008 → present (barely)
The note-taking app that wanted to be your "second brain" and ended up more like a junk drawer.
2008

Remember everything.

Evernote launched with a beautiful promise: just write notes. It synced across devices, had search that worked, and got out of your way. Tech reviewers called it essential. It reached 100M users.
Meeting notes — Product review
Discussed roadmap priorities for Q2. Key decisions: focus on sync performance...
Mar 14, 2009
Book notes — Getting Things Done
The two-minute rule: if it takes less than two minutes, do it now...
Mar 12, 2009
Recipe — Sourdough starter
Day 1: Mix 60g whole wheat flour with 60g water...
Mar 8, 2009
2012

"We're not a note-taking app. We're a platform."

Evernote's CEO declares the company will be a "100-year startup." They launch Evernote Food, Evernote Hello, Evernote Clearly, Evernote Peek, Evernote Web Clipper, Evernote Business, and a physical line of bags and wallets. The note-taking app starts selling socks.
2016

The everything dashboard

Opening Evernote now greets you with a "Home" dashboard showing widgets, shortcuts, scratch pads, recently captured items, pinned notes, and suggested content. You wanted to write a note. You got a mission control center. Meanwhile, sync is still slow.
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HomeNotesTasksCalendarSearch
New NoteNew TaskScratch PadWeb ClipperAudioScanSketch
Scratch Pad
Type quick notes here...
Recently Captured
3 web clips this week
Pinned Note
Q1 OKRs (outdated)
Calendar
3 meetings today
Meanwhile...

People switch to Apple Notes.

Apple Notes does almost nothing. Open it, type, close it. It syncs instantly. It's free. It has no dashboard, no widgets, no scratch pad, no business tier, no socks. By 2023, it's the most-used note app on iPhone. Sometimes less wins.

The pattern

Evernote didn't lose to a better note-taking app. It lost to a simpler one. While Evernote was adding tasks, calendars, home dashboards, and AI features, Apple Notes was doing the one thing users actually wanted: letting them write a note and find it later.


G

Google Search

1998 → present
The page that proved simplicity wins. Then slowly walked it back.
1998

A logo, a text box, and two buttons.

While Yahoo, AltaVista, and Excite crammed their homepages with news, weather, stocks, email, and ads, Google showed you almost nothing. A logo. A search box. "Google Search" and "I'm Feeling Lucky." It was radical in its restraint.
2012

The Knowledge Graph: answers, not just links.

Google starts answering questions directly on the results page. Useful, but it begins training users to never leave Google. Side panels, answer boxes, "People also ask" — the results page is becoming a destination, not a waypoint.
2024

AI Overviews, ads, and the infinite results page

Search for a recipe. You get: an AI Overview (often wrong), 4 ads, "People also ask," a featured snippet, a video carousel, more ads, and finally — maybe — the link you wanted. The "10 blue links" are buried under a wall of Google's own content.
AI Overview
To make sourdough bread, you'll need a starter, flour, water, and salt. Mix 500g bread flour with 375g water and 100g active starter. Let it autolyze for 30 minutes, then add 10g salt...
[This summary was generated by AI and may contain errors]
People also ask
How long does sourdough take to rise?
Is sourdough bread healthy?
Can I make sourdough without a starter?
Our test kitchen's favorite sourdough recipe uses a 75% hydration...

The pattern

Google won by being the calmest page on the internet. Now it's one of the noisiest results pages. The homepage is still clean — but the moment you search, you're navigating a maze of AI summaries, ads, and "People also ask" accordions before you find an actual link. The simplicity was the product. They forgot.