PackageManagement
Post #169 · source on Telegram
Upgrading pip removes pip, producing the classic Surprised Pikachu moment
Description
The meme is split vertically. The upper half is a white background with black monospace-style text that reads: "Me: pip install package Pip: pip needs to be updated. Me: python -m pip install --upgrade pip Pip: Success. Me: pip install package Bash: Command 'pip' not found. Me:". The lower half shows the well-known "Surprised Pikachu" reaction image - Pikachu’s yellow face with mouth agape and wide eyes - conveying stunned disbelief. Technically, the joke highlights how running "python -m pip install --upgrade pip" inside a shell can replace the pip executable on PATH, making the next "pip" invocation fail with Bash’s "command not found" error, a common Python environment and package-management pitfall for developers using the CLI
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Upgrading pip is the Python rite of passage where you realize pip is both everywhere in site-packages and nowhere on $PATH, as Bash calmly walks you through the concept of impermanence
Twenty years in, and I still explain to juniors that Python's package management isn't broken - it's just teaching us the importance of immutable infrastructure by making every dev environment unreproducible
Pip followed the upgrade instructions perfectly - it just considers its own existence an optional dependency
Ah yes, the classic pip upgrade ouroboros - where the tool designed to manage dependencies becomes its own circular dependency nightmare. It's the software equivalent of 'you need experience to get a job, but you need a job to get experience.' Senior devs know this dance well: pip breaks itself during upgrade, forcing you to use `python -m pip` as a workaround, which then mysteriously makes the `pip` command vanish from your PATH like it's entered witness protection. The real pro move? Having a shell alias for `python -m pip` ready before you even attempt the upgrade, because you've been burned enough times to know that pip's idea of 'Success' is more aspirational than factual. Virtual environments were supposed to solve this, but somehow we still end up in this Kafkaesque loop where the package manager needs to be managed by another invocation of itself
Upgrading pip is a raffle to decide which of your five Pythons owns the ‘pip’ shim - sometimes the winner is None
python -m pip upgrades the entrypoint into ~/.local/bin, bash still has /usr/bin/pip hashed, and suddenly the blocker is $PATH - package managers are the only tools that can uninstall themselves mid-upgrade
Pip upgrades: Fix the version, PATH the blame to Bash - classic Python shell sorcery