Does Challenging AI Make It Smarter?

A recent Medium article claims that adding challenge phrases like “I bet you can’t solve this” to AI prompts improves output quality by 45%, based on research by Li et al. (2023).

Quick Test Results

Testing these techniques on academic tasks—SQL queries, code debugging, and research synthesis—showed mixed but interesting results:

What worked: Challenge framing produced more thorough, systematic responses for complex multi-step problems. Confidence scoring (asking AI to rate certainty and re-evaluate if below 0.9) caught overconfident answers.

What didn’t: Simple factual queries showed no improvement.

The Why

High-stakes language doesn’t trigger AI emotions—it cues pattern-matching against higher-quality training examples where stakes were high.

Bottom Line

Worth trying for complex tasks, but expect higher token usage. Results are task-dependent, not universal.


Source: Li et al. (2023), arXiv:2307.11760

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Source: Li et al. (2023), arXiv:2307.11760

Streamlining macOS Application Management with Homebrew Cask

macOS users frequently face the challenge of efficiently managing application installations across multiple machines. The traditional approach involves manually downloading disk images, navigating installation wizards, and maintaining applications across systems. Homebrew Cask offers a command-line solution that significantly streamlines this process.

Understanding Homebrew Cask

Homebrew Cask is an extension of Homebrew, the widely-adopted package manager for macOS. While Homebrew manages command-line tools and libraries, Cask extends this functionality to graphical user interface (GUI) applications. This enables system administrators, developers, and power users to install, update, and manage standard macOS applications through terminal commands.

The conventional installation workflow requires multiple steps:

  1. Locating the official download source
  2. Downloading the disk image file
  3. Opening and mounting the disk image
  4. Transferring the application to the Applications folder
  5. Ejecting the disk image
  6. Managing the downloaded installer file
  7. Repeating this process for each required application

Homebrew Cask reduces this to a single command:

brew install --cask google-chrome

The application is then installed automatically with no further user interaction required.

Key Advantages for Professional Workflows

1. Accelerated System Provisioning

Organizations and individual users can maintain installation scripts containing all required applications. A typical enterprise development environment setup might include:

brew install --cask visual-studio-code
brew install --cask docker
brew install --cask slack
brew install --cask zoom
brew install --cask rectangle
brew install --cask iterm2
brew install --cask spotify
brew install --cask vlc

This approach reduces new machine setup time from several hours to approximately 15-20 minutes, depending on network bandwidth and the number of applications being installed.

2. Simplified Update Management

Maintaining current software versions is essential for security compliance and feature availability. Rather than monitoring and updating each application individually, administrators can execute a single command:

brew upgrade --cask

This command updates all Cask-managed applications to their latest versions, ensuring consistent patch management across the system.

3. Complete Application Removal

Standard macOS uninstallation methods often leave residual files including configuration data, cache files, and preference files distributed throughout the file system. Homebrew Cask performs thorough removal:

brew uninstall --cask docker

This ensures complete application removal without orphaned system files.

4. Automation and Standardization

Homebrew Cask’s command-line interface enables scripting and automation. Development teams can create standardized setup scripts ensuring consistent development environments. IT departments can implement automated workstation provisioning workflows. System configurations can be version-controlled in dotfiles repositories, enabling rapid deployment and rollback capabilities.

Recommended Applications by Category

The following applications represent commonly deployed tools across professional environments:

Development Tools

brew install --cask visual-studio-code
brew install --cask iterm2
brew install --cask docker
brew install --cask postman
brew install --cask dbeaver-community

Productivity Applications

brew install --cask rectangle        # Window management
brew install --cask alfred           # Enhanced search functionality
brew install --cask obsidian         # Knowledge management
brew install --cask notion           # Collaborative workspace

Communication Platforms

brew install --cask slack
brew install --cask zoom
brew install --cask discord

System Utilities

brew install --cask the-unarchiver
brew install --cask appcleaner
brew install --cask vlc

Implementation Guide

Organizations and users without an existing Homebrew installation can deploy it with a single command:

/bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)"

Once Homebrew is installed, Cask functionality is built right in. Just start using brew install --cask commands.

Useful Commands to Know

# Search for an app
brew search --cask chrome

# Get information about an app
brew info --cask visual-studio-code

# List all installed cask apps
brew list --cask

# Update all apps
brew upgrade --cask

# Uninstall an app
brew uninstall --cask slack

A Few Gotchas

Cask isn’t perfect. Here are some things to be aware of:

  • Not every app is available – Popular apps are well-covered, but niche or very new applications might not be in the repository yet
  • App Store apps aren’t included – Apps distributed exclusively through the Mac App Store can’t be installed via Cask
  • Some apps require manual steps – Occasionally, an app needs additional configuration or permissions that Cask can’t automate
  • Updates might lag slightly – Cask maintainers need to update formulas when new versions release, so there can be a brief delay

These are minor inconveniences compared to the time saved.

The Bottom Line

Homebrew Cask has fundamentally changed how I interact with my Mac. What started as a way to avoid repetitive downloads has become an essential part of my workflow. The ability to script, automate, and version-control my application setup means I’m never more than a few commands away from a productive environment.

If you spend any significant time on macOS, especially as a developer or power user, Homebrew Cask is worth learning. Your future self—the one setting up that next new machine—will thank you.

Try It Yourself

Pick three applications you use regularly and install them via Cask. I bet you’ll be hooked by the simplicity. Start with something like:

brew install --cask visual-studio-code
brew install --cask google-chrome  
brew install --cask rectangle

Welcome to a more efficient way of managing your Mac applications.


What’s your favorite Homebrew Cask application? Have you automated your Mac setup? Share your experiences in the comments below!

AI is displacing software engineers, but those in Singapore have the chance to fare better

https://www.straitstimes.com/business/ai-is-displacing-software-engineers-but-those-in-singapore-have-the-chance-to-fare-better?sfnsn=mo

The CEO Magazine: David Ellis: Why AI makes new graduates more valuable than ever

https://amp.theceomagazine.com/business/innovation-technology/david-ellis/

Ellis sees a different future. Rather than eliminating graduate positions, IBM Consulting is actively increasing them.

“So, for example, we are increasing, not decreasing, the number of graduate hires that we’re making here in Australia,” he says.

Investing in the future
The reasoning is both strategic and generational. Today’s graduates enter the workforce with a crucial advantage – they’ve been using AI longer than most experienced workers.

“We have people entering the workforce that have perhaps been using AI longer than many others. Maybe they’ve been using it through their studies. Maybe they’ve just got a deeper affinity to it,” Ellis explains.

When properly equipped and trained, these AI-native workers can be a huge asset to organizations.

“We can skill them, we can equip them, we can give them the confidence to be much more effective than you or I might have been at the beginning of our careers,” he says.

Automating oral argument

Back in January 2023, a company called DoNotPay offered “any lawyer or person $1,000,000 with an upcoming case in front of the United States Supreme Court to wear AirPods and let our robot lawyer argue the case by repeating exactly what it says.” At the time, everyone thought this was a silly gimmick.

https://adamunikowsky.substack.com/p/automating-oral-argument?utm_source=tldrai