Asks for status every 15-25 minutes to track where time goes. Traps USR2 to wake and prompt for status. Designed for Linux, works on OS X, needs tweaks for Windows. Uses JRuby, since it's the only easy-to-get cross-platform UI toolkit for Ruby.

whazzup.rb

require "java"
java_import javax.swing.JOptionPane

class Whazzup
  def initialize(file = "#{ENV['HOME']}/snippets.txt")
    @snippets ||= open(file, 'ab')
    log('[Starting up (ruby)]')

    thread_loop = Thread.current

    # Use the USR2 signal as a 'wake up'.
    Signal.trap("USR2") do
      thread_loop.run
    end
  end

  PROMPTS = ["What're you working on?",
             "What'cha up to?",
             "What's going on?",
             "How goes it?",
             "What's the plan?",
             "Where are you at?",
             "What's next?",
             "What've you been up to?",
             "Status:",
             "Anything I can help with?",
             "What's happening?",
             "What's on your mind?"]

  def log(msg)
    @snippets << Time.now.to_s << ': ' << msg << "\n"
    @snippets.flush
  end

  def ask
    picked = PROMPTS[rand*PROMPTS.length]

    answer = JOptionPane.showInputDialog(nil, picked)
    answer = '...' if answer.nil? || answer.empty?

    log(answer)
  end

  def run!
    while true
      ask

      # Sleep between 15 and 25 minutes
      sleep (((rand*10).to_i-5)+20)*60
    end
  end
end

whatsup = Whazzup.new
whatsup.run!