The author discusses their preference for choosing unconventional or "underdog" tech stacks, which they playfully term "**contrarian stacks**," as opposed to mainstream or "orthodox stacks." They share past experiences such as using Sinatra over Rails, MooTools over Prototype, and Solid over React. While contrarian stacks may present challenges like limited community support and the need for more self-troubleshooting, they also offer opportunities for deeper understanding and potential contributions to open-source projects. These stacks often emerge as reactions to perceived shortcomings in mainstream technologies, leading to innovative designs. Although assembling a contrarian stack can be complex, it provides valuable insights into the underlying technologies. The author argues that while mainstream stacks may be favored by current LLM trends, the learning opportunities from contrarian stacks remain invaluable, encouraging readers to explore less-traveled paths for unique insights and growth.