Remember lining up in the computer lab to die of dysentery? There's something that pixelated pioneer simulator understood about learning that we've forgotten in our rush to make everything accessible.

In this episode, I'm exploring why the best learning happens when failure is expected, feedback is immediate, and students choose to struggle because the struggle feels meaningful. We're diving into what's changed since 1985, why confusion has become a signal to rescue rather than persist, and how we've accidentally taught students that difficulty means they're doing something wrong.

We'll Discuss:

• Why removing struggle actually removes the mechanism of learning itself
• The critical difference between productive struggle and overwhelming frustration
• How AI and instant information access have rewired how students approach confusion
• Four concrete strategies for creating "Oregon Trail moments" in your English classroom
• Why faster feedback matters more than detailed feedback (and how to actually do it)
• How to use discussion as a productive struggle space without needing resolution

If you've noticed students shutting down at the first sign of difficulty, or if you're wondering why summarized versions don't stick, this episode reframes struggle as a feature—not a bug—of genuine learning.

Oregon Trail didn't have an easy mode. It had strategy. Let's bring that energy back to English class.