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July 25, 2025 28 mins

Most travelers walk away from a guided trip thinking, “That was amazing”—but they have no idea what it actually took to make it feel that way.

In Part 2 of my conversation with former REI Guide of the Year Chris Anderson, we go behind the curtain to uncover what guides really do:

  • How REI tried to flip the script and treat guiding as a real career—and why that model didn’t survive
  • The long hours, behind-the-scenes prep, and emotional labor that guests never see
  • The broken tipping culture—and why it puts guides in a tough, awkward position
  • What it really means to serve 10+ guests for 14+ hours a day with zero margin for error
  • How underprepared guests affect group dynamics, safety, and morale
  • The impossible math behind seasonal contracts, no PTO, and $100 day rates
  • Why the best guides make you feel like the trip ran itself—and how much effort that actually takes

If you’ve ever been on a guided trip—or plan to—this episode will change how you see your guide forever.

🎧 Start listening now—and maybe rethink that tip envelope.

Check out the LinkedIn post from Chris that sparked this two-part series…

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