This reminds me of "Tunnel In The Sky" by Robert Heinlein. Teenager goes on a "growing up quest" in the hopes of becoming some type of Ranger or "Space Colony

This reminds me of "Tunnel In The Sky" by Robert Heinlein. Teenager goes on a "growing up quest" in the hopes of becoming some type of Ranger or "Space Colony Guide". He and a group of others wormhole out to some planet and have to survive for a time before being wormholed back. On the front end, you have to show up with equipment you think you'll need. Since you don't know anything about what environment you'll be warped in to, you have to do your absolute "Boy Scout Best". Main character shows up with a parka, a knife, this-and-that. "Don't worry kid, you don't need that parka. Today you're not going to some arctic desert so you don't need it. Keep the knife though. I had to turn away some poor shit for bringing a space suit; regulations clearly stated a habitable environment. All set? Step on through."