As long as i get to be the frog
Group dynamics are different but if it was my group I think I would go around the group and ask about the degree of setbacks when they lose/retreat that they prefer. Maybe with a few hypothetical scenarios and then use that as the starting off point.So talking to one of my players he described a feeling of "not wanting retreat to always mean a lose." And that he feels the consequences of retreating are campaign ending.
I tried explaining that unfortunately retreating does pretty much mean youve lost. If your on a quest and you run away then youve generally failed that quest. I also tried to point out i explicitly do try and make consequences bad without being campaign ending.
At this point it looks like its mostly just a mismatch of expectations and styles with mostly one player. He has a habit of when things go wrong (he doesnt like a rule or ruling, he gets unlucky) of just shutting down and not trying and i think this might be an extension of that. Talking to my players and reading the replies on here have helped me realize i mostly just need to chat with him.
Now i just need to figure out how to do so without it feeling like im singleing him out or attacking him.
But all groups/players are different and what might work for mine might not for yours.